Genomic loci for this biosynthetic pathway

Cluster Type From To
The following clusters are from record BGC0001450.1:
Cluster 1Terpene12837
The following clusters are from record BGC0001450.2:
Cluster 2Terpene11725
The following clusters are from record BGC0001450.3:
Cluster 3Terpene11072
The following clusters are from record BGC0001450.4:
Cluster 4Terpene11013
The following clusters are from record BGC0001450.5:
Cluster 5Terpene15352
The following clusters are from record BGC0001450.6:
Cluster 6Terpene11850
The following clusters are from record BGC0001450.7:
Cluster 7Terpene11296
The following clusters are from record BGC0001450.8:
Cluster 8Terpene11059
The following clusters are from record BGC0001450.9:
Cluster 9Terpene1835
The following clusters are from record BGC0001450.10:
Cluster 10Terpene1833
The following clusters are from record BGC0001450.11:
Cluster 11Terpene11721

BGC0001450, macrophorin biosynthetic gene cluster from Penicillium terrestre. Locus 1. Full MIBiG entry.

Chemical compounds

Compound: macrophorin A
PubChem ID: 14526957
SMILES string: Copy to clipboard
Molecular formula: C22H32O4
Average molecular mass: 360.494 Da
Molecular activity: Antibacterial

Class-specific details

Biosynthetic class(es):
Terpene
Terpene subclass:
Other
Terpene subclass by size:
Sesquiterpene
Final isoprenoid precursor:
FPP
Terpene synthase/cyclase-encoding genes:
MF990004
Prenyltransferase-encoding genes:
MF989998

Gene cluster description

macrophorin (BGC0001450). Gene Cluster 1. Biosynthetic class = Terpene. GenBank MF989995. Click on genes for more information.

Legend:

biosynthetic genes
transport-related genes
regulatory genes
other genes

General MIBiG information on this cluster

Complete gene cluster sequence?complete
Evidence for cluster-compound connection:Gene expression correlated with compound production
MIxS-compliance:Unknown
Comments:This cluster is responsible for the biosynthesis of meroterpenoid macrophorins. The membrane-bound terpene cyclase, MacJ, was characterized to catalyze the cyclization of meroterpenoids via direct protonation of the terminal olefin in the linear isoprenoid chain.
Contact for this cluster:Mancheng Tang (UCLA)

Literature references

1. Man-Cheng Tang, Xiaoqing Cui, Xueqian He, Zhuang Ding, Tianjiao Zhu, Yi Tang, Dehai Li. (2017) Late-Stage Terpene Cyclization by an Integral Membrane Cyclase in the Biosynthesis of Isoprenoid Epoxycyclohexenone Natural Products. Organic Letters, vol. 19, no. 19, pp. 5376-5379
2. Haruhiro Fujimoto, Etsuko Nakamura, Yong-Pil Kim, Emi Okuyama, Masami Ishibashi, Takeshi Sassa. (2001) Immunomodulatory Constituents from an Ascomycete,Eupenicillium crustaceum, and Revised Absolute Structure of Macrophorin D. Journal of Natural Products, vol. 64, no. 9, pp. 1234-1237
3. Takeshi Sassa, Hajime Yoshikoshi. (1983) New Terpene-linked Cyclohexenone Epoxides, Macrophorin A, B and C, Produced by the Fungus CausedMacrophomaFruit Rot of Apple. Agricultural and Biological Chemistry, vol. 47, no. 1, pp. 187-189

BGC0001450, macrophorin biosynthetic gene cluster from Penicillium terrestre. Locus 2. Full MIBiG entry.

Chemical compounds

Compound: macrophorin A
PubChem ID: 14526957
SMILES string: Copy to clipboard
Molecular formula: C22H32O4
Average molecular mass: 360.494 Da
Molecular activity: Antibacterial

Class-specific details

Biosynthetic class(es):
Terpene
Terpene subclass:
Other
Terpene subclass by size:
Sesquiterpene
Final isoprenoid precursor:
FPP
Terpene synthase/cyclase-encoding genes:
MF990004
Prenyltransferase-encoding genes:
MF989998

Gene cluster description

macrophorin (BGC0001450). Gene Cluster 2. Biosynthetic class = Terpene. GenBank MF989996. Click on genes for more information.

