(1S,3E,4S,5S,6S)-4,5-dihydroxy-3-(3-methylbut-2-enylidene)-7-oxabicyclo[4.1.0]heptan-2-one

Details

• Internal ID: 06642dab-c67f-40f3-b13e-fb6e8a4623b2
• Taxonomy: Organoheterocyclic compounds > Oxepanes
• IUPAC Name: (1S,3E,4S,5S,6S)-4,5-dihydroxy-3-(3-methylbut-2-enylidene)-7-oxabicyclo[4.1.0]heptan-2-one
• SMILES (Canonical): CC(=CC=C1C(C(C2C(C1=O)O2)O)O)C
• SMILES (Isomeric): CC(=C/C=C/1\[C@@H]([C@@H]([C@H]2[C@@H](C1=O)O2)O)O)C
• InChI: InChI=1S/C11H14O4/c1-5(2)3-4-6-7(12)9(14)11-10(15-11)8(6)13/h3-4,7,9-12,14H,1-2H3/b6-4+/t7-,9-,10+,11-/m0/s1
• InChI Key: FZFOYVPJRYSIMY-UDOVHQHDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₄O₄
• Molecular Weight: 210.23 g/mol
• Exact Mass: 210.08920892 g/mol
• Topological Polar Surface Area (TPSA): 70.10 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): -0.05
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 31298-56-3

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9558	95.58%
Caco-2	-	0.6357	63.57%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6748	67.48%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8936	89.36%
OATP1B3 inhibitior	+	0.9734	97.34%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9181	91.81%
P-glycoprotein inhibitior	-	0.9359	93.59%
P-glycoprotein substrate	-	0.9602	96.02%
CYP3A4 substrate	-	0.5243	52.43%
CYP2C9 substrate	-	0.7917	79.17%
CYP2D6 substrate	-	0.8640	86.40%
CYP3A4 inhibition	-	0.8891	88.91%
CYP2C9 inhibition	-	0.8107	81.07%
CYP2C19 inhibition	-	0.6080	60.80%
CYP2D6 inhibition	-	0.9038	90.38%
CYP1A2 inhibition	-	0.8401	84.01%
CYP2C8 inhibition	-	0.9609	96.09%
CYP inhibitory promiscuity	-	0.8107	81.07%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.5889	58.89%
Eye corrosion	-	0.9491	94.91%
Eye irritation	-	0.6654	66.54%
Skin irritation	-	0.5292	52.92%
Skin corrosion	-	0.8781	87.81%
Ames mutagenesis	-	0.5364	53.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.8646	86.46%
Micronuclear	+	0.6500	65.00%
Hepatotoxicity	+	0.5802	58.02%
skin sensitisation	-	0.5928	59.28%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	+	0.7574	75.74%
Acute Oral Toxicity (c)	III	0.4587	45.87%
Estrogen receptor binding	-	0.5638	56.38%
Androgen receptor binding	-	0.7786	77.86%
Thyroid receptor binding	-	0.6912	69.12%
Glucocorticoid receptor binding	-	0.8140	81.40%
Aromatase binding	-	0.9164	91.64%
PPAR gamma	-	0.6788	67.88%
Honey bee toxicity	-	0.8654	86.54%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.8506	85.06%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.85%	91.11%
CHEMBL2581	P07339	Cathepsin D	90.68%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	89.33%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.62%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.46%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.61%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.75%	99.23%

Plants that contains it

• Duranta erecta
• Verbena officinalis

Cross-Links

• PubChem: 101306865
• NPASS: NPC128124