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Malindine

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

Canonical Smiles	C[C@H]1c2cnccc2C[C@@H]2[N@+]1(C)CCc1c2[nH]c2c1cccc2
InChI	InChI=1S/C20H22N3/c1-13-17-12-21-9-7-14(17)11-19-20-16(8-10-23(13,19)2)15-5-3-4-6-18(15)22-20/h3-7,9,12-13,19,22H,8,10-11H2,1-2H3/q+1/t13-,19-,23+/m0/s1
InChIKey	KXNXUEUDDUKJMK-CUKRAGERSA-N
Formula	C₂₀H₂₂N₃+
HBA	1
HBD	1
MW	304.42
Rotatable Bonds	0
TPSA	28.68
LogP	3.92
Number Rings	5
Number Aromatic Rings	3
Heavy Atom Count	23
Formal Charge	1
Fraction CSP3	0.35
Exact Mass	304.18
Number of Lipinski Rule Violations	0

#	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: 157739

Cas: 81161-28-6

Gnps: CCMSLIB00004680008

Chebi: 141921

Nmrshiftdb2: 70021279

No compound-protein relationship available.

SMILES: c1cccc2[nH]c(c3c12)C4[NH+](CC3)Cc5c(C4)ccnc5

Level: 0

Mol. Weight: 304.42 g/mol

Antimalarial

Absorption

Caco-2 (logPapp): -4.91
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.64
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -1.85

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.73
Plasma Protein Binding: 71.78
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 4.63
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 2.12
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.86
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 6.9
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: -3.4
Rat (Acute): 3.08
Rat (Chronic Oral): 1.07
Fathead Minnow: 4.13
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: 417.52
Hydration Free Energy: -8.43
Log(D) at pH=7.4: 1.85
Log(P): -0.68
Log S: -1.05
Log(Vapor Pressure): -9.29
Melting Point: 256.33
pKa Acid: 12.41
pKa Basic: 6.25

