Tilivalline

Details

• Internal ID: 70580a8c-0e55-45e3-aabe-5610eda3c1c6
• Taxonomy: Organoheterocyclic compounds > Benzodiazepines > 1,4-benzodiazepines
• IUPAC Name: (6S,6aS)-4-hydroxy-6-(1H-indol-3-yl)-5,6,6a,7,8,9-hexahydropyrrolo[2,1-c][1,4]benzodiazepin-11-one
• SMILES (Canonical): C1CC2C(NC3=C(C=CC=C3O)C(=O)N2C1)C4=CNC5=CC=CC=C54
• SMILES (Isomeric): C1C[C@H]2[C@@H](NC3=C(C=CC=C3O)C(=O)N2C1)C4=CNC5=CC=CC=C54
• InChI: InChI=1S/C20H19N3O2/c24-17-9-3-6-13-19(17)22-18(16-8-4-10-23(16)20(13)25)14-11-21-15-7-2-1-5-12(14)15/h1-3,5-7,9,11,16,18,21-22,24H,4,8,10H2/t16-,18-/m0/s1
• InChI Key: AJZNARCWDDMOPL-WMZOPIPTSA-N
• Popularity: 14 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₉N₃O₂
• Molecular Weight: 333.40 g/mol
• Exact Mass: 333.147726857 g/mol
• Topological Polar Surface Area (TPSA): 68.40 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 3.64
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• Epitilivalline
• 80279-24-9
• (6S,6aS)-4-hydroxy-6-(1H-indol-3-yl)-5,6,6a,7,8,9-hexahydropyrrolo[2,1-c][1,4]benzodiazepin-11-one
• (11s,11as)-9-hydroxy-11-(1h-indol-3-yl)-1,2,3,10,11,11a-hexahydro-5h-pyrrolo[2,1-c][1,4]benzodiazepin-5-one
• CHEBI:156292
• DTXSID401001138
• (7S,8S)-11-hydroxy-8-(1H-indol-3-yl)-3,9-diazatricyclo[8.4.0.0(3,7)]tetradeca-1(10),11,13-trien-2-one
• 5H-Pyrrolo(2,1-c)(1,4)benzodiazepin-5-one, 1,2,3,10,11,11a-hexahydro-9-hydroxy-11(1H-indol-3-yl)-, (11S-cis)-
• 9-Hydroxy-11-(1H-indol-3-yl)-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9574	95.74%
Caco-2	+	0.6000	60.00%
Blood Brain Barrier	+	0.7917	79.17%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7948	79.48%
OATP2B1 inhibitior	-	0.7153	71.53%
OATP1B1 inhibitior	+	0.8854	88.54%
OATP1B3 inhibitior	+	0.9415	94.15%
MATE1 inhibitior	-	0.6200	62.00%
OCT2 inhibitior	-	0.6383	63.83%
BSEP inhibitior	-	0.5681	56.81%
P-glycoprotein inhibitior	-	0.7693	76.93%
P-glycoprotein substrate	-	0.5136	51.36%
CYP3A4 substrate	+	0.6508	65.08%
CYP2C9 substrate	+	0.8187	81.87%
CYP2D6 substrate	-	0.7614	76.14%
CYP3A4 inhibition	-	0.5653	56.53%
CYP2C9 inhibition	-	0.6059	60.59%
CYP2C19 inhibition	-	0.5237	52.37%
CYP2D6 inhibition	-	0.6306	63.06%
CYP1A2 inhibition	+	0.5306	53.06%
CYP2C8 inhibition	-	0.6698	66.98%
CYP inhibitory promiscuity	+	0.7865	78.65%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.7005	70.05%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9905	99.05%
Skin irritation	-	0.7915	79.15%
Skin corrosion	-	0.9429	94.29%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4585	45.85%
Micronuclear	+	0.8200	82.00%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.8853	88.53%
Respiratory toxicity	+	0.9111	91.11%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.6580	65.80%
Acute Oral Toxicity (c)	III	0.5548	55.48%
Estrogen receptor binding	+	0.5765	57.65%
Androgen receptor binding	+	0.6601	66.01%
Thyroid receptor binding	-	0.5512	55.12%
Glucocorticoid receptor binding	+	0.6979	69.79%
Aromatase binding	+	0.5861	58.61%
PPAR gamma	+	0.7866	78.66%
Honey bee toxicity	-	0.9137	91.37%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.7173	71.73%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.06%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.96%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	96.09%	91.49%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	95.85%	93.03%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	94.97%	99.23%
CHEMBL1937	Q92769	Histone deacetylase 2	93.86%	94.75%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	93.39%	92.67%
CHEMBL217	P14416	Dopamine D2 receptor	93.02%	95.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.27%	95.89%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.99%	91.11%
CHEMBL213	P08588	Beta-1 adrenergic receptor	91.77%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.24%	89.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	90.27%	82.69%
CHEMBL3310	Q96DB2	Histone deacetylase 11	90.18%	88.56%
CHEMBL5103	Q969S8	Histone deacetylase 10	89.71%	90.08%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.82%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.49%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.11%	96.09%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	88.00%	93.40%
CHEMBL2535	P11166	Glucose transporter	86.88%	98.75%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	86.76%	97.64%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	86.57%	83.00%
CHEMBL5805	Q9NR97	Toll-like receptor 8	85.52%	96.25%
CHEMBL3192	Q9BY41	Histone deacetylase 8	84.73%	93.99%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	83.29%	96.39%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	83.03%	90.71%
CHEMBL5203	P33316	dUTP pyrophosphatase	83.02%	99.18%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	82.74%	80.78%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.35%	100.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	81.71%	95.83%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	80.50%	83.10%
CHEMBL321	P14780	Matrix metalloproteinase 9	80.11%	92.12%
CHEMBL333	P08253	Matrix metalloproteinase-2	80.11%	96.31%
CHEMBL228	P31645	Serotonin transporter	80.10%	95.51%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 128363
• LOTUS: LTS0169746
• wikiData: Q82994959