[(5R,7R,8R,9S,10S,11R,13S,17S)-7-acetyloxy-17-[(3S,5R)-5-[(1S)-1,2-dihydroxy-2-methylpropyl]-2-hydroxyoxolan-3-yl]-4,4,10,13-tetramethyl-3-oxo-6,7,8,9,11,12,16,17-octahydro-5H-cyclopenta[a]phenanthren-11-yl] (2R)-2-methylbutanoate

Details

• Internal ID: 6b59d896-9ddc-465b-8d24-302bec12e865
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: [(5R,7R,8R,9S,10S,11R,13S,17S)-7-acetyloxy-17-[(3S,5R)-5-[(1S)-1,2-dihydroxy-2-methylpropyl]-2-hydroxyoxolan-3-yl]-4,4,10,13-tetramethyl-3-oxo-6,7,8,9,11,12,16,17-octahydro-5H-cyclopenta[a]phenanthren-11-yl] (2R)-2-methylbutanoate
• SMILES (Canonical): CCC(C)C(=O)OC1CC2(C(CC=C2C3C1C4(C=CC(=O)C(C4CC3OC(=O)C)(C)C)C)C5CC(OC5O)C(C(C)(C)O)O)C
• SMILES (Isomeric): CC[C@@H](C)C(=O)O[C@@H]1C[C@]2([C@@H](CC=C2[C@H]3[C@H]1[C@]4(C=CC(=O)C([C@@H]4C[C@H]3OC(=O)C)(C)C)C)[C@@H]5C[C@@H](OC5O)[C@@H](C(C)(C)O)O)C
• InChI: InChI=1S/C36H54O9/c1-10-18(2)31(40)45-25-17-36(9)21(20-15-24(44-32(20)41)30(39)34(6,7)42)11-12-22(36)28-23(43-19(3)37)16-26-33(4,5)27(38)13-14-35(26,8)29(25)28/h12-14,18,20-21,23-26,28-30,32,39,41-42H,10-11,15-17H2,1-9H3/t18-,20+,21+,23-,24-,25-,26+,28-,29+,30+,32?,35+,36+/m1/s1
• InChI Key: MFNZNGKXWWARMF-GROFBYINSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₅₄O₉
• Molecular Weight: 630.80 g/mol
• Exact Mass: 630.37678330 g/mol
• Topological Polar Surface Area (TPSA): 140.00 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 4.51
• H-Bond Acceptor: 9
• H-Bond Donor: 3
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9915	99.15%
Caco-2	-	0.8172	81.72%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7407	74.07%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8230	82.30%
OATP1B3 inhibitior	-	0.2339	23.39%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9477	94.77%
P-glycoprotein inhibitior	+	0.7771	77.71%
P-glycoprotein substrate	+	0.7056	70.56%
CYP3A4 substrate	+	0.7295	72.95%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8941	89.41%
CYP3A4 inhibition	+	0.6588	65.88%
CYP2C9 inhibition	-	0.5763	57.63%
CYP2C19 inhibition	-	0.5943	59.43%
CYP2D6 inhibition	-	0.9370	93.70%
CYP1A2 inhibition	-	0.7542	75.42%
CYP2C8 inhibition	+	0.6893	68.93%
CYP inhibitory promiscuity	-	0.6579	65.79%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4966	49.66%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9300	93.00%
Skin irritation	-	0.5498	54.98%
Skin corrosion	-	0.9366	93.66%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4021	40.21%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	+	0.6033	60.33%
skin sensitisation	-	0.8310	83.10%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.6093	60.93%
Acute Oral Toxicity (c)	I	0.3967	39.67%
Estrogen receptor binding	+	0.7265	72.65%
Androgen receptor binding	+	0.7229	72.29%
Thyroid receptor binding	-	0.5112	51.12%
Glucocorticoid receptor binding	+	0.7249	72.49%
Aromatase binding	+	0.6627	66.27%
PPAR gamma	+	0.6816	68.16%
Honey bee toxicity	-	0.6581	65.81%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	99.56%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.63%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.44%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.83%	94.45%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	96.80%	96.77%
CHEMBL2581	P07339	Cathepsin D	96.16%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.84%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.50%	97.09%
CHEMBL2996	Q05655	Protein kinase C delta	90.17%	97.79%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.53%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	87.95%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.93%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.55%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	87.54%	90.17%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.46%	97.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.05%	100.00%
CHEMBL2179	P04062	Beta-glucocerebrosidase	86.74%	85.31%
CHEMBL220	P22303	Acetylcholinesterase	86.13%	94.45%
CHEMBL3922	P50579	Methionine aminopeptidase 2	86.13%	97.28%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	86.10%	96.90%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	85.94%	95.71%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	85.71%	94.08%
CHEMBL5028	O14672	ADAM10	85.59%	97.50%
CHEMBL3359	P21462	Formyl peptide receptor 1	84.32%	93.56%
CHEMBL2413	P32246	C-C chemokine receptor type 1	84.16%	89.50%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	82.69%	94.97%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	82.63%	97.21%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	81.78%	90.93%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.12%	99.23%

Plants that contains it

• Aglaia argentea

Cross-Links

• PubChem: 101711155
• LOTUS: LTS0242301
• wikiData: Q105162880