(+/-)-Asarinol A

Details

• Internal ID: 26c8e0e7-a009-4baa-96f0-b02d09f763b2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Bicyclic monoterpenoids
• IUPAC Name: (1R,5R,6S)-5-hydroxy-3,7,7-trimethylbicyclo[4.1.0]hept-3-en-2-one
• SMILES (Canonical): CC1=CC(C2C(C1=O)C2(C)C)O
• SMILES (Isomeric): CC1=C[C@H]([C@H]2[C@@H](C1=O)C2(C)C)O
• InChI: InChI=1S/C10H14O2/c1-5-4-6(11)7-8(9(5)12)10(7,2)3/h4,6-8,11H,1-3H3/t6-,7+,8+/m1/s1
• InChI Key: GVTFSJLFFJEHAD-CSMHCCOUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₄O₂
• Molecular Weight: 166.22 g/mol
• Exact Mass: 166.099379685 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.15
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• CHEBI:81356
• DTXSID901156663
• C17824
• Q27155294
• (1R,5R,6S)-5-Hydroxy-3,7,7-trimethylbicyclo[4.1.0]hepta-3-ene-2-one
• rel-(1R,5R,6S)-5-Hydroxy-3,7,7-trimethylbicyclo[4.1.0]hept-3-en-2-one
• 131896-45-2

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9960	99.60%
Caco-2	+	0.5342	53.42%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6929	69.29%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9119	91.19%
OATP1B3 inhibitior	+	0.9659	96.59%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9568	95.68%
P-glycoprotein inhibitior	-	0.9418	94.18%
P-glycoprotein substrate	-	0.9734	97.34%
CYP3A4 substrate	-	0.5391	53.91%
CYP2C9 substrate	-	0.6830	68.30%
CYP2D6 substrate	-	0.8758	87.58%
CYP3A4 inhibition	-	0.7838	78.38%
CYP2C9 inhibition	-	0.8934	89.34%
CYP2C19 inhibition	-	0.6910	69.10%
CYP2D6 inhibition	-	0.9111	91.11%
CYP1A2 inhibition	-	0.7590	75.90%
CYP2C8 inhibition	-	0.9801	98.01%
CYP inhibitory promiscuity	-	0.7990	79.90%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.7330	73.30%
Carcinogenicity (trinary)	Non-required	0.5973	59.73%
Eye corrosion	-	0.8608	86.08%
Eye irritation	+	0.9298	92.98%
Skin irritation	+	0.7007	70.07%
Skin corrosion	-	0.8526	85.26%
Ames mutagenesis	-	0.8300	83.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6691	66.91%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	+	0.6585	65.85%
skin sensitisation	+	0.8093	80.93%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	-	0.5556	55.56%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	+	0.7337	73.37%
Acute Oral Toxicity (c)	III	0.6791	67.91%
Estrogen receptor binding	-	0.8624	86.24%
Androgen receptor binding	-	0.6950	69.50%
Thyroid receptor binding	-	0.8379	83.79%
Glucocorticoid receptor binding	-	0.8898	88.98%
Aromatase binding	-	0.8641	86.41%
PPAR gamma	-	0.8485	84.85%
Honey bee toxicity	-	0.8967	89.67%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.8818	88.18%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	90.63%	98.95%
CHEMBL1937	Q92769	Histone deacetylase 2	89.47%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.99%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.33%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.13%	91.11%

Plants that contains it

• Aconitum episcopale
• Ardisia humilis
• Asarum heterotropoides
• Asarum sieboldii
• Garcinia oligantha
• Iris spuria
• Rubus trifidus

Cross-Links

• PubChem: 46174001
• NPASS: NPC111544
• LOTUS: LTS0209486
• wikiData: Q27155294