Microcarpine - Compound Card

Microcarpine

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Microcarpine

Structure
Zoomed Structure
  • Family: Plantae - Papaveraceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Isoquinoline Alkaloid
Canonical Smiles COc1c(OC)ccc2c1C(=O)O/C/2=C\c1c(CCN(C)C)cc2c(c1O)OCO2
InChI InChI=1S/C22H23NO7/c1-23(2)8-7-12-9-17-21(29-11-28-17)19(24)14(12)10-16-13-5-6-15(26-3)20(27-4)18(13)22(25)30-16/h5-6,9-10,24H,7-8,11H2,1-4H3/b16-10-
InChIKey JUQYFQUYIWWESV-YBEGLDIGSA-N
Formula C22H23NO7
HBA 8
HBD 1
MW 413.43
Rotatable Bonds 6
TPSA 86.69
LogP 2.91
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.32
Exact Mass 413.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Fumaria parviflora Fumariaceae Plantae 1464625
2 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]
Pubchem: 5833496
Nmrshiftdb2: 60032695

No compound-protein relationship available.

Structure

SMILES: O1COc(c12)ccc(c2)C=C3OC(=O)c(c34)cccc4

Level: 1

Mol. Weight: 413.43 g/mol

Structure

SMILES: C=C1OC(=O)c(c12)cccc2

Level: 0

Mol. Weight: 413.43 g/mol

Structure

SMILES: O1COc(c12)cccc2

Level: 0

Mol. Weight: 413.43 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.94
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.810
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.85

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.880
Plasma Protein Binding
46.94
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
16.630
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.060
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.710
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
9.780
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-43.820
Rat (Acute)
2.320
Rat (Chronic Oral)
1.920
Fathead Minnow
5.260
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
463.940
Hydration Free Energy
-4.410
Log(D) at pH=7.4
3.170
Log(P)
2.1
Log S
-3.36
Log(Vapor Pressure)
-9.61
Melting Point
151.16
pKa Acid
7.09
pKa Basic
8.09
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 0.9355
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.9328
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9208
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9197
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.9186
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.9059
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9012
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9003
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 3 0.8986
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8785
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8732
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8680
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8635
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.8622
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 4 0.8547
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8494
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8416
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.8410
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8405
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8383
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8372
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8357
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8256
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8222
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8183
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8142
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8140
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8130
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8129
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8097
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8091
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8035
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8034
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8026
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8025
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7981
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7979
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7955
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7946
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7897
Beta-secretase 2 Q9Y5Z0 BACE2_HUMAN Homo sapiens 3 0.7883
Ribosome-inactivating protein 3 P25891 RIP3_MAIZE Zea mays 3 0.7851
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7846
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7806
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7805
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7770
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7747
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7744
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7729
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7724
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7716
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7716
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7708
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7685
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7636
IOMT 3 Q06YR3 Q06YR3_MEDTR Medicago truncatula 3 0.7618
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7596
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7590
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7572
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7562
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7552
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7502
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7472
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7470
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7448
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7439
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7420
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7405
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7391
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 4 0.7381
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7376
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7338
Beta-hexosaminidase Q9KU37 NAGZ_VIBCH Vibrio cholerae serotype O1 3 0.7333
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7326
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7326
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7303
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7291
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7284
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7283
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7273
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7273
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7258
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7228
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7216
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7212
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7210
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7200
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7189
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7187
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7185
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7185
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7177
PTS system glucose-specific EIIA component P69783 PTGA_ECOLI Escherichia coli 3 0.7173
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7169
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7158
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7153
16S rRNA (adenine(1408)-N(1))-methyltransferase A8C927 NPMA_ECOLX Escherichia coli 3 0.7140
Adenylosuccinate synthetase, chloroplastic Q96529 PURA_ARATH Arabidopsis thaliana 4 0.7119
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7106
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7093
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7085
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7082
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7066
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7064
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7038
Antibiotic ABC transporter, ATP-binding protein, putative Q9X1C3 Q9X1C3_THEMA Thermotoga maritima 3 0.7034
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7028
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7023
GTPase HRas P01112 RASH_HUMAN Homo sapiens 4 0.7020
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7020
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7012
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7009
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7007

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