(3R,5S)-3-[(3S,5S,10S,13S,14R,16R,17R)-16-hydroxy-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,5,6,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-5-[(2R,3S)-3-methyl-2-propan-2-yloxiran-2-yl]oxolan-2-one

Details

• Internal ID: b0610307-1338-45fb-aa7d-1f875be588bf
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (3R,5S)-3-[(3S,5S,10S,13S,14R,16R,17R)-16-hydroxy-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,5,6,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-5-[(2R,3S)-3-methyl-2-propan-2-yloxiran-2-yl]oxolan-2-one
• SMILES (Canonical): CC1C(O1)(C2CC(C(=O)O2)C3C(CC4C3(CC=C5C4=CCC6C5(CCC(C6)OC7C(C(C(C(O7)CO)O)O)O)C)C)O)C(C)C
• SMILES (Isomeric): C[C@H]1[C@@](O1)([C@@H]2C[C@@H](C(=O)O2)[C@H]3[C@@H](C[C@@H]4[C@@]3(CC=C5C4=CC[C@@H]6[C@@]5(CC[C@@H](C6)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)C)C)O)C(C)C
• InChI: InChI=1S/C35H52O10/c1-16(2)35(17(3)45-35)26-13-21(31(41)44-26)27-24(37)14-23-20-7-6-18-12-19(8-10-33(18,4)22(20)9-11-34(23,27)5)42-32-30(40)29(39)28(38)25(15-36)43-32/h7,9,16-19,21,23-30,32,36-40H,6,8,10-15H2,1-5H3/t17-,18-,19-,21+,23-,24+,25+,26-,27-,28+,29-,30+,32+,33-,34-,35+/m0/s1
• InChI Key: XATNGESTVSBAGC-VMPFJVBPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₅₂O₁₀
• Molecular Weight: 632.80 g/mol
• Exact Mass: 632.35604785 g/mol
• Topological Polar Surface Area (TPSA): 158.00 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.39
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9244	92.44%
Caco-2	-	0.8479	84.79%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.8542	85.42%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8197	81.97%
OATP1B3 inhibitior	+	0.8961	89.61%
MATE1 inhibitior	-	0.9812	98.12%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.6073	60.73%
P-glycoprotein inhibitior	+	0.6757	67.57%
P-glycoprotein substrate	+	0.5905	59.05%
CYP3A4 substrate	+	0.7293	72.93%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8916	89.16%
CYP3A4 inhibition	-	0.7380	73.80%
CYP2C9 inhibition	-	0.7706	77.06%
CYP2C19 inhibition	-	0.8955	89.55%
CYP2D6 inhibition	-	0.9187	91.87%
CYP1A2 inhibition	-	0.8775	87.75%
CYP2C8 inhibition	+	0.5870	58.70%
CYP inhibitory promiscuity	-	0.8778	87.78%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5395	53.95%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.9250	92.50%
Skin irritation	-	0.5542	55.42%
Skin corrosion	-	0.9339	93.39%
Ames mutagenesis	-	0.6854	68.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.6836	68.36%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	-	0.6852	68.52%
skin sensitisation	-	0.8840	88.40%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.6569	65.69%
Acute Oral Toxicity (c)	I	0.6025	60.25%
Estrogen receptor binding	+	0.7468	74.68%
Androgen receptor binding	+	0.7293	72.93%
Thyroid receptor binding	-	0.5273	52.73%
Glucocorticoid receptor binding	+	0.6915	69.15%
Aromatase binding	+	0.6194	61.94%
PPAR gamma	+	0.6149	61.49%
Honey bee toxicity	-	0.6464	64.64%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9723	97.23%

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	99.08%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.29%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.04%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.92%	97.09%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	93.70%	94.23%
CHEMBL218	P21554	Cannabinoid CB1 receptor	93.16%	96.61%
CHEMBL2581	P07339	Cathepsin D	92.92%	98.95%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.38%	96.21%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.65%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.29%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.06%	85.14%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.55%	93.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.29%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	87.22%	94.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.19%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.96%	86.92%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.59%	89.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.89%	97.14%
CHEMBL220	P22303	Acetylcholinesterase	84.17%	94.45%
CHEMBL2996	Q05655	Protein kinase C delta	83.08%	97.79%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.02%	91.07%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.85%	94.00%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.77%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	82.61%	92.50%
CHEMBL5103	Q969S8	Histone deacetylase 10	80.49%	90.08%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.01%	95.89%

Plants that contains it

• Gymnanthemum amygdalinum

Cross-Links

• PubChem: 162858132
• LOTUS: LTS0234330
• wikiData: Q105324135