(3S,5R,8R,9R,10R,13R,14R,17S)-17-[(1S,2S,3R)-1,2-dihydroxy-3-(2-hydroxypropan-2-yl)cyclopentyl]-3-[(2S,3R,4S,5S)-5-hydroxy-4-[(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-4,4,8,10,14-pentamethyl-1,2,3,5,6,7,9,11,13,15,16,17-dodecahydrocyclopenta[a]phenanthren-12-one

Details

• Internal ID: bb9f37bc-4186-451d-84d6-ba1e0b966aa2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (3S,5R,8R,9R,10R,13R,14R,17S)-17-[(1S,2S,3R)-1,2-dihydroxy-3-(2-hydroxypropan-2-yl)cyclopentyl]-3-[(2S,3R,4S,5S)-5-hydroxy-4-[(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-4,4,8,10,14-pentamethyl-1,2,3,5,6,7,9,11,13,15,16,17-dodecahydrocyclopenta[a]phenanthren-12-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(COC2OC3CCC4(C(C3(C)C)CCC5(C4CC(=O)C6C5(CCC6C7(CCC(C7O)C(C)(C)O)O)C)C)C)O)OC8C(C(C(C(O8)CO)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](C3(C)C)CC[C@@]5([C@@H]4CC(=O)[C@H]6[C@]5(CC[C@@H]6[C@]7(CC[C@H]([C@@H]7O)C(C)(C)O)O)C)C)C)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O)O)O
• InChI: InChI=1S/C47H78O18/c1-20-30(51)32(53)34(55)39(61-20)65-37-36(64-40-35(56)33(54)31(52)25(18-48)62-40)24(50)19-60-41(37)63-28-12-13-44(6)26(42(28,2)3)11-15-45(7)27(44)17-23(49)29-21(9-14-46(29,45)8)47(59)16-10-22(38(47)57)43(4,5)58/h20-22,24-41,48,50-59H,9-19H2,1-8H3/t20-,21-,22+,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: ZHFXKWVRGIKIBN-CXKRXDECSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₇H₇₈O₁₈
• Molecular Weight: 931.10 g/mol
• Exact Mass: 930.51881563 g/mol
• Topological Polar Surface Area (TPSA): 295.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): -0.38
• H-Bond Acceptor: 18
• H-Bond Donor: 11
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6739	67.39%
Caco-2	-	0.8959	89.59%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7997	79.97%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7843	78.43%
OATP1B3 inhibitior	+	0.8901	89.01%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7287	72.87%
BSEP inhibitior	+	0.5735	57.35%
P-glycoprotein inhibitior	+	0.7530	75.30%
P-glycoprotein substrate	-	0.5401	54.01%
CYP3A4 substrate	+	0.7441	74.41%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8646	86.46%
CYP3A4 inhibition	-	0.9186	91.86%
CYP2C9 inhibition	-	0.8887	88.87%
CYP2C19 inhibition	-	0.9086	90.86%
CYP2D6 inhibition	-	0.9588	95.88%
CYP1A2 inhibition	-	0.9272	92.72%
CYP2C8 inhibition	+	0.6722	67.22%
CYP inhibitory promiscuity	-	0.9674	96.74%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6885	68.85%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9069	90.69%
Skin irritation	-	0.6974	69.74%
Skin corrosion	-	0.9528	95.28%
Ames mutagenesis	-	0.6124	61.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.7570	75.70%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.6927	69.27%
skin sensitisation	-	0.9346	93.46%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.9119	91.19%
Acute Oral Toxicity (c)	I	0.6197	61.97%
Estrogen receptor binding	+	0.7916	79.16%
Androgen receptor binding	+	0.7539	75.39%
Thyroid receptor binding	-	0.5959	59.59%
Glucocorticoid receptor binding	+	0.7111	71.11%
Aromatase binding	+	0.6637	66.37%
PPAR gamma	+	0.7848	78.48%
Honey bee toxicity	-	0.6245	62.45%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.8680	86.80%

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	98.28%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.52%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.37%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.90%	89.00%
CHEMBL2581	P07339	Cathepsin D	91.88%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.79%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.04%	94.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.74%	97.36%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.85%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.41%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	87.32%	94.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.02%	95.89%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	86.12%	91.24%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.00%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.93%	92.94%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.59%	97.14%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	83.73%	95.71%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.54%	93.04%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	82.20%	97.33%
CHEMBL2959	Q08881	Tyrosine-protein kinase ITK/TSK	81.82%	95.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.94%	99.23%

Plants that contains it

• Coleostephus myconis
• Dahlia pinnata
• Gynostemma pentaphyllum
• Synotis alata

Cross-Links

• PubChem: 46850028
• NPASS: NPC32016
• LOTUS: LTS0273719
• wikiData: Q105375710