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Strychnopentamine

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

Canonical Smiles	C=C[C@H]1CN2CCc3c([C@@H]2C[C@@H]1C[C@@H]1N(C)CCc2c1[nH]c1c2cccc1)[nH]c1c3ccc(c1[C@H]1CCCN1C)O
InChI	InChI=1S/C35H43N5O/c1-4-21-20-40-17-14-26-24-11-12-31(41)32(28-10-7-15-38(28)2)35(24)37-34(26)30(40)19-22(21)18-29-33-25(13-16-39(29)3)23-8-5-6-9-27(23)36-33/h4-6,8-9,11-12,21-22,28-30,36-37,41H,1,7,10,13-20H2,2-3H3/t21-,22-,28+,29-,30-/m0/s1
InChIKey	PHLJPJICTIGOKC-XKYMZAEISA-N
Formula	C₃₅H₄₃N₅O
HBA	4
HBD	3
MW	549.76
Rotatable Bonds	4
TPSA	61.53
LogP	6.46
Number Rings	8
Number Aromatic Rings	4
Heavy Atom Count	41
Formal Charge	0
Fraction CSP3	0.49
Exact Mass	549.35
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: 6712640

Gnps: CCMSLIB00004680061

Zinc: ZINC000006004505

Chebi: 141956

Nmrshiftdb2: 70053767

Chembl: CHEMBL1979186

No compound-protein relationship available.

SMILES: c1cccc2[nH]c(c3c12)C(NCC3)CC(C4)CCN(CC5)C4c(c5c67)[nH]c6c(ccc7)C8CCCN8

Level: 2

Mol. Weight: 549.76 g/mol

SMILES: c1cccc2[nH]c(c3c12)C(NCC3)CC(C4)CCN(CC5)C4c(c5c67)[nH]c6cccc7

Level: 1

Mol. Weight: 549.76 g/mol

SMILES: C1CCCN(CC2)C1c(c2c34)[nH]c3c(ccc4)C5CCCN5

Level: 1

Mol. Weight: 549.76 g/mol

SMILES: C1CCCN(CC2)C1c(c2c34)[nH]c3cccc4

Level: 0

Mol. Weight: 549.76 g/mol

SMILES: C1CNCc(c1c23)[nH]c2cccc3

Level: 0

Mol. Weight: 549.76 g/mol

SMILES: C1CCNC1

Level: 0

Mol. Weight: 549.76 g/mol

Antimalarial

Absorption

Caco-2 (logPapp): -5.74
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.37
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 18.1

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.85
Plasma Protein Binding: 90.36
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: 8.92
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.93
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -1.66
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 6.15
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: -32123.17
Rat (Acute): 2.79
Rat (Chronic Oral): 2.07
Fathead Minnow: 52.04
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: 608.04
Hydration Free Energy: -2.92
Log(D) at pH=7.4: 4.6
Log(P): 5.01
Log S: -4.84
Log(Vapor Pressure): -22.05
Melting Point: 228.13
pKa Acid: 10.69
pKa Basic: 7.08

