Norsuaveoline - Compound Card

Norsuaveoline

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Norsuaveoline

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Indole Alkaloid
Canonical Smiles CCc1cncc2c1C[C@@H]1N[C@H]2Cc2c1[nH]c1c2cccc1
InChI InChI=1S/C19H19N3/c1-2-11-9-20-10-15-13(11)7-18-19-14(8-17(15)21-18)12-5-3-4-6-16(12)22-19/h3-6,9-10,17-18,21-22H,2,7-8H2,1H3/t17-,18-/m0/s1
InChIKey BLVJRRBSOKQTFO-ROUUACIJSA-N
Formula C19H19N3
HBA 2
HBD 2
MW 289.38
Rotatable Bonds 1
TPSA 40.71
LogP 3.61
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.32
Exact Mass 289.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Rauvolfia caffra Apocynaceae Plantae 947877

Showing of synonyms

  • Bitombo AN, Zintchem AAA, et al. (2022). Antimicrobial and cytotoxic activities of indole alkaloids and other constituents from the stem barks of Rauvolfia caffra Sond (Apocynaceae). Natural product research,2022, 36(6), 1467-1475. [View] [PubMed]
Pubchem: 10957193
Nmrshiftdb2: 60062239

No compound-protein relationship available.

Structure

SMILES: c1cccc2[nH]c(c3c12)C4Cc5c(C(C3)N4)cncc5

Level: 0

Mol. Weight: 289.38 g/mol

Antimicrobial
Cytotoxic

Absorption

Caco-2 (logPapp)
-5.21
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.67
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.33

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.29
Plasma Protein Binding
71.06
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
5.59
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.08
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.58
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.99
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
-0.99
Rat (Acute)
3.09
Rat (Chronic Oral)
1.59
Fathead Minnow
4.22
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
418.76
Hydration Free Energy
-10.01
Log(D) at pH=7.4
3.06
Log(P)
2.82
Log S
-3.5
Log(Vapor Pressure)
-9.24
Melting Point
224.61
pKa Acid
17.05
pKa Basic
7.64
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.9218
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9042
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.9016
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 3 0.9008
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.8997
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8985
Prostaglandin E synthase 2 Q9N0A4 PGES2_MACFA Macaca fascicularis 3 0.8877
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8846
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.8786
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.8766
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.8711
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8673
Cytochrome P450 2C19 P33261 CP2CJ_HUMAN Homo sapiens 3 0.8620
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8539
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.8493
Casein kinase I isoform delta P48730 KC1D_HUMAN Homo sapiens 3 0.8414
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8403
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.8398
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.8343
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8273
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8262
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8253
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8249
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8231
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.8178
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8145
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8112
Endolysin P00720 ENLYS_BPT4 Enterobacteria phage T4 3 0.8094
E3 ubiquitin-protein ligase Mdm2 Q00987 MDM2_HUMAN Homo sapiens 3 0.8085
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.8081
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.8073
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.8058
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.8038
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8022
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8021
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8015
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8011
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7986
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7943
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7917
Casein kinase I isoform delta P48730 KC1D_HUMAN Homo sapiens 3 0.7894
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7883
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7857
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7833
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7823
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7774
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7771
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7771
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7763
Toll-like receptor 8 Q9NR97 TLR8_HUMAN Homo sapiens 3 0.7760
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7756
Progesterone receptor P06401 PRGR_HUMAN Homo sapiens 3 0.7754
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7730
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7727
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7695
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7663
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7659
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7658
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7652
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 3 0.7630
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 4 0.7625
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform O35904 PK3CD_MOUSE Mus musculus 3 0.7593
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7586
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 3 0.7577
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.7561
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7548
Tyrosine-protein kinase HCK P08631 HCK_HUMAN Homo sapiens 3 0.7548
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7530
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7528
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7515
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 3 0.7513
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7501
E3 ubiquitin-protein ligase Mdm2 P56273 MDM2_XENLA Xenopus laevis 3 0.7492
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7487
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 3 0.7485
Abscisic acid receptor PYL1 Q8VZS8 PYL1_ARATH Arabidopsis thaliana 3 0.7485
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7427
Casein kinase I isoform delta P48730 KC1D_HUMAN Homo sapiens 3 0.7426
glutaryl-CoA dehydrogenase (ETF) Q3JP94 Q3JP94_BURP1 Burkholderia pseudomallei 3 0.7424
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7422
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7402
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial Q15119 PDK2_HUMAN Homo sapiens 3 0.7388
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7378
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7371
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 4 0.7368
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7344
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7313
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7307
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7296
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7288
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7267
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7259
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7254
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7240
Metallo-beta-lactamase type 2 P52699 BLAB_SERMA Serratia marcescens 3 0.7237
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 2 0.7225
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 3 0.7204
Thyroxine-binding globulin P05543 THBG_HUMAN Homo sapiens 3 0.7200
Histamine N-methyltransferase P50135 HNMT_HUMAN Homo sapiens 3 0.7196
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 4 0.7191
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7191
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 3 0.7187
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7176
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 2 0.7175
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7173
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 4 0.7168
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7163
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7156
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7149
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7129
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7123
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 3 0.7119
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7118
Cholesterol 24-hydroxylase Q9Y6A2 CP46A_HUMAN Homo sapiens 3 0.7116
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7116
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 2 0.7115
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7103
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7098
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7072
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7063
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 4 0.7056
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7053
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7053
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7051
Beta-lactamase P00811 AMPC_ECOLI Escherichia coli 3 0.7050
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7041
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7039
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7028
Ribonuclease 4 P15468 RNAS4_PIG Sus scrofa 2 0.7028
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 3 0.7018
Mandelate racemase P11444 MANR_PSEPU Pseudomonas putida 3 0.7011
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.7010
Terminal oxygenase component of carbazole Q84II6 Q84II6_JANS3 Janthinobacterium sp 3 0.7002

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