Bicyclo[3.2.0]heptane-2,6-diol, 5-(2-hydroxyethyl)-3,3-dimethyl-6-vinyl-, (Z)-

Details

• Internal ID: 79873b5e-b670-49bd-b997-9405ed20b330
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Monoterpenoids > Bicyclic monoterpenoids
• IUPAC Name: 6-ethenyl-5-(2-hydroxyethyl)-3,3-dimethylbicyclo[3.2.0]heptane-2,6-diol
• SMILES (Canonical): CC1(CC2(C(C1O)CC2(C=C)O)CCO)C
• SMILES (Isomeric): CC1(CC2(C(C1O)CC2(C=C)O)CCO)C
• InChI: InChI=1S/C13H22O3/c1-4-13(16)7-9-10(15)11(2,3)8-12(9,13)5-6-14/h4,9-10,14-16H,1,5-8H2,2-3H3
• InChI Key: CBHVRILJVSEUEF-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₂₂O₃
• Molecular Weight: 226.31 g/mol
• Exact Mass: 226.15689456 g/mol
• Topological Polar Surface Area (TPSA): 60.70 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.08
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• Bicyclo[3.2.0]heptane-2,6-diol, 5-(2-hydroxyethyl)-3,3-dimethyl-6-vinyl-, (Z)-
• 5-(2-Hydroxyethyl)-3,3-dimethyl-6-vinylbicyclo[3.2.0]heptane-2,6-diol #

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9769	97.69%
Caco-2	+	0.5370	53.70%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5243	52.43%
OATP2B1 inhibitior	-	0.8439	84.39%
OATP1B1 inhibitior	+	0.9084	90.84%
OATP1B3 inhibitior	+	0.9499	94.99%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7083	70.83%
BSEP inhibitior	-	0.9295	92.95%
P-glycoprotein inhibitior	-	0.9641	96.41%
P-glycoprotein substrate	-	0.8661	86.61%
CYP3A4 substrate	+	0.5286	52.86%
CYP2C9 substrate	-	0.7574	75.74%
CYP2D6 substrate	-	0.7625	76.25%
CYP3A4 inhibition	-	0.8109	81.09%
CYP2C9 inhibition	-	0.8243	82.43%
CYP2C19 inhibition	-	0.8355	83.55%
CYP2D6 inhibition	-	0.9239	92.39%
CYP1A2 inhibition	-	0.7916	79.16%
CYP2C8 inhibition	-	0.8306	83.06%
CYP inhibitory promiscuity	-	0.9259	92.59%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.6594	65.94%
Eye corrosion	-	0.9723	97.23%
Eye irritation	-	0.6255	62.55%
Skin irritation	-	0.7000	70.00%
Skin corrosion	-	0.9414	94.14%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5198	51.98%
Micronuclear	-	0.9600	96.00%
Hepatotoxicity	-	0.6558	65.58%
skin sensitisation	-	0.6443	64.43%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.4641	46.41%
Acute Oral Toxicity (c)	III	0.7220	72.20%
Estrogen receptor binding	-	0.5422	54.22%
Androgen receptor binding	+	0.5616	56.16%
Thyroid receptor binding	-	0.5535	55.35%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.6379	63.79%
PPAR gamma	-	0.7355	73.55%
Honey bee toxicity	-	0.8520	85.20%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.9004	90.04%

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%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.44%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	88.83%	95.93%
CHEMBL221	P23219	Cyclooxygenase-1	88.17%	90.17%
CHEMBL4040	P28482	MAP kinase ERK2	87.83%	83.82%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.34%	97.09%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	82.46%	83.57%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.25%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.20%	100.00%
CHEMBL1977	P11473	Vitamin D receptor	80.63%	99.43%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.51%	95.50%
CHEMBL218	P21554	Cannabinoid CB1 receptor	80.35%	96.61%

Plants that contains it

• Artemisia annua
• Artemisia carvifolia

Cross-Links

• PubChem: 587017
• NPASS: NPC31396