(8R,19R)-8-hydroxy-1,11-diazapentacyclo[9.7.1.02,7.08,19.012,17]nonadeca-2,4,6,12,14,16-hexaene-10,18-dione

Details

• Internal ID: 54e762f1-9532-4cc8-bbbe-2b250dba0ea0
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Pyrroloindoles
• IUPAC Name: (8R,19R)-8-hydroxy-1,11-diazapentacyclo[9.7.1.02,7.08,19.012,17]nonadeca-2,4,6,12,14,16-hexaene-10,18-dione
• SMILES (Canonical): C1C(=O)N2C3C1(C4=CC=CC=C4N3C(=O)C5=CC=CC=C52)O
• SMILES (Isomeric): C1C(=O)N2[C@H]3[C@@]1(C4=CC=CC=C4N3C(=O)C5=CC=CC=C52)O
• InChI: InChI=1S/C17H12N2O3/c20-14-9-17(22)11-6-2-4-8-13(11)19-15(21)10-5-1-3-7-12(10)18(14)16(17)19/h1-8,16,22H,9H2/t16-,17-/m1/s1
• InChI Key: DMWBWCODLSCGLM-IAGOWNOFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₂N₂O₃
• Molecular Weight: 292.29 g/mol
• Exact Mass: 292.08479225 g/mol
• Topological Polar Surface Area (TPSA): 60.80 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.61
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• (5aR)-6-Hydroxy-5,6beta-ethano-5,5aalpha,6,12-tetrahydroindolo[2,1-b]quinazoline-12,14-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9941	99.41%
Caco-2	+	0.7410	74.10%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7128	71.28%
OATP2B1 inhibitior	-	0.8607	86.07%
OATP1B1 inhibitior	+	0.9501	95.01%
OATP1B3 inhibitior	+	0.9478	94.78%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8566	85.66%
BSEP inhibitior	+	0.6534	65.34%
P-glycoprotein inhibitior	-	0.8916	89.16%
P-glycoprotein substrate	-	0.8763	87.63%
CYP3A4 substrate	+	0.5108	51.08%
CYP2C9 substrate	-	0.8067	80.67%
CYP2D6 substrate	-	0.8210	82.10%
CYP3A4 inhibition	-	0.9106	91.06%
CYP2C9 inhibition	-	0.5771	57.71%
CYP2C19 inhibition	-	0.6615	66.15%
CYP2D6 inhibition	-	0.8344	83.44%
CYP1A2 inhibition	-	0.7055	70.55%
CYP2C8 inhibition	-	0.9544	95.44%
CYP inhibitory promiscuity	-	0.8922	89.22%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8200	82.00%
Carcinogenicity (trinary)	Non-required	0.5571	55.71%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.8715	87.15%
Skin irritation	-	0.8281	82.81%
Skin corrosion	-	0.9522	95.22%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.9373	93.73%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	+	0.5875	58.75%
skin sensitisation	-	0.8988	89.88%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.7973	79.73%
Acute Oral Toxicity (c)	III	0.4869	48.69%
Estrogen receptor binding	+	0.6420	64.20%
Androgen receptor binding	+	0.6917	69.17%
Thyroid receptor binding	-	0.5379	53.79%
Glucocorticoid receptor binding	+	0.7513	75.13%
Aromatase binding	+	0.6013	60.13%
PPAR gamma	+	0.8989	89.89%
Honey bee toxicity	-	0.9290	92.90%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	-	0.7817	78.17%

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	93.37%	91.11%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	93.09%	82.69%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.79%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.59%	96.09%
CHEMBL2581	P07339	Cathepsin D	87.31%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	85.49%	90.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.40%	99.23%
CHEMBL4208	P20618	Proteasome component C5	83.73%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.72%	86.33%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	81.63%	96.67%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.27%	97.09%

Plants that contains it

• Isatis tinctoria

Cross-Links

• PubChem: 60156156
• NPASS: NPC171934