2-alpha-Hydroxynagilactone

Details

• Internal ID: 0d78835a-9e6b-4416-9da7-20b7ae03fd27
• Taxonomy: Organoheterocyclic compounds > Naphthopyrans
• IUPAC Name: (1S,6R,9R,12S,14R,16R)-14-hydroxy-1,12-dimethyl-6-propan-2-yl-5,10-dioxatetracyclo[7.6.1.02,7.012,16]hexadeca-2,7-diene-4,11-dione
• SMILES (Canonical): CC(C)C1C2=CC3C4C(C2=CC(=O)O1)(CC(CC4(C(=O)O3)C)O)C
• SMILES (Isomeric): CC(C)[C@@H]1C2=C[C@@H]3[C@@H]4[C@@](C2=CC(=O)O1)(C[C@H](C[C@@]4(C(=O)O3)C)O)C
• InChI: InChI=1S/C19H24O5/c1-9(2)15-11-5-13-16-18(3,12(11)6-14(21)24-15)7-10(20)8-19(16,4)17(22)23-13/h5-6,9-10,13,15-16,20H,7-8H2,1-4H3/t10-,13-,15-,16-,18-,19+/m1/s1
• InChI Key: KEXSMNABMQFSDY-DEIJXFBXSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₄O₅
• Molecular Weight: 332.40 g/mol
• Exact Mass: 332.16237386 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 2.14
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 2-alpha-hydroxynagilactone
• CHEMBL519703

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9895	98.95%
Caco-2	+	0.4885	48.85%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7988	79.88%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8846	88.46%
OATP1B3 inhibitior	+	0.9389	93.89%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.8653	86.53%
P-glycoprotein inhibitior	-	0.7396	73.96%
P-glycoprotein substrate	-	0.6172	61.72%
CYP3A4 substrate	+	0.5868	58.68%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8828	88.28%
CYP3A4 inhibition	-	0.6654	66.54%
CYP2C9 inhibition	-	0.8493	84.93%
CYP2C19 inhibition	-	0.9278	92.78%
CYP2D6 inhibition	-	0.9450	94.50%
CYP1A2 inhibition	-	0.9178	91.78%
CYP2C8 inhibition	-	0.9119	91.19%
CYP inhibitory promiscuity	-	0.9248	92.48%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Danger	0.4182	41.82%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9771	97.71%
Skin irritation	-	0.5349	53.49%
Skin corrosion	-	0.8945	89.45%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8642	86.42%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	+	0.6908	69.08%
skin sensitisation	-	0.6501	65.01%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.6479	64.79%
Acute Oral Toxicity (c)	III	0.5645	56.45%
Estrogen receptor binding	+	0.6126	61.26%
Androgen receptor binding	+	0.6205	62.05%
Thyroid receptor binding	-	0.5227	52.27%
Glucocorticoid receptor binding	+	0.6538	65.38%
Aromatase binding	-	0.6043	60.43%
PPAR gamma	+	0.5333	53.33%
Honey bee toxicity	-	0.8327	83.27%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9645	96.45%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.87%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.38%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.44%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.16%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.90%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.37%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.13%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.95%	99.23%
CHEMBL2581	P07339	Cathepsin D	81.75%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.54%	95.89%

Plants that contains it

• Ileostylus micranthus
• Nageia nagi
• Podocarpus macrophyllus

Cross-Links

• PubChem: 14507409
• LOTUS: LTS0099064
• wikiData: Q105140248