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Showing metabocard for Tropolone (HMDB0259299)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 21:49:11 UTC
Update Date2021-10-01 23:44:17 UTC
HMDB IDHMDB0259299
Secondary Accession NumbersNone
Metabolite Identification
Common NameTropolone
Descriptiontropolone, also known as 2-hydroxytropone or purpurocatechol, belongs to the class of organic compounds known as tropolones. Tropolones are compounds containing tropone ring with a hydroxyl group at ring position 2. tropolone is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on tropolone. This compound has been identified in human blood as reported by (PMID: 31557052 ). Tropolone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Tropolone is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0259299 (Tropolone)

  Mrv1652304272018432D          

  9  9  0  0  0  0            999 V2000
    0.9507    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5927    0.7433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5927   -0.7433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2115    0.9268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2115   -0.9268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8566    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8566   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5998    0.7704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5998   -0.7704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  2  0  0  0  0
  4  6  2  0  0  0  0
  5  7  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  2  0  0  0  0
M  END
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3D MOL for HMDB0259299 (Tropolone)

HMDB0259299
     RDKit          3D
Tropolone
 15 15  0  0  0  0  0  0  0  0999 V2000
    0.6307   -2.5256    0.0868 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2545   -1.3277    0.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1224   -1.1216   -0.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8152    0.0525    0.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2647    1.3286    0.1279 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0137    1.7104   -0.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1691    0.9339   -0.3056 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2760   -0.4101   -0.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5329   -0.9415    0.1778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7427   -1.9777   -0.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8391   -0.0384    0.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9718    2.1011    0.3613 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1271    2.7366   -0.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0860    1.4036   -0.5954 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6660   -1.9240    0.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8  2  1  0
  3 10  1  0
  4 11  1  0
  5 12  1  0
  6 13  1  0
  7 14  1  0
  9 15  1  0
M  END
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3D SDF for HMDB0259299 (Tropolone)

  Mrv1652304272018432D          

  9  9  0  0  0  0            999 V2000
    0.9507    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5927    0.7433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5927   -0.7433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2115    0.9268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2115   -0.9268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8566    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8566   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5998    0.7704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5998   -0.7704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  2  0  0  0  0
  4  6  2  0  0  0  0
  5  7  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259299

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=CC=CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H6O2/c8-6-4-2-1-3-5-7(6)9/h1-5H,(H,8,9)

> <INCHI_KEY>
MDYOLVRUBBJPFM-UHFFFAOYSA-N

> <FORMULA>
C7H6O2

> <MOLECULAR_WEIGHT>
122.1213

> <EXACT_MASS>
122.036779436

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
11.894158901439784

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxycyclohepta-2,4,6-trien-1-one

> <ALOGPS_LOGP>
0.07

> <JCHEM_LOGP>
1.0874972376666665

> <ALOGPS_LOGS>
-0.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.260552133364282

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8028944968664637

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
38.119

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.36e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tropolone

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0259299 (Tropolone)

HMDB0259299
     RDKit          3D
Tropolone
 15 15  0  0  0  0  0  0  0  0999 V2000
    0.6307   -2.5256    0.0868 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2545   -1.3277    0.0069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1224   -1.1216   -0.0101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8152    0.0525    0.2341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2647    1.3286    0.1279 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0137    1.7104   -0.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1691    0.9339   -0.3056 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2760   -0.4101   -0.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5329   -0.9415    0.1778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7427   -1.9777   -0.2417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8391   -0.0384    0.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9718    2.1011    0.3613 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1271    2.7366   -0.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0860    1.4036   -0.5954 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6660   -1.9240    0.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8  2  1  0
  3 10  1  0
  4 11  1  0
  5 12  1  0
  6 13  1  0
  7 14  1  0
  9 15  1  0
M  END
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PDB for HMDB0259299 (Tropolone)

HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0       1.775   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.106   1.388   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.106  -1.388   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.395   1.730   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.395  -1.730   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.599   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.599  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.986   1.438   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -2.986  -1.438   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    7    8                                                  
CONECT    7    5    6    9                                                  
CONECT    8    6                                                            
CONECT    9    7                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for HMDB0259299 (Tropolone)

COMPND    HMDB0259299
HETATM    1  O1  UNL     1       0.631  -2.526   0.087  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.255  -1.328   0.007  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.122  -1.122  -0.010  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.815   0.052   0.234  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.265   1.329   0.128  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.014   1.710  -0.223  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.169   0.934  -0.306  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.276  -0.410  -0.051  1.00  0.00           C  
HETATM    9  O2  UNL     1       2.533  -0.942   0.178  1.00  0.00           O  
HETATM   10  H1  UNL     1      -1.743  -1.978  -0.242  1.00  0.00           H  
HETATM   11  H2  UNL     1      -2.839  -0.038   0.522  1.00  0.00           H  
HETATM   12  H3  UNL     1      -1.972   2.101   0.361  1.00  0.00           H  
HETATM   13  H4  UNL     1       0.127   2.737  -0.460  1.00  0.00           H  
HETATM   14  H5  UNL     1       2.086   1.404  -0.595  1.00  0.00           H  
HETATM   15  H6  UNL     1       2.666  -1.924   0.370  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    8
CONECT    3    4    4   10
CONECT    4    5   11
CONECT    5    6    6   12
CONECT    6    7   13
CONECT    7    8    8   14
CONECT    8    9
CONECT    9   15
END
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SMILES for HMDB0259299 (Tropolone)

OC1=CC=CC=CC1=O
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INCHI for HMDB0259299 (Tropolone)

InChI=1S/C7H6O2/c8-6-4-2-1-3-5-7(6)9/h1-5H,(H,8,9)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
2-Hydroxy-2,4,6-cycloheptatrien-1-oneChEBI
2-Hydroxycyclohepta-2,4,6-trienoneChEBI
2-HydroxytroponeChEBI
PurpurocatecholChEBI
Chemical FormulaC7H6O2
Average Molecular Weight122.1213
Monoisotopic Molecular Weight122.036779436
IUPAC Name2-hydroxycyclohepta-2,4,6-trien-1-one
Traditional Nametropolone
CAS Registry NumberNot Available
SMILES
OC1=CC=CC=CC1=O
InChI Identifier
InChI=1S/C7H6O2/c8-6-4-2-1-3-5-7(6)9/h1-5H,(H,8,9)
InChI KeyMDYOLVRUBBJPFM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tropolones. Tropolones are compounds containing tropone ring with a hydroxyl group at ring position 2.
KingdomOrganic compounds
Super ClassHydrocarbon derivatives
ClassTropones
Sub ClassTropolones
Direct ParentTropolones
Alternative Parents
Substituents
  • Tropolone
  • Cyclic ketone
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00011964
Chemspider ID10333
KEGG Compound IDC15474
BioCyc IDCPD-7024
BiGG IDNot Available
Wikipedia LinkTropolone
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID79966
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1295771
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Enzymes

