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1-carbomethoxy-beta-carboline

Family: Plantae - Apocynaceae
Kingdom: Plantae
Class: Alkaloid
- Subclass: Indole Alkaloid

Canonical Smiles	COC(=O)c1nccc2c1[nH]c1c2cccc1
InChI	InChI=1S/C13H10N2O2/c1-17-13(16)12-11-9(6-7-14-12)8-4-2-3-5-10(8)15-11/h2-7,15H,1H3
InChIKey	FRNCTTUBAHKEBZ-UHFFFAOYSA-N
Formula	C₁₃H₁₀N₂O₂
HBA	3
HBD	1
MW	226.24
Rotatable Bonds	1
TPSA	54.98
LogP	2.5
Number Rings	3
Number Aromatic Rings	3
Heavy Atom Count	17
Formal Charge	0
Fraction CSP3	0.08
Exact Mass	226.07
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Pleiocarpa pycnantha	Apocynaceae	Plantae	1220085

Showing of synonyms

Ndongo JT, Mbing JN, et al. (2018). Carbazole-, aspidofractinine-, and aspidocarpamine-type alkaloids from Pleiocarpa pycnantha.. Journal of natural products,2018, 81(5), 1193-1202. [View] [PubMed]

Pubchem: 597266

Cas: 3464-66-2

Zinc: ZINC000001095283

Nmrshiftdb2: 60022843

Chembl: CHEMBL2229719

Comptox: DTXSID70188208

No compound-protein relationship available.

SMILES: c1cncc(c1c23)[nH]c2cccc3

Level: 0

Mol. Weight: 226.24 g/mol

Cancer cell growth inhibitory

Absorption

Caco-2 (logPapp): -4.53
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.270
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.48

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.420
Plasma Protein Binding: 48.15
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 5.410
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: 0.610
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.280
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 3.930
Micronucleos: Toxic
NR-AhR: Toxic
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 3.270
Rat (Acute): 2.090
Rat (Chronic Oral): 2.030
Fathead Minnow: 4.300
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Toxic

General Properties

Boiling Point: 369.600
Hydration Free Energy: -11.050
Log(D) at pH=7.4: 2.770
Log(P): 2.3
Log S: -4.18
Log(Vapor Pressure): -6.82
Melting Point: 223.27
pKa Acid: 9.94
pKa Basic: 5.98

