(4aS,5S,6R,8aR)-5-[(E)-4-carboxy-3-methylbut-3-enyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid

Details

• Internal ID: a4e01c05-c966-43d7-b077-c4662073d538
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: (4aS,5S,6R,8aR)-5-[(E)-4-carboxy-3-methylbut-3-enyl]-5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid
• SMILES (Canonical): CC1CCC2(C(C1(C)CCC(=CC(=O)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)O)/C)CCC=C2C(=O)O)C
• InChI: InChI=1S/C20H30O4/c1-13(12-17(21)22)8-10-19(3)14(2)9-11-20(4)15(18(23)24)6-5-7-16(19)20/h6,12,14,16H,5,7-11H2,1-4H3,(H,21,22)(H,23,24)/b13-12+/t14-,16+,19+,20+/m1/s1
• InChI Key: FMWSHZRIJXQMOO-ADZBGDIPSA-N
• Popularity: 0 references 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): 74.60 Ų
• XlogP: 5.50
• Atomic LogP (AlogP): 4.66
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9711	97.11%
Caco-2	+	0.7703	77.03%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6915	69.15%
OATP2B1 inhibitior	-	0.8705	87.05%
OATP1B1 inhibitior	+	0.8787	87.87%
OATP1B3 inhibitior	-	0.2298	22.98%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7271	72.71%
BSEP inhibitior	-	0.6088	60.88%
P-glycoprotein inhibitior	-	0.6620	66.20%
P-glycoprotein substrate	-	0.8110	81.10%
CYP3A4 substrate	+	0.5505	55.05%
CYP2C9 substrate	-	0.7829	78.29%
CYP2D6 substrate	-	0.9180	91.80%
CYP3A4 inhibition	-	0.8364	83.64%
CYP2C9 inhibition	-	0.9278	92.78%
CYP2C19 inhibition	-	0.9376	93.76%
CYP2D6 inhibition	-	0.9321	93.21%
CYP1A2 inhibition	-	0.8218	82.18%
CYP2C8 inhibition	-	0.6622	66.22%
CYP inhibitory promiscuity	-	0.7879	78.79%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.6820	68.20%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9228	92.28%
Skin irritation	-	0.5564	55.64%
Skin corrosion	-	0.9780	97.80%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7427	74.27%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.5763	57.63%
skin sensitisation	+	0.7433	74.33%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.7188	71.88%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.5522	55.22%
Acute Oral Toxicity (c)	III	0.7456	74.56%
Estrogen receptor binding	+	0.8139	81.39%
Androgen receptor binding	+	0.5647	56.47%
Thyroid receptor binding	+	0.7573	75.73%
Glucocorticoid receptor binding	+	0.7379	73.79%
Aromatase binding	+	0.7606	76.06%
PPAR gamma	+	0.5802	58.02%
Honey bee toxicity	-	0.8591	85.91%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
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	95.16%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.18%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.32%	97.25%
CHEMBL4040	P28482	MAP kinase ERK2	90.37%	83.82%
CHEMBL2581	P07339	Cathepsin D	86.86%	98.95%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	86.85%	93.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.35%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.73%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.24%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.51%	94.45%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.12%	100.00%

Plants that contains it

• Haplopappus foliosus

Cross-Links

• PubChem: 162983069
• LOTUS: LTS0098743
• wikiData: Q104998107