(1R,3R,5R,6S,7S,8S,10S,11S,13R,14R)-13-[[(3S,4R,4aR,6aR,6bS,8S,8aR,9R,10R,12aS,14aR,14bR)-8,9-dihydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(Z)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-6,7,8,14-tetrahydroxy-5-(hydroxymethyl)-2,4,9,12-tetraoxatricyclo[8.4.0.03,8]tetradecane-11-carboxylic acid

Details

• Internal ID: 8b2f57b5-f17c-409e-afce-62aeaeee3dfb
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (1R,3R,5R,6S,7S,8S,10S,11S,13R,14R)-13-[[(3S,4R,4aR,6aR,6bS,8S,8aR,9R,10R,12aS,14aR,14bR)-8,9-dihydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(Z)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-6,7,8,14-tetrahydroxy-5-(hydroxymethyl)-2,4,9,12-tetraoxatricyclo[8.4.0.03,8]tetradecane-11-carboxylic acid
• SMILES (Canonical): CC=C(C)C(=O)OC1C(C2(C(CC1(C)C)C3=CCC4C5(CCC(C(C5CCC4(C3(CC2O)C)C)(C)CO)OC6C(C7C(C(O6)C(=O)O)OC8(C(C(C(OC8O7)CO)O)O)O)O)C)CO)O
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H]1[C@@H]([C@@]2([C@H](C[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H]([C@@]5(C)CO)O[C@H]6[C@@H]([C@@H]7[C@@H]([C@H](O6)C(=O)O)O[C@]8([C@H]([C@@H]([C@H](O[C@@H]8O7)CO)O)O)O)O)C)C)[C@@H]2CC1(C)C)C)O)CO)O
• InChI: InChI=1S/C47H72O18/c1-9-21(2)38(58)64-36-35(55)46(20-50)23(16-41(36,3)4)22-10-11-26-42(5)14-13-28(43(6,19-49)25(42)12-15-44(26,7)45(22,8)17-27(46)51)61-39-30(53)31-32(33(62-39)37(56)57)65-47(59)34(54)29(52)24(18-48)60-40(47)63-31/h9-10,23-36,39-40,48-55,59H,11-20H2,1-8H3,(H,56,57)/b21-9-/t23-,24+,25+,26+,27-,28-,29+,30+,31+,32-,33-,34-,35-,36-,39+,40+,42-,43-,44+,45+,46-,47-/m0/s1
• InChI Key: BWXKRPOYCALGJT-NFFNGUADSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₇H₇₂O₁₈
• Molecular Weight: 925.10 g/mol
• Exact Mass: 924.47186544 g/mol
• Topological Polar Surface Area (TPSA): 292.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 0.65
• H-Bond Acceptor: 17
• H-Bond Donor: 10
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7601	76.01%
Caco-2	-	0.8761	87.61%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8703	87.03%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8138	81.38%
OATP1B3 inhibitior	-	0.4610	46.10%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5026	50.26%
BSEP inhibitior	+	0.8549	85.49%
P-glycoprotein inhibitior	+	0.7524	75.24%
P-glycoprotein substrate	+	0.6196	61.96%
CYP3A4 substrate	+	0.7405	74.05%
CYP2C9 substrate	-	0.6097	60.97%
CYP2D6 substrate	-	0.8923	89.23%
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	+	0.7854	78.54%
CYP inhibitory promiscuity	-	0.9733	97.33%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6024	60.24%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9035	90.35%
Skin irritation	-	0.5876	58.76%
Skin corrosion	-	0.9441	94.41%
Ames mutagenesis	-	0.7778	77.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.7114	71.14%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.7194	71.94%
skin sensitisation	-	0.9013	90.13%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	+	0.7400	74.00%
Acute Oral Toxicity (c)	III	0.8023	80.23%
Estrogen receptor binding	+	0.7881	78.81%
Androgen receptor binding	+	0.7597	75.97%
Thyroid receptor binding	+	0.5219	52.19%
Glucocorticoid receptor binding	+	0.7579	75.79%
Aromatase binding	+	0.6266	62.66%
PPAR gamma	+	0.7966	79.66%
Honey bee toxicity	-	0.6502	65.02%
Biodegradation	-	0.7500	75.00%
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	97.30%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.65%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.12%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	94.08%	90.17%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	92.09%	93.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	91.52%	91.07%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.47%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.33%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.50%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.89%	89.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.61%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.07%	92.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.97%	100.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	82.94%	96.61%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.73%	97.36%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	82.72%	94.23%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.25%	95.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.24%	86.33%
CHEMBL5028	O14672	ADAM10	81.66%	97.50%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.66%	97.25%
CHEMBL2581	P07339	Cathepsin D	80.16%	98.95%

Plants that contains it

• Gymnema sylvestre

Cross-Links

• PubChem: 163014398
• LOTUS: LTS0065269
• wikiData: Q104947748