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Record Information
Version2.0
Created at2020-12-09 03:06:27 UTC
Updated at2021-07-15 16:53:38 UTC
NP-MRD IDNP0006028
Secondary Accession NumbersNone
Natural Product Identification
Common NameTetrahydrobisvertinolone
Provided ByNPAtlasNPAtlas Logo
Description Tetrahydrobisvertinolone is found in Penicillium terrestre. Tetrahydrobisvertinolone was first documented in 2005 (PMID: 16161481). Based on a literature review very few articles have been published on (1R,2R,6S,7R,9S)-4,13-bis[(4E)-hex-4-enoyl]-3,6,7,10,12-pentahydroxy-2,6,9,11-tetramethyl-8-oxatricyclo[7.4.0.0²,⁷]Trideca-3,10,12-trien-5-one.
Structure
Data?1624574597
SynonymsNot Available
Chemical FormulaC28H36O9
Average Mass516.5870 Da
Monoisotopic Mass516.23593 Da
IUPAC Name(1R,2R,6S,7R,9S)-4,13-bis[(4E)-hex-4-enoyl]-3,6,7,10,12-pentahydroxy-2,6,9,11-tetramethyl-8-oxatricyclo[7.4.0.0^{2,7}]trideca-3,10,12-trien-5-one
Traditional Name(1R,2R,6S,7R,9S)-4,13-bis[(4E)-hex-4-enoyl]-3,6,7,10,12-pentahydroxy-2,6,9,11-tetramethyl-8-oxatricyclo[7.4.0.0^{2,7}]trideca-3,10,12-trien-5-one
CAS Registry NumberNot Available
SMILES
C\C=C\CCC(=O)C1=C(O)C(C)=C(O)[C@@]2(C)O[C@]3(O)[C@](C)([C@@H]12)C(O)=C(C(=O)CC\C=C\C)C(=O)[C@]3(C)O
InChI Identifier
InChI=1S/C28H36O9/c1-7-9-11-13-16(29)18-20(31)15(3)22(32)26(5)21(18)25(4)23(33)19(17(30)14-12-10-8-2)24(34)27(6,35)28(25,36)37-26/h7-10,21,31-33,35-36H,11-14H2,1-6H3/b9-7+,10-8+/t21-,25-,26+,27+,28-/m1/s1
InChI KeyFEQQKMZNFKCWST-QCNVSJCTSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Penicillium terrestreNPAtlas
Chemical Taxonomy
ClassificationNot classified
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.24ALOGPS
logP2.95ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)3.12ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area161.59 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity141.42 m³·mol⁻¹ChemAxon
Polarizability54.47 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
NPAtlas IDNPA018375
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9447318
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11272310
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Liu W, Gu Q, Zhu W, Cui C, Fan G: Two new benzoquinone derivatives and two new bisorbicillinoids were isolated from a marine-derived fungus Penicillium terrestre. J Antibiot (Tokyo). 2005 Jul;58(7):441-6. doi: 10.1038/ja.2005.57. [PubMed:16161481 ]