(3S,5S,8R,9S,10S,13R,14R,17S)-3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-17-[(2R)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,14-tetramethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde

Details

• Internal ID: 7c2643ca-5a2a-4305-ad9d-885d8547eb0c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (3S,5S,8R,9S,10S,13R,14R,17S)-3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-17-[(2R)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,14-tetramethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
• SMILES (Canonical): CC(=CCCC(C)(C1CCC2(C1CCC3C2(CCC4C3(CCC(C4(C)C)OC5C(C(C(C(O5)CO)O)O)OC6C(C(C(C(O6)CO)O)O)O)C=O)C)C)O)C
• SMILES (Isomeric): CC(=CCC[C@](C)([C@H]1CC[C@@]2([C@@H]1CC[C@H]3[C@]2(CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C=O)C)C)O)C
• InChI: InChI=1S/C42H70O13/c1-22(2)9-8-15-41(7,51)24-12-16-39(5)23(24)10-11-28-40(39,6)17-13-27-38(3,4)29(14-18-42(27,28)21-45)54-37-35(33(49)31(47)26(20-44)53-37)55-36-34(50)32(48)30(46)25(19-43)52-36/h9,21,23-37,43-44,46-51H,8,10-20H2,1-7H3/t23-,24+,25-,26-,27+,28+,29+,30-,31-,32+,33+,34-,35-,36+,37+,39-,40-,41-,42-/m1/s1
• InChI Key: DOUGLYJWNNDEQP-BMFABALCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₇₀O₁₃
• Molecular Weight: 783.00 g/mol
• Exact Mass: 782.48164228 g/mol
• Topological Polar Surface Area (TPSA): 216.00 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 2.36
• H-Bond Acceptor: 13
• H-Bond Donor: 8
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7719	77.19%
Caco-2	-	0.8813	88.13%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.8134	81.34%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8153	81.53%
OATP1B3 inhibitior	-	0.2428	24.28%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6776	67.76%
BSEP inhibitior	+	0.6143	61.43%
P-glycoprotein inhibitior	+	0.7712	77.12%
P-glycoprotein substrate	-	0.7658	76.58%
CYP3A4 substrate	+	0.7202	72.02%
CYP2C9 substrate	-	0.7899	78.99%
CYP2D6 substrate	-	0.8421	84.21%
CYP3A4 inhibition	-	0.9469	94.69%
CYP2C9 inhibition	-	0.8637	86.37%
CYP2C19 inhibition	-	0.9118	91.18%
CYP2D6 inhibition	-	0.9391	93.91%
CYP1A2 inhibition	-	0.9069	90.69%
CYP2C8 inhibition	+	0.6761	67.61%
CYP inhibitory promiscuity	-	0.9514	95.14%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6516	65.16%
Eye corrosion	-	0.9913	99.13%
Eye irritation	-	0.9114	91.14%
Skin irritation	-	0.5512	55.12%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7853	78.53%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.5828	58.28%
skin sensitisation	-	0.9013	90.13%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	+	0.6555	65.55%
Acute Oral Toxicity (c)	I	0.4409	44.09%
Estrogen receptor binding	+	0.7540	75.40%
Androgen receptor binding	+	0.7544	75.44%
Thyroid receptor binding	-	0.5857	58.57%
Glucocorticoid receptor binding	+	0.6712	67.12%
Aromatase binding	+	0.6626	66.26%
PPAR gamma	+	0.7361	73.61%
Honey bee toxicity	-	0.5726	57.26%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9413	94.13%

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	97.24%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.97%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.84%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.89%	95.89%
CHEMBL218	P21554	Cannabinoid CB1 receptor	90.59%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.33%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.87%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.43%	100.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	88.34%	95.71%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	87.44%	91.24%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	86.47%	89.34%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.42%	86.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.32%	92.94%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.77%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.74%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	84.56%	94.73%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.28%	97.14%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.73%	100.00%
CHEMBL2243	O00519	Anandamide amidohydrolase	82.41%	97.53%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.07%	94.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.47%	99.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.05%	92.62%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.96%	97.36%
CHEMBL2581	P07339	Cathepsin D	80.65%	98.95%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.32%	96.90%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.12%	85.14%

Plants that contains it

• Gymnema sylvestre
• Gynostemma pentaphyllum

Cross-Links

• PubChem: 101618906
• LOTUS: LTS0223849
• wikiData: Q104398816