Np mrd loader

Record Information
Version2.0
Created at2021-06-21 00:49:58 UTC
Updated at2021-06-30 00:19:05 UTC
NP-MRD IDNP0043419
Secondary Accession NumbersNone
Natural Product Identification
Common Namecaesalpin C
Provided ByJEOL DatabaseJEOL Logo
DescriptionCHEMBL2386703 belongs to the class of organic compounds known as isocopalane and spongiane diterpenoids. These are diterpenoids with a structure based on the isocopalane (Tetradecahydro-1,1,4a,7,8,8a-hexamethylphenanthrene) or the 15,16-epoxyisocopalane skeleton. caesalpin C is found in Caesalpinia minax. It was first documented in 2002 (PMID: 29437326). Based on a literature review a significant number of articles have been published on CHEMBL2386703 (PMID: 27466641) (PMID: 27253005) (PMID: 26389468) (PMID: 26389426).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC28H42O10
Average Mass538.6340 Da
Monoisotopic Mass538.27780 Da
IUPAC Name(4S,4aS,4bS,8aR,9R,10S,10aR)-4,10-bis(acetyloxy)-7-(2,2-dimethoxyethyl)-10a-hydroxy-1,1,4a,8-tetramethyl-6-oxo-1,2,3,4,4a,4b,5,6,8a,9,10,10a-dodecahydrophenanthren-9-yl acetate
Traditional Name(4S,4aS,4bS,8aR,9R,10S,10aR)-4,10-bis(acetyloxy)-7-(2,2-dimethoxyethyl)-10a-hydroxy-1,1,4a,8-tetramethyl-6-oxo-2,3,4,4b,5,8a,9,10-octahydrophenanthren-9-yl acetate
CAS Registry NumberNot Available
SMILES
[H]O[C@@]12[C@@]([H])(OC(=O)C([H])([H])[H])[C@]([H])(OC(=O)C([H])([H])[H])[C@@]3([H])C(=C(C(=O)C([H])([H])[C@]3([H])[C@@]1(C([H])([H])[H])[C@@]([H])(OC(=O)C([H])([H])[H])C([H])([H])C([H])([H])C2(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])(OC([H])([H])[H])OC([H])([H])[H])C([H])([H])[H]
InChI Identifier
InChI=1S/C28H42O10/c1-14-18(12-22(34-8)35-9)20(32)13-19-23(14)24(37-16(3)30)25(38-17(4)31)28(33)26(5,6)11-10-21(27(19,28)7)36-15(2)29/h19,21-25,33H,10-13H2,1-9H3/t19-,21-,23-,24+,25-,27-,28+/m0/s1
InChI KeyULUPXGWQUJLMKD-VTVVOEPJSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 600 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Caesalpinia minaxJEOL database
    • Ma, G., et al, J. Nat. Prod. 76, 1025 (2013)
Chemical Taxonomy
Description Belongs to the class of organic compounds known as isocopalane and spongiane diterpenoids. These are diterpenoids with a structure based on the isocopalane (Tetradecahydro-1,1,4a,7,8,8a-hexamethylphenanthrene) or the 15,16-epoxyisocopalane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentIsocopalane and spongiane diterpenoids
Alternative Parents
Substituents
  • Isocopalane diterpenoid
  • Hydrophenanthrene
  • Phenanthrene
  • Tricarboxylic acid or derivatives
  • Cyclohexenone
  • Cyclic alcohol
  • Tertiary alcohol
  • Carboxylic acid ester
  • Ketone
  • Cyclic ketone
  • Acetal
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • 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
logP2.21ALOGPS
logP1.73ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)13.01ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area134.66 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity134.64 m³·mol⁻¹ChemAxon
Polarizability56.99 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
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 IDNot Available
Chemspider ID30827957
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound71725693
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Authors unspecified: Childhood Cancer Genomics (PDQ(R)): Health Professional Version. 2002. [PubMed:27466641 ]
  2. Authors unspecified: Thyroid Cancer Screening (PDQ(R)): Patient Version. 2002. [PubMed:29437326 ]
  3. Authors unspecified: Childhood Vascular Tumors Treatment (PDQ(R)): Patient Version. 2002. [PubMed:27253005 ]
  4. Authors unspecified: Stomach (Gastric) Cancer Prevention (PDQ(R)): Patient Version. 2002. [PubMed:26389468 ]
  5. Authors unspecified: Childhood Central Nervous System Atypical Teratoid/Rhabdoid Tumor Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389426 ]
  6. Ma, G., et al. (2013). Ma, G., et al, J. Nat. Prod. 76, 1025 (2013). J. Nat. Prod..