Legend:

biosynthetic genes
transport-related genes
regulatory genes
other genes

General MIBiG information on this cluster

Complete gene cluster sequence?complete
Evidence for cluster-compound connection:Gene expression correlated with compound production
MIxS-compliance:Unknown
Comments:This cluster is responsible for the biosynthesis of meroterpenoid macrophorins. The membrane-bound terpene cyclase, MacJ, was characterized to catalyze the cyclization of meroterpenoids via direct protonation of the terminal olefin in the linear isoprenoid chain.
Contact for this cluster:Mancheng Tang (UCLA)

Literature references

1. Man-Cheng Tang, Xiaoqing Cui, Xueqian He, Zhuang Ding, Tianjiao Zhu, Yi Tang, Dehai Li. (2017) Late-Stage Terpene Cyclization by an Integral Membrane Cyclase in the Biosynthesis of Isoprenoid Epoxycyclohexenone Natural Products. Organic Letters, vol. 19, no. 19, pp. 5376-5379
2. Haruhiro Fujimoto, Etsuko Nakamura, Yong-Pil Kim, Emi Okuyama, Masami Ishibashi, Takeshi Sassa. (2001) Immunomodulatory Constituents from an Ascomycete,Eupenicillium crustaceum, and Revised Absolute Structure of Macrophorin D. Journal of Natural Products, vol. 64, no. 9, pp. 1234-1237
3. Takeshi Sassa, Hajime Yoshikoshi. (1983) New Terpene-linked Cyclohexenone Epoxides, Macrophorin A, B and C, Produced by the Fungus CausedMacrophomaFruit Rot of Apple. Agricultural and Biological Chemistry, vol. 47, no. 1, pp. 187-189

BGC0001450, macrophorin biosynthetic gene cluster from Penicillium terrestre. Locus 3. Full MIBiG entry.

Chemical compounds

Compound: macrophorin A
PubChem ID: 14526957
SMILES string: Copy to clipboard
Molecular formula: C22H32O4
Average molecular mass: 360.494 Da
Molecular activity: Antibacterial

Class-specific details

Biosynthetic class(es):
Terpene
Terpene subclass:
Other
Terpene subclass by size:
Sesquiterpene
Final isoprenoid precursor:
FPP
Terpene synthase/cyclase-encoding genes:
MF990004
Prenyltransferase-encoding genes:
MF989998

Gene cluster description

macrophorin (BGC0001450). Gene Cluster 3. Biosynthetic class = Terpene. GenBank MF989997. Click on genes for more information.

Legend:

biosynthetic genes
transport-related genes
regulatory genes
other genes

General MIBiG information on this cluster

Complete gene cluster sequence?complete
Evidence for cluster-compound connection:Gene expression correlated with compound production
MIxS-compliance:Unknown
Comments:This cluster is responsible for the biosynthesis of meroterpenoid macrophorins. The membrane-bound terpene cyclase, MacJ, was characterized to catalyze the cyclization of meroterpenoids via direct protonation of the terminal olefin in the linear isoprenoid chain.
Contact for this cluster:Mancheng Tang (UCLA)

Literature references

1. Man-Cheng Tang, Xiaoqing Cui, Xueqian He, Zhuang Ding, Tianjiao Zhu, Yi Tang, Dehai Li. (2017) Late-Stage Terpene Cyclization by an Integral Membrane Cyclase in the Biosynthesis of Isoprenoid Epoxycyclohexenone Natural Products. Organic Letters, vol. 19, no. 19, pp. 5376-5379
2. Haruhiro Fujimoto, Etsuko Nakamura, Yong-Pil Kim, Emi Okuyama, Masami Ishibashi, Takeshi Sassa. (2001) Immunomodulatory Constituents from an Ascomycete,Eupenicillium crustaceum, and Revised Absolute Structure of Macrophorin D. Journal of Natural Products, vol. 64, no. 9, pp. 1234-1237
3. Takeshi Sassa, Hajime Yoshikoshi. (1983) New Terpene-linked Cyclohexenone Epoxides, Macrophorin A, B and C, Produced by the Fungus CausedMacrophomaFruit Rot of Apple. Agricultural and Biological Chemistry, vol. 47, no. 1, pp. 187-189

BGC0001450, macrophorin biosynthetic gene cluster from Penicillium terrestre. Locus 4. Full MIBiG entry.

