(Z)-5-[(1S,3aS,6R,6aS)-6-hydroxy-3-oxo-1,3a,4,5,6,6a-hexahydrocyclopenta[c]furan-1-yl]pent-4-enoic acid

Details

• Internal ID: dee73c23-fc10-4821-9f14-3a7753efd1a7
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Fatty acids and conjugates > Medium-chain fatty acids
• IUPAC Name: (Z)-5-[(1S,3aS,6R,6aS)-6-hydroxy-3-oxo-1,3a,4,5,6,6a-hexahydrocyclopenta[c]furan-1-yl]pent-4-enoic acid
• SMILES (Canonical): C1CC(C2C1C(=O)OC2C=CCCC(=O)O)O
• SMILES (Isomeric): C1C[C@H]([C@@H]2[C@H]1C(=O)O[C@H]2/C=C\CCC(=O)O)O
• InChI: InChI=1S/C12H16O5/c13-8-6-5-7-11(8)9(17-12(7)16)3-1-2-4-10(14)15/h1,3,7-9,11,13H,2,4-6H2,(H,14,15)/b3-1-/t7-,8+,9-,11-/m0/s1
• InChI Key: MBJGXBXSSPCMDR-XBCXFSRYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₆O₅
• Molecular Weight: 240.25 g/mol
• Exact Mass: 240.09977361 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): 0.72
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9377	93.77%
Caco-2	-	0.6089	60.89%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7027	70.27%
OATP2B1 inhibitior	-	0.8545	85.45%
OATP1B1 inhibitior	+	0.8619	86.19%
OATP1B3 inhibitior	+	0.9606	96.06%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9195	91.95%
P-glycoprotein inhibitior	-	0.9620	96.20%
P-glycoprotein substrate	-	0.9318	93.18%
CYP3A4 substrate	-	0.5355	53.55%
CYP2C9 substrate	-	0.8438	84.38%
CYP2D6 substrate	-	0.8348	83.48%
CYP3A4 inhibition	-	0.8551	85.51%
CYP2C9 inhibition	-	0.9579	95.79%
CYP2C19 inhibition	-	0.9373	93.73%
CYP2D6 inhibition	-	0.9498	94.98%
CYP1A2 inhibition	-	0.9010	90.10%
CYP2C8 inhibition	-	0.9196	91.96%
CYP inhibitory promiscuity	-	0.9773	97.73%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5311	53.11%
Eye corrosion	-	0.8150	81.50%
Eye irritation	-	0.7303	73.03%
Skin irritation	-	0.6554	65.54%
Skin corrosion	-	0.6669	66.69%
Ames mutagenesis	-	0.6570	65.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.8341	83.41%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	+	0.5399	53.99%
skin sensitisation	-	0.8795	87.95%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.7494	74.94%
Acute Oral Toxicity (c)	III	0.4480	44.80%
Estrogen receptor binding	-	0.5160	51.60%
Androgen receptor binding	-	0.7196	71.96%
Thyroid receptor binding	-	0.8242	82.42%
Glucocorticoid receptor binding	-	0.5772	57.72%
Aromatase binding	-	0.8070	80.70%
PPAR gamma	+	0.5367	53.67%
Honey bee toxicity	-	0.9394	93.94%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	-	0.6459	64.59%

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	92.71%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.36%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.10%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.53%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.12%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.05%	99.17%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.59%	93.00%
CHEMBL340	P08684	Cytochrome P450 3A4	80.77%	91.19%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 11172501
• LOTUS: LTS0171849
• wikiData: Q105160806