18, 19-dihydrousambarine - Compound Card

18, 19-dihydrousambarine

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18, 19-dihydrousambarine

Structure
Zoomed Structure
  • Family: Plantae - Loganiaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Indole Alkaloid
Canonical Smiles CC[C@H]1CN2CCc3c([C@@H]2C[C@@H]1C[C@@H]1N(C)CCc2c1[nH]c1c2cccc1)[nH]c1c3cccc1
InChI InChI=1S/C30H36N4/c1-3-19-18-34-15-13-24-22-9-5-7-11-26(22)32-30(24)28(34)17-20(19)16-27-29-23(12-14-33(27)2)21-8-4-6-10-25(21)31-29/h4-11,19-20,27-28,31-32H,3,12-18H2,1-2H3/t19-,20-,27-,28-/m0/s1
InChIKey QMPMOSMXZGIBBR-DXBSEXLMSA-N
Formula C30H36N4
HBA 2
HBD 2
MW 452.65
Rotatable Bonds 3
TPSA 38.06
LogP 6.21
Number Rings 7
Number Aromatic Rings 4
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.47
Exact Mass 452.29
Number of Lipinski Rule Violations 1
# 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]

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 452.65 g/mol

Structure

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

Level: 0

Mol. Weight: 452.65 g/mol

Structure

SMILES: C1CNCc(c1c23)[nH]c2cccc3

Level: 0

Mol. Weight: 452.65 g/mol

Antimalarial

Absorption

Caco-2 (logPapp)
-5.49
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.51
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.4

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.28
Plasma Protein Binding
89.92
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
Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.25
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.98
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.32
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.02
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
-987.33
Rat (Acute)
2.65
Rat (Chronic Oral)
1.73
Fathead Minnow
6.86
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
480.78
Hydration Free Energy
-2.98
Log(D) at pH=7.4
5.21
Log(P)
5.85
Log S
-5.1
Log(Vapor Pressure)
-9.0
Melting Point
213.87
pKa Acid
13.65
pKa Basic
6.84
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 0.9606
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.9562
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9516
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.9503
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.9411
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.9398
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.9375
clade A/E 93TH057 HIV-1 gp120 core A0A0M3KKW9 A0A0M3KKW9_9HIV1 Human immunodeficiency virus 1 3 0.9115
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.9084
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.9084
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.9007
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8875
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 3 0.8803
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8607
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.8357
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.8335
Aklanonic acid methyl ester cyclase AcmA O52646 DNRD_STRGJ Streptomyces galilaeus 3 0.8307
Dipeptidyl peptidase 4 P14740 DPP4_RAT Rattus norvegicus 3 0.8298
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 4 0.8290
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.8290
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 4 0.8284
Death-associated protein kinase 3 O43293 DAPK3_HUMAN Homo sapiens 3 0.8252
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.8231
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.8214
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8153
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8125
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8121
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8052
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 3 0.8030
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8027
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.8003
clade A/E 93TH057 HIV-1 gp120 core A0A0M3KKW9 A0A0M3KKW9_9HIV1 Human immunodeficiency virus 1 3 0.7992
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7985
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7936
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7934
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7925
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7918
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7903
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7873
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 4 0.7867
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7857
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 2 0.7839
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7818
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase O33877 FABA_PSEAE Pseudomonas aeruginosa 3 0.7789
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7783
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7751
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7718
mRNA cap guanine-N7 methyltransferase O43148 MCES_HUMAN Homo sapiens 3 0.7696
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7686
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7679
Carnitine O-palmitoyltransferase 2, mitochondrial P18886 CPT2_RAT Rattus norvegicus 2 0.7674
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase F6MZ55 F6MZ55_9FIRM Sporomusa ovata 3 0.7673
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 2 0.7646
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7635
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7627
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7620
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7612
Troponin C, slow skeletal and cardiac muscles P09860 TNNC1_CHICK Gallus gallus 3 0.7608
Carbonic anhydrase 13 Q8N1Q1 CAH13_HUMAN Homo sapiens 3 0.7604
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7597
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7590
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7584
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7575
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7567
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7566
Ribosomal protein S6 kinase beta-1 P23443 KS6B1_HUMAN Homo sapiens 3 0.7549
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7548
UDP-N-acetylenolpyruvoylglucosamine reductase P08373 MURB_ECOLI Escherichia coli 3 0.7547
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7537
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7502
Naphthalene 1,2-dioxygenase system, large oxygenase component P0A110 NDOB_PSEPU Pseudomonas putida 2 0.7492
Putative snRNP Sm-like protein Q8ZYG5 Q8ZYG5_PYRAE Pyrobaculum aerophilum 2 0.7490
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7482
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7463
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7457
Insulin-degrading enzyme P14735 IDE_HUMAN Homo sapiens 2 0.7415
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 3 0.7414
Antitumor antibiotic C-1027 apoprotein Q06110 CAGA_STRGL Streptomyces globisporus 2 0.7413
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7404
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7393
Glutathione S-transferase A1 P08263 GSTA1_HUMAN Homo sapiens 2 0.7389
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7389
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7387
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7384
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7381
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7371
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7364
Bromodomain testis-specific protein Q58F21 BRDT_HUMAN Homo sapiens 3 0.7353
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 2 0.7338
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7337
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 2 0.7333
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7330
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7326
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 2 0.7325
Histidinol dehydrogenase P06988 HISX_ECOLI Escherichia coli 2 0.7321
Glycoside Hydrolase Family 13 Q65MI2 Q65MI2_BACLD Bacillus licheniformis 2 0.7321
Genome polyprotein Q99AU2 Q99AU2_9HEPC Hepatitis C virus subtype 1b 3 0.7320
Carbonic anhydrase 13 Q8N1Q1 CAH13_HUMAN Homo sapiens 4 0.7317
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7314
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7304
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 3 0.7281
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7275
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7263
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7253
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7239
Hexokinase-4 P35557 HXK4_HUMAN Homo sapiens 3 0.7227
4-chlorobenzoyl CoA ligase Q8GN86 Q8GN86_9BURK Alcaligenes sp. AL3007 2 0.7227
Acidic mammalian chitinase Q9BZP6 CHIA_HUMAN Homo sapiens 2 0.7225
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 3 0.7224
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7216
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7216
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7204
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7195
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 3 0.7188
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7178
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7176
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7166
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.7156
Reticuline oxidase P30986 RETO_ESCCA Eschscholzia californica 4 0.7152
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7152
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.7143
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7142
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7134
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 2 0.7131
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7125
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 4 0.7121
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7120
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 2 0.7120
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7119
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7113
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 2 0.7113
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7110
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 2 0.7088
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7079
Acidic mammalian chitinase Q9BZP6 CHIA_HUMAN Homo sapiens 3 0.7075
Prostaglandin E synthase 2 Q9N0A4 PGES2_MACFA Macaca fascicularis 3 0.7067
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 3 0.7065
Karilysin D0EM77 KLY_TANFA Tannerella forsythia 2 0.7062
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7043
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7039
Archaeal actin homolog Q9HKL4 ACTH_THEAC Thermoplasma acidophilum 2 0.7031
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7025
Sterol 14-alpha demethylase Q7Z1V1 CP51_TRYCC Trypanosoma cruzi 4 0.7016
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7009
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7006
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7002

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