(7E)-3,10-dihydroxy-14H-benzo[e][2]benzazecin-13-one

Details

• Internal ID: 353b5d55-65a6-446e-91f8-a4071c26cb2e
• Taxonomy: Alkaloids and derivatives > Protopine alkaloids
• IUPAC Name: (7E)-3,10-dihydroxy-14H-benzo[e][2]benzazecin-13-one
• SMILES (Canonical): C1C2=C(C=C(C=C2)O)C=NC=CC3=C(C1=O)C=CC(=C3)O
• SMILES (Isomeric): C1C2=C(C=C(C=C2)O)C=N/C=C/C3=C(C1=O)C=CC(=C3)O
• InChI: InChI=1S/C17H13NO3/c19-14-2-1-11-9-17(21)16-4-3-15(20)7-12(16)5-6-18-10-13(11)8-14/h1-8,10,19-20H,9H2/b6-5+,18-10?
• InChI Key: PHTNPJUNCWXYDO-LZGHNAOBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₃NO₃
• Molecular Weight: 279.29 g/mol
• Exact Mass: 279.08954328 g/mol
• Topological Polar Surface Area (TPSA): 69.90 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.93
• 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	+	0.9974	99.74%
Caco-2	+	0.8295	82.95%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6768	67.68%
OATP2B1 inhibitior	-	0.5788	57.88%
OATP1B1 inhibitior	+	0.8758	87.58%
OATP1B3 inhibitior	+	0.9437	94.37%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6675	66.75%
P-glycoprotein inhibitior	-	0.9129	91.29%
P-glycoprotein substrate	-	0.7097	70.97%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7859	78.59%
CYP3A4 inhibition	+	0.6768	67.68%
CYP2C9 inhibition	-	0.5802	58.02%
CYP2C19 inhibition	+	0.5412	54.12%
CYP2D6 inhibition	-	0.7478	74.78%
CYP1A2 inhibition	+	0.8459	84.59%
CYP2C8 inhibition	-	0.7835	78.35%
CYP inhibitory promiscuity	+	0.7546	75.46%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7753	77.53%
Carcinogenicity (trinary)	Non-required	0.4709	47.09%
Eye corrosion	-	0.9859	98.59%
Eye irritation	+	0.7038	70.38%
Skin irritation	-	0.6022	60.22%
Skin corrosion	-	0.9752	97.52%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7051	70.51%
Micronuclear	+	0.6300	63.00%
Hepatotoxicity	+	0.6875	68.75%
skin sensitisation	-	0.5935	59.35%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	-	0.5571	55.71%
Nephrotoxicity	+	0.4580	45.80%
Acute Oral Toxicity (c)	III	0.4712	47.12%
Estrogen receptor binding	+	0.8813	88.13%
Androgen receptor binding	+	0.6623	66.23%
Thyroid receptor binding	+	0.6789	67.89%
Glucocorticoid receptor binding	+	0.9193	91.93%
Aromatase binding	+	0.8778	87.78%
PPAR gamma	+	0.8823	88.23%
Honey bee toxicity	-	0.9090	90.90%
Biodegradation	-	1.0000	100.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.7978	79.78%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	98.07%	91.49%
CHEMBL2581	P07339	Cathepsin D	94.44%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.40%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.67%	95.56%
CHEMBL4208	P20618	Proteasome component C5	85.15%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.97%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.91%	99.15%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.78%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.40%	86.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.69%	96.21%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	81.44%	93.10%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.39%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	81.34%	83.82%
CHEMBL2535	P11166	Glucose transporter	81.31%	98.75%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.16%	85.14%

Plants that contains it

• Aristolochia constricta

Cross-Links

• PubChem: 102091737
• LOTUS: LTS0143804
• wikiData: Q105209205