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Record Information
Version2.0
Created at2020-12-09 01:47:07 UTC
Updated at2021-07-15 16:48:44 UTC
NP-MRD IDNP0004271
Secondary Accession NumbersNone
Natural Product Identification
Common NameAzaspirene
Provided ByNPAtlasNPAtlas Logo
Description Azaspirene is found in Neosartorya sp. Azaspirene was first documented in 2002 (PMID: 12182570). Based on a literature review very few articles have been published on (5R,8R,9R)-8-benzyl-2-[(1E,3E)-hexa-1,3-dien-1-yl]-6,8,9-trihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]Nona-2,6-dien-4-one.
Structure
Data?1624574058
SynonymsNot Available
Chemical FormulaC21H23NO5
Average Mass369.4170 Da
Monoisotopic Mass369.15762 Da
IUPAC Name(5S,8R,9R)-8-benzyl-2-[(3E)-hexa-1,3-dien-1-yl]-8,9-dihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione
Traditional Name(5S,8R,9R)-8-benzyl-2-[(3E)-hexa-1,3-dien-1-yl]-8,9-dihydroxy-3-methyl-1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione
CAS Registry NumberNot Available
SMILES
CC\C=C\C=C\C1=C(C)C(=O)[C@@]2(O1)[C@@H](O)[C@](O)(CC1=CC=CC=C1)NC2=O
InChI Identifier
InChI=1S/C21H23NO5/c1-3-4-5-9-12-16-14(2)17(23)21(27-16)18(24)20(26,22-19(21)25)13-15-10-7-6-8-11-15/h4-12,18,24,26H,3,13H2,1-2H3,(H,22,25)/b5-4+,12-9+/t18-,20+,21+/m0/s1
InChI KeyQLKGRMRPKQNCRR-XXPFWKOGSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Neosartorya sp.NPAtlas
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
logP2.69ALOGPS
logP2.63ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)10.28ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area95.86 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity103.47 m³·mol⁻¹ChemAxon
Polarizability40.47 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA006799
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9265103
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11089957
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Asami Y, Kakeya H, Onose R, Yoshida A, Matsuzaki H, Osada H: Azaspirene: a novel angiogenesis inhibitor containing a 1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione skeleton produced by the fungus Neosartorya sp. Org Lett. 2002 Aug 22;4(17):2845-8. doi: 10.1021/ol020104+. [PubMed:12182570 ]