Cumingianoside D
PubChem CID
10327541
Structure
Molecular Formula
Synonyms
- cumingianoside D
- CHEBI:65692
- (3alpha,7alpha,17alpha,20S,23R,24R)-7-[(6-O-acetyl-beta-D-glucopyranosyl)oxy]-23,24-dihydroxy-13,30-cyclodammar-25-en-3-yl acetate
- [(2R,3S,4S,5R,6R)-6-[[(1S,2R,3R,5R,7R,10S,11R,14R,15S)-7-acetyloxy-15-[(2S,4R,5R)-4,5-dihydroxy-6-methylhept-6-en-2-yl]-2,6,6,10-tetramethyl-3-pentacyclo[12.3.1.01,14.02,11.05,10]octadecanyl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate
- 3-O-acetyl-3alpha,7alpha,23,24-tetrahydroxy-14,18-cycloapoeuph-25-enyl 7-O-beta-D-(6'-O-acetyl)glucopyranoside
Molecular Weight
720.9 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
- Create:2006-10-25
- Modify:2025-01-04
Description
Cumingianoside D is a triterpenoid saponin that is 13,30-cyclodammar-25-ene-3,7,23,24-tetrol esterified to the corresponding acetate at position 3 and attached to a 6-O-acetyl-beta-D-glucopyranosyl residue at position 7 via a glycosidic linkage. Isolated from Dysoxylum cumingianum, it exhibits antileukemic activity. It has a role as an antineoplastic agent and a plant metabolite. It is a beta-D-glucoside, an acetate ester, a monosaccharide derivative, a pentacyclic triterpenoid, a triterpenoid saponin and a secondary alcohol.
Chemical Structure Depiction
Conformer generation is disallowed since too many atoms
[(2R,3S,4S,5R,6R)-6-[[(1S,2R,3R,5R,7R,10S,11R,14R,15S)-7-acetyloxy-15-[(2S,4R,5R)-4,5-dihydroxy-6-methylhept-6-en-2-yl]-2,6,6,10-tetramethyl-3-pentacyclo[12.3.1.01,14.02,11.05,10]octadecanyl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.05.07)
InChI=1S/C40H64O11/c1-20(2)31(44)25(43)16-21(3)24-10-15-40-19-39(24,40)14-11-27-37(8)13-12-29(49-23(5)42)36(6,7)28(37)17-30(38(27,40)9)51-35-34(47)33(46)32(45)26(50-35)18-48-22(4)41/h21,24-35,43-47H,1,10-19H2,2-9H3/t21-,24-,25+,26+,27+,28-,29+,30+,31+,32+,33-,34+,35-,37+,38-,39+,40+/m0/s1
Computed by InChI 1.0.6 (PubChem release 2021.05.07)
PVMHLUQSCKSBOW-AJQNEZDESA-N
Computed by InChI 1.0.6 (PubChem release 2021.05.07)
C[C@@H](C[C@H]([C@@H](C(=C)C)O)O)[C@@H]1CC[C@@]23[C@@]1(C2)CC[C@H]4[C@]3([C@@H](C[C@@H]5[C@@]4(CC[C@H](C5(C)C)OC(=O)C)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)COC(=O)C)O)O)O)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C40H64O11
Computed by PubChem 2.1 (PubChem release 2021.05.07)
- cumingianoside D
- CHEBI:65692
- (3alpha,7alpha,17alpha,20S,23R,24R)-7-[(6-O-acetyl-beta-D-glucopyranosyl)oxy]-23,24-dihydroxy-13,30-cyclodammar-25-en-3-yl acetate
- [(2R,3S,4S,5R,6R)-6-[[(1S,2R,3R,5R,7R,10S,11R,14R,15S)-7-acetyloxy-15-[(2S,4R,5R)-4,5-dihydroxy-6-methylhept-6-en-2-yl]-2,6,6,10-tetramethyl-3-pentacyclo[12.3.1.01,14.02,11.05,10]octadecanyl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate
- 3-O-acetyl-3alpha,7alpha,23,24-tetrahydroxy-14,18-cycloapoeuph-25-enyl 7-O-beta-D-(6'-O-acetyl)glucopyranoside
- ((2R,3S,4S,5R,6R)-6-(((1S,2R,3R,5R,7R,10S,11R,14R,15S)-7-acetyloxy-15-((2S,4R,5R)-4,5-dihydroxy-6-methylhept-6-en-2-yl)-2,6,6,10-tetramethyl-3-pentacyclo(12.3.1.01,14.02,11.05,10)octadecanyl)oxy)-3,4,5-trihydroxyoxan-2-yl)methyl acetate
- (3alpha,7alpha,17alpha,20S,23R,24R)-7-((6-O-acetyl-beta-D-glucopyranosyl)oxy)-23,24-dihydroxy-13,30-cyclodammar-25-en-3-yl acetate
- CHEMBL510039
- Q27134176
- 3-O-Acetyl-3a,7a,23,24-tetrahydroxy-14,18-cycloapoeuph-25-enyl 7-O-b-D-(6'-O-acetyl)glucopyranoside
- 3-O-Acetyl-3I+-,7I+-,23,24-tetrahydroxy-14,18-cycloapoeuph-25-enyl 7-O-I2-D-(6'-O-acetyl)glucopyranoside
Property Name
Property Value
Reference
Property Name
Molecular Weight
Property Value
720.9 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
5.3
Reference
Computed by XLogP3 3.0 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Donor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Acceptor Count
Property Value
11
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Rotatable Bond Count
Property Value
12
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Exact Mass
Property Value
720.44486285 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
720.44486285 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
172 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Heavy Atom Count
Property Value
51
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
1370
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
17
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2019.01.04)
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Parent, Connectivity Count
Similar Compounds (2D)
Similar Conformers (3D)
Same Count
- ChEBICumingianoside Dhttps://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:65692
- ChEMBLLICENSEAccess to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).http://www.ebi.ac.uk/Information/termsofuse.html
- Metabolomics Workbench
- Natural Product Activity and Species Source (NPASS)Cumingianoside Dhttps://bidd.group/NPASS/compound.php?compoundID=NPC165405
- Wikidatacumingianoside Dhttps://www.wikidata.org/wiki/Q27134176
- PubChem
- LOTUS - the natural products occurrence databaseLICENSEThe code for LOTUS is released under the GNU General Public License v3.0.https://lotus.nprod.net/LOTUS Treehttps://lotus.naturalproducts.net/
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
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