[(2R,3R)-1-[(2R,3S,4S)-2,4-dimethyl-5-oxooxolan-3-yl]-3-hydroxy-3-[(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]butan-2-yl] acetate

Details

• Internal ID: 02b4d9ae-66cf-4045-a6e0-ce57fb426214
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: [(2R,3R)-1-[(2R,3S,4S)-2,4-dimethyl-5-oxooxolan-3-yl]-3-hydroxy-3-[(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]butan-2-yl] acetate
• SMILES (Canonical): CC1C(C(OC1=O)C)CC(C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)O)OC(=O)C
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H](OC1=O)C)C[C@H]([C@@](C)([C@H]2CC[C@@]3([C@@]2(CC[C@H]4C3=CC(=O)[C@H]5[C@@]4(C[C@@H]([C@@H](C5)O)O)C)C)O)O)OC(=O)C
• InChI: InChI=1S/C31H46O9/c1-15-18(16(2)39-27(15)36)11-26(40-17(3)32)30(6,37)25-8-10-31(38)20-12-22(33)21-13-23(34)24(35)14-28(21,4)19(20)7-9-29(25,31)5/h12,15-16,18-19,21,23-26,34-35,37-38H,7-11,13-14H2,1-6H3/t15-,16+,18-,19-,21-,23+,24-,25-,26+,28+,29+,30+,31+/m0/s1
• InChI Key: GFPSWBAAJFSDOH-OOTRXCNISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₆O₉
• Molecular Weight: 562.70 g/mol
• Exact Mass: 562.31418304 g/mol
• Topological Polar Surface Area (TPSA): 151.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 2.46
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9784	97.84%
Caco-2	-	0.7484	74.84%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8286	82.86%
OATP2B1 inhibitior	-	0.7161	71.61%
OATP1B1 inhibitior	+	0.8575	85.75%
OATP1B3 inhibitior	+	0.8592	85.92%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.6053	60.53%
BSEP inhibitior	+	0.7891	78.91%
P-glycoprotein inhibitior	+	0.6509	65.09%
P-glycoprotein substrate	+	0.6592	65.92%
CYP3A4 substrate	+	0.7351	73.51%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9076	90.76%
CYP3A4 inhibition	+	0.6360	63.60%
CYP2C9 inhibition	-	0.7326	73.26%
CYP2C19 inhibition	-	0.7291	72.91%
CYP2D6 inhibition	-	0.9151	91.51%
CYP1A2 inhibition	-	0.6703	67.03%
CYP2C8 inhibition	+	0.5735	57.35%
CYP inhibitory promiscuity	-	0.8829	88.29%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5595	55.95%
Eye corrosion	-	0.9926	99.26%
Eye irritation	-	0.9231	92.31%
Skin irritation	+	0.6740	67.40%
Skin corrosion	-	0.9278	92.78%
Ames mutagenesis	-	0.7670	76.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4015	40.15%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	+	0.5916	59.16%
skin sensitisation	-	0.8710	87.10%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.6809	68.09%
Acute Oral Toxicity (c)	IV	0.4607	46.07%
Estrogen receptor binding	+	0.7433	74.33%
Androgen receptor binding	+	0.7411	74.11%
Thyroid receptor binding	-	0.5294	52.94%
Glucocorticoid receptor binding	+	0.7541	75.41%
Aromatase binding	+	0.7006	70.06%
PPAR gamma	+	0.6220	62.20%
Honey bee toxicity	-	0.6998	69.98%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.9946	99.46%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.15%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.61%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.18%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.66%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.07%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.46%	97.09%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	92.46%	91.07%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	91.29%	82.69%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.63%	94.45%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	89.41%	95.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.90%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.81%	100.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	88.63%	97.28%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.31%	97.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.08%	86.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.61%	96.77%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.23%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.39%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.99%	94.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.30%	95.89%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.87%	93.56%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.44%	89.50%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.28%	96.95%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	80.07%	94.78%

Plants that contains it

• Ajuga taiwanensis
• Ajuga turkestancia

Cross-Links

• PubChem: 101355227
• LOTUS: LTS0245185
• wikiData: Q104251673