[(2S)-2-[(4bS)-3-acetyloxy-9-hydroxy-4b,8,8-trimethyl-1,4,10-trioxo-6,7-dihydro-5H-phenanthren-2-yl]propyl] acetate

Details

• Internal ID: ac5f850a-4c31-4e66-8449-f4fbe4c13608
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: [(2S)-2-[(4bS)-3-acetyloxy-9-hydroxy-4b,8,8-trimethyl-1,4,10-trioxo-6,7-dihydro-5H-phenanthren-2-yl]propyl] acetate
• SMILES (Canonical): CC(COC(=O)C)C1=C(C(=O)C2=C(C1=O)C(=O)C(=C3C2(CCCC3(C)C)C)O)OC(=O)C
• SMILES (Isomeric): C[C@H](COC(=O)C)C1=C(C(=O)C2=C(C1=O)C(=O)C(=C3[C@@]2(CCCC3(C)C)C)O)OC(=O)C
• InChI: InChI=1S/C24H28O8/c1-11(10-31-12(2)25)14-17(27)15-16(19(29)21(14)32-13(3)26)24(6)9-7-8-23(4,5)22(24)20(30)18(15)28/h11,30H,7-10H2,1-6H3/t11-,24-/m1/s1
• InChI Key: UUVKKHSAZOSIOH-YDGUKXNOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₈O₈
• Molecular Weight: 444.50 g/mol
• Exact Mass: 444.17841785 g/mol
• Topological Polar Surface Area (TPSA): 124.00 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.06
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9862	98.62%
Caco-2	-	0.5571	55.71%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8750	87.50%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8324	83.24%
OATP1B3 inhibitior	-	0.2427	24.27%
MATE1 inhibitior	+	0.7200	72.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.5550	55.50%
P-glycoprotein inhibitior	-	0.4524	45.24%
P-glycoprotein substrate	-	0.6918	69.18%
CYP3A4 substrate	+	0.6006	60.06%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8972	89.72%
CYP3A4 inhibition	-	0.9256	92.56%
CYP2C9 inhibition	-	0.6531	65.31%
CYP2C19 inhibition	-	0.8506	85.06%
CYP2D6 inhibition	-	0.8956	89.56%
CYP1A2 inhibition	-	0.6111	61.11%
CYP2C8 inhibition	-	0.7629	76.29%
CYP inhibitory promiscuity	-	0.8331	83.31%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6128	61.28%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.8063	80.63%
Skin irritation	+	0.5287	52.87%
Skin corrosion	-	0.9603	96.03%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7216	72.16%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	+	0.5307	53.07%
skin sensitisation	-	0.7536	75.36%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	+	0.4767	47.67%
Acute Oral Toxicity (c)	III	0.8224	82.24%
Estrogen receptor binding	+	0.7049	70.49%
Androgen receptor binding	+	0.6496	64.96%
Thyroid receptor binding	+	0.5682	56.82%
Glucocorticoid receptor binding	+	0.6986	69.86%
Aromatase binding	+	0.5710	57.10%
PPAR gamma	+	0.7105	71.05%
Honey bee toxicity	-	0.8195	81.95%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9963	99.63%

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	99.39%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.33%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.85%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.04%	96.09%
CHEMBL1937	Q92769	Histone deacetylase 2	94.42%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.89%	95.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.37%	82.69%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	87.85%	98.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.53%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.09%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.01%	89.00%

Plants that contains it

• Plectranthus xanthanthus

Cross-Links

• PubChem: 162989978
• LOTUS: LTS0061192
• wikiData: Q105279622