Chemical compounds

Compound: macrophorin A
PubChem ID: 14526957
SMILES string: Copy to clipboard
Molecular formula: C22H32O4
Average molecular mass: 360.494 Da
Molecular activity: Antibacterial

Class-specific details

Biosynthetic class(es):
Terpene
Terpene subclass:
Other
Terpene subclass by size:
Sesquiterpene
Final isoprenoid precursor:
FPP
Terpene synthase/cyclase-encoding genes:
MF990004
Prenyltransferase-encoding genes:
MF989998

Gene cluster description

macrophorin (BGC0001450). Gene Cluster 4. Biosynthetic class = Terpene. GenBank MF989998. Click on genes for more information.

Legend:

biosynthetic genes
transport-related genes
regulatory genes
other genes

General MIBiG information on this cluster

Complete gene cluster sequence?complete
Evidence for cluster-compound connection:Gene expression correlated with compound production
MIxS-compliance:Unknown
Comments:This cluster is responsible for the biosynthesis of meroterpenoid macrophorins. The membrane-bound terpene cyclase, MacJ, was characterized to catalyze the cyclization of meroterpenoids via direct protonation of the terminal olefin in the linear isoprenoid chain.
Contact for this cluster:Mancheng Tang (UCLA)

Literature references

1. Man-Cheng Tang, Xiaoqing Cui, Xueqian He, Zhuang Ding, Tianjiao Zhu, Yi Tang, Dehai Li. (2017) Late-Stage Terpene Cyclization by an Integral Membrane Cyclase in the Biosynthesis of Isoprenoid Epoxycyclohexenone Natural Products. Organic Letters, vol. 19, no. 19, pp. 5376-5379
2. Haruhiro Fujimoto, Etsuko Nakamura, Yong-Pil Kim, Emi Okuyama, Masami Ishibashi, Takeshi Sassa. (2001) Immunomodulatory Constituents from an Ascomycete,Eupenicillium crustaceum, and Revised Absolute Structure of Macrophorin D. Journal of Natural Products, vol. 64, no. 9, pp. 1234-1237
3. Takeshi Sassa, Hajime Yoshikoshi. (1983) New Terpene-linked Cyclohexenone Epoxides, Macrophorin A, B and C, Produced by the Fungus CausedMacrophomaFruit Rot of Apple. Agricultural and Biological Chemistry, vol. 47, no. 1, pp. 187-189

BGC0001450, macrophorin biosynthetic gene cluster from Penicillium terrestre. Locus 5. Full MIBiG entry.

Chemical compounds

Compound: macrophorin A
PubChem ID: 14526957
SMILES string: Copy to clipboard
Molecular formula: C22H32O4
Average molecular mass: 360.494 Da
Molecular activity: Antibacterial

Class-specific details

Biosynthetic class(es):
Terpene
Terpene subclass:
Other
Terpene subclass by size:
Sesquiterpene
Final isoprenoid precursor:
FPP
Terpene synthase/cyclase-encoding genes:
MF990004
Prenyltransferase-encoding genes:
MF989998

Gene cluster description

macrophorin (BGC0001450). Gene Cluster 5. Biosynthetic class = Terpene. GenBank MF989999. Click on genes for more information.

