N-methylstylopine - Compound Card

N-methylstylopine

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N-methylstylopine

Structure
Zoomed Structure
  • Family: Plantae - Fumariaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Isoquinoline Alkaloid
Canonical Smiles C[N@@+]12CCc3c([C@H]2Cc2c(C1)c1OCOc1cc2)cc1c(c3)OCO1
InChI InChI=1S/C20H20NO4/c1-21-5-4-13-7-18-19(24-10-23-18)8-14(13)16(21)6-12-2-3-17-20(15(12)9-21)25-11-22-17/h2-3,7-8,16H,4-6,9-11H2,1H3/q+1/t16-,21-/m1/s1
InChIKey GBUUKFRQPCPYPW-IIBYNOLFSA-N
Formula C20H20NO4+
HBA 4
HBD 0
MW 338.38
Rotatable Bonds 0
TPSA 36.92
LogP 2.94
Number Rings 6
Number Aromatic Rings 2
Heavy Atom Count 25
Formal Charge 1
Fraction CSP3 0.4
Exact Mass 338.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Fumaria parviflora Fumariaceae 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]
Pubchem: 14335855

No compound-protein relationship available.

Structure

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

Level: 0

Mol. Weight: 338.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.16
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.57
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.83

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.19
Plasma Protein Binding
68.42
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
14.47
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.23
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.01
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
6.23
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
-3.92
Rat (Acute)
2.6
Rat (Chronic Oral)
0.72
Fathead Minnow
4.39
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
463.82
Hydration Free Energy
-5.64
Log(D) at pH=7.4
2.36
Log(P)
0.08
Log S
-1.14
Log(Vapor Pressure)
-11.33
Melting Point
252.59
pKa Acid
10.66
pKa Basic
2.87
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9610
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.9457
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.9259
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9205
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.9186
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8965
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8942
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8931
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8815
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8677
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8581
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8554
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8533
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8466
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8396
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.8367
S-norcoclaurine synthase Q67A25 NCS_THLFG Thalictrum flavum subsp. glaucum 3 0.8215
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8208
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.8205
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8120
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.8051
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7973
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7966
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7938
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7925
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7908
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7898
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7886
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7878
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7863
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7829
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 2 0.7789
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7696
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.7674
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7625
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 2 0.7620
Beta-adrenergic receptor kinase 1 P25098 ARBK1_HUMAN Homo sapiens 3 0.7569
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7556
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7548
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 2 0.7534
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7523
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7521
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7503
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7490
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7467
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7458
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 2 0.7445
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7444
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 2 0.7416
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7416
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7412
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7378
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7377
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 2 0.7376
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7369
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 3 0.7337
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7332
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7329
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7325
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7319
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7309
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7303
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7301
Putative cytochrome P450 Q70AS3 Q70AS3_STRPE Streptomyces peucetius 3 0.7296
Rifampin ADP-ribosyl transferase A0QRS5 A0QRS5_MYCS2 Mycolicibacterium smegmatis155) 3 0.7293
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7284
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7280
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 3 0.7267
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7254
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7254
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7245
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7243
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.7237
3-hydroxybenzoate 4-monooxygenase Q6SSJ6 MOBA_COMTE Comamonas testosteroni 2 0.7227
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7218
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7201
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 2 0.7193
Prostaglandin G/H synthase 1 P05979 PGH1_SHEEP Ovis aries 3 0.7185
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7181
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7176
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7167
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7157
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7154
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7153
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7148
Protein mono-ADP-ribosyltransferase PARP15 Q460N3 PAR15_HUMAN Homo sapiens 3 0.7127
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7115
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7112
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 3 0.7110
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7101
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7099
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7089
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7087
Histidine kinase 4 Q9C5U0 AHK4_ARATH Arabidopsis thaliana 3 0.7078
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7063
Ferric enterobactin-binding periplasmic protein FepB P0AEL6 FEPB_ECOLI Escherichia coli 3 0.7060
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 2 0.7057
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7053
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7038
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7030
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7030
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7016
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7016
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7012
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 2 0.7010
Ribosome-inactivating protein 3 P25891 RIP3_MAIZE Zea mays 2 0.7009

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