Dihydro-joubertiamine - Compound Card

Dihydro-joubertiamine

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Dihydro-joubertiamine

Structure
Zoomed Structure
  • Family: Plantae - Mesembryanthemaceae-Aizoaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Mesemberine Alkaloid
Canonical Smiles CN(CCC1(CCC(=O)CC1)c1ccc(cc1)O)C
InChI InChI=1S/C16H23NO2/c1-17(2)12-11-16(9-7-15(19)8-10-16)13-3-5-14(18)6-4-13/h3-6,18H,7-12H2,1-2H3
InChIKey JKAPXMKAOLCRPY-UHFFFAOYSA-N
Formula C16H23NO2
HBA 3
HBD 1
MW 261.37
Rotatable Bonds 4
TPSA 40.54
LogP 2.72
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 19
Formal Charge 0
Fraction CSP3 0.56
Exact Mass 261.17
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]
Pubchem: 14219251
Nmrshiftdb2: 70068434

No compound-protein relationship available.

Structure

SMILES: O=C1CCC(CC1)c2ccccc2

Level: 1

Mol. Weight: 261.37 g/mol

Structure

SMILES: O=C1CCCCC1

Level: 0

Mol. Weight: 261.37 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 261.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.74
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.68
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.88

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.25
Plasma Protein Binding
31.82
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
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
15.55
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.6
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.02
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.0
Micronucleos
Safe
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
3.11
Rat (Acute)
2.43
Rat (Chronic Oral)
1.63
Fathead Minnow
3.94
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
335.69
Hydration Free Energy
-10.16
Log(D) at pH=7.4
0.33
Log(P)
1.56
Log S
-1.97
Log(Vapor Pressure)
-6.27
Melting Point
152.71
pKa Acid
8.88
pKa Basic
8.24
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8907
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 3 0.8840
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8746
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8742
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8684
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8663
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.8635
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8632
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8585
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8565
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8559
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.8493
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.8429
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8407
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8321
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8314
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 3 0.8261
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8241
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8225
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8221
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8209
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8152
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8127
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.8115
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8089
Beta-galactoside-specific lectin 1 P81446 ML1_VISAL Viscum album 3 0.7959
Histidinol dehydrogenase P06988 HISX_ECOLI Escherichia coli 3 0.7959
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7896
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 3 0.7813
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7783
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7763
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7705
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7702
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7657
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 2 0.7633
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7601
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7507
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7489
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7486
4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase 1, chloroplastic P49235 HGGL1_MAIZE Zea mays 2 0.7477
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7457
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7451
Probable bifunctional SAT/APS kinase O67174 SATC_AQUAE Aquifex aeolicus 3 0.7432
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7427
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7420
Class 10 plant pathogenesis-related protein 2B Q9LLQ2 P102B_LUPLU Lupinus luteus 2 0.7409
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7405
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7403
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7388
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7372
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7368
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7366
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7356
Ribonuclease TTHA0252 Q5SLP1 RNSE_THET8 Thermus thermophilus 3 0.7355
Phosphoglycerate kinase 1 P00558 PGK1_HUMAN Homo sapiens 3 0.7354
Uridine phosphorylase P0A1F6 UDP_SALTY Salmonella typhimurium 3 0.7352
Large structural protein Q91L20 Q91L20_9MONO Human metapneumovirus 3 0.7351
RNA-directed RNA polymerase lambda-3 P0CK31 RDRP_REOVD Reovirus type 3 3 0.7347
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7340
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7329
Cobalt-precorrin-4 C(11)-methyltransferase O87696 CBIF_BACME Priestia megaterium 3 0.7327
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7324
DNA (cytosine-5)-methyltransferase 1 Q9AXT8 H32_ARATH Zea mays 3 0.7320
16S rRNA (guanine(1405)-N(7))-methyltransferase Q763K9 Q763K9_ECOLX Escherichia coli 3 0.7303
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7299
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7286
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7276
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7273
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7268
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7266
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7258
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7256
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7252
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 2 0.7244
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 2 0.7240
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7236
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7235
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7235
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7233
Galactoside O-acetyltransferase P07464 THGA_ECOLI Escherichia coli 3 0.7228
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7227
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7225
Putative S-adenosyl-L-methionine-dependent methyltransferase ML2640 Q9CCZ4 Y2640_MYCLE Mycobacterium leprae 3 0.7223
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7218
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7211
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7209
L-seryl-tRNA(Sec) kinase Q58933 PSTK_METJA Methanocaldococcus jannaschii 2 0.7204
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7194
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7186
Biotin carboxylase P43873 ACCC_HAEIN Haemophilus influenzae 2 0.7181
Leucine--tRNA ligase P07813 SYL_ECOLI Escherichia coli 3 0.7180
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7179
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7175
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7169
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7155
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7147
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 O88703 HCN2_MOUSE Mus musculus 2 0.7143
Polyamine aminopropyltransferase Q5SK28 SPEE_THET8 Thermus thermophilus 3 0.7140
(R)-S-adenosyl-L-methionine hydrolase O58212 O58212_PYRHO Pyrococcus horikoshii OT3 3 0.7136
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7135
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7126
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7125
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7122
Purine nucleoside phosphorylase Q9BMI9 Q9BMI9_SCHMA Schistosoma mansoni 3 0.7121
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 2 0.7116
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7108
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7106
Three-prime repair exonuclease 1 Q91XB0 TREX1_MOUSE Mus musculus 2 0.7105
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7099
Receptor-interacting serine/threonine-protein kinase 1 Q13546 RIPK1_HUMAN Homo sapiens 3 0.7098
Myosin heavy chain, striated muscle P24733 MYS_ARGIR Argopecten irradians 3 0.7097
Adenylate cyclase P94182 P94182_9NOST Anabaena sp 3 0.7091
Angiotensin-converting enzyme P12821 ACE_HUMAN Homo sapiens 2 0.7091
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7091
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7086
Glycoside Hydrolase Family 13 Q65MI2 Q65MI2_BACLD Bacillus licheniformis 2 0.7085
Nucleoside diphosphate kinase Q5HFV4 NDK_STAAC Staphylococcus aureus 2 0.7083
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7080
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7071
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 2 0.7057
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7050
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 2 0.7048
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7042
Protein claret segregational P20480 NCD_DROME Drosophila melanogaster 2 0.7028
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7025
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7016
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 2 0.7014
Chaperone protein ClpB Q9RA63 CLPB_THET8 Thermus thermophilus 3 0.7013
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7010
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7008
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7006
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7005
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 2 0.7002

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