(2R,3R,4S,5S,6R)-2-[[(2R,3S,4S,5R,6S)-6-[(E,2S)-6-hydroperoxy-6-methyl-2-[(2R,3R,5R,8R,9R,10R,12R,13R,14R,17S)-2,3,12-trihydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]hept-4-en-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: eb532712-4230-4045-827b-49c7d7e17b4c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[[(2R,3S,4S,5R,6S)-6-[(E,2S)-6-hydroperoxy-6-methyl-2-[(2R,3R,5R,8R,9R,10R,12R,13R,14R,17S)-2,3,12-trihydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]hept-4-en-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC1(C2CCC3(C(C2(CC(C1O)O)C)CC(C4C3(CCC4C(C)(CC=CC(C)(C)OO)OC5C(C(C(C(O5)COC6C(C(C(C(O6)CO)O)O)O)O)O)O)C)O)C)C
• SMILES (Isomeric): C[C@@]12CC[C@@H]3[C@@]([C@H]1C[C@H]([C@H]4[C@]2(CC[C@@H]4[C@](C)(C/C=C/C(C)(C)OO)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O)O)O)C)O)(C[C@H]([C@@H](C3(C)C)O)O)C
• InChI: InChI=1S/C42H72O16/c1-37(2,58-53)12-9-13-42(8,57-36-33(51)31(49)29(47)24(56-36)19-54-35-32(50)30(48)28(46)23(18-43)55-35)20-10-14-41(7)27(20)21(44)16-26-39(5)17-22(45)34(52)38(3,4)25(39)11-15-40(26,41)6/h9,12,20-36,43-53H,10-11,13-19H2,1-8H3/b12-9+/t20-,21+,22+,23+,24+,25-,26+,27-,28+,29+,30-,31-,32+,33+,34-,35+,36-,39-,40+,41+,42-/m0/s1
• InChI Key: OUZGLMQJFNSAPO-GXCPRVIISA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₇₂O₁₆
• Molecular Weight: 833.00 g/mol
• Exact Mass: 832.48203620 g/mol
• Topological Polar Surface Area (TPSA): 269.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 0.59
• H-Bond Acceptor: 16
• H-Bond Donor: 11
• Rotatable Bonds: 11

Synonyms

• BDBM50090476

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5627	56.27%
Caco-2	-	0.8811	88.11%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6365	63.65%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8045	80.45%
OATP1B3 inhibitior	+	0.8884	88.84%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.6268	62.68%
P-glycoprotein inhibitior	+	0.7641	76.41%
P-glycoprotein substrate	-	0.5852	58.52%
CYP3A4 substrate	+	0.7175	71.75%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8308	83.08%
CYP3A4 inhibition	-	0.9413	94.13%
CYP2C9 inhibition	-	0.8698	86.98%
CYP2C19 inhibition	-	0.8543	85.43%
CYP2D6 inhibition	-	0.9414	94.14%
CYP1A2 inhibition	-	0.8765	87.65%
CYP2C8 inhibition	+	0.6848	68.48%
CYP inhibitory promiscuity	-	0.9524	95.24%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6368	63.68%
Eye corrosion	-	0.9863	98.63%
Eye irritation	-	0.9074	90.74%
Skin irritation	-	0.6823	68.23%
Skin corrosion	-	0.9304	93.04%
Ames mutagenesis	-	0.5817	58.17%
Human Ether-a-go-go-Related Gene inhibition	+	0.7344	73.44%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.5076	50.76%
skin sensitisation	-	0.8898	88.98%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	+	0.4778	47.78%
Acute Oral Toxicity (c)	I	0.4658	46.58%
Estrogen receptor binding	+	0.7330	73.30%
Androgen receptor binding	+	0.7351	73.51%
Thyroid receptor binding	-	0.5231	52.31%
Glucocorticoid receptor binding	+	0.6409	64.09%
Aromatase binding	+	0.6476	64.76%
PPAR gamma	+	0.7397	73.97%
Honey bee toxicity	-	0.6377	63.77%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9060	90.60%

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	99.03%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.55%	97.25%
CHEMBL218	P21554	Cannabinoid CB1 receptor	96.83%	96.61%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.02%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.91%	97.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	93.06%	82.69%
CHEMBL226	P30542	Adenosine A1 receptor	91.55%	95.93%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.60%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.92%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.91%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.46%	95.89%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	87.05%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.08%	95.56%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.91%	100.00%
CHEMBL259	P32245	Melanocortin receptor 4	84.88%	95.38%
CHEMBL2996	Q05655	Protein kinase C delta	83.68%	97.79%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.43%	94.45%
CHEMBL1937	Q92769	Histone deacetylase 2	83.26%	94.75%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.62%	97.14%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	81.51%	94.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.48%	89.00%
CHEMBL1977	P11473	Vitamin D receptor	81.28%	99.43%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	80.55%	100.00%

Plants that contains it

• Gynostemma pentaphyllum

Cross-Links

• PubChem: 122179020
• LOTUS: LTS0192037
• wikiData: Q105200553