(1R,5S)-4-(hydroxymethyl)-1-propan-2-ylbicyclo[3.1.0]hex-3-en-2-one

Details

• Internal ID: ac6b0174-04ab-4629-b46c-9442fa56ce7b
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Bicyclic monoterpenoids
• IUPAC Name: (1R,5S)-4-(hydroxymethyl)-1-propan-2-ylbicyclo[3.1.0]hex-3-en-2-one
• SMILES (Canonical): CC(C)C12CC1C(=CC2=O)CO
• SMILES (Isomeric): CC(C)[C@]12C[C@H]1C(=CC2=O)CO
• InChI: InChI=1S/C10H14O2/c1-6(2)10-4-8(10)7(5-11)3-9(10)12/h3,6,8,11H,4-5H2,1-2H3/t8-,10+/m0/s1
• InChI Key: GFMJTKMWLNEZHB-WCBMZHEXSA-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: 0.30
• Atomic LogP (AlogP): 1.15
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 159645-34-8

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9956	99.56%
Caco-2	+	0.6088	60.88%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6984	69.84%
OATP2B1 inhibitior	-	0.8462	84.62%
OATP1B1 inhibitior	+	0.9220	92.20%
OATP1B3 inhibitior	+	0.9446	94.46%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.9522	95.22%
P-glycoprotein inhibitior	-	0.9816	98.16%
P-glycoprotein substrate	-	0.8791	87.91%
CYP3A4 substrate	-	0.5731	57.31%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8886	88.86%
CYP3A4 inhibition	-	0.9169	91.69%
CYP2C9 inhibition	-	0.8211	82.11%
CYP2C19 inhibition	-	0.6962	69.62%
CYP2D6 inhibition	-	0.8791	87.91%
CYP1A2 inhibition	-	0.6821	68.21%
CYP2C8 inhibition	-	0.9956	99.56%
CYP inhibitory promiscuity	-	0.6841	68.41%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8030	80.30%
Carcinogenicity (trinary)	Non-required	0.6659	66.59%
Eye corrosion	-	0.9477	94.77%
Eye irritation	+	0.8207	82.07%
Skin irritation	-	0.5742	57.42%
Skin corrosion	-	0.9276	92.76%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7500	75.00%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	+	0.5783	57.83%
skin sensitisation	+	0.5771	57.71%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.5907	59.07%
Acute Oral Toxicity (c)	III	0.6219	62.19%
Estrogen receptor binding	-	0.9329	93.29%
Androgen receptor binding	+	0.5517	55.17%
Thyroid receptor binding	-	0.8516	85.16%
Glucocorticoid receptor binding	-	0.7446	74.46%
Aromatase binding	-	0.8400	84.00%
PPAR gamma	-	0.8548	85.48%
Honey bee toxicity	-	0.9552	95.52%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.9694	96.94%

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	94.58%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.16%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.49%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.78%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.03%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.78%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.70%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.48%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.46%	100.00%

Plants that contains it

• Coptis omeiensis
• Umbellularia californica

Cross-Links

• PubChem: 92466631
• NPASS: NPC130820
• LOTUS: LTS0146190
• wikiData: Q105007637