(5R,7S)-5,7-dihydroxy-7-methyl-1,4,4a,5,6,7a-hexahydrocyclopenta[c]pyran-3-one

Details

• Internal ID: 7103631d-0a34-4244-b7a3-2a25fa03c5f8
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (5R,7S)-5,7-dihydroxy-7-methyl-1,4,4a,5,6,7a-hexahydrocyclopenta[c]pyran-3-one
• SMILES (Canonical): CC1(CC(C2C1COC(=O)C2)O)O
• SMILES (Isomeric): C[C@@]1(C[C@H](C2C1COC(=O)C2)O)O
• InChI: InChI=1S/C9H14O4/c1-9(12)3-7(10)5-2-8(11)13-4-6(5)9/h5-7,10,12H,2-4H2,1H3/t5?,6?,7-,9+/m1/s1
• InChI Key: LKZXAOPEOQRJLJ-URUNJKECSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₄O₄
• Molecular Weight: 186.20 g/mol
• Exact Mass: 186.08920892 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -0.32
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9322	93.22%
Caco-2	-	0.5764	57.64%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5597	55.97%
OATP2B1 inhibitior	-	0.8493	84.93%
OATP1B1 inhibitior	+	0.9277	92.77%
OATP1B3 inhibitior	+	0.9447	94.47%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9271	92.71%
P-glycoprotein inhibitior	-	0.9672	96.72%
P-glycoprotein substrate	-	0.7698	76.98%
CYP3A4 substrate	+	0.5189	51.89%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8338	83.38%
CYP3A4 inhibition	-	0.9126	91.26%
CYP2C9 inhibition	-	0.9238	92.38%
CYP2C19 inhibition	-	0.9212	92.12%
CYP2D6 inhibition	-	0.9552	95.52%
CYP1A2 inhibition	-	0.7293	72.93%
CYP2C8 inhibition	-	0.9728	97.28%
CYP inhibitory promiscuity	-	0.9863	98.63%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6469	64.69%
Eye corrosion	-	0.9837	98.37%
Eye irritation	-	0.6274	62.74%
Skin irritation	-	0.7004	70.04%
Skin corrosion	-	0.9315	93.15%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7249	72.49%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.5964	59.64%
skin sensitisation	-	0.8940	89.40%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.6588	65.88%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	+	0.5060	50.60%
Acute Oral Toxicity (c)	III	0.5496	54.96%
Estrogen receptor binding	-	0.6304	63.04%
Androgen receptor binding	-	0.7328	73.28%
Thyroid receptor binding	-	0.8185	81.85%
Glucocorticoid receptor binding	-	0.7110	71.10%
Aromatase binding	-	0.8912	89.12%
PPAR gamma	-	0.8274	82.74%
Honey bee toxicity	-	0.8060	80.60%
Biodegradation	+	0.5500	55.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.7572	75.72%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.97%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.22%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.43%	91.11%
CHEMBL2581	P07339	Cathepsin D	91.36%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	91.27%	95.93%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.92%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.72%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.93%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.71%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.22%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.66%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.62%	94.45%

Plants that contains it

• Rehmannia glutinosa

Cross-Links

• PubChem: 5318708
• NPASS: NPC123400