(3S)-5-[(1R,2S,4aR,8aR)-1,2,4a,5-tetramethyl-3,7-dioxo-2,4,8,8a-tetrahydronaphthalen-1-yl]-3-methylpentanoic acid

Details

• Internal ID: 391ece16-0cb3-448a-99ef-9763af915187
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: (3S)-5-[(1R,2S,4aR,8aR)-1,2,4a,5-tetramethyl-3,7-dioxo-2,4,8,8a-tetrahydronaphthalen-1-yl]-3-methylpentanoic acid
• SMILES (Canonical): CC1C(=O)CC2(C(C1(C)CCC(C)CC(=O)O)CC(=O)C=C2C)C
• SMILES (Isomeric): C[C@@H]1C(=O)C[C@@]2([C@@H]([C@@]1(C)CC[C@H](C)CC(=O)O)CC(=O)C=C2C)C
• InChI: InChI=1S/C20H30O4/c1-12(8-18(23)24)6-7-19(4)14(3)16(22)11-20(5)13(2)9-15(21)10-17(19)20/h9,12,14,17H,6-8,10-11H2,1-5H3,(H,23,24)/t12-,14+,17+,19-,20-/m0/s1
• InChI Key: WCWSAYZIPUPYKD-SVMSGLSLSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₄
• Molecular Weight: 334.40 g/mol
• Exact Mass: 334.21440943 g/mol
• Topological Polar Surface Area (TPSA): 71.40 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 4.03
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9885	98.85%
Caco-2	+	0.7282	72.82%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8059	80.59%
OATP2B1 inhibitior	-	0.8653	86.53%
OATP1B1 inhibitior	+	0.8849	88.49%
OATP1B3 inhibitior	+	0.9181	91.81%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.7021	70.21%
BSEP inhibitior	+	0.5650	56.50%
P-glycoprotein inhibitior	-	0.6438	64.38%
P-glycoprotein substrate	-	0.6541	65.41%
CYP3A4 substrate	+	0.5852	58.52%
CYP2C9 substrate	-	0.8078	80.78%
CYP2D6 substrate	-	0.9114	91.14%
CYP3A4 inhibition	-	0.6463	64.63%
CYP2C9 inhibition	-	0.9571	95.71%
CYP2C19 inhibition	-	0.9609	96.09%
CYP2D6 inhibition	-	0.9441	94.41%
CYP1A2 inhibition	-	0.9245	92.45%
CYP2C8 inhibition	-	0.8806	88.06%
CYP inhibitory promiscuity	-	0.9408	94.08%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7096	70.96%
Eye corrosion	-	0.9960	99.60%
Eye irritation	-	0.8975	89.75%
Skin irritation	+	0.7565	75.65%
Skin corrosion	-	0.9581	95.81%
Ames mutagenesis	-	0.8154	81.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7941	79.41%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.5395	53.95%
skin sensitisation	-	0.6387	63.87%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.5538	55.38%
Acute Oral Toxicity (c)	III	0.8649	86.49%
Estrogen receptor binding	+	0.6260	62.60%
Androgen receptor binding	+	0.6980	69.80%
Thyroid receptor binding	+	0.7114	71.14%
Glucocorticoid receptor binding	+	0.7611	76.11%
Aromatase binding	+	0.7558	75.58%
PPAR gamma	+	0.5502	55.02%
Honey bee toxicity	-	0.8804	88.04%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9955	99.55%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.00%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.56%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.85%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	90.96%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.85%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.04%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.17%	94.45%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.75%	93.04%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.43%	93.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.07%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.76%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.54%	97.25%

Plants that contains it

• Nuxia sphaerocephala

Cross-Links

• PubChem: 11508272
• LOTUS: LTS0035204
• wikiData: Q105302146