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Record Information
Version1.0
Created at2022-09-06 09:33:10 UTC
Updated at2022-09-06 09:33:10 UTC
NP-MRD IDNP0229479
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3,4,5-trihydroxy-6-{[4-methoxy-3a,6,6,9b,11a-pentamethyl-1-(6-methylhept-5-en-2-yl)-7-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthren-2-yl]oxy}oxan-2-yl)methyl acetate
Description (3,4,5-trihydroxy-6-{[4-methoxy-3a,6,6,9b,11a-pentamethyl-1-(6-methylhept-5-en-2-yl)-7-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthren-2-yl]oxy}oxan-2-yl)methyl acetate is found in Hebeloma vinosophyllum. It was first documented in 1992 (PMID: 1292745).
Structure
Thumb
Synonyms
ValueSource
(+)-LactoseChEBI
(Gal)1 (GLC)1ChEBI
1-beta-D-Galactopyranosyl-4-D-glucopyranoseChEBI
4-(beta-D-Galactosido)-D-glucoseChEBI
4-O-beta-D-Galactopyranosyl-D-glucoseChEBI
beta-D-Gal-(1->4)-D-GLCChEBI
beta-D-Galp-(1->4)-D-GLCPChEBI
beta-Gal1,4-GLCChEBI
D-LactoseChEBI
Galbeta1-4GLCChEBI
LacChEBI
LactobioseChEBI
LaktobioseChEBI
LaktoseChEBI
MilchzuckerChEBI
Milk sugarChEBI
Lactose, anhydrousKegg
1-b-D-Galactopyranosyl-4-D-glucopyranoseGenerator
1-Β-D-galactopyranosyl-4-D-glucopyranoseGenerator
4-(b-D-Galactosido)-D-glucoseGenerator
4-(Β-D-galactosido)-D-glucoseGenerator
4-O-b-D-Galactopyranosyl-D-glucoseGenerator
4-O-Β-D-galactopyranosyl-D-glucoseGenerator
b-D-Gal-(1->4)-D-GLCGenerator
Β-D-gal-(1->4)-D-GLCGenerator
b-D-Galp-(1->4)-D-GLCPGenerator
Β-D-galp-(1->4)-D-GLCPGenerator
b-Gal1,4-GLCGenerator
Β-gal1,4-GLCGenerator
3beta,16beta-Dihydroxy-7beta-methoxycucurbita-5,24-diene-3-O-beta-D-xylopyranoside-16-O-(6-O-acetyl)-beta-D-glucopyranosideHMDB
GM(m)HMDB
GMMHMDB
(3,4,5-Trihydroxy-6-{[9-methoxy-1,6,6,11,15-pentamethyl-14-(6-methylhept-5-en-2-yl)-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-13-yl]oxy}oxan-2-yl)methyl acetic acidGenerator
Chemical FormulaC44H72O13
Average Mass809.0347 Da
Monoisotopic Mass808.49729 Da
IUPAC Name(3,4,5-trihydroxy-6-{[9-methoxy-1,6,6,11,15-pentamethyl-14-(6-methylhept-5-en-2-yl)-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-13-yl]oxy}oxan-2-yl)methyl acetate
Traditional Name(3,4,5-trihydroxy-6-{[9-methoxy-1,6,6,11,15-pentamethyl-14-(6-methylhept-5-en-2-yl)-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-13-yl]oxy}oxan-2-yl)methyl acetate
CAS Registry NumberNot Available
SMILES
COC1C=C2C(CCC(OC3OCC(O)C(O)C3O)C2(C)C)C2(C)CCC3(C)C(C(C)CCC=C(C)C)C(CC3(C)C12)OC1OC(COC(C)=O)C(O)C(O)C1O
InChI Identifier
InChI=1S/C44H72O13/c1-22(2)12-11-13-23(3)32-29(55-40-37(51)35(49)34(48)30(56-40)21-53-24(4)45)19-44(9)38-28(52-10)18-26-25(42(38,7)16-17-43(32,44)8)14-15-31(41(26,5)6)57-39-36(50)33(47)27(46)20-54-39/h12,18,23,25,27-40,46-51H,11,13-17,19-21H2,1-10H3
InChI KeyPEVRNEDRRNBORS-UHFFFAOYSA-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 Origin
Species NameSourceReference
Hebeloma vinosophyllumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentO-glycosyl compounds
Alternative Parents
Substituents
  • O-glycosyl compound
  • Disaccharide
  • Oxane
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
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
logP3.69ALOGPS
logP3.46ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)11.93ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area193.83 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity210.61 m³·mol⁻¹ChemAxon
Polarizability89.73 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDDB04465
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001145
KNApSAcK IDC00001136
Chemspider IDNot Available
KEGG Compound IDC00243
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLactose
METLIN IDNot Available
PubChem Compound440995
PDB IDNot Available
ChEBI ID17716
Good Scents IDNot Available
References
General References
  1. Tanaka K, Yamamoto M, Matsumoto M, Saito M, Funabashi M, Yoshimatsu S: [An outbreak of food poisoning suspected due to Aeromonas and characteristics of the isolated strains]. Nihon Koshu Eisei Zasshi. 1992 Sep;39(9):707-13. [PubMed:1292745 ]
  2. Nakatani S, Mano H, Im R, Shimizu J, Wada M: Glucosamine regulates differentiation of a chondrogenic cell line, ATDC5. Biol Pharm Bull. 2007 Mar;30(3):433-8. doi: 10.1248/bpb.30.433. [PubMed:17329833 ]
  3. Buchini S, Buschiazzo A, Withers SG: A new generation of specific Trypanosoma cruzi trans-sialidase inhibitors. Angew Chem Int Ed Engl. 2008;47(14):2700-3. doi: 10.1002/anie.200705435. [PubMed:18300214 ]
  4. Delaine T, Cumpstey I, Ingrassia L, Le Mercier M, Okechukwu P, Leffler H, Kiss R, Nilsson UJ: Galectin-inhibitory thiodigalactoside ester derivatives have antimigratory effects in cultured lung and prostate cancer cells. J Med Chem. 2008 Dec 25;51(24):8109-14. doi: 10.1021/jm801077j. [PubMed:19053747 ]
  5. Adhya M, Singha B, Chatterjee BP: Macoma birmanica agglutinin recognizes glycoside clusters of beta-GlcNAc/Glc and alpha-Man. Carbohydr Res. 2009 Dec 14;344(18):2489-95. doi: 10.1016/j.carres.2009.08.043. Epub 2009 Sep 30. [PubMed:19846069 ]
  6. LOTUS database [Link]