(4aS,5R,6S,8aS)-5,6,8a-trimethyl-5-[(Z)-3-methyl-5-oxopent-3-enyl]-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid

Details

• Internal ID: 0451cb73-4fc0-4074-b4bb-fe2024e72961
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: (4aS,5R,6S,8aS)-5,6,8a-trimethyl-5-[(Z)-3-methyl-5-oxopent-3-enyl]-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid
• SMILES (Canonical): CC1CCC2(C(C1(C)CCC(=CC=O)C)CCC=C2C(=O)O)C
• SMILES (Isomeric): C[C@H]1CC[C@]2([C@H]([C@]1(C)CC/C(=C\C=O)/C)CCC=C2C(=O)O)C
• InChI: InChI=1S/C20H30O3/c1-14(10-13-21)8-11-19(3)15(2)9-12-20(4)16(18(22)23)6-5-7-17(19)20/h6,10,13,15,17H,5,7-9,11-12H2,1-4H3,(H,22,23)/b14-10-/t15-,17-,19+,20+/m0/s1
• InChI Key: DJYLWRPYQJKCDU-JUUFGKLUSA-N
• Popularity: 0 references 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: 5.40
• 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	+	0.9902	99.02%
Caco-2	+	0.8704	87.04%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6377	63.77%
OATP2B1 inhibitior	-	0.8670	86.70%
OATP1B1 inhibitior	+	0.8646	86.46%
OATP1B3 inhibitior	+	0.8031	80.31%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	+	0.6440	64.40%
P-glycoprotein inhibitior	-	0.6441	64.41%
P-glycoprotein substrate	-	0.7840	78.40%
CYP3A4 substrate	+	0.5550	55.50%
CYP2C9 substrate	-	0.7859	78.59%
CYP2D6 substrate	-	0.9118	91.18%
CYP3A4 inhibition	-	0.8222	82.22%
CYP2C9 inhibition	-	0.8053	80.53%
CYP2C19 inhibition	-	0.8264	82.64%
CYP2D6 inhibition	-	0.9361	93.61%
CYP1A2 inhibition	-	0.8204	82.04%
CYP2C8 inhibition	-	0.6393	63.93%
CYP inhibitory promiscuity	-	0.7823	78.23%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.6396	63.96%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.9469	94.69%
Skin irritation	-	0.5258	52.58%
Skin corrosion	-	0.9751	97.51%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8056	80.56%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.5638	56.38%
skin sensitisation	+	0.7215	72.15%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.5567	55.67%
Acute Oral Toxicity (c)	III	0.7824	78.24%
Estrogen receptor binding	+	0.7912	79.12%
Androgen receptor binding	-	0.5208	52.08%
Thyroid receptor binding	+	0.6911	69.11%
Glucocorticoid receptor binding	+	0.5810	58.10%
Aromatase binding	+	0.6265	62.65%
PPAR gamma	-	0.5283	52.83%
Honey bee toxicity	-	0.8989	89.89%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7400	74.00%
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
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.18%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.14%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.92%	95.56%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	88.39%	93.00%
CHEMBL2581	P07339	Cathepsin D	87.46%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.39%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.90%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.35%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.57%	97.09%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.18%	100.00%
CHEMBL5028	O14672	ADAM10	80.13%	97.50%

Plants that contains it

• Haplopappus glutinosus

Cross-Links

• PubChem: 162902695
• LOTUS: LTS0250672
• wikiData: Q104982916