(4S,4aR,7aS)-4,7-bis(hydroxymethyl)-4,4a,5,7a-tetrahydro-1H-cyclopenta[c]pyran-3-one

Details

• Internal ID: 3037ac18-7d7b-4111-ba12-4aab5e524ef2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (4S,4aR,7aS)-4,7-bis(hydroxymethyl)-4,4a,5,7a-tetrahydro-1H-cyclopenta[c]pyran-3-one
• SMILES (Canonical): C1C=C(C2C1C(C(=O)OC2)CO)CO
• SMILES (Isomeric): C1C=C([C@@H]2[C@@H]1[C@H](C(=O)OC2)CO)CO
• InChI: InChI=1S/C10H14O4/c11-3-6-1-2-7-8(4-12)10(13)14-5-9(6)7/h1,7-9,11-12H,2-5H2/t7-,8+,9+/m0/s1
• InChI Key: RQRMWYOWQUEKAS-DJLDLDEBSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₄O₄
• Molecular Weight: 198.22 g/mol
• Exact Mass: 198.08920892 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -0.29
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8999	89.99%
Caco-2	-	0.7382	73.82%
Blood Brain Barrier	+	0.6178	61.78%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6014	60.14%
OATP2B1 inhibitior	-	0.8499	84.99%
OATP1B1 inhibitior	+	0.9391	93.91%
OATP1B3 inhibitior	+	0.9644	96.44%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9404	94.04%
P-glycoprotein inhibitior	-	0.9816	98.16%
P-glycoprotein substrate	-	0.8832	88.32%
CYP3A4 substrate	-	0.5940	59.40%
CYP2C9 substrate	-	0.6159	61.59%
CYP2D6 substrate	-	0.8130	81.30%
CYP3A4 inhibition	-	0.8617	86.17%
CYP2C9 inhibition	-	0.8809	88.09%
CYP2C19 inhibition	-	0.7718	77.18%
CYP2D6 inhibition	-	0.9037	90.37%
CYP1A2 inhibition	-	0.7228	72.28%
CYP2C8 inhibition	-	0.9496	94.96%
CYP inhibitory promiscuity	-	0.8259	82.59%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9413	94.13%
Carcinogenicity (trinary)	Non-required	0.6807	68.07%
Eye corrosion	-	0.9337	93.37%
Eye irritation	+	0.5786	57.86%
Skin irritation	-	0.6770	67.70%
Skin corrosion	-	0.9402	94.02%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7923	79.23%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	+	0.5408	54.08%
skin sensitisation	-	0.8286	82.86%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	-	0.5889	58.89%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.5845	58.45%
Acute Oral Toxicity (c)	III	0.4393	43.93%
Estrogen receptor binding	-	0.8454	84.54%
Androgen receptor binding	+	0.7105	71.05%
Thyroid receptor binding	-	0.8339	83.39%
Glucocorticoid receptor binding	-	0.6604	66.04%
Aromatase binding	-	0.8752	87.52%
PPAR gamma	-	0.7455	74.55%
Honey bee toxicity	-	0.8666	86.66%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9207	92.07%

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	94.14%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.88%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.43%	97.25%
CHEMBL2581	P07339	Cathepsin D	86.90%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.57%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.93%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	82.95%	83.82%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.89%	86.92%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.01%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.11%	94.45%

Plants that contains it

• Cymbaria mongolica
• Genipa americana

Cross-Links

• PubChem: 160701616
• LOTUS: LTS0174516
• wikiData: Q105243531