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Strychnophylline

Family: Loganiaceae
Kingdom: Plantae
Class: Alkaloid
- Subclass: Oxindole Alkaloid

Canonical Smiles	C=C[C@@H]1CN2CC[C@]3([C@@H]2C[C@@H]1C[C@@H]1N(C)CCc2c1[nH]c1c2cccc1)CNc1c3ccc(c1[C@H]1CCCN1C)O
InChI	InChI=1S/C35H45N5O/c1-4-22-20-40-17-14-35(21-36-34-26(35)11-12-30(41)32(34)28-10-7-15-38(28)2)31(40)19-23(22)18-29-33-25(13-16-39(29)3)24-8-5-6-9-27(24)37-33/h4-6,8-9,11-12,22-23,28-29,31,36-37,41H,1,7,10,13-21H2,2-3H3/t22-,23+,28-,29+,31+,35+/m1/s1
InChIKey	LLNJYWAPDLBDRC-DKNITUKRSA-N
Formula	C₃₅H₄₅N₅O
HBA	5
HBD	3
MW	551.78
Rotatable Bonds	4
TPSA	57.77
LogP	5.82
Number Rings	8
Number Aromatic Rings	3
Heavy Atom Count	41
Formal Charge	0
Fraction CSP3	0.54
Exact Mass	551.36
Number of Lipinski Rule Violations	2

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Strychnos usambarensis	Loganiaceae	Plantae	992791

Showing of synonyms

Frederich M, Hayette MP, et al. (1999). In vitro activities of Strychnos alkaloids and extracts against Plasmodium falciparum.. Antimicrobial agents and chemotherapy,1999, 43(9), 2328-31. [View] [PubMed]

Pubchem: 49863860

Zinc: ZINC000058541817

Chembl: CHEMBL1214313

No compound-protein relationship available.

SMILES: c1cccc2[nH]c(c3c12)C(NCC3)CC(C4)CCN(CC5)C4C56c7c(NC6)c(ccc7)C8CCCN8

Level: 2

Mol. Weight: 481.69 g/mol

SMILES: c1cccc2[nH]c(c3c12)C(NCC3)CC(C4)CCN(CC5)C4C56c7c(NC6)cccc7

Level: 1

Mol. Weight: 412.58 g/mol

SMILES: N1CCCC1c(ccc2)c(NC3)c2C34C5N(CC4)CCCC5

Level: 1

Mol. Weight: 297.45 g/mol

SMILES: c1cccc(NC2)c1C23C4N(CC3)CCCC4

Level: 0

Mol. Weight: 228.34 g/mol

SMILES: C1CNCc(c1c23)[nH]c2cccc3

Level: 0

Mol. Weight: 172.23 g/mol

SMILES: C1CCNC1

Level: 0

Mol. Weight: 71.12 g/mol

Antimalarial

Absorption

Caco-2 (logPapp): -5.67
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.27
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 17.44

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.87
Plasma Protein Binding: 89.78
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 6.78
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.71
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -1.77
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 6.23
Micronucleos: Toxic
NR-AhR: Safe
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: -31760.92
Rat (Acute): 2.88
Rat (Chronic Oral): 1.77
Fathead Minnow: 50.62
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 743.14
Hydration Free Energy: -2.92
Log(D) at pH=7.4: 3.88
Log(P): 4.11
Log S: -4.28
Log(Vapor Pressure): -18.16
Melting Point: 195.11
pKa Acid: 8.9
pKa Basic: 7.52

