(+)-naucleofficine D - Compound Card

(+)-naucleofficine D

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(+)-naucleofficine D

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Monoterpenoid Indole Alkaloid
Canonical Smiles C/C=C/1\CO/C(=C\O)/[C@@H]2[C@H]1C[C@@H]1N(C2=O)CCc2c1[nH]c1c2cccc1
InChI InChI=1S/C21H22N2O3/c1-2-12-11-26-18(10-24)19-15(12)9-17-20-14(7-8-23(17)21(19)25)13-5-3-4-6-16(13)22-20/h2-6,10,15,17,19,22,24H,7-9,11H2,1H3/b12-2+,18-10-/t15-,17-,19-/m0/s1
InChIKey NWDOFPSTQNBQHB-HOAFHCTMSA-N
Formula C21H22N2O3
HBA 3
HBD 2
MW 350.42
Rotatable Bonds 0
TPSA 65.56
LogP 3.61
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.38
Exact Mass 350.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Nauclea latifolia Rubiaceae Plantae 43573

Showing of synonyms

  • Kezetas Bankeu JJ, Kenou Kagho DU, et al. (2019). Constituents from Nauclea latifolia with Anti-Haemophilus influenzae Type b Inhibitory Activities.. Journal of natural products,2019, 82(9), 2580-2585. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C=C1OCC(=C)C(C2)C1C(=O)N(CC3)C2c(c3c45)[nH]c4cccc5

Level: 0

Mol. Weight: 350.42 g/mol

Antibacterial

Absorption

Caco-2 (logPapp)
-4.99
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.79
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.81

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.44
Plasma Protein Binding
64.65
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-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
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
10.44
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
-0.5
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.43
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.34
Micronucleos
Toxic
NR-AhR
Toxic
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
-9.21
Rat (Acute)
3.18
Rat (Chronic Oral)
2.2
Fathead Minnow
4.24
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
455.05
Hydration Free Energy
-7.76
Log(D) at pH=7.4
2.22
Log(P)
2.43
Log S
-3.85
Log(Vapor Pressure)
-10.26
Melting Point
215.22
pKa Acid
9.28
pKa Basic
6.26
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9167
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9145
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.9083
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.9018
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8907
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8857
Nitric oxide synthase, inducible P35228 NOS2_HUMAN Homo sapiens 3 0.8831
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8724
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8698
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8686
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8547
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8512
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8509
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8480
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8325
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.8325
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.8262
Retinol-binding protein 4 P18902 RET4_BOVIN Bos taurus 3 0.8225
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.8072
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8058
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8042
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.8025
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8003
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 O88703 HCN2_MOUSE Mus musculus 3 0.7995
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7958
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7947
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7890
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7873
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7870
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.7869
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7867
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7866
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7849
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 2 0.7806
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7772
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7769
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7745
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7739
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7704
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7701
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7691
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7673
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7658
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7652
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7651
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7649
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7647
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7608
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7586
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7585
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7584
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7540
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7526
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7514
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7507
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7506
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7494
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7494
Hexokinase-4 P35557 HXK4_HUMAN Homo sapiens 3 0.7488
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase O33877 FABA_PSEAE Pseudomonas aeruginosa 3 0.7478
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7465
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7463
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7462
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7456
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7453
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7447
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7446
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7436
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7433
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7397
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7387
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7386
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7381
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7379
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7372
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7367
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7363
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7357
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7303
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7285
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7273
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7271
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7261
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7258
Alcohol dehydrogenase 1C P00326 ADH1G_HUMAN Homo sapiens 2 0.7248
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7236
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7227
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7217
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7207
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.7205
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7198
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7179
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7175
Lactoylglutathione lyase Q04760 LGUL_HUMAN Homo sapiens 2 0.7174
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7174
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7172
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7171
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 2 0.7159
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 2 0.7156
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7154
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7143
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7140
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 2 0.7137
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 2 0.7136
Beta-hexosaminidase Q9KU37 NAGZ_VIBCH Vibrio cholerae serotype O1 3 0.7124
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7096
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7093
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7075
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7075
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7065
Chorismate pyruvate-lyase P26602 UBIC_ECOLI Escherichia coli 2 0.7063
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 2 0.7046
Purine nucleoside phosphorylase, putative A2E7Y6 A2E7Y6_TRIVA Trichomonas vaginalis 2 0.7042
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7038
Adenosylmethionine-8-amino-7-oxononanoate aminotransferase P12995 BIOA_ECOLI Escherichia coli 2 0.7032
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7031
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 3 0.7029
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7029
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7017
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7010
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7006
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7000

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