Enzyme Details
1. 3-methylorcinaldehyde synthase
General function:
Not Available
Specific function:
Non-reducing polyketide synthase; part of the gene cluster that mediates the biosynthesis of xenovulene A, an unusual meroterpenoid that has potent inhibitory effects on the human gamma-aminobutyrate A (GABAA) benzodiazepine receptor (PubMed:17912413, PubMed:29773797, PubMed:20552126). The first step of xenovulene A biosynthesis is the biosynthesis of 3-methylorcinaldehyde performed by the non-reducing polyketide synthase aspks1 (PubMed:17912413, PubMed:29773797, PubMed:20552126). The salicylate hydroxylase asL1 then catalyzes the oxidative dearomatization of 3-methylorcinaldehyde to yield a dearomatized hydroxycyclohexadione (PubMed:29773797). The 2-oxoglutarate-dependent dioxygenase asL3 further catalyzes the oxidative ring expansion to provide the first tropolone metabolite (PubMed:29773797). The cytochrome P450 monooxygenase asR2 allows the synthesis of tropolone hemiacetal (PubMed:29773797). In parallel, a previously unrecognised class of terpene cyclase, asR6, produces alpha-humulene from farnesylpyrophosphate (FPP) (PubMed:29773797). The putative Diels-Alderase asR5 probably catalyzes the formation of the tropolone-humulene skeleton by linking humulene and the polyketide moiety (PubMed:29773797). Oxidative-ring contractions catalyzed by asL4 and asL6 then processively remove carbon atoms from the polyketide to yield xenovulene A (PubMed:29773797).
Gene Name:
ASPKS1
Uniprot ID:
A5PHD6
Molecular weight:
296112.47
Enzyme Details
2. Cytochrome P450 monooxygenase asR2
General function:
Not Available
Specific function:
Cytochrome P450 monooxygenase; part of the gene cluster that mediates the biosynthesis of xenovulene A, an unusual meroterpenoid that has potent inhibitory effects on the human gamma-aminobutyrate A (GABAA) benzodiazepine receptor (PubMed:29773797). The first step of xenovulene A biosynthesis is the biosynthesis of 3-methylorcinaldehyde performed by the non-reducing polyketide synthase aspks1 (PubMed:17912413, PubMed:29773797, PubMed:20552126). The salicylate hydroxylase asL1 then catalyzes the oxidative dearomatization of 3-methylorcinaldehyde to yield a dearomatized hydroxycyclohexadione (PubMed:29773797). The 2-oxoglutarate-dependent dioxygenase asL3 further catalyzes the oxidative ring expansion to provide the first tropolone metabolite (PubMed:29773797). The cytochrome P450 monooxygenase asR2 allows the synthesis of tropolone hemiacetal (PubMed:29773797). In parallel, a previously unrecognised class of terpene cyclase, asR6, produces alpha-humulene from farnesylpyrophosphate (FPP) (PubMed:29773797). The putative Diels-Alderase asR5 probably catalyzes the formation of the tropolone-humulene skeleton by linking humulene and the polyketide moiety (PubMed:29773797). Oxidative-ring contractions catalyzed by asL4 and asL6 then processively remove carbon atoms from the polyketide to yield xenovulene A (PubMed:29773797).
Gene Name:
ASR2
Uniprot ID:
A0A2U8U2M8
Molecular weight:
59131.855
Enzyme Details
3. FAD-dependent monooxygenase asL4
General function:
Not Available
Specific function:
Flavin-dependent monooxygenase; part of the gene cluster that mediates the biosynthesis of xenovulene A, an unusual meroterpenoid that has potent inhibitory effects on the human gamma-aminobutyrate A (GABAA) benzodiazepine receptor (PubMed:29773797). The first step of xenovulene A biosynthesis is the biosynthesis of 3-methylorcinaldehyde performed by the non-reducing polyketide synthase aspks1 (PubMed:17912413, PubMed:29773797, PubMed:20552126). The salicylate hydroxylase asL1 then catalyzes the oxidative dearomatization of 3-methylorcinaldehyde to yield a dearomatized hydroxycyclohexadione (PubMed:29773797). The 