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.9587
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	3	0.9544
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.9338
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.9323
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9212
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.9178
Norsolorinic acid synthase	Q12053	AFLC_ASPPU	Aspergillus parasiticus	3	0.9098
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9046
clade A/E 93TH057 HIV-1 gp120 core	A0A0M3KKW9	A0A0M3KKW9_9HIV1	Human immunodeficiency virus 1	3	0.9044
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.9005
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.8881
Cytidine and deoxycytidylate deaminase zinc-binding region	Q82Y41	Q82Y41_NITEU	Nitrosomonas europaea	3	0.8813
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8704
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	3	0.8702
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8689
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8663
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.8661
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8647
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8599
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8548
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8546
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8529
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.8510
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8492
Cyclomaltodextrin glucanotransferase	P05618	CDGT_BACS0	Bacillus sp	3	0.8472
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8443
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8434
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	3	0.8411
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.8390
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8386
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8347
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8322
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.8296
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	3	0.8265
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.8185
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8180
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	3	0.8088
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8071
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8033
Kallikrein-4	Q9Y5K2	KLK4_HUMAN	Homo sapiens	3	0.7990
Trichosurin	Q29147	TRIC_TRIVU	Trichosurus vulpecula	3	0.7945
Serine/threonine-protein kinase toxin HipA	P23874	HIPA_ECOLI	Escherichia coli	3	0.7938
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	P0AF12	MTNN_ECOLI	Escherichia coli	3	0.7906
N-acetyltransferase domain-containing protein	Q9HV14	Q9HV14_PSEAE	Pseudomonas aeruginosa	3	0.7870
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7851
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	3	0.7846
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7825
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7768
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	3	0.7760
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase	O33877	FABA_PSEAE	Pseudomonas aeruginosa	3	0.7739
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7735
Proline iminopeptidase	O32449	PIP_SERMA	Serratia marcescens	3	0.7733
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7731
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7728
Proline iminopeptidase	O32449	PIP_SERMA	Serratia marcescens	3	0.7714
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.7688
Glycogen phosphorylase, muscle form	P00489	PYGM_RABIT	Oryctolagus cuniculus	3	0.7683
Toluene-4-monooxygenase system, hydroxylase component subunit alpha	Q00456	TMOA_PSEME	Pseudomonas mendocina	3	0.7643
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	2	0.7617
Streptavidin	P22629	SAV_STRAV	Streptomyces avidinii	3	0.7605
Annexin A5	P08758	ANXA5_HUMAN	Homo sapiens	2	0.7601
Proline iminopeptidase	O32449	PIP_SERMA	Serratia marcescens	3	0.7591
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	4	0.7551
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	3	0.7544
Ribosome-inactivating protein 3	P25891	RIP3_MAIZE	Zea mays	3	0.7533
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7523
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	2	0.7520
Thiamine-monophosphate kinase	O67883	THIL_AQUAE	Aquifex aeolicus	3	0.7498
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.7491
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase	Q84HC8	NCSB1_STRCZ	Streptomyces carzinostaticus	2	0.7473
Flavin-dependent thymidylate synthase	Q9WYT0	THYX_THEMA	Thermotoga maritima	3	0.7457
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	3	0.7450
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	2	0.7429
rRNA methylase	Q8DSS3	Q8DSS3_STRMU	Streptococcus mutans serotype c	2	0.7412
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7405
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7403
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7388
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7375
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7374
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7350
Epothilone C/D epoxidase	Q9KIZ4	C167_SORCE	Sorangium cellulosum	3	0.7342
Thiamine-phosphate synthase	P39594	THIE_BACSU	Bacillus subtilis	2	0.7338
Glutathione S-transferase P	P09211	GSTP1_HUMAN	Homo sapiens	2	0.7330
4-chlorobenzoyl CoA ligase	Q8GN86	Q8GN86_9BURK	Alcaligenes sp. AL3007	2	0.7310
Dihydrofolate reductase	P0ABQ4	DYR_ECOLI	Escherichia coli	3	0.7308
Acidic mammalian chitinase	Q9BZP6	CHIA_HUMAN	Homo sapiens	2	0.7305
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7300
Casein kinase II subunit alpha'	P19784	CSK22_HUMAN	Homo sapiens	2	0.7299
histone deacetylase	A5H660	A5H660_SCHMA	Schistosoma mansoni	3	0.7266
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.7266
Dihydrofolate reductase	P0ABQ4	DYR_ECOLI	Escherichia coli	3	0.7255
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7250
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	4	0.7249
Dicamba O-demethylase, oxygenase component	Q5S3I3	DDMC_STEMA	Stenotrophomonas maltophilia	2	0.7241
clade A/E 93TH057 HIV-1 gp120 core	A0A0M3KKW9	A0A0M3KKW9_9HIV1	Human immunodeficiency virus 1	3	0.7237
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7233
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase	Q84HC8	NCSB1_STRCZ	Streptomyces carzinostaticus	2	0.7222
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7222
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	3	0.7216
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7215
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7204
Enoyl-[acyl-carrier-protein] reductase [NADH]	P9WGR1	INHA_MYCTU	Mycobacterium tuberculosis	3	0.7202
Histamine N-methyltransferase	P50135	HNMT_HUMAN	Homo sapiens	3	0.7197
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7189
Phospholipase A2, major isoenzyme	P00592	PA21B_PIG	Sus scrofa	3	0.7184
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7179
Glycoside Hydrolase Family 13	Q65MI2	Q65MI2_BACLD	Bacillus licheniformis	2	0.7173
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	2	0.7171
Thiamine pyrophosphokinase	P35202	THI80_YEAST	Saccharomyces cerevisiae	3	0.7171
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7157
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.7155
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7152
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7149
Achbp	I6L8L2	I6L8L2_CAPTE	Capitella teleta	2	0.7137
Endoplasmic reticulum aminopeptidase 2	Q6P179	ERAP2_HUMAN	Homo sapiens	3	0.7136
Tetracycline repressor protein class B from transposon Tn10	P04483	TETR2_ECOLX	Escherichia coli	3	0.7128
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7125
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	2	0.7118
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7113
Dual specificity mitogen-activated protein kinase kinase 1	Q02750	MP2K1_HUMAN	Homo sapiens	2	0.7110
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7108
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7103
Tissue factor	P13726	TF_HUMAN	Homo sapiens	3	0.7088
Ribonuclease 4	P15468	RNAS4_PIG	Sus scrofa	2	0.7088
Purine nucleoside phosphorylase	P55859	PNPH_BOVIN	Bos taurus	2	0.7086
Myosin heavy chain kinase A	P42527	MHCKA_DICDI	Dictyostelium discoideum	3	0.7081
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7081
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7074
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	3	0.7072
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7070
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7059
Nucleoside 2-deoxyribosyltransferase	Q8RLY5	Q8RLY5_LACHE	Lactobacillus helveticus	2	0.7050
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7032
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7031
prolyl oligopeptidase	Q9X6R4	Q9X6R4_AERCA	Aeromonas caviae	2	0.7031
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7030
Dipeptidyl peptidase 4	P14740	DPP4_RAT	Rattus norvegicus	3	0.7027
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7027
Integrin alpha-IIb	P08514	ITA2B_HUMAN	Homo sapiens	3	0.7008
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7003
Adenosine receptor A2a	P29274	AA2AR_HUMAN	Homo sapiens	4	0.7001

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