CID 11672401

Details

• Internal ID: 5b7f8711-61e4-4686-baa8-3976920df551
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-[(2S,3R,4S,5S)-4-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(COC2OC3CCC4(C5CCC6C7C(CCC7(CCC6(C5(CCC4C3(C)C)C)C)C(=O)O)C(=C)C)C)OC8C(C(C(C(O8)CO)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]3CC[C@@]4([C@H]5CC[C@@H]6[C@H]7[C@@H](CC[C@@]7(CC[C@]6([C@@]5(CC[C@H]4C3(C)C)C)C)C(=O)O)C(=C)C)C)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O)O)O)O
• InChI: InChI=1S/C47H76O16/c1-21(2)23-11-16-47(42(56)57)18-17-45(7)24(30(23)47)9-10-28-44(6)14-13-29(43(4,5)27(44)12-15-46(28,45)8)62-41-38(63-39-36(54)34(52)31(49)22(3)59-39)33(51)26(20-58-41)61-40-37(55)35(53)32(50)25(19-48)60-40/h22-41,48-55H,1,9-20H2,2-8H3,(H,56,57)/t22-,23-,24+,25+,26-,27-,28+,29-,30+,31-,32+,33-,34+,35-,36+,37+,38+,39-,40-,41-,44-,45+,46+,47-/m0/s1
• InChI Key: WOOPUJXMROOOPP-KSYIBZFCSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₇H₇₆O₁₆
• Molecular Weight: 897.10 g/mol
• Exact Mass: 896.51333633 g/mol
• Topological Polar Surface Area (TPSA): 255.00 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 2.23
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 9

Synonyms

• (1R,3As,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-[(2S,3R,4S,5S)-4-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
• CHEMBL500097
• WOOPUJXMROOOPP-KSYIBZFCSA-N
• Betulinic acid 3beta-O-alpha-L-rhamnopyranosyl-(1->2)-[beta-D-glucopyranosyl-(1->4)]-alpha-L-arabinopyranoside
• 3beta-(2-O-alpha-L-Rhamnopyranosyl-4-O-beta-D-glucopyranosyl-alpha-L-arabinopyranosyloxy)lupa-20(29)-ene-28-oic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7051	70.51%
Caco-2	-	0.8828	88.28%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.8157	81.57%
OATP2B1 inhibitior	-	0.8768	87.68%
OATP1B1 inhibitior	+	0.8240	82.40%
OATP1B3 inhibitior	-	0.2904	29.04%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7276	72.76%
BSEP inhibitior	+	0.5656	56.56%
P-glycoprotein inhibitior	+	0.7491	74.91%
P-glycoprotein substrate	-	0.5283	52.83%
CYP3A4 substrate	+	0.7369	73.69%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8798	87.98%
CYP3A4 inhibition	-	0.9486	94.86%
CYP2C9 inhibition	-	0.8350	83.50%
CYP2C19 inhibition	-	0.8719	87.19%
CYP2D6 inhibition	-	0.9385	93.85%
CYP1A2 inhibition	-	0.8703	87.03%
CYP2C8 inhibition	+	0.7166	71.66%
CYP inhibitory promiscuity	-	0.9201	92.01%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6772	67.72%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9062	90.62%
Skin irritation	-	0.5790	57.90%
Skin corrosion	-	0.9435	94.35%
Ames mutagenesis	-	0.6370	63.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7099	70.99%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.8375	83.75%
skin sensitisation	-	0.8913	89.13%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.8946	89.46%
Acute Oral Toxicity (c)	III	0.5802	58.02%
Estrogen receptor binding	+	0.7718	77.18%
Androgen receptor binding	+	0.7488	74.88%
Thyroid receptor binding	-	0.6010	60.10%
Glucocorticoid receptor binding	+	0.6461	64.61%
Aromatase binding	+	0.6710	67.10%
PPAR gamma	+	0.7553	75.53%
Honey bee toxicity	-	0.5905	59.05%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9799	97.99%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3714130	P46095	G-protein coupled receptor 6	93.59%	97.36%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.85%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.80%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.65%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.02%	86.33%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	89.12%	97.33%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	88.75%	91.24%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.23%	92.94%
CHEMBL233	P35372	Mu opioid receptor	87.23%	97.93%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.34%	99.17%
CHEMBL340	P08684	Cytochrome P450 3A4	86.09%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.07%	97.09%
CHEMBL5255	O00206	Toll-like receptor 4	84.64%	92.50%
CHEMBL5028	O14672	ADAM10	84.61%	97.50%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	84.55%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.29%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.96%	89.00%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	83.48%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	82.15%	95.93%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	81.43%	82.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.41%	100.00%
CHEMBL2095194	P08709	Coagulation factor VII/tissue factor	81.26%	99.17%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.82%	94.33%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.12%	95.50%

Plants that contains it

• Pulsatilla cernua

Cross-Links

• PubChem: 11672401
• NPASS: NPC204392
• LOTUS: LTS0270455
• wikiData: Q105309624