4,5-dihydro-4'-O-methylsceletenone - Compound Card

4,5-dihydro-4'-O-methylsceletenone

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4,5-dihydro-4'-O-methylsceletenone

Structure
Zoomed Structure
  • Family: Mesembryanthemaceae-Aizoaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Mesemberine Alkaloid
Canonical Smiles COc1ccc(cc1)[C@]12CCC(=O)C[C@@H]2N(CC1)C
InChI InChI=1S/C16H21NO2/c1-17-10-9-16(8-7-13(18)11-15(16)17)12-3-5-14(19-2)6-4-12/h3-6,15H,7-11H2,1-2H3/t15-,16-/m0/s1
InChIKey UENZJOLIHBPSCD-HOTGVXAUSA-N
Formula C16H21NO2
HBA 3
HBD 0
MW 259.35
Rotatable Bonds 2
TPSA 29.54
LogP 2.39
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.56
Exact Mass 259.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Mesembryanthemum cordifolium-Aptenia cordifolia Mesembryanthemaceae-Aizoaceae Plantae 3543

Showing of synonyms

  • Said A.A.E, Ali T.F.S, et al. (2021). Antidepressant potential of Mesembryanthemum cordifolium roots assisted by metabolomic analysis and virtual screening. Natural product research, 2021, 35(23), 5493-5497. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1CC(=O)CC(NCC2)C12c3ccccc3

Level: 1

Mol. Weight: 215.3 g/mol

Structure

SMILES: C1CNC(C12)CC(=O)CC2

Level: 0

Mol. Weight: 139.2 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.68
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.740
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.36

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.280
Plasma Protein Binding
49.88
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
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
9.860
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.570
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.030
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
8.030
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
0.680
Rat (Acute)
2.920
Rat (Chronic Oral)
1.500
Fathead Minnow
3.690
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
316.970
Hydration Free Energy
-8.710
Log(D) at pH=7.4
1.030
Log(P)
1.74
Log S
-1.49
Log(Vapor Pressure)
-6.04
Melting Point
128.24
pKa Acid
9.64
pKa Basic
8.23
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9714
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.9130
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8908
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8885
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8838
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8593
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8585
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8466
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.8192
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.8170
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 2 0.8074
Thymidylate synthase Q4JQW2 TYSY_VZVO Varicella-zoster virus 3 0.7856
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7786
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7632
Rho-associated protein kinase 1 Q13464 ROCK1_HUMAN Homo sapiens 3 0.7617
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7617
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7604
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7580
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7559
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7543
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7541
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7512
Beta-glucosidase Q8T0W7 Q8T0W7_9NEOP Neotermes koshunensis 3 0.7494
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7493
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7452
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7443
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7441
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7440
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 2 0.7440
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 2 0.7438
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7428
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 3 0.7423
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7409
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 3 0.7409
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7409
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7406
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7403
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7394
Indole-3-glycerol phosphate synthase P9WFX7 TRPC_MYCTU Mycobacterium tuberculosis 2 0.7386
Thymidylate synthase P13100 TYSY_PNECA Pneumocystis carinii 4 0.7382
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7380
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7374
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7373
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7372
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7367
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7361
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7346
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7345
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7344
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7341
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 2 0.7333
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7316
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7314
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7307
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 2 0.7303
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7302
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7298
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 2 0.7289
Nucleoside permease Q9KPL5 Q9KPL5_VIBCH Vibrio cholerae serotype O1 3 0.7288
Methionine--tRNA ligase P00959 SYM_ECOLI Escherichia coli 3 0.7281
Myosin heavy chain kinase A P42527 MHCKA_DICDI Dictyostelium discoideum 2 0.7271
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7270
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7270
Adenosine kinase Q9TVW2 ADK_TOXGO Toxoplasma gondii 2 0.7266
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7260
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7257
Ribosome-inactivating protein 3 P25891 RIP3_MAIZE Zea mays 2 0.7251
Biotin carboxylase P43873 ACCC_HAEIN Haemophilus influenzae 2 0.7251
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7241
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7229
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7229
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7224
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7223
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 2 0.7220
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 2 0.7219
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7217
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7214
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7214
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7212
Orotidine 5'-phosphate decarboxylase O26232 PYRF_METTH Methanothermobacter thermautotrophicus 3 0.7209
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 2 0.7209
Beta-glucosidase 12 B8AVF0 BGL12_ORYSI Oryza sativa subsp. indica 2 0.7209
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7206
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7201
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7200
L-seryl-tRNA(Sec) kinase Q58933 PSTK_METJA Methanocaldococcus jannaschii 2 0.7198
Nucleoside diphosphate kinase A5J299 A5J299_PENVA Penaeus vannamei 3 0.7196
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7177
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 2 0.7170
BMP-2-inducible protein kinase Q9NSY1 BMP2K_HUMAN Homo sapiens 2 0.7169
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7166
Aminopeptidase N P15145 AMPN_PIG Sus scrofa 2 0.7165
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7147
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7131
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7130
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7123
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7122
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7119
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7119
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7118
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7110
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 O88703 HCN2_MOUSE Mus musculus 2 0.7109
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7104
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7104
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 2 0.7100
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7099
Uridine phosphorylase P0A1F6 UDP_SALTY Salmonella typhimurium 3 0.7098
Disintegrin and metalloproteinase domain-containing protein 17 P78536 ADA17_HUMAN Homo sapiens 2 0.7098
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7097
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7096
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 2 0.7085
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7073
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7072
Matrix metalloproteinase-20 O60882 MMP20_HUMAN Homo sapiens 2 0.7069
Ribonuclease 4 P15468 RNAS4_PIG Sus scrofa 2 0.7065
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 2 0.7063
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7058
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7056
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7051
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 2 0.7051
Adenosine deaminase P56658 ADA_BOVIN Bos taurus 3 0.7046
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7045
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7039
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7032
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 2 0.7032
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7028
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 2 0.7027
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 2 0.7022
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 2 0.7020
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7019
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7015
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7011
Three-prime repair exonuclease 1 Q91XB0 TREX1_MOUSE Mus musculus 2 0.7002

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