N-methylstylopine - Compound Card

N-methylstylopine

Select a section from the left sidebar

N-methylstylopine

Structure
Zoomed Structure
  • Family: Plantae - Papaveraceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Isoquinoline Alkaloid
Canonical Smiles C[N@+]12CCc3c([C@]2(C)Cc2c(C1)c1OCOc1cc2)cc1c(c3)OCO1
InChI InChI=1S/C21H22NO4/c1-21-9-14-3-4-17-20(26-12-23-17)15(14)10-22(21,2)6-5-13-7-18-19(8-16(13)21)25-11-24-18/h3-4,7-8H,5-6,9-12H2,1-2H3/q+1/t21-,22-/m0/s1
InChIKey SVTHGHHVRVFAOR-VXKWHMMOSA-N
Formula C21H22NO4+
HBA 4
HBD 0
MW 352.41
Rotatable Bonds 0
TPSA 36.92
LogP 3.12
Number Rings 6
Number Aromatic Rings 2
Heavy Atom Count 26
Formal Charge 1
Fraction CSP3 0.43
Exact Mass 352.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Fumaria parviflora Papaveraceae Plantae 1464625

Showing of synonyms

  • Elsaid M.B, Elnaggar D.M, et al. (2022). Production of isoquinoline alkaloids from the in vitro conserved Fumaria parviflora and their in vitro wound healing activity. Natural product research, 2022, 36(10), 2575-2579. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: O1COc(c12)ccc3c2C[NH+]4C(C3)c5c(CC4)cc6c(c5)OCO6

Level: 0

Mol. Weight: 352.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.13
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.54
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.85

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.97
Plasma Protein Binding
71.31
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
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
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.02
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.47
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.86
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
7.93
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
-9.57
Rat (Acute)
2.83
Rat (Chronic Oral)
0.43
Fathead Minnow
4.45
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
455.47
Hydration Free Energy
-6.28
Log(D) at pH=7.4
2.52
Log(P)
0.03
Log S
-1.13
Log(Vapor Pressure)
-10.56
Melting Point
247.97
pKa Acid
10.09
pKa Basic
4.07
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9741
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.9359
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9208
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.9174
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9159
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9035
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8976
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8838
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8708
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8557
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.8515
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.8473
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8461
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.8419
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8351
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8342
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.8276
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8273
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8124
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8086
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.8049
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.8002
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7980
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7969
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7958
S-norcoclaurine synthase Q67A25 NCS_THLFG Thalictrum flavum subsp. glaucum 3 0.7840
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7821
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7807
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7806
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7791
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7765
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7740
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7731
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7724
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7722
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7715
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7702
Putative cytochrome P450 Q70AS3 Q70AS3_STRPE Streptomyces peucetius 3 0.7694
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7599
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7588
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7562
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7562
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7561
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 3 0.7546
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7545
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7519
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 2 0.7504
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7504
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7501
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7494
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7487
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7484
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7441
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7431
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 3 0.7395
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 3 0.7380
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7374
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7368
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7360
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7359
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7346
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7331
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7327
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 2 0.7313
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7287
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 3 0.7285
Chitinase Q54276 Q54276_SERMA Serratia marcescens 2 0.7278
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7274
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7273
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7263
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7239
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7224
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7223
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7207
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7198
Thymidylate synthase P45352 TYSY_RAT Rattus norvegicus 2 0.7196
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7193
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7189
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7188
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7184
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7183
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q3JRA0 ISPF_BURP1 Burkholderia pseudomallei 3 0.7176
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7169
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7164
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 2 0.7163
F420-dependent NADP reductase O29370 FNO_ARCFU Archaeoglobus fulgidus 3 0.7161
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7150
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 2 0.7149
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7135
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7131
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7126
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7120
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7112
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7109
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7107
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7101
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7098
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7098
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7089
Beta-ketoacyl-[acyl-carrier-protein] synthase III Q820T1 FABH_ENTFA Enterococcus faecalis 2 0.7089
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7089
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7088
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 2 0.7081
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7073
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7068
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 2 0.7068
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 2 0.7059
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7058
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 2 0.7050
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7049
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7021
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7018
UDP-N-acetylglucosamine 1-carboxyvinyltransferase P33038 MURA_ENTCC Enterobacter cloacae subsp. cloacae 2 0.7006
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7002
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 2 0.7002

Download SDF