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Record Information
Version2.0
Created at2022-09-12 04:29:39 UTC
Updated at2022-09-12 04:29:39 UTC
NP-MRD IDNP0324424
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2e,6r)-6-[(1r,3r,3ar,5ar,7r,9as,11ar)-3,7-bis(acetyloxy)-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid
DescriptionGanodermic acid S, also known as ganodermate S, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (2e,6r)-6-[(1r,3r,3ar,5ar,7r,9as,11ar)-3,7-bis(acetyloxy)-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid was first documented in 1990 (PMID: 1966354). Based on a literature review a small amount of articles have been published on Ganodermic acid S (PMID: 10946087) (PMID: 10413295) (PMID: 10064905) (PMID: 1649599).
Structure
Thumb
Synonyms
ValueSource
Ganodermate SGenerator
Ganodermic acid S, (3alpha,15alpha,24E)-isomerMeSH
Ganoderic acid RMeSH
Ganodermic acid DMMeSH
Ganodermic acid S, (3alpha,22S,24E)-isomerMeSH
Lanosta-7,9(11),24-trien-3,15-diacetoxy-26-Oic acidMeSH
Chemical FormulaC34H50O6
Average Mass554.7680 Da
Monoisotopic Mass554.36074 Da
IUPAC Name(2E,6R)-6-[(2S,5R,7R,11R,12R,14R,15R)-5,12-bis(acetyloxy)-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(17),9-dien-14-yl]-2-methylhept-2-enoic acid
Traditional Name(2E,6R)-6-[(2S,5R,7R,11R,12R,14R,15R)-5,12-bis(acetyloxy)-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(17),9-dien-14-yl]-2-methylhept-2-enoic acid
CAS Registry NumberNot Available
SMILES
C[C@H](CC\C=C(/C)C(O)=O)[C@H]1C[C@@H](OC(C)=O)[C@@]2(C)C3=CC[C@H]4C(C)(C)[C@@H](CC[C@]4(C)C3=CC[C@]12C)OC(C)=O
InChI Identifier
InChI=1S/C34H50O6/c1-20(11-10-12-21(2)30(37)38)26-19-29(40-23(4)36)34(9)25-13-14-27-31(5,6)28(39-22(3)35)16-17-32(27,7)24(25)15-18-33(26,34)8/h12-13,15,20,26-29H,10-11,14,16-19H2,1-9H3,(H,37,38)/b21-12+/t20-,26-,27+,28-,29-,32-,33-,34-/m1/s1
InChI KeyOTUZGGSAOMCYNC-HQGDWPTRSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • Cholane-skeleton
  • Bile acid, alcohol, or derivatives
  • Steroid ester
  • Steroid acid
  • 14-alpha-methylsteroid
  • Delta-7-steroid
  • Steroid
  • Tricarboxylic acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • 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
logP6.19ChemAxon
pKa (Strongest Acidic)4.66ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area89.9 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity157.2 m³·mol⁻¹ChemAxon
Polarizability64.56 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00056476
Chemspider ID78441229
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound139586622
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Su C, Shiao M, Wang C: Potentiation of ganodermic acid S on prostaglandin E(1)-induced cyclic AMP elevation in human platelets. Thromb Res. 2000 Jul 15;99(2):135-45. doi: 10.1016/s0049-3848(00)00250-4. [PubMed:10946087 ]
  2. Su CY, Shiao MS, Wang CT: Differential effects of ganodermic acid S on the thromboxane A2-signaling pathways in human platelets. Biochem Pharmacol. 1999 Aug 15;58(4):587-95. doi: 10.1016/s0006-2952(99)00136-7. [PubMed:10413295 ]
  3. Su CY, Shiao MS, Wang CT: Predominant inhibition of ganodermic acid S on the thromboxane A2-dependent pathway in human platelets response to collagen. Biochim Biophys Acta. 1999 Feb 25;1437(2):223-34. doi: 10.1016/s1388-1981(98)00012-2. [PubMed:10064905 ]
  4. Wang CN, Chen JC, Shiao MS, Wang CT: The inhibition of human platelet function by ganodermic acids. Biochem J. 1991 Jul 1;277 ( Pt 1)(Pt 1):189-97. doi: 10.1042/bj2770189. [PubMed:1649599 ]
  5. Wang CN, Chen JC, Shiao MS, Wang CT: The effect of ganodermic acid S on human platelets. Adv Exp Med Biol. 1990;281:265-9. doi: 10.1007/978-1-4615-3806-6_27. [PubMed:1966354 ]
  6. LOTUS database [Link]