gordonoside M

Details

Top
Internal ID 65d4969f-cfe9-4058-abba-a1e7f21423c2
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
IUPAC Name (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8R,8aR,12aS,14aR,14bR)-8-hydroxy-4,4,6a,6b,11,11,14b-heptamethyl-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3,5-dihydroxyoxane-2-carboxylic acid
SMILES (Canonical) CC1C(C(C(C(O1)OC2C(C(COC2OC3C(C(OC(C3O)OC4CCC5(C(C4(C)C)CCC6(C5CC=C7C6(CC(C8(C7CC(CC8)(C)C)C(=O)OC9C(C(C(C(O9)CO)O)O)O)O)C)C)C)C(=O)O)O)O)O)O)O)O
SMILES (Isomeric) C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@H](CO[C@H]2O[C@H]3[C@@H]([C@H](O[C@H]([C@@H]3O)O[C@H]4CC[C@]5([C@H](C4(C)C)CC[C@@]6([C@@H]5CC=C7[C@]6(C[C@H]([C@@]8([C@H]7CC(CC8)(C)C)C(=O)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)O)C)C)C)C(=O)O)O)O)O)O)O)O
InChI InChI=1S/C53H84O23/c1-21-30(57)33(60)35(62)43(70-21)75-41-31(58)24(55)20-69-46(41)73-39-37(64)40(42(66)67)74-45(38(39)65)72-29-12-13-50(6)26(49(29,4)5)11-14-51(7)27(50)10-9-22-23-17-48(2,3)15-16-53(23,28(56)18-52(22,51)8)47(68)76-44-36(63)34(61)32(59)25(19-54)71-44/h9,21,23-41,43-46,54-65H,10-20H2,1-8H3,(H,66,67)/t21-,23-,24-,25+,26-,27+,28+,29-,30-,31-,32+,33+,34-,35+,36+,37-,38+,39-,40-,41+,43-,44-,45+,46-,50-,51+,52+,53+/m0/s1
InChI Key PNVAFUMGIGXLFN-IJUOOPMQSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

Top
Molecular Formula C53H84O23
Molecular Weight 1089.20 g/mol
Exact Mass 1088.54033892 g/mol
Topological Polar Surface Area (TPSA) 371.00 Ų
XlogP 1.10
Atomic LogP (AlogP) -1.31
H-Bond Acceptor 22
H-Bond Donor 13
Rotatable Bonds 10

Synonyms

Top
CHEBI:67501
CHEMBL1782846
DTXSID901099512
Q27135969
(3beta,16alpha)-28-(beta-D-Glucopyranosyloxy)-16-hydroxy-28-oxoolean-12-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-->2)-O-alpha-L-arabinopyranosyl-(1-->3)-beta-D-glucopyranosiduronic acid
1-O-[(3beta,16alpha)-3-{[6-Deoxy-alpha-L-mannopyranosyl-(1->2)-alpha-L-arabinopyranosyl-(1->3)-beta-D-glucopyranuronosyl]oxy}-16-hydroxy-28-oxoolean-12-en-28-yl]-beta-D-glucopyranose
1293918-35-0

2D Structure

Top
2D Structure of gordonoside M

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7601 76.01%
Caco-2 - 0.8816 88.16%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.8286 82.86%
Subcellular localzation Mitochondria 0.8703 87.03%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior - 0.4855 48.55%
OATP1B3 inhibitior - 0.4610 46.10%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.5026 50.26%
BSEP inhibitior + 0.8895 88.95%
P-glycoprotein inhibitior + 0.7475 74.75%
P-glycoprotein substrate - 0.5368 53.68%
CYP3A4 substrate + 0.7366 73.66%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8776 87.76%
CYP3A4 inhibition - 0.8310 83.10%
CYP2C9 inhibition - 0.8704 87.04%
CYP2C19 inhibition - 0.9216 92.16%
CYP2D6 inhibition - 0.9491 94.91%
CYP1A2 inhibition - 0.9009 90.09%
CYP2C8 inhibition + 0.7516 75.16%
CYP inhibitory promiscuity - 0.9733 97.33%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.6024 60.24%
Eye corrosion - 0.9896 98.96%
Eye irritation - 0.9003 90.03%
Skin irritation - 0.5876 58.76%
Skin corrosion - 0.9441 94.41%
Ames mutagenesis - 0.7100 71.00%
Human Ether-a-go-go-Related Gene inhibition + 0.7180 71.80%
Micronuclear - 0.7800 78.00%
Hepatotoxicity - 0.9500 95.00%
skin sensitisation - 0.9013 90.13%
Respiratory toxicity + 0.5222 52.22%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity - 0.6250 62.50%
Nephrotoxicity - 0.9695 96.95%
Acute Oral Toxicity (c) III 0.8023 80.23%
Estrogen receptor binding + 0.7845 78.45%
Androgen receptor binding + 0.7348 73.48%
Thyroid receptor binding + 0.5787 57.87%
Glucocorticoid receptor binding + 0.7893 78.93%
Aromatase binding + 0.6467 64.67%
PPAR gamma + 0.8257 82.57%
Honey bee toxicity - 0.6579 65.79%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity - 0.5555 55.55%
Fish aquatic toxicity + 0.9585 95.85%

Targets

Top

Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.04% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.47% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 94.91% 86.33%
CHEMBL3714130 P46095 G-protein coupled receptor 6 92.11% 97.36%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 90.38% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.16% 95.56%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.01% 97.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 87.00% 89.00%
CHEMBL226 P30542 Adenosine A1 receptor 86.08% 95.93%
CHEMBL2716 Q8WUI4 Histone deacetylase 7 85.97% 89.44%
CHEMBL5028 O14672 ADAM10 85.22% 97.50%
CHEMBL2581 P07339 Cathepsin D 85.03% 98.95%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.63% 100.00%
CHEMBL1937 Q92769 Histone deacetylase 2 83.03% 94.75%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 82.08% 86.92%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 81.56% 93.00%
CHEMBL221 P23219 Cyclooxygenase-1 81.08% 90.17%

Plants that contains it

Top
Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Polyspora chrysandra

Cross-Links

Top
PubChem 54584202
LOTUS LTS0265387
wikiData Q27135969