Brevicolline

Details

• Internal ID: 512598fe-17bc-4d56-9538-c5ea88fd92d7
• Taxonomy: Alkaloids and derivatives > Harmala alkaloids
• IUPAC Name: 1-methyl-4-[(2S)-1-methylpyrrolidin-2-yl]-9H-pyrido[3,4-b]indole
• SMILES (Canonical): CC1=NC=C(C2=C1NC3=CC=CC=C32)C4CCCN4C
• SMILES (Isomeric): CC1=NC=C(C2=C1NC3=CC=CC=C32)[C@@H]4CCCN4C
• InChI: InChI=1S/C17H19N3/c1-11-17-16(12-6-3-4-7-14(12)19-17)13(10-18-11)15-8-5-9-20(15)2/h3-4,6-7,10,15,19H,5,8-9H2,1-2H3/t15-/m0/s1
• InChI Key: DIZAFWUMCZPYGF-HNNXBMFYSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₉N₃
• Molecular Weight: 265.35 g/mol
• Exact Mass: 265.157897619 g/mol
• Topological Polar Surface Area (TPSA): 31.90 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.79
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 20069-02-7
• 1-methyl-4-[(2S)-1-methylpyrrolidin-2-yl]-9H-pyrido[3,4-b]indole
• 1-methyl-4-((2S)-1-methylpyrrolidin-2-yl)-9H-pyrido(3,4-b)indole
• RefChem:907677
• 1-Methyl-4-((2S)-1-methyl-2-pyrrolidinyl)-9H-pyrido(3,4-b)indole
• C09083
• AC1NQYDZ
• SureCN13017534
• CHEBI:3174
• SCHEMBL13017534
• DTXSID10942088
• Q27105973
• 1-methyl-4-(1-methylpyrrolidin-2-yl)-9H-pyrido[3,4-b]indole

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9897	98.97%
Caco-2	+	0.6049	60.49%
Blood Brain Barrier	+	0.9500	95.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5008	50.08%
OATP2B1 inhibitior	-	0.8553	85.53%
OATP1B1 inhibitior	+	0.9135	91.35%
OATP1B3 inhibitior	+	0.9455	94.55%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	+	0.5500	55.00%
BSEP inhibitior	-	0.4805	48.05%
P-glycoprotein inhibitior	-	0.7947	79.47%
P-glycoprotein substrate	+	0.5183	51.83%
CYP3A4 substrate	+	0.6618	66.18%
CYP2C9 substrate	-	0.5733	57.33%
CYP2D6 substrate	+	0.6623	66.23%
CYP3A4 inhibition	+	0.6252	62.52%
CYP2C9 inhibition	-	0.8673	86.73%
CYP2C19 inhibition	-	0.8074	80.74%
CYP2D6 inhibition	-	0.6803	68.03%
CYP1A2 inhibition	-	0.5956	59.56%
CYP2C8 inhibition	-	0.6174	61.74%
CYP inhibitory promiscuity	-	0.5150	51.50%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7425	74.25%
Eye corrosion	-	0.9935	99.35%
Eye irritation	-	0.9981	99.81%
Skin irritation	-	0.5496	54.96%
Skin corrosion	-	0.8843	88.43%
Ames mutagenesis	+	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6964	69.64%
Micronuclear	-	0.5200	52.00%
Hepatotoxicity	+	0.5803	58.03%
skin sensitisation	-	0.9214	92.14%
Respiratory toxicity	+	0.9111	91.11%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.8899	88.99%
Acute Oral Toxicity (c)	II	0.6244	62.44%
Estrogen receptor binding	-	0.4784	47.84%
Androgen receptor binding	+	0.7460	74.60%
Thyroid receptor binding	+	0.6103	61.03%
Glucocorticoid receptor binding	+	0.6399	63.99%
Aromatase binding	-	0.6276	62.76%
PPAR gamma	-	0.5758	57.58%
Honey bee toxicity	-	0.9378	93.78%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	+	0.7900	79.00%
Fish aquatic toxicity	+	0.9035	90.35%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.01%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.03%	96.09%
CHEMBL5103	Q969S8	Histone deacetylase 10	93.89%	90.08%
CHEMBL2581	P07339	Cathepsin D	93.24%	98.95%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	92.48%	90.71%
CHEMBL5203	P33316	dUTP pyrophosphatase	92.34%	99.18%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.33%	85.14%
CHEMBL3310	Q96DB2	Histone deacetylase 11	92.14%	88.56%
CHEMBL3192	Q9BY41	Histone deacetylase 8	90.92%	93.99%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	89.42%	93.65%
CHEMBL3524	P56524	Histone deacetylase 4	89.18%	92.97%
CHEMBL228	P31645	Serotonin transporter	89.05%	95.51%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.82%	95.89%
CHEMBL240	Q12809	HERG	88.58%	89.76%
CHEMBL1951	P21397	Monoamine oxidase A	87.79%	91.49%
CHEMBL2094121	P14867	GABA-A receptor; alpha-1/beta-3/gamma-2	86.52%	95.50%
CHEMBL4302	P08183	P-glycoprotein 1	86.18%	92.98%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.43%	89.00%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	84.44%	98.46%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.26%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.65%	99.23%
CHEMBL2535	P11166	Glucose transporter	83.40%	98.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.40%	97.09%
CHEMBL5805	Q9NR97	Toll-like receptor 8	83.34%	96.25%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	83.20%	85.49%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	82.92%	92.67%
CHEMBL2693	Q9UIQ6	Cystinyl aminopeptidase	82.43%	97.64%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	82.31%	93.40%
CHEMBL1937	Q92769	Histone deacetylase 2	82.01%	94.75%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	81.39%	96.39%
CHEMBL264	Q9Y5N1	Histamine H3 receptor	81.06%	91.43%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	80.96%	98.33%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	80.61%	96.47%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	80.16%	97.50%

Plants that contains it

• Carex brevicollis

Cross-Links

• PubChem: 5281361
• LOTUS: LTS0255866
• wikiData: Q27105973