(4aR,4bS)-1,3,9-trihydroxy-4b,8,8-trimethyl-4a-(2-oxopropyl)-2-propan-2-yl-6,7-dihydro-5H-phenanthrene-4,10-dione

Details

• Internal ID: a063f6e2-f0c8-439e-9e6e-4c65eedefe06
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (4aR,4bS)-1,3,9-trihydroxy-4b,8,8-trimethyl-4a-(2-oxopropyl)-2-propan-2-yl-6,7-dihydro-5H-phenanthrene-4,10-dione
• SMILES (Canonical): CC(C)C1=C(C(=O)C2(C(=C1O)C(=O)C(=C3C2(CCCC3(C)C)C)O)CC(=O)C)O
• SMILES (Isomeric): CC(C)C1=C(C(=O)[C@]2(C(=C1O)C(=O)C(=C3[C@@]2(CCCC3(C)C)C)O)CC(=O)C)O
• InChI: InChI=1S/C23H30O6/c1-11(2)13-15(25)14-17(27)18(28)19-21(4,5)8-7-9-22(19,6)23(14,10-12(3)24)20(29)16(13)26/h11,25-26,28H,7-10H2,1-6H3/t22-,23+/m0/s1
• InChI Key: NWHYUWBUXYIDNR-XZOQPEGZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₀O₆
• Molecular Weight: 402.50 g/mol
• Exact Mass: 402.20423867 g/mol
• Topological Polar Surface Area (TPSA): 112.00 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 4.43
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9801	98.01%
Caco-2	+	0.6289	62.89%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.8094	80.94%
OATP2B1 inhibitior	-	0.8563	85.63%
OATP1B1 inhibitior	+	0.8207	82.07%
OATP1B3 inhibitior	+	0.8338	83.38%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.6314	63.14%
BSEP inhibitior	-	0.4864	48.64%
P-glycoprotein inhibitior	-	0.7148	71.48%
P-glycoprotein substrate	-	0.7821	78.21%
CYP3A4 substrate	+	0.5555	55.55%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8675	86.75%
CYP3A4 inhibition	-	0.7172	71.72%
CYP2C9 inhibition	-	0.8892	88.92%
CYP2C19 inhibition	-	0.9094	90.94%
CYP2D6 inhibition	-	0.9363	93.63%
CYP1A2 inhibition	-	0.8531	85.31%
CYP2C8 inhibition	-	0.8819	88.19%
CYP inhibitory promiscuity	-	0.8255	82.55%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6908	69.08%
Eye corrosion	-	0.9923	99.23%
Eye irritation	-	0.5531	55.31%
Skin irritation	+	0.5920	59.20%
Skin corrosion	-	0.9457	94.57%
Ames mutagenesis	-	0.5454	54.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6120	61.20%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.5158	51.58%
skin sensitisation	-	0.7075	70.75%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.5678	56.78%
Acute Oral Toxicity (c)	III	0.5722	57.22%
Estrogen receptor binding	+	0.6719	67.19%
Androgen receptor binding	+	0.6267	62.67%
Thyroid receptor binding	+	0.5885	58.85%
Glucocorticoid receptor binding	+	0.7550	75.50%
Aromatase binding	+	0.6243	62.43%
PPAR gamma	+	0.6725	67.25%
Honey bee toxicity	-	0.8946	89.46%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.8200	82.00%
Fish aquatic toxicity	+	0.9935	99.35%

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	98.95%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.92%	94.45%
CHEMBL2581	P07339	Cathepsin D	93.85%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.68%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.62%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.65%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.79%	96.77%
CHEMBL1937	Q92769	Histone deacetylase 2	85.59%	94.75%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.42%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.11%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	80.08%	91.19%

Plants that contains it

• Plectranthus grandidentatus

Cross-Links

• PubChem: 11661337
• LOTUS: LTS0147718
• wikiData: Q105186612