Nauclefidine - Compound Card

Nauclefidine

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Nauclefidine

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Indole Alkaloid
Canonical Smiles [NH3+]Cc1nnc([n-]1)c1ccc(cc1)Br
InChI InChI=1S/C9H8BrN4/c10-7-3-1-6(2-4-7)9-12-8(5-11)13-14-9/h1-4H,5,11H2/q-1/p+1
InChIKey DSSQLHQBWKAKTM-UHFFFAOYSA-O
Formula C9H9BrN4
HBA 2
HBD 1
MW 253.1
Rotatable Bonds 2
TPSA 67.52
LogP 0.61
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 14
Formal Charge 0
Fraction CSP3 0.11
Exact Mass 252.0
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Mitragyna inermis Rubiaceae Plantae 170023

Showing of synonyms

  • Donfack E, Lenta B, et al. (2012). Naucleactonin D, an Indole Alkaloid and other Chemical Constituents from Roots and Fruits of Mitragyna inermis. Zeitschrift für Naturforschung B. 2012, 67(11), 1159-1165. [View]
Pubchem: 52370094

No compound-protein relationship available.

Structure

SMILES: n1nc[n-]c1-c2ccccc2

Level: 1

Mol. Weight: 253.1 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 253.1 g/mol

Structure

SMILES: c1[n-]cnn1

Level: 0

Mol. Weight: 253.1 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.83
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.170
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.03

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.490
Plasma Protein Binding
55.33
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
6.570
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.430
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.550
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.000
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
4.150
Rat (Acute)
2.530
Rat (Chronic Oral)
1.230
Fathead Minnow
4.470
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
301.130
Hydration Free Energy
-12.900
Log(D) at pH=7.4
1.530
Log(P)
-0.18
Log S
-1.38
Log(Vapor Pressure)
-6.3
Melting Point
245.15
pKa Acid
7.55
pKa Basic
0.81
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.9582
Cyclin-dependent kinase 6 Q00534 CDK6_HUMAN Homo sapiens 3 0.9418
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.9374
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.9280
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.9242
Biphenyl-2,3-diol 1,2-dioxygenase P47228 BPHC_PARXL Paraburkholderia xenovorans 3 0.9238
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.9216
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.9214
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.9212
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.9167
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.9162
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.9092
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.9044
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.9033
D(3) dopamine receptor P35462 DRD3_HUMAN Homo sapiens 3 0.9007
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.8835
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.8789
Catalase-peroxidase 2 O59651 KATG2_HALMA Haloarcula marismortui 3 0.8689
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.8622
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 3 0.8587
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.8540
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.8529
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 3 0.8508
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.8458
Purine nucleoside phosphorylase Q8I3X4 Q8I3X4_PLAF7 Plasmodium falciparum 3 0.8286
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.8238
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8213
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 3 0.8188
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.8154
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.8061
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.8014
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.7979
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7975
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7947
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 3 0.7938
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7934
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7910
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7862
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7858
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7845
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7837
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7825
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7825
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7802
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7780
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7776
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7775
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7759
Cathepsin S P25774 CATS_HUMAN Homo sapiens 2 0.7739
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7737
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7734
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7731
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7725
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 2 0.7693
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7687
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7643
Prostaglandin G/H synthase 2 Q05769 PGH2_MOUSE Mus musculus 2 0.7642
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7634
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7629
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7623
Putative cytochrome P450 Q70AS3 Q70AS3_STRPE Streptomyces peucetius 3 0.7606
Tyrosine-protein kinase ITK/TSK Q08881 ITK_HUMAN Homo sapiens 3 0.7605
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7602
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7602
Glutamate receptor 2 P42262 GRIA2_HUMAN Homo sapiens 2 0.7597
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 2 0.7596
Thymidylate synthase ThyA P9WFR9 TYSY_MYCTU Mycobacterium tuberculosis 3 0.7574
Collagenase 3 P45452 MMP13_HUMAN Homo sapiens 3 0.7551
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.7544
Lactoylglutathione lyase Q04760 LGUL_HUMAN Homo sapiens 2 0.7538
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.7511
Acyl-coenzyme A synthetase ACSM2A, mitochondrial Q08AH3 ACS2A_HUMAN Homo sapiens 2 0.7511
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 2 0.7508
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7498
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7477
Lipoprotein E P26093 HEL_HAEIN Haemophilus influenzae 3 0.7468
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 2 0.7468
Carbonic anhydrase 4 P22748 CAH4_HUMAN Homo sapiens 3 0.7467
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 2 0.7437
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7435
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 2 0.7420
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 2 0.7401
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7399
Dihydrofolate reductase Q81R22 Q81R22_BACAN Bacillus anthracis 3 0.7397
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7391
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7367
Hexokinase-4 P35557 HXK4_HUMAN Homo sapiens 3 0.7353
Estrogen receptor beta Q92731 ESR2_HUMAN Homo sapiens 3 0.7352
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7342
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7340
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase O33877 FABA_PSEAE Pseudomonas aeruginosa 2 0.7337
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7317
Transthyretin P02766 TTHY_HUMAN Homo sapiens 3 0.7315
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7307
Prostaglandin G/H synthase 1 P05979 PGH1_SHEEP Ovis aries 2 0.7307
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7292
Dihydrofolate reductase P00374 DYR_HUMAN Homo sapiens 3 0.7275
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7266
Dihydrofolate reductase P00381 DYR_LACCA Lacticaseibacillus casei 3 0.7262
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7251
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7244
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7234
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B Q13370 PDE3B_HUMAN Homo sapiens 3 0.7228
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7226
Dihydrofolate reductase type 1 from Tn4003 P13955 DYRA_STAAU Staphylococcus aureus 3 0.7226
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7224
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7206
Thymidylate synthase P45352 TYSY_RAT Rattus norvegicus 2 0.7203
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 2 0.7193
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 2 0.7191
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 3 0.7190
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7185
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 3 0.7184
Dihydrofolate reductase O30463 O30463_MYCAV Mycobacterium avium 3 0.7182
Beta-2 adrenergic receptor P07550 ADRB2_HUMAN Homo sapiens 2 0.7164
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7162
Odorant binding protein ASP1 Q8WRW5 Q8WRW5_APIME Apis mellifera 2 0.7144
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7139
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 2 0.7134
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 2 0.7129
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 2 0.7124
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7122
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 2 0.7106
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 2 0.7106
Cholinesterase P06276 CHLE_HUMAN Homo sapiens 2 0.7100
D-alanine--D-alanine ligase Q5HEB7 DDL_STAAC Staphylococcus aureus 3 0.7093
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7083
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 2 0.7072
Sepiapterin reductase Q64105 SPRE_MOUSE Mus musculus 3 0.7063
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7061
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7060
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7059
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 2 0.7056
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7043
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7030
Dihydrofolate reductase Q81R22 Q81R22_BACAN Bacillus anthracis 3 0.7025
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7010
Tyrosine 3-monooxygenase P04177 TY3H_RAT Rattus norvegicus 3 0.7007
Estrogen receptor beta Q92731 ESR2_HUMAN Homo sapiens 3 0.7003

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