2-oxoglutarate-dependent dioxygenase asL3 further catalyzes the oxidative ring expansion to provide the first tropolone metabolite (PubMed:29773797). The cytochrome P450 monooxygenase asR2 allows the synthesis of tropolone hemiacetal (PubMed:29773797). In parallel, a previously unrecognised class of terpene cyclase, asR6, produces alpha-humulene from farnesylpyrophosphate (FPP) (PubMed:29773797). The putative Diels-Alderase asR5 probably catalyzes the formation of the tropolone-humulene skeleton by linking humulene and the polyketide moiety (PubMed:29773797). Oxidative-ring contractions catalyzed by asL4 and asL6 then processively remove carbon atoms from the polyketide to yield xenovulene A (PubMed:29773797).
Gene Name:
ASL4
Uniprot ID:
A0A2U8U2L4
Molecular weight:
47732.665
Enzyme Details
4. Oxidoreductase asL5
General function:
Not Available
Specific function:
Oxidoreductase; part of the gene cluster that mediates the biosynthesis of xenovulene A, an unusual meroterpenoid that has potent inhibitory effects on the human gamma-aminobutyrate A (GABAA) benzodiazepine receptor (PubMed:29773797). The first step of xenovulene A biosynthesis is the biosynthesis of 3-methylorcinaldehyde performed by the non-reducing polyketide synthase aspks1 (PubMed:17912413, PubMed:29773797, PubMed:20552126). The salicylate hydroxylase asL1 then catalyzes the oxidative dearomatization of 3-methylorcinaldehyde to yield a dearomatized hydroxycyclohexadione (PubMed:29773797). The 2-oxoglutarate-dependent dioxygenase asL3 further catalyzes the oxidative ring expansion to provide the first tropolone metabolite (PubMed:29773797). The cytochrome P450 monooxygenase asR2 allows the synthesis of tropolone hemiacetal (PubMed:29773797). In parallel, a previously unrecognised class of terpene cyclase, asR6, produces alpha-humulene from farnesylpyrophosphate (FPP) (PubMed:29773797). The putative Diels-Alderase asR5 probably catalyzes the formation of the tropolone-humulene skeleton by linking humulene and the polyketide moiety (PubMed:29773797). Oxidative-ring contractions catalyzed by asL4 and asL6 then processively remove carbon atoms from the polyketide to yield xenovulene A (PubMed:29773797).
Gene Name:
ASL5
Uniprot ID:
A0A2U8U2K8
Molecular weight:
25469.86
Enzyme Details
5. Xenovulene A biosynthesis cluster protein asL2
General function:
Not Available
Specific function:
Part of the gene cluster that mediates the biosynthesis of xenovulene A, an unusual meroterpenoid that has potent inhibitory effects on the human gamma-aminobutyrate A (GABAA) benzodiazepine receptor (PubMed:29773797). The first step of xenovulene A biosynthesis is the biosynthesis of 3-methylorcinaldehyde performed by the non-reducing polyketide synthase aspks1 (PubMed:17912413, PubMed:29773797, PubMed:20552126). The salicylate hydroxylase asL1 then catalyzes the oxidative dearomatization of 3-methylorcinaldehyde to yield a dearomatized hydroxycyclohexadione (PubMed:29773797). The 2-oxoglutarate-dependent dioxygenase asL3 further catalyzes the oxidative ring expansion to provide the first tropolone metabolite (PubMed:29773797). The cytochrome P450 monooxygenase asR2 allows the synthesis of tropolone hemiacetal (PubMed:29773797). In parallel, a previously unrecognised class of terpene cyclase, asR6, produces alpha-humulene from farnesylpyrophosphate (FPP) (PubMed:29773797). The putative Diels-Alderase asR5 probably catalyzes the formation of the tropolone-humulene skeleton by linking humulene and the polyketide moiety (PubMed:29773797). Oxidative-ring contractions catalyzed by asL4 and asL6 then processively remove carbon atoms from the polyketide to yield xenovulene A (PubMed:29773797).
Gene Name:
ASL2
Uniprot ID:
A0A2U8U2L2
Molecular weight:
12582.36
