[(1R,4aS,10aR)-5,6-dihydroxy-1,4a-dimethyl-9-oxo-7-propan-2-yl-3,4,10,10a-tetrahydro-2H-phenanthren-1-yl]methyl acetate

Details

• Internal ID: ce5f3c70-db3e-41e5-813a-f00c55e2e0c7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(1R,4aS,10aR)-5,6-dihydroxy-1,4a-dimethyl-9-oxo-7-propan-2-yl-3,4,10,10a-tetrahydro-2H-phenanthren-1-yl]methyl acetate
• SMILES (Canonical): CC(C)C1=C(C(=C2C(=C1)C(=O)CC3C2(CCCC3(C)COC(=O)C)C)O)O
• SMILES (Isomeric): CC(C)C1=C(C(=C2C(=C1)C(=O)C[C@@H]3[C@@]2(CCC[C@@]3(C)COC(=O)C)C)O)O
• InChI: InChI=1S/C22H30O5/c1-12(2)14-9-15-16(24)10-17-21(4,11-27-13(3)23)7-6-8-22(17,5)18(15)20(26)19(14)25/h9,12,17,25-26H,6-8,10-11H2,1-5H3/t17-,21-,22-/m0/s1
• InChI Key: MWKQZQOBWYIJHX-HSQYWUDLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₀O₅
• Molecular Weight: 374.50 g/mol
• Exact Mass: 374.20932405 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 4.40
• Atomic LogP (AlogP): 4.43
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9645	96.45%
Caco-2	+	0.6212	62.12%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.9439	94.39%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8395	83.95%
OATP1B3 inhibitior	+	0.8558	85.58%
MATE1 inhibitior	-	0.6000	60.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.6521	65.21%
P-glycoprotein inhibitior	-	0.7135	71.35%
P-glycoprotein substrate	-	0.5859	58.59%
CYP3A4 substrate	+	0.6449	64.49%
CYP2C9 substrate	-	0.5773	57.73%
CYP2D6 substrate	-	0.8441	84.41%
CYP3A4 inhibition	-	0.7871	78.71%
CYP2C9 inhibition	-	0.7851	78.51%
CYP2C19 inhibition	-	0.8299	82.99%
CYP2D6 inhibition	-	0.9490	94.90%
CYP1A2 inhibition	+	0.5968	59.68%
CYP2C8 inhibition	+	0.4620	46.20%
CYP inhibitory promiscuity	-	0.9004	90.04%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.6631	66.31%
Eye corrosion	-	0.9941	99.41%
Eye irritation	-	0.8569	85.69%
Skin irritation	-	0.7414	74.14%
Skin corrosion	-	0.9706	97.06%
Ames mutagenesis	-	0.6754	67.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.5658	56.58%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.8931	89.31%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.8004	80.04%
Acute Oral Toxicity (c)	III	0.6717	67.17%
Estrogen receptor binding	+	0.6388	63.88%
Androgen receptor binding	+	0.5422	54.22%
Thyroid receptor binding	+	0.6131	61.31%
Glucocorticoid receptor binding	+	0.8154	81.54%
Aromatase binding	+	0.5456	54.56%
PPAR gamma	+	0.6435	64.35%
Honey bee toxicity	-	0.7325	73.25%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7150	71.50%
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
CHEMBL2581	P07339	Cathepsin D	98.91%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.79%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.17%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.11%	97.25%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.92%	96.77%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.99%	94.45%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	92.25%	96.38%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	91.05%	82.69%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	90.62%	91.65%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	90.61%	90.71%
CHEMBL340	P08684	Cytochrome P450 3A4	90.59%	91.19%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.35%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.43%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.66%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.65%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.51%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.40%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.75%	97.09%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	83.40%	95.71%
CHEMBL236	P41143	Delta opioid receptor	81.82%	99.35%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.63%	94.00%
CHEMBL3437	Q16853	Amine oxidase, copper containing	81.03%	94.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.67%	100.00%

Plants that contains it

• Salvia ballotiflora

Cross-Links

• PubChem: 162820090
• LOTUS: LTS0095680
• wikiData: Q103815804