(4aR,5S,6R,8aS)-8a-(hydroxymethyl)-5-[(3S)-5-hydroxy-3-methylpentyl]-5,6-dimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid

Details

• Internal ID: eb1dadda-bf4c-48bf-bc11-e8a577fc5d78
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids > Colensane and clerodane diterpenoids
• IUPAC Name: (4aR,5S,6R,8aS)-8a-(hydroxymethyl)-5-[(3S)-5-hydroxy-3-methylpentyl]-5,6-dimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid
• SMILES (Canonical): CC1CCC2(C(C1(C)CCC(C)CCO)CCC=C2C(=O)O)CO
• SMILES (Isomeric): C[C@@H]1CC[C@@]2([C@@H]([C@@]1(C)CC[C@H](C)CCO)CCC=C2C(=O)O)CO
• InChI: InChI=1S/C20H34O4/c1-14(9-12-21)7-10-19(3)15(2)8-11-20(13-22)16(18(23)24)5-4-6-17(19)20/h5,14-15,17,21-22H,4,6-13H2,1-3H3,(H,23,24)/t14-,15+,17+,19-,20+/m0/s1
• InChI Key: OJYNMAREYBQEPO-JQZTVVIASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₄O₄
• Molecular Weight: 338.50 g/mol
• Exact Mass: 338.24570956 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 4.20
• Atomic LogP (AlogP): 3.62
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9782	97.82%
Caco-2	+	0.7443	74.43%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7079	70.79%
OATP2B1 inhibitior	-	0.8654	86.54%
OATP1B1 inhibitior	+	0.8893	88.93%
OATP1B3 inhibitior	+	0.8392	83.92%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.5215	52.15%
BSEP inhibitior	+	0.6765	67.65%
P-glycoprotein inhibitior	-	0.8746	87.46%
P-glycoprotein substrate	-	0.7315	73.15%
CYP3A4 substrate	+	0.5446	54.46%
CYP2C9 substrate	-	0.8008	80.08%
CYP2D6 substrate	-	0.9158	91.58%
CYP3A4 inhibition	-	0.6752	67.52%
CYP2C9 inhibition	-	0.8994	89.94%
CYP2C19 inhibition	-	0.9152	91.52%
CYP2D6 inhibition	-	0.9240	92.40%
CYP1A2 inhibition	-	0.8981	89.81%
CYP2C8 inhibition	-	0.8290	82.90%
CYP inhibitory promiscuity	-	0.8711	87.11%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6756	67.56%
Eye corrosion	-	0.9878	98.78%
Eye irritation	-	0.9317	93.17%
Skin irritation	-	0.7205	72.05%
Skin corrosion	-	0.9791	97.91%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4816	48.16%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	-	0.6434	64.34%
skin sensitisation	-	0.6900	69.00%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7077	70.77%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.6013	60.13%
Acute Oral Toxicity (c)	III	0.6374	63.74%
Estrogen receptor binding	+	0.8876	88.76%
Androgen receptor binding	-	0.5113	51.13%
Thyroid receptor binding	+	0.7862	78.62%
Glucocorticoid receptor binding	+	0.7286	72.86%
Aromatase binding	+	0.7355	73.55%
PPAR gamma	-	0.5332	53.32%
Honey bee toxicity	-	0.8989	89.89%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.8700	87.00%
Fish aquatic toxicity	+	0.9928	99.28%

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	97.08%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.67%	97.25%
CHEMBL2581	P07339	Cathepsin D	90.76%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.75%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.08%	97.09%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.96%	93.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.21%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.29%	95.56%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.22%	100.00%
CHEMBL4072	P07858	Cathepsin B	81.76%	93.67%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.74%	93.56%

Plants that contains it

• Olearia teretifolia

Cross-Links

• PubChem: 163021628
• LOTUS: LTS0120266
• wikiData: Q105193402