Enzyme Details
6. 2-oxoglutarate-dependent dioxygenase asL3
General function:
Not Available
Specific function:
2-oxoglutarate-dependent dioxygenase; part of the gene cluster that mediates the biosynthesis of xenovulene A, an unusual meroterpenoid that has potent inhibitory effects on the human gamma-aminobutyrate A (GABAA) benzodiazepine receptor (PubMed:29773797). The first step of xenovulene A biosynthesis is the biosynthesis of 3-methylorcinaldehyde performed by the non-reducing polyketide synthase aspks1 (PubMed:17912413, PubMed:29773797, PubMed:20552126). The salicylate hydroxylase asL1 then catalyzes the oxidative dearomatization of 3-methylorcinaldehyde to yield a dearomatized hydroxycyclohexadione (PubMed:29773797). The 2-oxoglutarate-dependent dioxygenase asL3 further catalyzes the oxidative ring expansion to provide the first tropolone metabolite (PubMed:29773797). The cytochrome P450 monooxygenase asR2 allows the synthesis of tropolone hemiacetal (PubMed:29773797). In parallel, a previously unrecognised class of terpene cyclase, asR6, produces alpha-humulene from farnesylpyrophosphate (FPP) (PubMed:29773797). The putative Diels-Alderase asR5 probably catalyzes the formation of the tropolone-humulene skeleton by linking humulene and the polyketide moiety (PubMed:29773797). Oxidative-ring contractions catalyzed by asL4 and asL6 then processively remove carbon atoms from the polyketide to yield xenovulene A (PubMed:29773797).
Gene Name:
ASL3
Uniprot ID:
A0A2U8U2L3
Molecular weight:
37709.775
Enzyme Details
7. FAD-dependent monooxygenase asL6
General function:
Not Available
Specific function:
FAD-dependent monooxygenase; part of the gene cluster that mediates the biosynthesis of xenovulene A, an unusual meroterpenoid that has potent inhibitory effects on the human gamma-aminobutyrate A (GABAA) benzodiazepine receptor (PubMed:29773797). The first step of xenovulene A biosynthesis is the biosynthesis of 3-methylorcinaldehyde performed by the non-reducing polyketide synthase aspks1 (PubMed:17912413, PubMed:29773797, PubMed:20552126). The salicylate hydroxylase asL1 then catalyzes the oxidative dearomatization of 3-methylorcinaldehyde to yield a dearomatized hydroxycyclohexadione (PubMed:29773797). The 2-oxoglutarate-dependent dioxygenase asL3 further catalyzes the oxidative ring expansion to provide the first tropolone metabolite (PubMed:29773797). The cytochrome P450 monooxygenase asR2 allows the synthesis of tropolone hemiacetal (PubMed:29773797). In parallel, a previously unrecognised class of terpene cyclase, asR6, produces alpha-humulene from farnesylpyrophosphate (FPP) (PubMed:29773797). The putative Diels-Alderase asR5 probably catalyzes the formation of the tropolone-humulene skeleton by linking humulene and the polyketide moiety (PubMed:29773797). Oxidative-ring contractions catalyzed by asL4 and asL6 then processively remove carbon atoms from the polyketide to yield xenovulene A (PubMed:29773797).
Gene Name:
ASL6
Uniprot ID:
A0A2U8U2L0
Molecular weight:
46997.68
Enzyme Details
8. Putative hetero-Diels-Alderase asR5
General function:
Not Available
Specific function:
Putative hetero-Diels-Alderase; part of the gene cluster that mediates the biosynthesis of xenovulene A, an unusual meroterpenoid that has potent inhibitory effects on the human gamma-aminobutyrate A (GABAA) benzodiazepine receptor (PubMed:29773797). The first step of xenovulene A biosynthesis is the biosynthesis of 3-methylorcinaldehyde performed by the non-reducing polyketide synthase aspks1 (PubMed:17912413, PubMed:29773797, PubMed:20552126). The salicylate hydroxylase asL1 then catalyzes the oxidative dearomatization of 3-methylorcinaldehyde to yield a dearomatized hydroxycyclohexadione (PubMed:29773797). The 2-oxoglutarate-dependent