O-methylpapyramine - Compound Card

O-methylpapyramine

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O-methylpapyramine

Structure
Zoomed Structure
  • Family: Plantae - Amaryllidaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Amaryllidaceae Alkaloid
Canonical Smiles CO[C@@H]1C=C[C@]23C(C1)N(CC2)C(c1c3cc(OC)c(c1)OC)OC
InChI InChI=1S/C19H25NO4/c1-21-12-5-6-19-7-8-20(17(19)9-12)18(24-4)13-10-15(22-2)16(23-3)11-14(13)19/h5-6,10-12,17-18H,7-9H2,1-4H3/t12-,17?,18?,19+/m1/s1
InChIKey BFKPTPKHPWTRAO-ZUBVFAKQSA-N
Formula C19H25NO4
HBA 5
HBD 0
MW 331.41
Rotatable Bonds 4
TPSA 40.16
LogP 2.65
Number Rings 4
Number Aromatic Rings 1
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.58
Exact Mass 331.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Narcissus species Amaryllidaceae Plantae 54843

Showing of synonyms

  • Shawky E, Abou-Donia AH, et al. (2015). HPTLC and GC/MS study of Amaryllidaceae alkaloids of two Narcissus species. Chemistry and Biodiversity,2015,12(8),1184-1199. [View] [PubMed]
Pubchem: 162984881
Nmrshiftdb2: 80005091

No compound-protein relationship available.

Structure

SMILES: C1=CCCC(C123)N(CC2)Cc4c3cccc4

Level: 0

Mol. Weight: 331.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.64
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.570
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.75

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.650
Plasma Protein Binding
18.79
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
Non-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
3.340
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.770
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.350
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
9.050
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
-3.320
Rat (Acute)
2.970
Rat (Chronic Oral)
1.500
Fathead Minnow
4.240
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
347.570
Hydration Free Energy
-7.020
Log(D) at pH=7.4
2.040
Log(P)
1.89
Log S
-1.15
Log(Vapor Pressure)
-6.24
Melting Point
131.0
pKa Acid
11.02
pKa Basic
7.29
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9805
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9805
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9538
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9538
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9321
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9321
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9136
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9136
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.9115
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.9115
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8964
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8964
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8664
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8664
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8653
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8653
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8612
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8612
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8545
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8545
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.8511
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.8511
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8416
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8416
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8350
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8350
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8331
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8331
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8244
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8244
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8222
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8222
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8220
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8220
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8112
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.8112
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7874
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7874
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 3 0.7836
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 3 0.7836
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7724
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7724
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7611
Steroid 21-hydroxylase P08686 CP21A_HUMAN Homo sapiens 3 0.7611
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7600
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7600
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7579
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7579
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7509
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7509
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7409
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7409
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7362
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7362
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7351
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7351
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7306
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7306
Cytochrome P450 2A6 P11509 CP2A6_HUMAN Homo sapiens 3 0.7293
Cytochrome P450 2A6 P11509 CP2A6_HUMAN Homo sapiens 3 0.7293
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7281
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7281
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7222
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7222
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7206
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7206
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7200
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7200
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7200
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7200
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7199
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7199
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7183
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7183
Thymidylate synthase Q4JQW2 TYSY_VZVO Varicella-zoster virus 3 0.7150
Thymidylate synthase Q4JQW2 TYSY_VZVO Varicella-zoster virus 3 0.7150
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7120
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7120
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7019
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7019
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7015
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7015

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