14-Hydroxyhypocretenolide

Details

• Internal ID: 16eb0703-089a-4b15-b219-e4f9ea481bea
• Taxonomy: Organoheterocyclic compounds > Lactones > Delta valerolactones
• IUPAC Name: (1S,9R)-6-(hydroxymethyl)-2-methyl-10-methylidene-12-oxatricyclo[7.3.1.01,5]trideca-2,5-diene-4,11-dione
• SMILES (Canonical): CC1=CC(=O)C2=C(CCC3CC12OC(=O)C3=C)CO
• SMILES (Isomeric): CC1=CC(=O)C2=C(CC[C@@H]3C[C@]12OC(=O)C3=C)CO
• InChI: InChI=1S/C15H16O4/c1-8-5-12(17)13-11(7-16)4-3-10-6-15(8,13)19-14(18)9(10)2/h5,10,16H,2-4,6-7H2,1H3/t10-,15+/m1/s1
• InChI Key: SPZKJZJNPQNEKT-BMIGLBTASA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₄
• Molecular Weight: 260.28 g/mol
• Exact Mass: 260.10485899 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): 1.46
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 14-Hydroxyhypocretenolide
• CHEMBL365306

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9663	96.63%
Caco-2	+	0.6640	66.40%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8121	81.21%
OATP2B1 inhibitior	-	0.8584	85.84%
OATP1B1 inhibitior	+	0.9019	90.19%
OATP1B3 inhibitior	+	0.9489	94.89%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.5732	57.32%
BSEP inhibitior	-	0.8903	89.03%
P-glycoprotein inhibitior	-	0.9397	93.97%
P-glycoprotein substrate	-	0.8403	84.03%
CYP3A4 substrate	+	0.5958	59.58%
CYP2C9 substrate	-	0.8205	82.05%
CYP2D6 substrate	-	0.8931	89.31%
CYP3A4 inhibition	-	0.9072	90.72%
CYP2C9 inhibition	-	0.8781	87.81%
CYP2C19 inhibition	-	0.8778	87.78%
CYP2D6 inhibition	-	0.9355	93.55%
CYP1A2 inhibition	-	0.7268	72.68%
CYP2C8 inhibition	-	0.7459	74.59%
CYP inhibitory promiscuity	-	0.9503	95.03%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7028	70.28%
Eye corrosion	-	0.9777	97.77%
Eye irritation	+	0.7333	73.33%
Skin irritation	-	0.5993	59.93%
Skin corrosion	-	0.9274	92.74%
Ames mutagenesis	-	0.6470	64.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.6916	69.16%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	+	0.6033	60.33%
skin sensitisation	-	0.8423	84.23%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.4636	46.36%
Estrogen receptor binding	-	0.7181	71.81%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	-	0.6796	67.96%
Glucocorticoid receptor binding	+	0.5956	59.56%
Aromatase binding	-	0.7303	73.03%
PPAR gamma	-	0.6163	61.63%
Honey bee toxicity	-	0.9225	92.25%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9582	95.82%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	95.41%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.27%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.10%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.65%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.11%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	85.20%	95.93%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.09%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.42%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.24%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.00%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.75%	89.00%

Plants that contains it

• Crepis aurea
• Leontodon hispidus

Cross-Links

• PubChem: 15378302
• LOTUS: LTS0275205
• wikiData: Q105257697