(1aS,7aR)-3,6-dihydroxy-1a-(3-methylbut-2-enyl)-7aH-naphtho[2,3-b]oxirene-2,7-dione

Details

• Internal ID: 73809458-e440-4b6b-9fda-7b2f01224607
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Quinone and hydroquinone lipids > Vitamin K compounds
• IUPAC Name: (1aS,7aR)-3,6-dihydroxy-1a-(3-methylbut-2-enyl)-7aH-naphtho[2,3-b]oxirene-2,7-dione
• SMILES (Canonical): CC(=CCC12C(O1)C(=O)C3=C(C=CC(=C3C2=O)O)O)C
• SMILES (Isomeric): CC(=CC[C@@]12[C@@H](O1)C(=O)C3=C(C=CC(=C3C2=O)O)O)C
• InChI: InChI=1S/C15H14O5/c1-7(2)5-6-15-13(19)11-9(17)4-3-8(16)10(11)12(18)14(15)20-15/h3-5,14,16-17H,6H2,1-2H3/t14-,15+/m0/s1
• InChI Key: TWESJUCJKWFWQV-LSDHHAIUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₄O₅
• Molecular Weight: 274.27 g/mol
• Exact Mass: 274.08412354 g/mol
• Topological Polar Surface Area (TPSA): 87.10 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 1.97
• H-Bond Acceptor: 5
• 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	+	0.9929	99.29%
Caco-2	+	0.6879	68.79%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6913	69.13%
OATP2B1 inhibitior	-	0.7193	71.93%
OATP1B1 inhibitior	+	0.9188	91.88%
OATP1B3 inhibitior	+	0.9609	96.09%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.8696	86.96%
P-glycoprotein inhibitior	-	0.9295	92.95%
P-glycoprotein substrate	-	0.9312	93.12%
CYP3A4 substrate	-	0.5372	53.72%
CYP2C9 substrate	-	0.6148	61.48%
CYP2D6 substrate	-	0.8335	83.35%
CYP3A4 inhibition	-	0.8694	86.94%
CYP2C9 inhibition	+	0.6016	60.16%
CYP2C19 inhibition	+	0.5705	57.05%
CYP2D6 inhibition	-	0.7432	74.32%
CYP1A2 inhibition	-	0.5858	58.58%
CYP2C8 inhibition	-	0.8955	89.55%
CYP inhibitory promiscuity	+	0.5938	59.38%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9418	94.18%
Carcinogenicity (trinary)	Non-required	0.6199	61.99%
Eye corrosion	-	0.9867	98.67%
Eye irritation	+	0.5849	58.49%
Skin irritation	-	0.6484	64.84%
Skin corrosion	-	0.8805	88.05%
Ames mutagenesis	+	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6862	68.62%
Micronuclear	-	0.5041	50.41%
Hepatotoxicity	+	0.6228	62.28%
skin sensitisation	-	0.5360	53.60%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.7888	78.88%
Acute Oral Toxicity (c)	III	0.5232	52.32%
Estrogen receptor binding	+	0.6128	61.28%
Androgen receptor binding	+	0.6422	64.22%
Thyroid receptor binding	+	0.5237	52.37%
Glucocorticoid receptor binding	+	0.7488	74.88%
Aromatase binding	-	0.6492	64.92%
PPAR gamma	+	0.6476	64.76%
Honey bee toxicity	-	0.9230	92.30%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9878	98.78%

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	98.33%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	94.45%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.28%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	93.03%	91.49%
CHEMBL2581	P07339	Cathepsin D	92.63%	98.95%
CHEMBL3038469	P24941	CDK2/Cyclin A	88.14%	91.38%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.53%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.67%	89.00%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	84.55%	83.10%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.17%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.56%	86.33%

Plants that contains it

• Pisonia aculeata
• Sesamum indicum

Cross-Links

• PubChem: 21591349
• LOTUS: LTS0101992
• wikiData: Q104976826