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N-methylurabaine

Family: Plantae - Annonaceae
Kingdom: Plantae
Class: Alkaloid
- Subclass: Indole Sesquiterpene Alkaloid

Canonical Smiles	COc1c(OC)cc2c3c1c1ccccc1c(c3NCC2)c1c2N(C)CCc3c2c(c2c1cccc2)c(c(c3)OC)OC
InChI	InChI=1S/C37H34N2O4/c1-39-17-15-21-19-27(41-3)37(43-5)33-25-13-9-7-11-23(25)31(35(39)29(21)33)30-22-10-6-8-12-24(22)32-28-20(14-16-38-34(28)30)18-26(40-2)36(32)42-4/h6-13,18-19,38H,14-17H2,1-5H3
InChIKey	OZRPTHFYXIEDGN-UHFFFAOYSA-N
Formula	C₃₇H₃₄N₂O₄
HBA	6
HBD	1
MW	570.69
Rotatable Bonds	5
TPSA	52.19
LogP	7.96
Number Rings	8
Number Aromatic Rings	6
Heavy Atom Count	43
Formal Charge	0
Fraction CSP3	0.24
Exact Mass	570.25
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Polyalthia oliveri	Annonaceae	Plantae	296858

Showing of synonyms

Kouam SF, Ngouonpe AW, et al. (2014). Indolosesquiterpene alkaloids from the Cameroonian medicinal plant Polyalthia oliveri (Annonaceae).. Phytochemistry,2014, 105, 52-59. [View] [PubMed]

Pubchem: 13992204

Gnps: CCMSLIB00009918408

Zinc: ZINC000085977085

Nmrshiftdb2: 70017020

No compound-protein relationship available.

SMILES: c1ccc2CCNc3c(c(c4c1c23)cccc4)-c(c(c5c6c78)cccc5)c7NCCc8ccc6

Level: 1

Mol. Weight: 570.69 g/mol

SMILES: c1cccc(c1c2c34)cc4NCCc3ccc2

Level: 0

Mol. Weight: 570.69 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.56
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.560
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 37.0

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 2.040
Plasma Protein Binding: 80.84
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 9.510
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Toxic
Bee: Toxic
Bioconcentration Factor: 2.560
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.500
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 7.060
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: Toxic
T. Pyriformis: -69522.870
Rat (Acute): 3.330
Rat (Chronic Oral): 2.100
Fathead Minnow: 104.150
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: 3323.740
Hydration Free Energy: -2.920
Log(D) at pH=7.4: 3.590
Log(P): 6.87
Log S: -5.26
Log(Vapor Pressure): -164.26
Melting Point: 225.33
pKa Acid: 12.09
pKa Basic: 8.5

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.9661
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.9638
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.9524
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.9437
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9391
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	3	0.9225
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.9093
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.8817
DNA polymerase III subunit epsilon	P03007	DPO3E_ECOLI	Escherichia coli	3	0.8751
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.8729
Geranylgeranyl transferase type-2 subunit alpha	Q08602	PGTA_RAT	Rattus norvegicus	3	0.8694
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8545
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	4	0.8529
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8471
Serine/threonine-protein kinase PLK2	Q9NYY3	PLK2_HUMAN	Homo sapiens	3	0.8414
Serine/threonine-protein kinase PLK2	Q9NYY3	PLK2_HUMAN	Homo sapiens	3	0.8406
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8391
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8390
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8353
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.8290
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8238
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8215
Protein LlR18A	P52778	L18A_LUPLU	Lupinus luteus	3	0.8148
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	O02697	PK3CG_PIG	Sus scrofa	3	0.8130
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7963
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7955
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7913
Phosphodiesterase	Q8WQX9	Q8WQX9_9TRYP	Trypanosoma brucei	4	0.7904
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7882
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7879
Transthyretin	Q9PTT3	Q9PTT3_SPAAU	Sparus aurata	3	0.7856
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7842
Aldo-keto reductase family 1 member B10	O60218	AK1BA_HUMAN	Homo sapiens	3	0.7814
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7804
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7787
Catalase-peroxidase 2	O59651	KATG2_HALMA	Haloarcula marismortui	2	0.7769
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.7688
Renin	P00797	RENI_HUMAN	Homo sapiens	3	0.7653
Calmodulin	P62157	CALM_BOVIN	Bos taurus	3	0.7639
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7632
Aldo-keto reductase family 1 member A1	P50578	AK1A1_PIG	Sus scrofa	3	0.7616
Nucleoside diphosphate kinase A 2	P52175	NDKA2_BOVIN	Bos taurus	3	0.7591
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7560
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7541
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7538
Carbonic anhydrase 4	P22748	CAH4_HUMAN	Homo sapiens	3	0.7526
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7524
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7497
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7495
Proto-oncogene tyrosine-protein kinase Src	P12931	SRC_HUMAN	Homo sapiens	3	0.7460
NAD(P)H dehydrogenase [quinone] 1	P15559	NQO1_HUMAN	Homo sapiens	3	0.7450
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7432
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	4	0.7425
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7402
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7383
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7360
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7350
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7332
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7330
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase	Q84HC8	NCSB1_STRCZ	Streptomyces carzinostaticus	3	0.7302
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1	O50008	METE1_ARATH	Arabidopsis thaliana	2	0.7295
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7284
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7284
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7273
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7272
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7271
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7266
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7254
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7250
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7212
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7208
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7198
Beta-hexosaminidase	Q9KU37	NAGZ_VIBCH	Vibrio cholerae serotype O1	3	0.7196
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7193
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	2	0.7185
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7181
Serine/threonine-protein kinase Nek2	P51955	NEK2_HUMAN	Homo sapiens	4	0.7166
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	4	0.7157
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	2	0.7147
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.7140
Polyprotein	Q80J95	Q80J95_9CALI	Murine norovirus 1	2	0.7139
Proto-oncogene tyrosine-protein kinase receptor Ret	P07949	RET_HUMAN	Homo sapiens	3	0.7129
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7107
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7102
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7087
Aminopeptidase N	P15145	AMPN_PIG	Sus scrofa	2	0.7086
Liver carboxylesterase 1	P23141	EST1_HUMAN	Homo sapiens	2	0.7073
N-terminal acetyltransferase A complex subunit NAT1	P12945	NAT1_YEAST	Saccharomyces cerevisiae	2	0.7065
Angiotensin-converting enzyme 2	Q9BYF1	ACE2_HUMAN	Homo sapiens	2	0.7062
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7057
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	2	0.7055
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7054
Bifunctional protein GlmU	P43889	GLMU_HAEIN	Haemophilus influenzae	4	0.7033
Aldo-keto reductase family 1 member B1	P80276	ALDR_PIG	Sus scrofa	3	0.7021
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7020
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7015
Aldo-keto reductase family 1 member B10	O60218	AK1BA_HUMAN	Homo sapiens	4	0.7008
Polymerase acidic protein	Q5EP34	Q5EP34_9INFA	Influenza A virus	2	0.7004

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