(1S,2R,4aR,8aR)-1,4a,5-trimethyl-1-[(E)-3-methyl-5-oxopent-3-enyl]-2,3,4,7,8,8a-hexahydronaphthalene-2-carboxylic acid

Details

• Internal ID: 21e99c39-8ebe-44b1-bae5-da3a576126f8
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: (1S,2R,4aR,8aR)-1,4a,5-trimethyl-1-[(E)-3-methyl-5-oxopent-3-enyl]-2,3,4,7,8,8a-hexahydronaphthalene-2-carboxylic acid
• SMILES (Canonical): CC1=CCCC2C1(CCC(C2(C)CCC(=CC=O)C)C(=O)O)C
• SMILES (Isomeric): CC1=CCC[C@H]2[C@]1(CC[C@H]([C@@]2(C)CC/C(=C/C=O)/C)C(=O)O)C
• InChI: InChI=1S/C20H30O3/c1-14(10-13-21)8-11-20(4)16(18(22)23)9-12-19(3)15(2)6-5-7-17(19)20/h6,10,13,16-17H,5,7-9,11-12H2,1-4H3,(H,22,23)/b14-10+/t16-,17-,19-,20+/m0/s1
• InChI Key: CCRJBYFBLSIAHK-OMXBKVJCSA-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: 4.70
• 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	+	0.9934	99.34%
Caco-2	+	0.8105	81.05%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7068	70.68%
OATP2B1 inhibitior	-	0.8627	86.27%
OATP1B1 inhibitior	+	0.8907	89.07%
OATP1B3 inhibitior	-	0.2588	25.88%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.7923	79.23%
P-glycoprotein inhibitior	-	0.5977	59.77%
P-glycoprotein substrate	-	0.7856	78.56%
CYP3A4 substrate	+	0.5994	59.94%
CYP2C9 substrate	-	0.7859	78.59%
CYP2D6 substrate	-	0.9118	91.18%
CYP3A4 inhibition	-	0.7823	78.23%
CYP2C9 inhibition	-	0.7325	73.25%
CYP2C19 inhibition	-	0.7709	77.09%
CYP2D6 inhibition	-	0.9456	94.56%
CYP1A2 inhibition	-	0.8590	85.90%
CYP2C8 inhibition	-	0.5895	58.95%
CYP inhibitory promiscuity	-	0.8119	81.19%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.6267	62.67%
Eye corrosion	-	0.9874	98.74%
Eye irritation	-	0.9327	93.27%
Skin irritation	-	0.6040	60.40%
Skin corrosion	-	0.9771	97.71%
Ames mutagenesis	-	0.6254	62.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7138	71.38%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.5547	55.47%
skin sensitisation	+	0.7761	77.61%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.6023	60.23%
Acute Oral Toxicity (c)	III	0.6652	66.52%
Estrogen receptor binding	+	0.7405	74.05%
Androgen receptor binding	+	0.6175	61.75%
Thyroid receptor binding	+	0.6139	61.39%
Glucocorticoid receptor binding	+	0.6071	60.71%
Aromatase binding	+	0.5330	53.30%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.9364	93.64%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7200	72.00%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.89%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.06%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.27%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.02%	94.45%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.57%	93.00%
CHEMBL5028	O14672	ADAM10	83.95%	97.50%
CHEMBL2581	P07339	Cathepsin D	83.79%	98.95%
CHEMBL4208	P20618	Proteasome component C5	83.07%	90.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.54%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.11%	100.00%

Plants that contains it

• Jungermannia infusca
• Symphyopappus reticulatus

Cross-Links

• PubChem: 162962336
• LOTUS: LTS0127443
• wikiData: Q104953742