Naucleidinal dimethyl acetal - Compound Card

Naucleidinal dimethyl acetal

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Naucleidinal dimethyl acetal

Structure
Zoomed Structure
  • Family: Plantae - Rubiaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Monoterpenoid Indole Alkaloid
Canonical Smiles COC(C[C@H]1OC=C2[C@H]([C@@H]1C=O)C[C@@H]1N(C2=O)CCc2c1[nH]c1c2cccc1)OC
InChI InChI=1S/C23H26N2O5/c1-28-21(29-2)10-20-16(11-26)15-9-19-22-14(13-5-3-4-6-18(13)24-22)7-8-25(19)23(27)17(15)12-30-20/h3-6,11-12,15-16,19-21,24H,7-10H2,1-2H3/t15-,16-,19-,20+/m0/s1
InChIKey OUAFRZDEMWOGGD-CPLUKWAASA-N
Formula C23H26N2O5
HBA 5
HBD 1
MW 410.47
Rotatable Bonds 5
TPSA 80.86
LogP 2.72
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.48
Exact Mass 410.18
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: c1cccc2[nH]c(c3c12)C4N(CC3)C(=O)C=5C(C4)CCOC5

Level: 0

Mol. Weight: 410.47 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.03
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.870
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.99

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.540
Plasma Protein Binding
40.63
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-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
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.390
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.030
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.940
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.310
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
Toxic
T. Pyriformis
-71.480
Rat (Acute)
3.370
Rat (Chronic Oral)
1.620
Fathead Minnow
4.200
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
476.080
Hydration Free Energy
-2.740
Log(D) at pH=7.4
2.070
Log(P)
1.84
Log S
-3.62
Log(Vapor Pressure)
-9.34
Melting Point
192.94
pKa Acid
8.09
pKa Basic
5.9
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.9224
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.9180
Nitric oxide synthase, inducible P35228 NOS2_HUMAN Homo sapiens 3 0.9171
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.9153
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8963
Integrin alpha-L P20701 ITAL_HUMAN Homo sapiens 3 0.8846
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8728
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8672
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8666
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8656
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8627
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8588
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8587
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.8555
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 3 0.8488
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8458
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.8453
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8360
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8277
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8164
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8056
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.8045
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8027
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7997
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7974
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 3 0.7955
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7908
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7877
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7874
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7872
17-beta-hydroxysteroid dehydrogenase 14 Q9BPX1 DHB14_HUMAN Homo sapiens 2 0.7870
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7859
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7795
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7785
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7784
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7770
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7767
rRNA methylase Q8DSS3 Q8DSS3_STRMU Streptococcus mutans serotype c 2 0.7760
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7752
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7727
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7724
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7722
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7720
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7710
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 O88703 HCN2_MOUSE Mus musculus 3 0.7699
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7693
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7692
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7662
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7649
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7622
Class 10 plant pathogenesis-related protein 2B Q9LLQ2 P102B_LUPLU Lupinus luteus 2 0.7610
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7598
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7594
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7588
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7552
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7543
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7536
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7527
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7522
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7520
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7519
Lethal factor P15917 LEF_BACAN Bacillus anthracis 3 0.7485
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7475
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7470
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7439
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7427
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7420
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7411
Epoxide hydrolase Q41415 Q41415_SOLTU Solanum tuberosum 3 0.7396
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7392
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7378
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7376
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7368
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 3 0.7364
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7359
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7359
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7356
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7347
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 2 0.7346
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7334
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7314
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase O33877 FABA_PSEAE Pseudomonas aeruginosa 3 0.7310
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7300
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7271
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7269
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7265
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7262
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 2 0.7261
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7246
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7239
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7238
Probable esterase KAI2 Q9SZU7 KAI2_ARATH Arabidopsis thaliana 2 0.7233
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7231
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 3 0.7227
Beta-2 adrenergic receptor P07550 ADRB2_HUMAN Homo sapiens 3 0.7219
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7211
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7194
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 2 0.7194
Lactoylglutathione lyase Q04760 LGUL_HUMAN Homo sapiens 2 0.7186
Casein kinase I isoform gamma-2 P78368 KC1G2_HUMAN Homo sapiens 3 0.7176
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7166
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7158
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 2 0.7152
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7149
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7144
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 2 0.7141
Polymerase acidic protein Q5EP34 Q5EP34_9INFA Influenza A virus 2 0.7141
Pantothenate kinase P9WPA7 COAA_MYCTU Mycobacterium tuberculosis 3 0.7140
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 2 0.7137
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7126
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7125
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7116
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7111
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7105
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7098
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7097
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7090
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7088
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 2 0.7088
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7087
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 2 0.7077
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 3 0.7071
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7066
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 2 0.7058
Adenosylmethionine-8-amino-7-oxononanoate aminotransferase P12995 BIOA_ECOLI Escherichia coli 2 0.7052
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7049
Lethal factor P15917 LEF_BACAN Bacillus anthracis 3 0.7042
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 2 0.7036
NPC intracellular cholesterol transporter 1 O15118 NPC1_HUMAN Homo sapiens 2 0.7030
Steroid 17-alpha-hydroxylase/17,20 lyase P05093 CP17A_HUMAN Homo sapiens 2 0.7030
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 2 0.7030
Purine nucleoside phosphorylase, putative A2E7Y6 A2E7Y6_TRIVA Trichomonas vaginalis 2 0.7029
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7028
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7026
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7021
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7018
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7012

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