Legend:

biosynthetic genes
transport-related genes
regulatory genes
other genes

Domain annotation

General MIBiG information on this cluster

Complete gene cluster sequence?complete
Evidence for cluster-compound connection:Gene expression correlated with compound production
MIxS-compliance:Unknown
Comments:This cluster is responsible for the biosynthesis of meroterpenoid macrophorins. The membrane-bound terpene cyclase, MacJ, was characterized to catalyze the cyclization of meroterpenoids via direct protonation of the terminal olefin in the linear isoprenoid chain.
Contact for this cluster:Mancheng Tang (UCLA)

Literature references

1. Man-Cheng Tang, Xiaoqing Cui, Xueqian He, Zhuang Ding, Tianjiao Zhu, Yi Tang, Dehai Li. (2017) Late-Stage Terpene Cyclization by an Integral Membrane Cyclase in the Biosynthesis of Isoprenoid Epoxycyclohexenone Natural Products. Organic Letters, vol. 19, no. 19, pp. 5376-5379
2. Haruhiro Fujimoto, Etsuko Nakamura, Yong-Pil Kim, Emi Okuyama, Masami Ishibashi, Takeshi Sassa. (2001) Immunomodulatory Constituents from an Ascomycete,Eupenicillium crustaceum, and Revised Absolute Structure of Macrophorin D. Journal of Natural Products, vol. 64, no. 9, pp. 1234-1237
3. Takeshi Sassa, Hajime Yoshikoshi. (1983) New Terpene-linked Cyclohexenone Epoxides, Macrophorin A, B and C, Produced by the Fungus CausedMacrophomaFruit Rot of Apple. Agricultural and Biological Chemistry, vol. 47, no. 1, pp. 187-189

BGC0001450, macrophorin biosynthetic gene cluster from Penicillium terrestre. Locus 6. Full MIBiG entry.

Chemical compounds

Compound: macrophorin A
PubChem ID: 14526957
SMILES string: Copy to clipboard
Molecular formula: C22H32O4
Average molecular mass: 360.494 Da
Molecular activity: Antibacterial

Class-specific details

Biosynthetic class(es):
Terpene
Terpene subclass:
Other
Terpene subclass by size:
Sesquiterpene
Final isoprenoid precursor:
FPP
Terpene synthase/cyclase-encoding genes:
MF990004
Prenyltransferase-encoding genes:
MF989998

Gene cluster description

macrophorin (BGC0001450). Gene Cluster 6. Biosynthetic class = Terpene. GenBank MF990000. Click on genes for more information.

Legend:

biosynthetic genes
transport-related genes
regulatory genes
other genes

General MIBiG information on this cluster

Complete gene cluster sequence?complete
Evidence for cluster-compound connection:Gene expression correlated with compound production
MIxS-compliance:Unknown
Comments:This cluster is responsible for the biosynthesis of meroterpenoid macrophorins. The membrane-bound terpene cyclase, MacJ, was characterized to catalyze the cyclization of meroterpenoids via direct protonation of the terminal olefin in the linear isoprenoid chain.
Contact for this cluster:Mancheng Tang (UCLA)

Literature references

1. Man-Cheng Tang, Xiaoqing Cui, Xueqian He, Zhuang Ding, Tianjiao Zhu, Yi Tang, Dehai Li. (2017) Late-Stage Terpene Cyclization by an Integral Membrane Cyclase in the Biosynthesis of Isoprenoid Epoxycyclohexenone Natural Products. Organic Letters, vol. 19, no. 19, pp. 5376-5379
2. Haruhiro Fujimoto, Etsuko Nakamura, Yong-Pil Kim, Emi Okuyama, Masami Ishibashi, Takeshi Sassa. (2001) Immunomodulatory Constituents from an Ascomycete,Eupenicillium crustaceum, and Revised Absolute Structure of Macrophorin D. Journal of Natural Products, vol. 64, no. 9, pp. 1234-1237
3. Takeshi Sassa, Hajime Yoshikoshi. (1983) New Terpene-linked Cyclohexenone Epoxides, Macrophorin A, B and C, Produced by the Fungus CausedMacrophomaFruit Rot of Apple. Agricultural and Biological Chemistry, vol. 47, no. 1, pp. 187-189

BGC0001450, macrophorin biosynthetic gene cluster from Penicillium terrestre. Locus 7. Full MIBiG entry.