dioxygenase asL3 further catalyzes the oxidative ring expansion to provide the first tropolone metabolite (PubMed:29773797). The cytochrome P450 monooxygenase asR2 allows the synthesis of tropolone hemiacetal (PubMed:29773797). In parallel, a previously unrecognised class of terpene cyclase, asR6, produces alpha-humulene from farnesylpyrophosphate (FPP) (PubMed:29773797). The putative Diels-Alderase asR5 probably catalyzes the formation of the tropolone-humulene skeleton by linking humulene and the polyketide moiety (PubMed:29773797). Oxidative-ring contractions catalyzed by asL4 and asL6 then processively remove carbon atoms from the polyketide to yield xenovulene A (PubMed:29773797).
Gene Name:
ASR5
Uniprot ID:
A0A2U8U2M1
Molecular weight:
44333.67
Enzyme Details
9. Salicylate hydroxylase asL1
General function:
Not Available
Specific function:
Salicylate hydroxylase; part of the gene cluster that mediates the biosynthesis of xenovulene A, an unusual meroterpenoid that has potent inhibitory effects on the human gamma-aminobutyrate A (GABAA) benzodiazepine receptor (PubMed:29773797). The first step of xenovulene A biosynthesis is the biosynthesis of 3-methylorcinaldehyde performed by the non-reducing polyketide synthase aspks1 (PubMed:17912413, PubMed:29773797, PubMed:20552126). The salicylate hydroxylase asL1 then catalyzes the oxidative dearomatization of 3-methylorcinaldehyde to yield a dearomatized hydroxycyclohexadione (PubMed:29773797). The 2-oxoglutarate-dependent dioxygenase asL3 further catalyzes the oxidative ring expansion to provide the first tropolone metabolite (PubMed:29773797). The cytochrome P450 monooxygenase asR2 allows the synthesis of tropolone hemiacetal (PubMed:29773797). In parallel, a previously unrecognised class of terpene cyclase, asR6, produces alpha-humulene from farnesylpyrophosphate (FPP) (PubMed:29773797). The putative Diels-Alderase asR5 probably catalyzes the formation of the tropolone-humulene skeleton by linking humulene and the polyketide moiety (PubMed:29773797). Oxidative-ring contractions catalyzed by asL4 and asL6 then processively remove carbon atoms from the polyketide to yield xenovulene A (PubMed:29773797).
Gene Name:
ASL1
Uniprot ID:
A0A2U8U2L6
Molecular weight:
53344.835
Enzyme Details
10. Alpha-humulene synthase asR6
General function:
Not Available
Specific function:
Alpha-humulene synthase; part of the gene cluster that mediates the biosynthesis of xenovulene A, an unusual meroterpenoid that has potent inhibitory effects on the human gamma-aminobutyrate A (GABAA) benzodiazepine receptor (PubMed:29773797). The first step of xenovulene A biosynthesis is the biosynthesis of 3-methylorcinaldehyde performed by the non-reducing polyketide synthase aspks1 (PubMed:17912413, PubMed:29773797, PubMed:20552126). The salicylate hydroxylase asL1 then catalyzes the oxidative dearomatization of 3-methylorcinaldehyde to yield a dearomatized hydroxycyclohexadione (PubMed:29773797). The 2-oxoglutarate-dependent dioxygenase asL3 further catalyzes the oxidative ring expansion to provide the first tropolone metabolite (PubMed:29773797). The cytochrome P450 monooxygenase asR2 allows the synthesis of tropolone hemiacetal (PubMed:29773797). In parallel, a previously unrecognised class of terpene cyclase, asR6, produces alpha-humulene from farnesylpyrophosphate (FPP) (PubMed:29773797). The putative Diels-Alderase asR5 probably catalyzes the formation of the tropolone-humulene skeleton by linking humulene and the polyketide moiety (PubMed:29773797). Oxidative-ring contractions catalyzed by asL4 and asL6 then processively remove carbon atoms from the polyketide to yield xenovulene A (PubMed:29773797).
Gene Name:
ASR6
Uniprot ID:
A0A2U8U2L5
Molecular weight:
48386.605