(1S,2S,4R,6S,9S,11S)-2,11-dihydroxy-4-methyl-13-azatetracyclo[7.7.0.01,6.02,13]hexadec-14-en-8-one

Details

• Internal ID: 895d10f2-c8e3-40d4-8df3-bc8e3d309e75
• Taxonomy: Organoheterocyclic compounds > Azepanes
• IUPAC Name: (1S,2S,4R,6S,9S,11S)-2,11-dihydroxy-4-methyl-13-azatetracyclo[7.7.0.01,6.02,13]hexadec-14-en-8-one
• SMILES (Canonical): CC1CC2CC(=O)C3C24CC=CN(C4(C1)O)CC(C3)O
• SMILES (Isomeric): C[C@@H]1C[C@H]2CC(=O)[C@@H]3[C@]24CC=CN([C@@]4(C1)O)C[C@H](C3)O
• InChI: InChI=1S/C16H23NO3/c1-10-5-11-6-14(19)13-7-12(18)9-17-4-2-3-15(11,13)16(17,20)8-10/h2,4,10-13,18,20H,3,5-9H2,1H3/t10-,11+,12+,13-,15+,16+/m1/s1
• InChI Key: GQAHQMIJHHYCCJ-XDJSOMLNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₃NO₃
• Molecular Weight: 277.36 g/mol
• Exact Mass: 277.16779360 g/mol
• Topological Polar Surface Area (TPSA): 60.80 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.28
• 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	+	0.9810	98.10%
Caco-2	+	0.6570	65.70%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5584	55.84%
OATP2B1 inhibitior	-	0.8559	85.59%
OATP1B1 inhibitior	+	0.9335	93.35%
OATP1B3 inhibitior	+	0.9491	94.91%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8064	80.64%
BSEP inhibitior	+	0.6448	64.48%
P-glycoprotein inhibitior	-	0.9512	95.12%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.5926	59.26%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8002	80.02%
CYP3A4 inhibition	-	0.8513	85.13%
CYP2C9 inhibition	-	0.8157	81.57%
CYP2C19 inhibition	-	0.7411	74.11%
CYP2D6 inhibition	-	0.8703	87.03%
CYP1A2 inhibition	-	0.8753	87.53%
CYP2C8 inhibition	-	0.9291	92.91%
CYP inhibitory promiscuity	-	0.7918	79.18%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9613	96.13%
Carcinogenicity (trinary)	Non-required	0.5506	55.06%
Eye corrosion	-	0.9876	98.76%
Eye irritation	-	0.9503	95.03%
Skin irritation	-	0.7515	75.15%
Skin corrosion	-	0.9168	91.68%
Ames mutagenesis	-	0.7278	72.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.6807	68.07%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.8547	85.47%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.6063	60.63%
Acute Oral Toxicity (c)	III	0.6009	60.09%
Estrogen receptor binding	-	0.5071	50.71%
Androgen receptor binding	+	0.6894	68.94%
Thyroid receptor binding	-	0.4891	48.91%
Glucocorticoid receptor binding	+	0.5990	59.90%
Aromatase binding	-	0.6048	60.48%
PPAR gamma	-	0.6358	63.58%
Honey bee toxicity	-	0.8897	88.97%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.6400	64.00%
Fish aquatic toxicity	-	0.5067	50.67%

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	96.12%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.63%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.01%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.61%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.87%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.28%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.07%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	84.36%	90.17%
CHEMBL2581	P07339	Cathepsin D	84.01%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.14%	100.00%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	81.34%	94.78%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.27%	89.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.04%	90.71%

Plants that contains it

• Huperzia serrata

Cross-Links

• PubChem: 163104173
• LOTUS: LTS0007343
• wikiData: Q105015283