(4aR,5R)-5-hydroxy-7-(hydroxymethyl)-4,4a,5,6-tetrahydro-3H-cyclopenta[c]pyran-1-one

Details

• Internal ID: decebf0c-b84c-4158-909a-9739b1734741
• Taxonomy: Organoheterocyclic compounds > Lactones > Delta valerolactones
• IUPAC Name: (4aR,5R)-5-hydroxy-7-(hydroxymethyl)-4,4a,5,6-tetrahydro-3H-cyclopenta[c]pyran-1-one
• SMILES (Canonical): C1COC(=O)C2=C(CC(C21)O)CO
• SMILES (Isomeric): C1COC(=O)C2=C(C[C@H]([C@@H]21)O)CO
• InChI: InChI=1S/C9H12O4/c10-4-5-3-7(11)6-1-2-13-9(12)8(5)6/h6-7,10-11H,1-4H2/t6-,7+/m0/s1
• InChI Key: QISJSHBLMHINFW-NKWVEPMBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₂O₄
• Molecular Weight: 184.19 g/mol
• Exact Mass: 184.07355886 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): -0.40
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9479	94.79%
Caco-2	-	0.7103	71.03%
Blood Brain Barrier	-	0.5892	58.92%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7859	78.59%
OATP2B1 inhibitior	-	0.8452	84.52%
OATP1B1 inhibitior	+	0.9347	93.47%
OATP1B3 inhibitior	+	0.9581	95.81%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.7570	75.70%
BSEP inhibitior	-	0.9460	94.60%
P-glycoprotein inhibitior	-	0.9787	97.87%
P-glycoprotein substrate	-	0.9165	91.65%
CYP3A4 substrate	-	0.5593	55.93%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8489	84.89%
CYP3A4 inhibition	-	0.9275	92.75%
CYP2C9 inhibition	-	0.9416	94.16%
CYP2C19 inhibition	-	0.8140	81.40%
CYP2D6 inhibition	-	0.8530	85.30%
CYP1A2 inhibition	-	0.7526	75.26%
CYP2C8 inhibition	-	0.9458	94.58%
CYP inhibitory promiscuity	-	0.9283	92.83%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6980	69.80%
Eye corrosion	-	0.9574	95.74%
Eye irritation	+	0.7944	79.44%
Skin irritation	-	0.7881	78.81%
Skin corrosion	-	0.9578	95.78%
Ames mutagenesis	-	0.5170	51.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6247	62.47%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	+	0.5212	52.12%
skin sensitisation	-	0.8355	83.55%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.5797	57.97%
Acute Oral Toxicity (c)	III	0.5966	59.66%
Estrogen receptor binding	-	0.8873	88.73%
Androgen receptor binding	-	0.5635	56.35%
Thyroid receptor binding	-	0.7792	77.92%
Glucocorticoid receptor binding	-	0.6473	64.73%
Aromatase binding	-	0.8536	85.36%
PPAR gamma	-	0.6163	61.63%
Honey bee toxicity	-	0.9444	94.44%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	-	0.4939	49.39%

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	92.65%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.32%	97.09%
CHEMBL2581	P07339	Cathepsin D	90.28%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.32%	85.14%
CHEMBL226	P30542	Adenosine A1 receptor	86.21%	95.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.78%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.71%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.60%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.65%	95.89%

Plants that contains it

• Vitex cymosa
• Vitex rotundifolia

Cross-Links

• PubChem: 10607533
• LOTUS: LTS0093639
• wikiData: Q105221756