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	0.9599
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	3	0.9457
Death-associated protein kinase 3	O43293	DAPK3_HUMAN	Homo sapiens	3	0.9394
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.9116
clade A/E 93TH057 HIV-1 gp120 core	A0A0M3KKW9	A0A0M3KKW9_9HIV1	Human immunodeficiency virus 1	3	0.9101
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9QYJ6	PDE10_RAT	Rattus norvegicus	3	0.9025
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.8938
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8912
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8901
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8899
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8781
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8748
Purine nucleoside phosphorylase DeoD-type	O34925	DEOD_BACSU	Bacillus subtilis	3	0.8743
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	3	0.8720
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8698
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.8665
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.8530
Coniferyl alcohol 9-O-methyltransferase	A6XNE6	A6XNE6_9ROSI	Linum nodiflorum	3	0.8495
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8477
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8473
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8435
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.8427
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8424
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	3	0.8412
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.8409
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8396
Glutathione S-transferase F2	P46422	GSTF2_ARATH	Arabidopsis thaliana	3	0.8370
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8366
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8353
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.8320
Casein kinase II subunit alpha	P68400	CSK21_HUMAN	Homo sapiens	3	0.8305
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8298
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8241
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8231
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8208
Dipeptidyl peptidase 4	P14740	DPP4_RAT	Rattus norvegicus	3	0.8205
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.8176
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	3	0.8157
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8139
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8135
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	3	0.8103
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.8083
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8052
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.8045
Pteridine reductase 1	Q01782	PTR1_LEIMA	Leishmania major	3	0.8040
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	3	0.8027
Trichosurin	Q29147	TRIC_TRIVU	Trichosurus vulpecula	3	0.8015
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8005
clade A/E 93TH057 HIV-1 gp120 core	A0A0M3KKW9	A0A0M3KKW9_9HIV1	Human immunodeficiency virus 1	3	0.7964
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7949
Dihydrofolate reductase	P00374	DYR_HUMAN	Homo sapiens	4	0.7931
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7930
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	3	0.7911
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	3	0.7896
Seed lectin subunit I	P05045	LEC1_VIGUC	Vigna unguiculata subsp. cylindrica	3	0.7894
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	F6MZ55	F6MZ55_9FIRM	Sporomusa ovata	3	0.7866
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	3	0.7866
Orf1a polyprotein	Q692E5	Q692E5_CVHSA	SARS coronavirus TJF	3	0.7839
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7812
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7797
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase	O33877	FABA_PSEAE	Pseudomonas aeruginosa	3	0.7790
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	3	0.7760
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7742
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	3	0.7737
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7698
Cyclomaltodextrin glucanotransferase	P05618	CDGT_BACS0	Bacillus sp	3	0.7693
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	P0AF12	MTNN_ECOLI	Escherichia coli	3	0.7676
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7676
Aldose reductase-related protein 2	P45377	ALD2_MOUSE	Mus musculus	3	0.7674
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7660
Poly [ADP-ribose] polymerase 1	P09874	PARP1_HUMAN	Homo sapiens	3	0.7644
Gag-Pol polyprotein	P03369	POL_HV1A2	Human immunodeficiency virus type 1 group M subtype B	3	0.7619
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7607
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	3	0.7606
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7603
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7592
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	2	0.7584
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7560
Integrin alpha-IIb	P08514	ITA2B_HUMAN	Homo sapiens	3	0.7550
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7541
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7527
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7525
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7482
Dihydrofolate reductase	P00374	DYR_HUMAN	Homo sapiens	4	0.7460
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7452
Thiamine-monophosphate kinase	O67883	THIL_AQUAE	Aquifex aeolicus	3	0.7452
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7451
adenine phosphoribosyltransferase	Q967M2	Q967M2_GIAIN	Giardia intestinalis	3	0.7414
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	3	0.7409
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7401
mRNA cap guanine-N7 methyltransferase	O43148	MCES_HUMAN	Homo sapiens	3	0.7399
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7381
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	3	0.7381
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7366
4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase, chloroplastic	Q9FYS3	HGGL_SECCE	Secale cereale	3	0.7360
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7350
HTH-type transcriptional regulator QacR	P0A0N3	QACR_STAAM	Staphylococcus aureus	3	0.7339
RAC-alpha serine/threonine-protein kinase	P31749	AKT1_HUMAN	Homo sapiens	3	0.7336
Subunit alpha of sarocosine oxidase	Q50LF0	Q50LF0_9CORY	Corynebacterium sp. U-96	4	0.7320
histone deacetylase	A5H660	A5H660_SCHMA	Schistosoma mansoni	3	0.7317
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.7314
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7310
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7306
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7303
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7268
Ethylene receptor 1	P49333	ETR1_ARATH	Arabidopsis thaliana	3	0.7257
Flavonoid 3-O-glucosyltransferase	A6XNC6	UGFGT_MEDTR	Medicago truncatula	3	0.7251
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7246
TGF-beta-activated kinase 1 and MAP3K7-binding protein 1	Q15750	TAB1_HUMAN	Homo sapiens	3	0.7239
Nickel-binding periplasmic protein	P33590	NIKA_ECOLI	Escherichia coli	2	0.7208
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	4	0.7207
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7188
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7172
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7172
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	3	0.7167
histidine kinase	Q9WZV7	Q9WZV7_THEMA	Thermotoga maritima	3	0.7154
GMP reductase	Q81JJ9	GUAC_BACAN	Bacillus anthracis	2	0.7153
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7151
Polyamine oxidase FMS1	P50264	FMS1_YEAST	Saccharomyces cerevisiae	3	0.7130
Vascular endothelial growth factor receptor 2	P35968	VGFR2_HUMAN	Homo sapiens	3	0.7124
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7114
43.2 kDa salivary protein	Q5WPU9	Q5WPU9_LUTLO	Lutzomyia longipalpis	3	0.7109
Gag-Pol polyprotein	P03369	POL_HV1A2	Human immunodeficiency virus type 1 group M subtype B	3	0.7098
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	3	0.7063
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	2	0.7059
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7042
Ephrin type-B receptor 4	P54760	EPHB4_HUMAN	Homo sapiens	3	0.7036
Short form salivary protein D7R4	Q7PNF2	Q9BIH3_ANOGA	Anopheles gambiae	3	0.7036
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	2	0.7031
Ribonuclease 4	P15468	RNAS4_PIG	Sus scrofa	2	0.7029
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7028
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7025
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7019
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	3	0.7006
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7000

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