Chemical compounds

Compound: macrophorin A
PubChem ID: 14526957
SMILES string: Copy to clipboard
Molecular formula: C22H32O4
Average molecular mass: 360.494 Da
Molecular activity: Antibacterial

Class-specific details

Biosynthetic class(es):
Terpene
Terpene subclass:
Other
Terpene subclass by size:
Sesquiterpene
Final isoprenoid precursor:
FPP
Terpene synthase/cyclase-encoding genes:
MF990004
Prenyltransferase-encoding genes:
MF989998

Gene cluster description

macrophorin (BGC0001450). Gene Cluster 7. Biosynthetic class = Terpene. GenBank MF990001. Click on genes for more information.

Legend:

biosynthetic genes
transport-related genes
regulatory genes
other genes

General MIBiG information on this cluster

Complete gene cluster sequence?complete
Evidence for cluster-compound connection:Gene expression correlated with compound production
MIxS-compliance:Unknown
Comments:This cluster is responsible for the biosynthesis of meroterpenoid macrophorins. The membrane-bound terpene cyclase, MacJ, was characterized to catalyze the cyclization of meroterpenoids via direct protonation of the terminal olefin in the linear isoprenoid chain.
Contact for this cluster:Mancheng Tang (UCLA)

Literature references

1. Man-Cheng Tang, Xiaoqing Cui, Xueqian He, Zhuang Ding, Tianjiao Zhu, Yi Tang, Dehai Li. (2017) Late-Stage Terpene Cyclization by an Integral Membrane Cyclase in the Biosynthesis of Isoprenoid Epoxycyclohexenone Natural Products. Organic Letters, vol. 19, no. 19, pp. 5376-5379
2. Haruhiro Fujimoto, Etsuko Nakamura, Yong-Pil Kim, Emi Okuyama, Masami Ishibashi, Takeshi Sassa. (2001) Immunomodulatory Constituents from an Ascomycete,Eupenicillium crustaceum, and Revised Absolute Structure of Macrophorin D. Journal of Natural Products, vol. 64, no. 9, pp. 1234-1237
3. Takeshi Sassa, Hajime Yoshikoshi. (1983) New Terpene-linked Cyclohexenone Epoxides, Macrophorin A, B and C, Produced by the Fungus CausedMacrophomaFruit Rot of Apple. Agricultural and Biological Chemistry, vol. 47, no. 1, pp. 187-189

BGC0001450, macrophorin biosynthetic gene cluster from Penicillium terrestre. Locus 8. Full MIBiG entry.

Chemical compounds

Compound: macrophorin A
PubChem ID: 14526957
SMILES string: Copy to clipboard
Molecular formula: C22H32O4
Average molecular mass: 360.494 Da
Molecular activity: Antibacterial

Class-specific details

Biosynthetic class(es):
Terpene
Terpene subclass:
Other
Terpene subclass by size:
Sesquiterpene
Final isoprenoid precursor:
FPP
Terpene synthase/cyclase-encoding genes:
MF990004
Prenyltransferase-encoding genes:
MF989998

Gene cluster description

macrophorin (BGC0001450). Gene Cluster 8. Biosynthetic class = Terpene. GenBank MF990002. Click on genes for more information.

Legend:

biosynthetic genes
transport-related genes
regulatory genes
other genes

General MIBiG information on this cluster

Complete gene cluster sequence?complete
Evidence for cluster-compound connection:Gene expression correlated with compound production
MIxS-compliance:Unknown
Comments:This cluster is responsible for the biosynthesis of meroterpenoid macrophorins. The membrane-bound terpene cyclase, MacJ, was characterized to catalyze the cyclization of meroterpenoids via direct protonation of the terminal olefin in the linear isoprenoid chain.
Contact for this cluster:Mancheng Tang (UCLA)

