(4S,4aS,7aS)-4,7-bis(hydroxymethyl)-4-methyl-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-3-one

Details

• Internal ID: 25d91ff6-cd10-4f6c-9418-989ed6b2714c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (4S,4aS,7aS)-4,7-bis(hydroxymethyl)-4-methyl-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-3-one
• SMILES (Canonical): CC1(C2CC=C(C2COC1=O)CO)CO
• SMILES (Isomeric): C[C@]1([C@H]2CC=C([C@H]2COC1=O)CO)CO
• InChI: InChI=1S/C11H16O4/c1-11(6-13)9-3-2-7(4-12)8(9)5-15-10(11)14/h2,8-9,12-13H,3-6H2,1H3/t8-,9+,11-/m1/s1
• InChI Key: BTTOWNPBHGPOLE-WCABBAIRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₆O₄
• Molecular Weight: 212.24 g/mol
• Exact Mass: 212.10485899 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): 0.10
• 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	+	0.9342	93.42%
Caco-2	+	0.5321	53.21%
Blood Brain Barrier	+	0.6031	60.31%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5343	53.43%
OATP2B1 inhibitior	-	0.8472	84.72%
OATP1B1 inhibitior	+	0.9147	91.47%
OATP1B3 inhibitior	+	0.9527	95.27%
MATE1 inhibitior	-	0.9012	90.12%
OCT2 inhibitior	-	0.8817	88.17%
BSEP inhibitior	-	0.8923	89.23%
P-glycoprotein inhibitior	-	0.9842	98.42%
P-glycoprotein substrate	-	0.8862	88.62%
CYP3A4 substrate	+	0.5103	51.03%
CYP2C9 substrate	-	0.7907	79.07%
CYP2D6 substrate	-	0.8148	81.48%
CYP3A4 inhibition	-	0.8864	88.64%
CYP2C9 inhibition	-	0.8893	88.93%
CYP2C19 inhibition	-	0.8286	82.86%
CYP2D6 inhibition	-	0.9300	93.00%
CYP1A2 inhibition	-	0.6508	65.08%
CYP2C8 inhibition	-	0.9038	90.38%
CYP inhibitory promiscuity	-	0.8745	87.45%
UGT catelyzed	-	0.6638	66.38%
Carcinogenicity (binary)	-	0.9413	94.13%
Carcinogenicity (trinary)	Non-required	0.5969	59.69%
Eye corrosion	-	0.9765	97.65%
Eye irritation	-	0.6303	63.03%
Skin irritation	-	0.6290	62.90%
Skin corrosion	-	0.9403	94.03%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7605	76.05%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	+	0.5328	53.28%
skin sensitisation	-	0.8139	81.39%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	-	0.5556	55.56%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.4688	46.88%
Acute Oral Toxicity (c)	III	0.5291	52.91%
Estrogen receptor binding	-	0.7638	76.38%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.8161	81.61%
Glucocorticoid receptor binding	-	0.5786	57.86%
Aromatase binding	-	0.8033	80.33%
PPAR gamma	-	0.7462	74.62%
Honey bee toxicity	-	0.9223	92.23%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9829	98.29%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.17%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.78%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.28%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	88.29%	83.82%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.65%	97.09%
CHEMBL2581	P07339	Cathepsin D	87.57%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.30%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.22%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.35%	94.45%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.47%	96.77%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.50%	96.61%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.15%	89.00%

Plants that contains it

• Garcinia gummi-gutta
• Gardenia jasminoides

Cross-Links

• PubChem: 5317525
• NPASS: NPC290207