(E)-3-[(1R,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]prop-2-enoic acid

Details

• Internal ID: daa45015-cc05-47cb-a179-04aa766d2971
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Cyclic alcohols and derivatives
• IUPAC Name: (E)-3-[(1R,4aS,5R,6R,8aR)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]prop-2-enoic acid
• SMILES (Canonical): CC12CCC(C(C1CCC(=C)C2C=CC(=O)O)(C)CO)O
• SMILES (Isomeric): C[C@@]12CC[C@H]([C@@]([C@H]1CCC(=C)[C@H]2/C=C/C(=O)O)(C)CO)O
• InChI: InChI=1S/C17H26O4/c1-11-4-6-13-16(2,12(11)5-7-15(20)21)9-8-14(19)17(13,3)10-18/h5,7,12-14,18-19H,1,4,6,8-10H2,2-3H3,(H,20,21)/b7-5+/t12-,13+,14-,16+,17+/m1/s1
• InChI Key: ABRILZQPRHWMRY-JOAVWQPASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₆O₄
• Molecular Weight: 294.40 g/mol
• Exact Mass: 294.18310931 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.37
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9738	97.38%
Caco-2	+	0.6981	69.81%
Blood Brain Barrier	+	0.5777	57.77%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7475	74.75%
OATP2B1 inhibitior	-	0.8589	85.89%
OATP1B1 inhibitior	+	0.9183	91.83%
OATP1B3 inhibitior	+	0.7954	79.54%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5650	56.50%
BSEP inhibitior	-	0.8585	85.85%
P-glycoprotein inhibitior	-	0.9400	94.00%
P-glycoprotein substrate	-	0.8284	82.84%
CYP3A4 substrate	+	0.6310	63.10%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9071	90.71%
CYP3A4 inhibition	-	0.7762	77.62%
CYP2C9 inhibition	-	0.8671	86.71%
CYP2C19 inhibition	-	0.9002	90.02%
CYP2D6 inhibition	-	0.9277	92.77%
CYP1A2 inhibition	-	0.8770	87.70%
CYP2C8 inhibition	-	0.7342	73.42%
CYP inhibitory promiscuity	-	0.9062	90.62%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7118	71.18%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.8976	89.76%
Skin irritation	-	0.5321	53.21%
Skin corrosion	-	0.9589	95.89%
Ames mutagenesis	-	0.8354	83.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4010	40.10%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.8400	84.00%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.6035	60.35%
Acute Oral Toxicity (c)	III	0.6551	65.51%
Estrogen receptor binding	-	0.5553	55.53%
Androgen receptor binding	+	0.5560	55.60%
Thyroid receptor binding	-	0.4881	48.81%
Glucocorticoid receptor binding	+	0.6642	66.42%
Aromatase binding	+	0.5178	51.78%
PPAR gamma	-	0.6155	61.55%
Honey bee toxicity	-	0.8881	88.81%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9921	99.21%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	91.68%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.09%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.51%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.76%	95.56%
CHEMBL5028	O14672	ADAM10	81.77%	97.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.20%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	80.94%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.13%	97.09%

Plants that contains it

• Andrographis paniculata

Cross-Links

• PubChem: 44577210
• NPASS: NPC79945
• ChEMBL: CHEMBL503611
• LOTUS: LTS0177856
• wikiData: Q104908770