2-[(2R,4aS,6R,8S,8aR)-6,8-dihydroxy-4a-methyl-2,3,4,5,6,7,8,8a-octahydro-1H-naphthalen-2-yl]prop-2-enoic acid

Details

• Internal ID: 7c3e2c5c-0db3-4d3d-a1ae-71ab024ba848
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Cyclic alcohols and derivatives
• IUPAC Name: 2-[(2R,4aS,6R,8S,8aR)-6,8-dihydroxy-4a-methyl-2,3,4,5,6,7,8,8a-octahydro-1H-naphthalen-2-yl]prop-2-enoic acid
• SMILES (Canonical): CC12CCC(CC1C(CC(C2)O)O)C(=C)C(=O)O
• SMILES (Isomeric): C[C@@]12CC[C@H](C[C@H]1[C@H](C[C@@H](C2)O)O)C(=C)C(=O)O
• InChI: InChI=1S/C14H22O4/c1-8(13(17)18)9-3-4-14(2)7-10(15)6-12(16)11(14)5-9/h9-12,15-16H,1,3-7H2,2H3,(H,17,18)/t9-,10+,11+,12+,14+/m1/s1
• InChI Key: JDGJBTMARDZISJ-FGPLHTHASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₂₂O₄
• Molecular Weight: 254.32 g/mol
• Exact Mass: 254.15180918 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.57
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9836	98.36%
Caco-2	+	0.5116	51.16%
Blood Brain Barrier	-	0.7223	72.23%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6716	67.16%
OATP2B1 inhibitior	-	0.8521	85.21%
OATP1B1 inhibitior	+	0.9141	91.41%
OATP1B3 inhibitior	-	0.2299	22.99%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6478	64.78%
BSEP inhibitior	-	0.9366	93.66%
P-glycoprotein inhibitior	-	0.9498	94.98%
P-glycoprotein substrate	-	0.8225	82.25%
CYP3A4 substrate	+	0.6182	61.82%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8817	88.17%
CYP3A4 inhibition	-	0.7659	76.59%
CYP2C9 inhibition	-	0.8379	83.79%
CYP2C19 inhibition	-	0.8673	86.73%
CYP2D6 inhibition	-	0.9350	93.50%
CYP1A2 inhibition	-	0.7487	74.87%
CYP2C8 inhibition	-	0.8069	80.69%
CYP inhibitory promiscuity	-	0.9490	94.90%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5869	58.69%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.6872	68.72%
Skin irritation	+	0.5154	51.54%
Skin corrosion	-	0.9237	92.37%
Ames mutagenesis	-	0.6837	68.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.6596	65.96%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.6302	63.02%
skin sensitisation	-	0.6525	65.25%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.8254	82.54%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.4755	47.55%
Acute Oral Toxicity (c)	III	0.4482	44.82%
Estrogen receptor binding	+	0.8374	83.74%
Androgen receptor binding	-	0.5153	51.53%
Thyroid receptor binding	-	0.5333	53.33%
Glucocorticoid receptor binding	+	0.7067	70.67%
Aromatase binding	-	0.5092	50.92%
PPAR gamma	+	0.5650	56.50%
Honey bee toxicity	-	0.8544	85.44%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9918	99.18%

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	95.72%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.24%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	91.57%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.30%	97.09%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	86.85%	96.38%
CHEMBL284	P27487	Dipeptidyl peptidase IV	86.74%	95.69%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.68%	96.95%
CHEMBL340	P08684	Cytochrome P450 3A4	84.38%	91.19%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.69%	100.00%
CHEMBL237	P41145	Kappa opioid receptor	80.39%	98.10%

Plants that contains it

• Dittrichia graveolens

Cross-Links

• PubChem: 162816936
• LOTUS: LTS0040191
• wikiData: Q105125446