(1aS,3R,4R,4aR,6S,7R,8aS)-7-Chloro-3,6-dihydroxy-3,4a,8,8-tetramethyl-octahydro-1aH-naphtho[1-b]oxirene-4-carboxylic acid

Details

• Internal ID: a34a0c1b-92b8-4cd7-bc0f-391c00073727
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Abscisic acids and derivatives
• IUPAC Name: (1aS,3R,4R,4aR,6S,7R,8aS)-7-chloro-3,6-dihydroxy-3,4a,8,8-tetramethyl-1a,2,4,5,6,7-hexahydronaphtho[4,4a-b]oxirene-4-carboxylic acid
• SMILES (Canonical): CC1(C(C(CC2(C13C(O3)CC(C2C(=O)O)(C)O)C)O)Cl)C
• SMILES (Isomeric): C[C@]12C[C@@H]([C@@H](C([C@]13[C@@H](O3)C[C@@]([C@@H]2C(=O)O)(C)O)(C)C)Cl)O
• InChI: InChI=1S/C15H23ClO5/c1-12(2)10(16)7(17)5-13(3)9(11(18)19)14(4,20)6-8-15(12,13)21-8/h7-10,17,20H,5-6H2,1-4H3,(H,18,19)/t7-,8-,9+,10-,13+,14+,15+/m0/s1
• InChI Key: QUHIFZVMNSLMAB-ZEBSVQATSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₃ClO₅
• Molecular Weight: 318.79 g/mol
• Exact Mass: 318.1234015 g/mol
• Topological Polar Surface Area (TPSA): 90.30 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.38
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9439	94.39%
Caco-2	+	0.5056	50.56%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Lysosomes	0.5410	54.10%
OATP2B1 inhibitior	-	0.8518	85.18%
OATP1B1 inhibitior	+	0.9136	91.36%
OATP1B3 inhibitior	+	0.9420	94.20%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.8888	88.88%
P-glycoprotein inhibitior	-	0.9003	90.03%
P-glycoprotein substrate	-	0.8568	85.68%
CYP3A4 substrate	+	0.6081	60.81%
CYP2C9 substrate	-	0.8135	81.35%
CYP2D6 substrate	-	0.8466	84.66%
CYP3A4 inhibition	-	0.6861	68.61%
CYP2C9 inhibition	-	0.7910	79.10%
CYP2C19 inhibition	-	0.8367	83.67%
CYP2D6 inhibition	-	0.9101	91.01%
CYP1A2 inhibition	-	0.8293	82.93%
CYP2C8 inhibition	-	0.8721	87.21%
CYP inhibitory promiscuity	-	0.9049	90.49%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.8451	84.51%
Carcinogenicity (trinary)	Non-required	0.4489	44.89%
Eye corrosion	-	0.9855	98.55%
Eye irritation	-	0.9048	90.48%
Skin irritation	-	0.6491	64.91%
Skin corrosion	-	0.8920	89.20%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6288	62.88%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	-	0.6052	60.52%
skin sensitisation	-	0.7539	75.39%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.7088	70.88%
Acute Oral Toxicity (c)	III	0.4041	40.41%
Estrogen receptor binding	+	0.7500	75.00%
Androgen receptor binding	+	0.6450	64.50%
Thyroid receptor binding	+	0.6835	68.35%
Glucocorticoid receptor binding	+	0.7243	72.43%
Aromatase binding	+	0.5229	52.29%
PPAR gamma	-	0.6691	66.91%
Honey bee toxicity	-	0.8107	81.07%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9618	96.18%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	95.15%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.39%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	92.18%	96.61%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.07%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	85.52%	91.19%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.36%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.09%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.00%	95.56%

Plants that contains it

• Adenocarpus foliolosus

Cross-Links

• PubChem: 11688306
• LOTUS: LTS0149604
• wikiData: Q105228185