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Record Information
Version1.0
Created at2021-06-20 18:06:54 UTC
Updated at2021-06-30 00:04:42 UTC
NP-MRD IDNP0034364
Secondary Accession NumbersNone
Natural Product Identification
Common Namehexanorcucurbitacin D 2-O-beta-D-glucopyranoside
Provided ByJEOL DatabaseJEOL Logo
DescriptionCHEMBL538690 belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton. hexanorcucurbitacin D 2-O-beta-D-glucopyranoside is found in Cucumis melo. It was first documented in 2002 (PMID: 33651529). Based on a literature review very few articles have been published on CHEMBL538690 (PMID: 33079503) (PMID: 26389513) (PMID: 26389498) (PMID: 26389454).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC30H44O10
Average Mass564.6720 Da
Monoisotopic Mass564.29345 Da
IUPAC Name(1R,2R,4S,10S,11S,13R,14R,15R)-14-acetyl-13-hydroxy-1,6,6,11,15-pentamethyl-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,17-dione
Traditional Name(1R,2R,4S,10S,11S,13R,14R,15R)-14-acetyl-13-hydroxy-1,6,6,11,15-pentamethyl-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,17-dione
CAS Registry NumberNot Available
SMILES
[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(O[C@]2([H])C(=O)C(C3=C([H])C([H])([H])[C@@]4([H])[C@]5(C([H])([H])[H])C([H])([H])[C@@]([H])(O[H])[C@]([H])(C(=O)C([H])([H])[H])[C@@]5(C([H])([H])[H])C([H])([H])C(=O)[C@@]4(C([H])([H])[H])[C@]3([H])C2([H])[H])(C([H])([H])[H])C([H])([H])[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]
InChI Identifier
InChI=1S/C30H44O10/c1-13(32)21-16(33)10-28(4)19-8-7-14-15(30(19,6)20(34)11-29(21,28)5)9-17(25(38)27(14,2)3)39-26-24(37)23(36)22(35)18(12-31)40-26/h7,15-19,21-24,26,31,33,35-37H,8-12H2,1-6H3/t15-,16-,17+,18-,19+,21+,22-,23+,24-,26-,28+,29-,30+/m1/s1
InChI KeyZPPOLNNGEVBQFA-CVVUTLENSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cucumis meloJEOL database
    • Chen, C., et al, J. Nat. Prod. 72, 824 (2009)
Chemical Taxonomy
Description Belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal glycosides
Direct ParentSteroidal glycosides
Alternative Parents
Substituents
  • Diterpene glycoside
  • Steroidal glycoside
  • 20-oxosteroid
  • Diterpenoid
  • 3-oxo-delta-5-steroid
  • 3-oxosteroid
  • 14-alpha-methylsteroid
  • Hydroxysteroid
  • 16-hydroxysteroid
  • 16-alpha-hydroxysteroid
  • 11-oxosteroid
  • Oxosteroid
  • Delta-5-steroid
  • Terpene glycoside
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Oxane
  • Monosaccharide
  • Cyclic alcohol
  • Cyclic ketone
  • Ketone
  • Secondary alcohol
  • Acetal
  • Polyol
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Primary alcohol
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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
logP1.73ALOGPS
logP0.65ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)12.21ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area170.82 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity142.39 m³·mol⁻¹ChemAxon
Polarizability60.04 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24611519
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44139738
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Authors unspecified: Curcumin (Curcuma, Turmeric) and Cancer (PDQ(R)): Health Professional Version. 2002. [PubMed:33651529 ]
  2. Authors unspecified: Cancer Therapy Interactions With Foods and Dietary Supplements (PDQ(R)): Health Professional Version. 2002. [PubMed:33079503 ]
  3. Authors unspecified: Planning the Transition to End-of-Life Care in Advanced Cancer (PDQ(R)): Health Professional Version. 2002. [PubMed:26389513 ]
  4. Authors unspecified: Childhood Central Nervous System Germ Cell Tumors Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389498 ]
  5. Authors unspecified: Childhood Acute Myeloid Leukemia/Other Myeloid Malignancies Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389454 ]
  6. Chen, C., et al. (2009). Chen, C., et al, J. Nat. Prod. 72, 824 (2009). J. Nat. Prod..