5-[(1S,2R,4aR,8aR)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylidene-4-oxopentanoic acid

Details

• Internal ID: 4a685aff-aafc-4822-88f5-72dc2675e23b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: 5-[(1S,2R,4aR,8aR)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylidene-4-oxopentanoic acid
• SMILES (Canonical): CC1CCC2(C(C1(C)CC(=O)C(=C)CC(=O)O)CCC=C2C)C
• SMILES (Isomeric): C[C@@H]1CC[C@@]2([C@@H]([C@@]1(C)CC(=O)C(=C)CC(=O)O)CCC=C2C)C
• InChI: InChI=1S/C20H30O3/c1-13(11-18(22)23)16(21)12-20(5)15(3)9-10-19(4)14(2)7-6-8-17(19)20/h7,15,17H,1,6,8-12H2,2-5H3,(H,22,23)/t15-,17+,19+,20+/m1/s1
• InChI Key: ZCSPQXGZOGRGDG-LQJIQPLVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₃
• Molecular Weight: 318.40 g/mol
• Exact Mass: 318.21949481 g/mol
• Topological Polar Surface Area (TPSA): 54.40 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 4.78
• H-Bond Acceptor: 2
• 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	+	0.9938	99.38%
Caco-2	+	0.6224	62.24%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6377	63.77%
OATP2B1 inhibitior	-	0.8636	86.36%
OATP1B1 inhibitior	+	0.9045	90.45%
OATP1B3 inhibitior	+	0.9207	92.07%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.5320	53.20%
P-glycoprotein inhibitior	-	0.6097	60.97%
P-glycoprotein substrate	-	0.8723	87.23%
CYP3A4 substrate	+	0.5584	55.84%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8928	89.28%
CYP3A4 inhibition	-	0.5271	52.71%
CYP2C9 inhibition	-	0.8906	89.06%
CYP2C19 inhibition	-	0.8969	89.69%
CYP2D6 inhibition	-	0.9481	94.81%
CYP1A2 inhibition	-	0.8901	89.01%
CYP2C8 inhibition	-	0.6836	68.36%
CYP inhibitory promiscuity	-	0.9058	90.58%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8500	85.00%
Carcinogenicity (trinary)	Non-required	0.6654	66.54%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.8804	88.04%
Skin irritation	+	0.5696	56.96%
Skin corrosion	-	0.9648	96.48%
Ames mutagenesis	-	0.7866	78.66%
Human Ether-a-go-go-Related Gene inhibition	+	0.6915	69.15%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.6157	61.57%
skin sensitisation	+	0.6026	60.26%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.7355	73.55%
Acute Oral Toxicity (c)	III	0.8386	83.86%
Estrogen receptor binding	+	0.6440	64.40%
Androgen receptor binding	-	0.4863	48.63%
Thyroid receptor binding	+	0.6602	66.02%
Glucocorticoid receptor binding	+	0.6204	62.04%
Aromatase binding	+	0.7524	75.24%
PPAR gamma	+	0.7071	70.71%
Honey bee toxicity	-	0.9308	93.08%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.9975	99.75%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.55%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.30%	91.11%
CHEMBL2581	P07339	Cathepsin D	88.19%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.37%	95.56%
CHEMBL221	P23219	Cyclooxygenase-1	85.74%	90.17%
CHEMBL340	P08684	Cytochrome P450 3A4	85.30%	91.19%
CHEMBL5028	O14672	ADAM10	82.93%	97.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.36%	97.09%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.12%	93.03%
CHEMBL4040	P28482	MAP kinase ERK2	80.06%	83.82%

Plants that contains it

• Premna schimperi
• Scrophularia deserti
• Scrophularia ilwensis

Cross-Links

• PubChem: 10381227
• LOTUS: LTS0204319
• wikiData: Q105341481