Np mrd loader

Record Information
Version2.0
Created at2021-01-06 01:40:25 UTC
Updated at2021-07-15 17:23:39 UTC
NP-MRD IDNP0016776
Secondary Accession NumbersNone
Natural Product Identification
Common NameSpirograterpene A
Provided ByNPAtlasNPAtlas Logo
Description Spirograterpene A is found in Penicillium and Penicillium granulatum. Spirograterpene A was first documented in 2017 (PMID: 28692272). Based on a literature review very few articles have been published on Spirograterpene A (PMID: 34094343).
Structure
Data?1624506279
Synonyms
ValueSource
(1R,1'r,2R,3R,5R,8'r,11's)-3-Hydroxy-2,5,8',11'-tetramethylspiro[cyclopentane-1,5'-tricyclo[6.3.0.0,]undecan]-2'(6')-ene-11'-carboxylateGenerator
Chemical FormulaC20H30O3
Average Mass318.4570 Da
Monoisotopic Mass318.21949 Da
IUPAC Name(1R,1'R,2R,3R,5R,8'R,11'S)-3-hydroxy-2,5,8',11'-tetramethylspiro[cyclopentane-1,5'-tricyclo[6.3.0.0^{2,6}]undecan]-2'(6')-ene-11'-carboxylic acid
Traditional Name(1R,1'R,2R,3R,5R,8'R,11'S)-3-hydroxy-2,5,8',11'-tetramethylspiro[cyclopentane-1,5'-tricyclo[6.3.0.0^{2,6}]undecan]-2'(6')-ene-11'-carboxylic acid
CAS Registry NumberNot Available
SMILES
C[C@@H]1C[C@@H](O)[C@H](C)[C@@]11CCC2=C1C[C@@]1(C)CC[C@@](C)([C@@H]21)C(O)=O
InChI Identifier
InChI=1S/C20H30O3/c1-11-9-15(21)12(2)20(11)6-5-13-14(20)10-18(3)7-8-19(4,16(13)18)17(22)23/h11-12,15-16,21H,5-10H2,1-4H3,(H,22,23)/t11-,12+,15-,16+,18-,19+,20-/m1/s1
InChI KeyIXEKUSSTAAFIKN-FKBRWOSRSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
PenicilliumNPAtlas
Penicillium granulatumLOTUS Database
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
logP3.34ALOGPS
logP3.24ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)4.7ChemAxon
pKa (Strongest Basic)-0.94ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity89.71 m³·mol⁻¹ChemAxon
Polarizability36.43 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA022396
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID78441650
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound139589750
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Niu S, Fan ZW, Xie CL, Liu Q, Luo ZH, Liu G, Yang XW: Spirograterpene A, a Tetracyclic Spiro-Diterpene with a Fused 5/5/5/5 Ring System from the Deep-Sea-Derived Fungus Penicillium granulatum MCCC 3A00475. J Nat Prod. 2017 Jul 28;80(7):2174-2177. doi: 10.1021/acs.jnatprod.7b00475. Epub 2017 Jul 10. [PubMed:28692272 ]
  2. Chi HM, Cole CJF, Hu P, Taylor CA, Snyder SA: Total syntheses of spiroviolene and spirograterpene A: a structural reassignment with biosynthetic implications. Chem Sci. 2020 Sep 30;11(40):10939-10944. doi: 10.1039/d0sc04686h. [PubMed:34094343 ]