gordonoside P

Details

• Internal ID: 876223da-c7f0-4176-afe2-3248cc7efc96
• 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]-5-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3-hydroxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-2-carboxylic acid
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(OC(C2O)OC3C(C(C(OC3OC4CCC5(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)OC1C(C(C(CO1)O)O)O)CO)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](O[C@H]([C@@H]2O)O[C@@H]3[C@H]([C@@H]([C@H](O[C@H]3O[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[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O)CO)O)O)O)O
• InChI: InChI=1S/C59H94O28/c1-22-32(64)36(68)39(71)49(79-22)83-43-35(67)27(20-61)81-51(42(43)74)86-46-44(84-48-38(70)33(65)25(62)21-78-48)41(73)45(47(75)76)85-52(46)82-31-12-13-56(6)28(55(31,4)5)11-14-57(7)29(56)10-9-23-24-17-54(2,3)15-16-59(24,30(63)18-58(23,57)8)53(77)87-50-40(72)37(69)34(66)26(19-60)80-50/h9,22,24-46,48-52,60-74H,10-21H2,1-8H3,(H,75,76)/t22-,24-,25+,26+,27+,28-,29+,30+,31-,32-,33-,34+,35+,36+,37-,38+,39+,40+,41-,42+,43-,44-,45-,46+,48-,49-,50-,51-,52+,56-,57+,58+,59+/m0/s1
• InChI Key: LPBOZSLWWLQGRY-DLZLHNPUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₉H₉₄O₂₈
• Molecular Weight: 1251.40 g/mol
• Exact Mass: 1250.59316234 g/mol
• Topological Polar Surface Area (TPSA): 450.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -3.48
• H-Bond Acceptor: 27
• H-Bond Donor: 16
• Rotatable Bonds: 13

Synonyms

• CHEBI:67504
• CHEMBL1782849
• Q27135972
• 1-O-[(3beta,16alpha)-3-{[6-Deoxy-alpha-L-mannopyranosyl-(1->3)-beta-D-glucopyranosyl-(1->2)-[beta-D-xylopyranosyl-(1->3)]-beta-D-glucopyranuronosyl]oxy}-16-hydroxy-28-oxoolean-12-en-28-yl]-beta-D-glucopyranose

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7601	76.01%
Caco-2	-	0.8772	87.72%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.8703	87.03%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.4524	45.24%
OATP1B3 inhibitior	-	0.4610	46.10%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5026	50.26%
BSEP inhibitior	+	0.9226	92.26%
P-glycoprotein inhibitior	+	0.7455	74.55%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.7381	73.81%
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	+	0.7690	76.90%
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	-	0.8986	89.86%
Skin irritation	-	0.5876	58.76%
Skin corrosion	-	0.9441	94.41%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7366	73.66%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.9250	92.50%
skin sensitisation	-	0.9013	90.13%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.9724	97.24%
Acute Oral Toxicity (c)	III	0.8023	80.23%
Estrogen receptor binding	+	0.7555	75.55%
Androgen receptor binding	+	0.7421	74.21%
Thyroid receptor binding	+	0.6262	62.62%
Glucocorticoid receptor binding	+	0.8071	80.71%
Aromatase binding	+	0.6450	64.50%
PPAR gamma	+	0.8249	82.49%
Honey bee toxicity	-	0.6532	65.32%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5455	54.55%
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	98.32%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.58%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.95%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.35%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.16%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.22%	97.36%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.41%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.90%	97.09%
CHEMBL2581	P07339	Cathepsin D	85.07%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	84.89%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.63%	100.00%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	84.46%	89.44%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.95%	93.00%
CHEMBL5255	O00206	Toll-like receptor 4	81.77%	92.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.22%	99.17%
CHEMBL5028	O14672	ADAM10	80.73%	97.50%

Plants that contains it

• Polyspora chrysandra

Cross-Links

• PubChem: 54585161
• LOTUS: LTS0108975
• wikiData: Q27135972