(1R,2R,5S,6S)-3-(3-methylbut-2-enyl)-7-oxabicyclo[4.1.0]hept-3-ene-2,5-diol

Details

• Internal ID: 0e0473db-2d06-4155-a38f-0680a90d2044
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Secondary alcohols
• IUPAC Name: (1R,2R,5S,6S)-3-(3-methylbut-2-enyl)-7-oxabicyclo[4.1.0]hept-3-ene-2,5-diol
• SMILES (Canonical): CC(=CCC1=CC(C2C(C1O)O2)O)C
• SMILES (Isomeric): CC(=CCC1=C[C@@H]([C@H]2[C@@H]([C@@H]1O)O2)O)C
• InChI: InChI=1S/C11H16O3/c1-6(2)3-4-7-5-8(12)10-11(14-10)9(7)13/h3,5,8-13H,4H2,1-2H3/t8-,9+,10-,11+/m0/s1
• InChI Key: XNQYNBDARWOHSB-ZRUFSTJUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₆O₃
• Molecular Weight: 196.24 g/mol
• Exact Mass: 196.109944368 g/mol
• Topological Polar Surface Area (TPSA): 53.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 0.77
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 31298-59-6

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9747	97.47%
Caco-2	-	0.7748	77.48%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.5906	59.06%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8833	88.33%
OATP1B3 inhibitior	+	0.9659	96.59%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9358	93.58%
P-glycoprotein inhibitior	-	0.9648	96.48%
P-glycoprotein substrate	-	0.9204	92.04%
CYP3A4 substrate	-	0.6433	64.33%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6878	68.78%
CYP3A4 inhibition	-	0.9059	90.59%
CYP2C9 inhibition	-	0.6747	67.47%
CYP2C19 inhibition	-	0.5661	56.61%
CYP2D6 inhibition	-	0.8386	83.86%
CYP1A2 inhibition	-	0.7776	77.76%
CYP2C8 inhibition	-	0.9548	95.48%
CYP inhibitory promiscuity	-	0.5564	55.64%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.5996	59.96%
Eye corrosion	-	0.9495	94.95%
Eye irritation	-	0.7919	79.19%
Skin irritation	-	0.5642	56.42%
Skin corrosion	-	0.8283	82.83%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8036	80.36%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	+	0.6375	63.75%
skin sensitisation	-	0.5450	54.50%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.4811	48.11%
Acute Oral Toxicity (c)	III	0.4886	48.86%
Estrogen receptor binding	-	0.8710	87.10%
Androgen receptor binding	-	0.8408	84.08%
Thyroid receptor binding	-	0.7078	70.78%
Glucocorticoid receptor binding	-	0.7638	76.38%
Aromatase binding	-	0.9292	92.92%
PPAR gamma	+	0.5282	52.82%
Honey bee toxicity	-	0.8957	89.57%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.8683	86.83%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3401	O75469	Pregnane X receptor	91.74%	94.73%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.86%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.13%	96.09%

Plants that contains it

• Duranta erecta
• Verbena officinalis

Cross-Links

• PubChem: 101967074
• NPASS: NPC46042