3-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-12-hydroxy-17-[2-hydroxy-6-methyl-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhept-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: bc01b722-7e14-43a0-9612-936bd7fd6ab0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: 3-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-12-hydroxy-17-[2-hydroxy-6-methyl-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhept-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): CC1C(C(C(C(O1)OC2C(C(COC2OC3CCC4(C(C3(C)C)CCC5(C4CC(C6C5(CCC6C(CCC=C(C)C)(COC7C(C(C(C(O7)CO)O)O)O)O)C)O)C)C=O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H](C(O1)O[C@@H]2[C@H]([C@H](CO[C@H]2OC3CCC4(C(C3(C)C)CCC5(C4CC(C6C5(CCC6C(CCC=C(C)C)(CO[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O)C)O)C)C=O)O)O)O)O)O
• InChI: InChI=1S/C47H78O18/c1-22(2)9-8-13-47(59,21-61-40-37(57)36(56)34(54)27(18-48)63-40)24-10-14-45(7)31(24)25(50)17-29-44(45,6)15-11-28-43(4,5)30(12-16-46(28,29)20-49)64-42-39(33(53)26(51)19-60-42)65-41-38(58)35(55)32(52)23(3)62-41/h9,20,23-42,48,50-59H,8,10-19,21H2,1-7H3/t23-,24?,25?,26-,27+,28?,29?,30?,31?,32-,33-,34+,35+,36-,37+,38+,39+,40+,41?,42-,44?,45?,46?,47?/m0/s1
• InChI Key: XFPBYUCYWVUISN-RTSVSFOISA-N
• Popularity: 0 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): -0.21
• H-Bond Acceptor: 18
• H-Bond Donor: 11
• Rotatable Bonds: 13

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	-	0.8916	89.16%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.8134	81.34%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7927	79.27%
OATP1B3 inhibitior	-	0.2428	24.28%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6776	67.76%
BSEP inhibitior	+	0.8786	87.86%
P-glycoprotein inhibitior	+	0.7534	75.34%
P-glycoprotein substrate	+	0.5278	52.78%
CYP3A4 substrate	+	0.7361	73.61%
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	+	0.7733	77.33%
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	-	0.9055	90.55%
Skin irritation	-	0.5512	55.12%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7990	79.90%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.6575	65.75%
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	+	0.5795	57.95%
Acute Oral Toxicity (c)	I	0.4409	44.09%
Estrogen receptor binding	+	0.8119	81.19%
Androgen receptor binding	+	0.7410	74.10%
Thyroid receptor binding	-	0.5285	52.85%
Glucocorticoid receptor binding	+	0.7424	74.24%
Aromatase binding	+	0.6388	63.88%
PPAR gamma	+	0.8006	80.06%
Honey bee toxicity	-	0.5622	56.22%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
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	97.49%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.50%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	93.90%	92.94%
CHEMBL3714130	P46095	G-protein coupled receptor 6	93.45%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.10%	86.33%
CHEMBL226	P30542	Adenosine A1 receptor	90.65%	95.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.40%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.18%	100.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	89.17%	91.24%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.48%	97.25%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	87.01%	92.88%
CHEMBL1951	P21397	Monoamine oxidase A	86.62%	91.49%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.92%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.85%	89.00%
CHEMBL1937	Q92769	Histone deacetylase 2	85.00%	94.75%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	84.21%	95.58%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	84.11%	92.78%
CHEMBL2243	O00519	Anandamide amidohydrolase	83.85%	97.53%
CHEMBL5028	O14672	ADAM10	83.18%	97.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.77%	95.56%
CHEMBL2094128	P24941	Cyclin-dependent kinase 2/cyclin A	82.23%	97.25%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.50%	95.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.34%	91.07%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.69%	100.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.60%	96.90%

Plants that contains it

• Gynostemma pentaphyllum

Cross-Links

• PubChem: 11968532
• NPASS: NPC182868