gordonoside I

Details

• Internal ID: 9bd8d30e-deb6-440b-abea-0048a7f1d7d2
• 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,9S,12aS,14aR,14bR)-8-hydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-9-[(Z)-2-methylbut-2-enoyl]oxy-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,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-3-hydroxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
• SMILES (Canonical): CC=C(C)C(=O)OC1CC(CC2C1(C(CC3(C2=CCC4C3(CCC5C4(CCC(C5(C)C)OC6C(C(C(C(O6)C(=O)O)O)OC7C(C(C(CO7)O)O)OC8C(C(C(CO8)O)O)O)OC9C(C(C(C(O9)CO)O)O)O)C)C)C)O)CO)(C)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H]1CC(C[C@@H]2[C@]1([C@@H](C[C@@]3(C2=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O)O[C@H]7[C@@H]([C@H]([C@H](CO7)O)O)O[C@H]8[C@@H]([C@H]([C@@H](CO8)O)O)O)O[C@H]9[C@@H]([C@H]([C@H]([C@H](O9)CO)O)O)O)C)C)C)O)CO)(C)C
• InChI: InChI=1S/C57H90O24/c1-10-24(2)47(72)76-34-19-52(3,4)17-26-25-11-12-31-54(7)15-14-33(53(5,6)30(54)13-16-55(31,8)56(25,9)18-32(62)57(26,34)23-59)77-51-45(81-49-40(68)38(66)37(65)29(20-58)75-49)42(41(69)43(79-51)46(70)71)78-50-44(36(64)28(61)22-74-50)80-48-39(67)35(63)27(60)21-73-48/h10-11,26-45,48-51,58-69H,12-23H2,1-9H3,(H,70,71)/b24-10-/t26-,27+,28-,29+,30-,31+,32+,33-,34-,35-,36-,37-,38-,39+,40+,41-,42-,43-,44+,45+,48-,49-,50-,51+,54-,55+,56+,57-/m0/s1
• InChI Key: BHKKNGSHLSYLPN-KOYGLFPPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₇H₉₀O₂₄
• Molecular Weight: 1159.30 g/mol
• Exact Mass: 1158.58220373 g/mol
• Topological Polar Surface Area (TPSA): 380.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): -0.73
• H-Bond Acceptor: 23
• H-Bond Donor: 13
• Rotatable Bonds: 13

Synonyms

• CHEBI:67497
• 1293918-31-6
• beta-D-Glucopyranosiduronic acid, (3beta,16alpha,22alpha)-16,28-dihydroxy-22-[[(2Z)-2-methyl-1-oxo-2-buten-1-yl]oxy]olean-12-en-3-yl O-beta-D-xylopyranosyl-(1-->2)-O-alpha-L-arabinopyranosyl-(1-->3)-O-[beta-D-galactopyranosyl-(1-->2)]-
• CHEMBL1782843
• DTXSID501098348
• Q27135965
• (3beta,16alpha,22alpha)-16,28-Dihydroxy-22-[[(2Z)-2-methyl-1-oxo-2-buten-1-yl]oxy]olean-12-en-3-yl O-beta-D-xylopyranosyl-(1-->2)-O-alpha-L-arabinopyranosyl-(1-->3)-O-[beta-D-galactopyranosyl-(1-->2)]-beta-D-glucopyranosiduronic acid
• (3beta,16alpha,22alpha)-16,28-dihydroxy-22-{[(2Z)-2-methylbut-2-enoyl]oxy}olean-12-en-3-yl beta-D-galactopyranosyl-(1->2)-[beta-D-xylopyranosyl-(1->2)-alpha-L-arabinopyranosyl-(1->3)]-beta-D-glucopyranosiduronic acid
• 3-O-beta-D-xylopyranosyl-(1->2)-alpha-L-arabinopyranosyl-(1->3)-[beta-D-galactopyranosyl-(1->2)]-beta-D-glucuronopyranosyl-22alpha-angeloyloxyolean-12-ene-16alpha,28-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7601	76.01%
Caco-2	-	0.8726	87.26%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.8703	87.03%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7234	72.34%
OATP1B3 inhibitior	-	0.4610	46.10%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5026	50.26%
BSEP inhibitior	+	0.9667	96.67%
P-glycoprotein inhibitior	+	0.7469	74.69%
P-glycoprotein substrate	-	0.5168	51.68%
CYP3A4 substrate	+	0.7404	74.04%
CYP2C9 substrate	-	0.8018	80.18%
CYP2D6 substrate	-	0.8966	89.66%
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	+	0.7702	77.02%
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	-	0.8992	89.92%
Skin irritation	-	0.5876	58.76%
Skin corrosion	-	0.9441	94.41%
Ames mutagenesis	-	0.6978	69.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.7486	74.86%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.8875	88.75%
skin sensitisation	-	0.9013	90.13%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.8287	82.87%
Acute Oral Toxicity (c)	III	0.8023	80.23%
Estrogen receptor binding	+	0.7647	76.47%
Androgen receptor binding	+	0.7543	75.43%
Thyroid receptor binding	+	0.6057	60.57%
Glucocorticoid receptor binding	+	0.7940	79.40%
Aromatase binding	+	0.6441	64.41%
PPAR gamma	+	0.8214	82.14%
Honey bee toxicity	-	0.6281	62.81%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
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	97.94%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.49%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	94.26%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.33%	94.45%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	90.10%	93.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.79%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.61%	86.33%
CHEMBL2581	P07339	Cathepsin D	88.24%	98.95%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.70%	95.50%
CHEMBL226	P30542	Adenosine A1 receptor	85.62%	95.93%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.59%	96.21%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.53%	97.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	84.85%	97.36%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.59%	100.00%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	83.28%	89.44%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.97%	91.07%
CHEMBL5028	O14672	ADAM10	82.82%	97.50%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.76%	97.25%
CHEMBL1937	Q92769	Histone deacetylase 2	82.61%	94.75%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.56%	91.24%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.81%	89.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.18%	94.33%
CHEMBL5255	O00206	Toll-like receptor 4	81.14%	92.50%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.98%	95.50%

Plants that contains it

• Polyspora chrysandra

Cross-Links

• PubChem: 54581244
• LOTUS: LTS0067636
• wikiData: Q27135965