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Record Information
Version2.0
Created at2022-04-28 19:47:56 UTC
Updated at2022-04-28 19:47:56 UTC
NP-MRD IDNP0074514
Secondary Accession NumbersNone
Natural Product Identification
Common NameTriptoquinone A
DescriptionTriptoquinone A belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton. Triptoquinone A is found in Tripterygium doianum and Tripterygium wilfordii . Triptoquinone A was first documented in 2014 (PMID: 25047514). Based on a literature review a small amount of articles have been published on triptoquinone A (PMID: 28948738) (PMID: 28875643).
Structure
Thumb
Synonyms
ValueSource
(4AS-trans)-3,4,4a,5,8,9,10,10a-octahydro-1,4a-dimethyl-7-(1-methylethyl)-5,8-dioxo-2-phenanthrenecarboxylic acidChEBI
(4AS-trans)-3,4,4a,5,8,9,10,10a-octahydro-1,4a-dimethyl-7-(1-methylethyl)-5,8-dioxo-2-phenanthrenecarboxylateGenerator
Chemical FormulaC20H24O4
Average Mass328.4080 Da
Monoisotopic Mass328.16746 Da
IUPAC Name(4aS,10aS)-1,4a-dimethyl-5,8-dioxo-7-(propan-2-yl)-3,4,4a,5,8,9,10,10a-octahydrophenanthrene-2-carboxylic acid
Traditional Name(4aS,10aS)-7-isopropyl-1,4a-dimethyl-5,8-dioxo-4,9,10,10a-tetrahydro-3H-phenanthrene-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC(C)C1=CC(=O)C2=C(CC[C@H]3C(C)=C(CC[C@]23C)C(O)=O)C1=O
InChI Identifier
InChI=1S/C20H24O4/c1-10(2)14-9-16(21)17-13(18(14)22)5-6-15-11(3)12(19(23)24)7-8-20(15,17)4/h9-10,15H,5-8H2,1-4H3,(H,23,24)/t15-,20-/m0/s1
InChI KeyPDPFWAJAYGLYHD-YWZLYKJASA-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
Tripterygium doianumPlant
Tripterygium wilfordiiPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassOxosteroids
Direct ParentOxosteroids
Alternative Parents
Substituents
  • Abietane diterpenoid
  • Diterpenoid
  • 17-oxosteroid
  • Oxosteroid
  • Hydrophenanthrene
  • Phenanthrene
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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
logP2.81ALOGPS
logP3.98ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)4.35ChemAxon
pKa (Strongest Basic)-8.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area71.44 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity93.02 m³·mol⁻¹ChemAxon
Polarizability36.27 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00035774
Chemspider ID117013
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound132524
PDB IDNot Available
ChEBI ID132352
Good Scents IDNot Available
References
General References
  1. Ji JZ, Lao KJ, Hu J, Pang T, Jiang ZZ, Yuan HL, Miao JS, Chen X, Ning SS, Xiang H, Guo YM, Yan M, Zhang LY: Discovery of novel aromatase inhibitors using a homogeneous time-resolved fluorescence assay. Acta Pharmacol Sin. 2014 Aug;35(8):1082-92. doi: 10.1038/aps.2014.53. Epub 2014 Jul 21. [PubMed:25047514 ]
  2. Chen YL, Liu X, Qu XY, Yao YY, Li N, Liang XM, Zhang YY, Yang DJ, Zhang XM: [Studies on difference of chemical compositions in plant species of Tripterygium genus]. Zhongguo Zhong Yao Za Zhi. 2017 Jan;42(2):319-325. doi: 10.19540/j.cnki.cjcmm.20161222.011. [PubMed:28948738 ]
  3. Zhang XM, Chen YL, Yao YY, Li N, Liu YP, Liang XM: [Simultaneous determination of 5 compounds in Tripterygium hypoglaucum based on ultrasound-assisted ionic liquid coupled with HPLC]. Zhongguo Zhong Yao Za Zhi. 2016 Mar;41(5):879-886. doi: 10.4268/cjcmm20160520. [PubMed:28875643 ]