Literature references

1. Man-Cheng Tang, Xiaoqing Cui, Xueqian He, Zhuang Ding, Tianjiao Zhu, Yi Tang, Dehai Li. (2017) Late-Stage Terpene Cyclization by an Integral Membrane Cyclase in the Biosynthesis of Isoprenoid Epoxycyclohexenone Natural Products. Organic Letters, vol. 19, no. 19, pp. 5376-5379
2. Haruhiro Fujimoto, Etsuko Nakamura, Yong-Pil Kim, Emi Okuyama, Masami Ishibashi, Takeshi Sassa. (2001) Immunomodulatory Constituents from an Ascomycete,Eupenicillium crustaceum, and Revised Absolute Structure of Macrophorin D. Journal of Natural Products, vol. 64, no. 9, pp. 1234-1237
3. Takeshi Sassa, Hajime Yoshikoshi. (1983) New Terpene-linked Cyclohexenone Epoxides, Macrophorin A, B and C, Produced by the Fungus CausedMacrophomaFruit Rot of Apple. Agricultural and Biological Chemistry, vol. 47, no. 1, pp. 187-189

BGC0001450, macrophorin biosynthetic gene cluster from Penicillium terrestre. Locus 9. Full MIBiG entry.

Chemical compounds

Compound: macrophorin A
PubChem ID: 14526957
SMILES string: Copy to clipboard
Molecular formula: C22H32O4
Average molecular mass: 360.494 Da
Molecular activity: Antibacterial

Class-specific details

Biosynthetic class(es):
Terpene
Terpene subclass:
Other
Terpene subclass by size:
Sesquiterpene
Final isoprenoid precursor:
FPP
Terpene synthase/cyclase-encoding genes:
MF990004
Prenyltransferase-encoding genes:
MF989998

Gene cluster description

macrophorin (BGC0001450). Gene Cluster 9. Biosynthetic class = Terpene. GenBank MF990003. Click on genes for more information.

Legend:

biosynthetic genes
transport-related genes
regulatory genes
other genes

General MIBiG information on this cluster

Complete gene cluster sequence?complete
Evidence for cluster-compound connection:Gene expression correlated with compound production
MIxS-compliance:Unknown
Comments:This cluster is responsible for the biosynthesis of meroterpenoid macrophorins. The membrane-bound terpene cyclase, MacJ, was characterized to catalyze the cyclization of meroterpenoids via direct protonation of the terminal olefin in the linear isoprenoid chain.
Contact for this cluster:Mancheng Tang (UCLA)

Literature references

1. Man-Cheng Tang, Xiaoqing Cui, Xueqian He, Zhuang Ding, Tianjiao Zhu, Yi Tang, Dehai Li. (2017) Late-Stage Terpene Cyclization by an Integral Membrane Cyclase in the Biosynthesis of Isoprenoid Epoxycyclohexenone Natural Products. Organic Letters, vol. 19, no. 19, pp. 5376-5379
2. Haruhiro Fujimoto, Etsuko Nakamura, Yong-Pil Kim, Emi Okuyama, Masami Ishibashi, Takeshi Sassa. (2001) Immunomodulatory Constituents from an Ascomycete,Eupenicillium crustaceum, and Revised Absolute Structure of Macrophorin D. Journal of Natural Products, vol. 64, no. 9, pp. 1234-1237
3. Takeshi Sassa, Hajime Yoshikoshi. (1983) New Terpene-linked Cyclohexenone Epoxides, Macrophorin A, B and C, Produced by the Fungus CausedMacrophomaFruit Rot of Apple. Agricultural and Biological Chemistry, vol. 47, no. 1, pp. 187-189

BGC0001450, macrophorin biosynthetic gene cluster from Penicillium terrestre. Locus 10. Full MIBiG entry.

Chemical compounds

Compound: macrophorin A
PubChem ID: 14526957
SMILES string: Copy to clipboard
Molecular formula: C22H32O4
Average molecular mass: 360.494 Da
Molecular activity: Antibacterial

Class-specific details

Biosynthetic class(es):
Terpene
Terpene subclass:
Other
Terpene subclass by size:
Sesquiterpene
Final isoprenoid precursor:
FPP
Terpene synthase/cyclase-encoding genes:
MF990004
Prenyltransferase-encoding genes:
MF989998

Gene cluster description

macrophorin (BGC0001450). Gene Cluster 10. Biosynthetic class = Terpene. GenBank MF990004. Click on genes for more information.

