N-formyldihydrochelerythrine - Compound Card

N-formyldihydrochelerythrine

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N-formyldihydrochelerythrine

Structure
Zoomed Structure
  • Family: Plantae - Flacourtiaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Benzophenanthridine Alkaloid
Canonical Smiles O=CN1Cc2c(c3c1c1cc4OCOc4cc1cc3)ccc(c2OC)OC
InChI InChI=1S/C21H17NO5/c1-24-17-6-5-13-14-4-3-12-7-18-19(27-11-26-18)8-15(12)20(14)22(10-23)9-16(13)21(17)25-2/h3-8,10H,9,11H2,1-2H3
InChIKey OWMXMOAPTQPIGX-UHFFFAOYSA-N
Formula C21H17NO5
HBA 5
HBD 0
MW 363.37
Rotatable Bonds 3
TPSA 57.23
LogP 3.73
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.19
Exact Mass 363.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Caloncoba glauca Flacourtiaceae Plantae 2806806

Showing of synonyms

  • Agbo J, Mpetga J, et al. (2017). A New Benzophenanthridine Alkaloid from Caloncoba Glauca.. Natural Product Communications, 2017, 12(3), 367-368. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: O1COc(c12)cc3c(c2)c4c(cc3)c5c(CN4)cccc5

Level: 0

Mol. Weight: 363.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.09
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.42
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.91

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.46
Plasma Protein Binding
79.0
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
12.05
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.52
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.15
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.93
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
-13.55
Rat (Acute)
2.47
Rat (Chronic Oral)
1.59
Fathead Minnow
5.56
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
513.88
Hydration Free Energy
-6.21
Log(D) at pH=7.4
2.72
Log(P)
3.57
Log S
-4.87
Log(Vapor Pressure)
-9.1
Melting Point
198.46
pKa Acid
10.44
pKa Basic
1.67
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9801
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.9682
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9458
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9323
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9117
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 4 0.8900
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8864
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8864
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.8847
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8835
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8815
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.8790
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8775
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8766
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8689
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8678
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8677
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8662
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8649
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.8646
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8523
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.8509
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.8473
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.8417
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.8399
Metapyrocatechase Q7WYF5 Q7WYF5_9PSED Pseudomonas alkylphenolica 3 0.8388
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8387
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8373
Cytochrome P450 2B4 P00178 CP2B4_RABIT Oryctolagus cuniculus 3 0.8370
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8363
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8347
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8290
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.8274
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8258
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8255
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.8230
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8135
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8104
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8102
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8048
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8042
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8026
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7976
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7922
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 4 0.7918
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 4 0.7900
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 4 0.7900
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7892
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7871
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7866
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7855
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7853
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7769
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7761
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7757
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7746
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7745
Enterochelin uptake periplasmic binding protein Q0P8Q4 Q0P8Q4_CAMJE Campylobacter jejuni subsp. jejuni serotype O:2 4 0.7735
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7732
Beta-2 adrenergic receptor P07550 ADRB2_HUMAN Homo sapiens 2 0.7726
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7717
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7708
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 4 0.7686
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7683
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7678
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7637
Estrogen receptor beta Q92731 ESR2_HUMAN Homo sapiens 4 0.7632
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7628
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 3 0.7604
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7584
Bromodomain protein, putative Q8I240 Q8I240_PLAF7 Plasmodium falciparum 4 0.7560
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7558
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7547
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7540
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7533
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7521
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7510
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7508
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7498
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7480
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7463
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7442
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7424
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7419
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7415
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7415
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7400
Mitogen-activated protein kinase 1 P63086 MK01_RAT Rattus norvegicus 3 0.7366
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7356
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7355
Carbonic anhydrase 4 P22748 CAH4_HUMAN Homo sapiens 3 0.7351
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7350
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 3 0.7337
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7333
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7328
Sulfotransferase 1E1 P49888 ST1E1_HUMAN Homo sapiens 3 0.7325
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7309
Interstitial collagenase P03956 MMP1_HUMAN Homo sapiens 3 0.7302
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 3 0.7301
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7292
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7253
(RS)-norcoclaurine 6-O-methyltransferase Q5C9L7 6OMT_THLFG Thalictrum flavum subsp. glaucum 3 0.7252
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7244
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7205
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.7201
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7201
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7184
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7181
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7177
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7176
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7152
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7149
AGAP003309-PA A0A1U7F4W2 A0A1U7F4W2_ANOGA Anopheles gambiae 3 0.7145
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7130
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7130
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7114
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7105
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7099
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7088
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7087
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7086
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7081
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7079
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7077
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7074
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7059
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7058
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7056
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7051
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7051
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7041
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 3 0.7029
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7019
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 2 0.7018
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7009
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7000

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