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9824
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9728
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9674
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9523
Caspase-7	P55210	CASP7_HUMAN	Homo sapiens	3	0.9381
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.9313
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9294
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9231
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.9091
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.9061
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.9060
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.9054
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.9042
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.9022
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.9003
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8871
Terminal oxygenase component of carbazole	Q84II6	Q84II6_JANS3	Janthinobacterium sp	3	0.8842
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.8668
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.8582
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8510
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8452
Cytochrome P450 2C5	P00179	CP2C5_RABIT	Oryctolagus cuniculus	3	0.8441
Matrix metalloproteinase-9	P14780	MMP9_HUMAN	Homo sapiens	3	0.8415
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8408
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8312
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8296
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.8276
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	3	0.8155
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8131
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.8079
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.8076
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8069
Casein kinase II subunit alpha'	P19784	CSK22_HUMAN	Homo sapiens	3	0.8057
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7999
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7999
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7996
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7995
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7991
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7991
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7989
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7973
Aldo-keto reductase family 1 member B10	O60218	AK1BA_HUMAN	Homo sapiens	3	0.7968
Focal adhesion kinase 1	Q00944	FAK1_CHICK	Gallus gallus	3	0.7967
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7949
NAD(P)H dehydrogenase [quinone] 1	P15559	NQO1_HUMAN	Homo sapiens	3	0.7946
Cell division cycle 7-related protein kinase	O00311	CDC7_HUMAN	Homo sapiens	3	0.7934
Aldehyde dehydrogenase, dimeric NADP-preferring	P30838	AL3A1_HUMAN	Homo sapiens	3	0.7934
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7927
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7911
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7892
Tubulin alpha chain	D0VWZ0	D0VWZ0_SHEEP	Ovis aries	3	0.7884
Acetylcholine-binding protein	P58154	ACHP_LYMST	Lymnaea stagnalis	3	0.7878
Putative ketoacyl reductase	P16544	ACT3_STRCO	Streptomyces coelicolor / M145)	3	0.7869
Achbp	I6L8L2	I6L8L2_CAPTE	Capitella teleta	3	0.7849
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7831
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.7808
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.7781
Bifunctional dihydrofolate reductase-thymidylate synthase	O02604	DRTS_PLAVI	Plasmodium vivax	2	0.7778
Alcohol dehydrogenase E chain	P00327	ADH1E_HORSE	Equus caballus	4	0.7749
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7743
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	2	0.7735
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	3	0.7713
Renin	P00797	RENI_HUMAN	Homo sapiens	3	0.7699
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7692
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7674
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7673
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.7671
Sulfotransferase 1A1	P50225	ST1A1_HUMAN	Homo sapiens	2	0.7669
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7666
cGMP-dependent protein kinase, putative	A5K0N4	A5K0N4_PLAVS	Plasmodium vivax	3	0.7650
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7642
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.7606
Beta sliding clamp	P0A988	DPO3B_ECOLI	Escherichia coli	2	0.7593
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7589
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7586
Nucleoprotein	P33469	NCAP_CVHOC	Human coronavirus OC43	3	0.7577
Enoyl-ACP reductase	Q9BJJ9	Q9BJJ9_PLAFA	Plasmodium falciparum	3	0.7572
Abscisic acid receptor PYL9	Q84MC7	PYL9_ARATH	Arabidopsis thaliana	3	0.7547
Fatty acid-binding protein 10-A, liver basic	Q9I8L5	FA10A_DANRE	Danio rerio	2	0.7525
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	2	0.7522
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	3	0.7517
Alcohol dehydrogenase 1C	P00326	ADH1G_HUMAN	Homo sapiens	2	0.7512
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7468
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7464
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7461
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	2	0.7459
Catalase-peroxidase 2	O59651	KATG2_HALMA	Haloarcula marismortui	2	0.7451
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7449
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7445
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7440
Cytochrome P450 2A6	P11509	CP2A6_HUMAN	Homo sapiens	3	0.7439
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7432
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7426
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7387
Dihydroorotate dehydrogenase (quinone), mitochondrial	Q08210	PYRD_PLAF7	Plasmodium falciparum	3	0.7355
Fatty acid-binding protein, adipocyte	P04117	FABP4_MOUSE	Mus musculus	2	0.7355
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	3	0.7341
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7340
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7339
Aromatase	P11511	CP19A_HUMAN	Homo sapiens	2	0.7327
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7304
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7288
Glutathione S-transferase A1	P08263	GSTA1_HUMAN	Homo sapiens	2	0.7288
Alcohol dehydrogenase E chain	P00327	ADH1E_HORSE	Equus caballus	3	0.7286
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7285
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7283
ADP-ribosylation factor 1	P84080	ARF1_BOVIN	Bos taurus	3	0.7278
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7258
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7255
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7240
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7233
Aldo-keto reductase family 1 member B1	P80276	ALDR_PIG	Sus scrofa	3	0.7232
Alcohol dehydrogenase E chain	P00327	ADH1E_HORSE	Equus caballus	3	0.7231
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7231
Dihydroorotate dehydrogenase (quinone), mitochondrial	Q02127	PYRD_HUMAN	Homo sapiens	3	0.7230
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7218
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7217
Hematopoietic prostaglandin D synthase	O60760	HPGDS_HUMAN	Homo sapiens	2	0.7216
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	2	0.7201
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7190
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7178
UDP-glycosyltransferase 72B1	Q9M156	U72B1_ARATH	Arabidopsis thaliana	3	0.7155
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7153
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase	Q3JRA0	ISPF_BURP1	Burkholderia pseudomallei	3	0.7135
Abscisic acid receptor PYL3	Q9SSM7	PYL3_ARATH	Arabidopsis thaliana	2	0.7129
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7126
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.7124
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7121
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7119
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7119
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7117
Protein S100-A13	Q99584	S10AD_HUMAN	Homo sapiens	2	0.7111
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	3	0.7110
Eugenol synthase 1	Q15GI4	EGS1_OCIBA	Ocimum basilicum	3	0.7107
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7102
A disintegrin and metalloproteinase with thrombospondin motifs 5	Q9UNA0	ATS5_HUMAN	Homo sapiens	3	0.7090
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7088
Aldo-keto reductase family 1 member B1	P80276	ALDR_PIG	Sus scrofa	3	0.7081
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	2	0.7079
Collagenase 3	P45452	MMP13_HUMAN	Homo sapiens	3	0.7078
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7067
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7067
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7066
F420-dependent methylenetetrahydromethanopterin dehydrogenase	P94951	MTD_METKA	Methanopyrus kandleri	2	0.7062
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7061
Cholinesterase	P06276	CHLE_HUMAN	Homo sapiens	2	0.7058
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7056
Aldo-keto reductase family 1 member A1	P50578	AK1A1_PIG	Sus scrofa	3	0.7053
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	2	0.7051
Acyl-coenzyme A synthetase ACSM2A, mitochondrial	Q08AH3	ACS2A_HUMAN	Homo sapiens	2	0.7048
glutaryl-CoA dehydrogenase (ETF)	Q3JP94	Q3JP94_BURP1	Burkholderia pseudomallei	2	0.7041
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7037
Nitroreductase domain-containing protein	Q8DW21	Q8DW21_STRMU	Streptococcus mutans serotype c	3	0.7037
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	2	0.7023
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7019
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7011
Prolyl tripeptidyl peptidase	Q7MUW6	PTP_PORGI	Porphyromonas gingivalis	2	0.7011
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7006
Pyridoxal kinase	O00764	PDXK_HUMAN	Homo sapiens	2	0.7005
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7000

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