Legend:

biosynthetic genes
transport-related genes
regulatory genes
other genes

General MIBiG information on this cluster

Complete gene cluster sequence?complete
Evidence for cluster-compound connection:Gene expression correlated with compound production
MIxS-compliance:Unknown
Comments:This cluster is responsible for the biosynthesis of meroterpenoid macrophorins. The membrane-bound terpene cyclase, MacJ, was characterized to catalyze the cyclization of meroterpenoids via direct protonation of the terminal olefin in the linear isoprenoid chain.
Contact for this cluster:Mancheng Tang (UCLA)

Literature references

1. Man-Cheng Tang, Xiaoqing Cui, Xueqian He, Zhuang Ding, Tianjiao Zhu, Yi Tang, Dehai Li. (2017) Late-Stage Terpene Cyclization by an Integral Membrane Cyclase in the Biosynthesis of Isoprenoid Epoxycyclohexenone Natural Products. Organic Letters, vol. 19, no. 19, pp. 5376-5379
2. Haruhiro Fujimoto, Etsuko Nakamura, Yong-Pil Kim, Emi Okuyama, Masami Ishibashi, Takeshi Sassa. (2001) Immunomodulatory Constituents from an Ascomycete,Eupenicillium crustaceum, and Revised Absolute Structure of Macrophorin D. Journal of Natural Products, vol. 64, no. 9, pp. 1234-1237
3. Takeshi Sassa, Hajime Yoshikoshi. (1983) New Terpene-linked Cyclohexenone Epoxides, Macrophorin A, B and C, Produced by the Fungus CausedMacrophomaFruit Rot of Apple. Agricultural and Biological Chemistry, vol. 47, no. 1, pp. 187-189

BGC0001450, macrophorin biosynthetic gene cluster from Penicillium terrestre. Locus 11. Full MIBiG entry.

Chemical compounds

Compound: macrophorin A
PubChem ID: 14526957
SMILES string: Copy to clipboard
Molecular formula: C22H32O4
Average molecular mass: 360.494 Da
Molecular activity: Antibacterial

Class-specific details

Biosynthetic class(es):
Terpene
Terpene subclass:
Other
Terpene subclass by size:
Sesquiterpene
Final isoprenoid precursor:
FPP
Terpene synthase/cyclase-encoding genes:
MF990004
Prenyltransferase-encoding genes:
MF989998

Gene cluster description

macrophorin (BGC0001450). Gene Cluster 11. Biosynthetic class = Terpene. GenBank MF990005. Click on genes for more information.

Legend:

biosynthetic genes
transport-related genes
regulatory genes
other genes

General MIBiG information on this cluster

Complete gene cluster sequence?complete
Evidence for cluster-compound connection:Gene expression correlated with compound production
MIxS-compliance:Unknown
Comments:This cluster is responsible for the biosynthesis of meroterpenoid macrophorins. The membrane-bound terpene cyclase, MacJ, was characterized to catalyze the cyclization of meroterpenoids via direct protonation of the terminal olefin in the linear isoprenoid chain.
Contact for this cluster:Mancheng Tang (UCLA)

Literature references

1. Man-Cheng Tang, Xiaoqing Cui, Xueqian He, Zhuang Ding, Tianjiao Zhu, Yi Tang, Dehai Li. (2017) Late-Stage Terpene Cyclization by an Integral Membrane Cyclase in the Biosynthesis of Isoprenoid Epoxycyclohexenone Natural Products. Organic Letters, vol. 19, no. 19, pp. 5376-5379
2. Haruhiro Fujimoto, Etsuko Nakamura, Yong-Pil Kim, Emi Okuyama, Masami Ishibashi, Takeshi Sassa. (2001) Immunomodulatory Constituents from an Ascomycete,Eupenicillium crustaceum, and Revised Absolute Structure of Macrophorin D. Journal of Natural Products, vol. 64, no. 9, pp. 1234-1237
3. Takeshi Sassa, Hajime Yoshikoshi. (1983) New Terpene-linked Cyclohexenone Epoxides, Macrophorin A, B and C, Produced by the Fungus CausedMacrophomaFruit Rot of Apple. Agricultural and Biological Chemistry, vol. 47, no. 1, pp. 187-189