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Beta-2-microglobulin	P61769	B2MG_HUMAN	Homo sapiens	3	0.9611
AGAP001556-PA	Q7PXT9	Q7PXT9_ANOGA	Anopheles gambiae	3	0.9420
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.9362
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.9221
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9170
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.8744
Enoyl-[acyl-carrier-protein] reductase [NADH]	Q5NGQ3	Q5NGQ3_FRATT	Francisella tularensis subsp. tularensis	3	0.8512
Acidic mammalian chitinase	Q9BZP6	CHIA_HUMAN	Homo sapiens	3	0.8407
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.8352
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.8262
Mitogen-activated protein kinase 10	P53779	MK10_HUMAN	Homo sapiens	3	0.8213
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.8190
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase	O33877	FABA_PSEAE	Pseudomonas aeruginosa	3	0.8178
Dihydroorotate dehydrogenase (quinone), mitochondrial	Q08210	PYRD_PLAF7	Plasmodium falciparum	3	0.8121
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.8055
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.8027
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8020
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	2	0.7994
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	2	0.7976
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7910
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7880
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7874
Carbonic anhydrase 13	Q8N1Q1	CAH13_HUMAN	Homo sapiens	3	0.7844
Protease	O38896	O38896_9HIV1	Human immunodeficiency virus 1	2	0.7839
cytokinin dehydrogenase	E3T1W8	E3T1W8_MAIZE	Zea mays	3	0.7822
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.7813
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	3	0.7808
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7802
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	3	0.7751
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7740
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7734
Scytalone dehydratase	P56221	SCYD_MAGO7	Pyricularia oryzae	3	0.7727
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7707
Hut operon positive regulatory protein	P10943	HUTP_BACSU	Bacillus subtilis	3	0.7667
11-beta-hydroxysteroid dehydrogenase 1	P28845	DHI1_HUMAN	Homo sapiens	2	0.7665
Amine oxidase [flavin-containing] B	P27338	AOFB_HUMAN	Homo sapiens	3	0.7662
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	2	0.7661
Cyclic dipeptide N-prenyltransferase	D1D8L6	D1D8L6_ASPFM	Neosartorya fumigata	2	0.7649
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	2	0.7645
Cytochrome b-c1 complex subunit 1, mitochondrial	P31800	QCR1_BOVIN	Bos taurus	3	0.7642
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7641
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7640
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	2	0.7634
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7614
Scytalone dehydratase	P56221	SCYD_MAGO7	Pyricularia oryzae	3	0.7605
Hexokinase-4	P35557	HXK4_HUMAN	Homo sapiens	3	0.7605
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	3	0.7599
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7585
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7584
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7583
Tyrosine-protein kinase Lyn	P25911	LYN_MOUSE	Mus musculus	3	0.7569
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	2	0.7562
Decaprenylphosphoryl-beta-D-ribose oxidase	I6X8C4	I6X8C4_MYCTU	Mycobacterium tuberculosis	2	0.7559
L-lactate dehydrogenase A chain	P13491	LDHA_RABIT	Oryctolagus cuniculus	2	0.7557
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7556
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7548
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7546
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7538
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	2	0.7519
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7519
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	2	0.7513
Glutamate receptor 2	P19491	GRIA2_RAT	Rattus norvegicus	2	0.7508
Glutathione S-transferase F2	P46422	GSTF2_ARATH	Arabidopsis thaliana	2	0.7505
CREB-binding protein	Q92793	CBP_HUMAN	Homo sapiens	2	0.7497
Poly [ADP-ribose] polymerase tankyrase-1	O95271	TNKS1_HUMAN	Homo sapiens	2	0.7495
Proto-oncogene tyrosine-protein kinase Src	P00523	SRC_CHICK	Gallus gallus	2	0.7476
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7469
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7462
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	2	0.7455
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7446
DNA gyrase subunit B	Q839Z1	GYRB_ENTFA	Enterococcus faecalis	2	0.7429
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	2	0.7426
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	3	0.7424
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7416
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	2	0.7410
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7404
Histone deacetylase 8	Q9BY41	HDAC8_HUMAN	Homo sapiens	2	0.7384
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7378
Caspase-3	P42574	CASP3_HUMAN	Homo sapiens	2	0.7362
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7362
Glycogen phosphorylase, liver form	P06737	PYGL_HUMAN	Homo sapiens	3	0.7360
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	2	0.7357
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7356
Macrophage metalloelastase	P39900	MMP12_HUMAN	Homo sapiens	2	0.7348
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	2	0.7347
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7336
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7334
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase	Q8DNV6	Q8DNV6_STRR6	Streptococcus pneumoniae	2	0.7333
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	2	0.7330
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7327
Beta-lactamase	Q79MP6	Q79MP6_PSEAI	Pseudomonas aeruginosa	2	0.7327
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	2	0.7326
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7310
Proto-oncogene tyrosine-protein kinase receptor Ret	P07949	RET_HUMAN	Homo sapiens	3	0.7309
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	2	0.7301
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7295
Beta-lactamase	Q79MP6	Q79MP6_PSEAI	Pseudomonas aeruginosa	2	0.7266
Soluble cytochrome b562	P0ABE7	C562_ECOLX	Escherichia coli	2	0.7255
Mitogen-activated protein kinase kinase kinase 5	Q99683	M3K5_HUMAN	Homo sapiens	3	0.7249
Formate--tetrahydrofolate ligase	Q2RM91	FTHS_MOOTA	Moorella thermoacetica	2	0.7248
Botulinum neurotoxin type A	P0DPI0	BXA1_CLOBO	Clostridium botulinum	2	0.7244
Nicotinamide phosphoribosyltransferase	P43490	NAMPT_HUMAN	Homo sapiens	2	0.7244
Fumarate reductase subunit D	P0A8Q3	FRDD_ECOLI	Escherichia coli	2	0.7243
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7229
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7229
Heat shock protein HSP 90-beta	P08238	HS90B_HUMAN	Homo sapiens	2	0.7229
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7221
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7219
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7217
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	2	0.7217
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	2	0.7210
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7210
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7202
Sterol 14-alpha demethylase	Q7Z1V1	CP51_TRYCC	Trypanosoma cruzi	3	0.7198
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	2	0.7198
Fibroblast growth factor receptor 1	P11362	FGFR1_HUMAN	Homo sapiens	2	0.7198
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase	Q84HC8	NCSB1_STRCZ	Streptomyces carzinostaticus	2	0.7195
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7177
D-alanine--D-alanine ligase	Q5HEB7	DDL_STAAC	Staphylococcus aureus	2	0.7170
Transthyretin	P02767	TTHY_RAT	Rattus norvegicus	2	0.7168
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7168
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	2	0.7166
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7161
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	2	0.7161
Thiamine-phosphate synthase	P39594	THIE_BACSU	Bacillus subtilis	2	0.7156
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	2	0.7152
17beta-hydroxysteroid dehydrogenase	O93874	O93874_COCLU	Cochliobolus lunatus	2	0.7151
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7150
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7149
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7143
Casein kinase II subunit alpha'	P19784	CSK22_HUMAN	Homo sapiens	2	0.7141
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7132
Putative lanosterol 14-alpha-demethylase	A2TEF2	A2TEF2_LEIIN	Leishmania infantum	3	0.7122
Glycylpeptide N-tetradecanoyltransferase	A5K1A2	A5K1A2_PLAVS	Plasmodium vivax	2	0.7120
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7098
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7098
Endoplasmic reticulum aminopeptidase 2	Q6P179	ERAP2_HUMAN	Homo sapiens	2	0.7094
Urokinase-type plasminogen activator	P00749	UROK_HUMAN	Homo sapiens	2	0.7087
3',5'-cyclic-AMP phosphodiesterase 4B	Q07343	PDE4B_HUMAN	Homo sapiens	3	0.7086
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7081
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7081
Sulfide-quinone reductase	B7JBP8	SQRD_ACIF2	Acidithiobacillus ferrooxidans)	2	0.7080
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7079
Genome polyprotein	Q9WMX2	POLG_HCVCO	Hepatitis C virus genotype 1b	3	0.7076
Abscisic acid receptor PYR1	O49686	PYR1_ARATH	Arabidopsis thaliana	2	0.7072
ABC-type polar amino acid transport system, ATPase component	Q8RCC2	Q8RCC2_CALS4	Caldanaerobacter subterraneus subsp. tengcongensis	2	0.7069
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7062
Major pollen allergen Bet v 1-A	P15494	BEV1A_BETPN	Betula pendula	2	0.7056
Karilysin	D0EM77	KLY_TANFA	Tannerella forsythia	2	0.7042
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	2	0.7039
NTPase P4	Q94M05	Q94M05_9VIRU	Pseudomonas phage phi12	2	0.7027
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	2	0.7025
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7022
Caffeic acid 3-O-methyltransferase	P28002	COMT1_MEDSA	Medicago sativa	2	0.7013

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