gordonoside M

Details

• 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

• 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

• 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

ADMET Properties (via admetSAR 2)

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

Proven Targets:

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

• Polyspora chrysandra

Cross-Links

• PubChem: 54584202
• LOTUS: LTS0265387
• wikiData: Q27135969