Structure

Physi-Chem Properties

Molecular Weight:  155.07
Volume:  146.437
LogP:  -3.186
LogD:  -1.514
LogS:  -0.875
# Rotatable Bonds:  3
TPSA:  92.0
# H-Bond Aceptor:  5
# H-Bond Donor:  4
# Rings:  1
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.541
Synthetic Accessibility Score:  3.192
Fsp3:  0.333
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.56
MDCK Permeability:  2.077493627439253e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.067
Human Intestinal Absorption (HIA):  0.014
20% Bioavailability (F20%):  0.001
30% Bioavailability (F30%):  0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.86
Plasma Protein Binding (PPB):  8.2584228515625%
Volume Distribution (VD):  0.486
Pgp-substrate:  96.71338653564453%

ADMET: Metabolism

CYP1A2-inhibitor:  0.012
CYP1A2-substrate:  0.123
CYP2C19-inhibitor:  0.046
CYP2C19-substrate:  0.059
CYP2C9-inhibitor:  0.013
CYP2C9-substrate:  0.59
CYP2D6-inhibitor:  0.018
CYP2D6-substrate:  0.054
CYP3A4-inhibitor:  0.057
CYP3A4-substrate:  0.044

ADMET: Excretion

Clearance (CL):  9.116
Half-life (T1/2):  0.886

ADMET: Toxicity

hERG Blockers:  0.07
Human Hepatotoxicity (H-HT):  0.068
Drug-inuced Liver Injury (DILI):  0.027
AMES Toxicity:  0.017
Rat Oral Acute Toxicity:  0.164
Maximum Recommended Daily Dose:  0.019
Skin Sensitization:  0.815
Carcinogencity:  0.018
Eye Corrosion:  0.004
Eye Irritation:  0.086
Respiratory Toxicity:  0.098

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Similar NPs/Drugs  

  Natural Product: NPC18223

Natural Product ID:  NPC18223
Common Name*:   D-Histidine
IUPAC Name:   (2R)-2-amino-3-(1H-imidazol-5-yl)propanoic acid
Synonyms:   D-His; D-Histamine; D-Histidine
Standard InCHIKey:  HNDVDQJCIGZPNO-RXMQYKEDSA-N
Standard InCHI:  InChI=1S/C6H9N3O2/c7-5(6(10)11)1-4-2-8-3-9-4/h2-3,5H,1,7H2,(H,8,9)(H,10,11)/t5-/m1/s1
SMILES:  C(c1cnc[nH]1)[C@H](C(=O)O)N
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL104875
PubChem CID:   71083
6971048
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0000265] Carboxylic acids and derivatives
        • [CHEMONTID:0000013] Amino acids, peptides, and analogues
          • [CHEMONTID:0000347] Amino acids and derivatives
            • [CHEMONTID:0000060] Alpha amino acids and derivatives
              • [CHEMONTID:0004311] Histidine and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/0003-9861(62)90112-1]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[11035032]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[11599360]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[12902239]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[13835567]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[14389294]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[1449509]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[14607989]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[15375647]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[15744050]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[16850348]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[17439666]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota n.a. seed n.a. PMID[21381697]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[22031445]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[2405251]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[24305546]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[24678285]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[24733517]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[24831709]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[24981409]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[2687322]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[3289762]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[4266242]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[4616942]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[5764336]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[6306574]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[767332]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[7929110]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[8017107]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[8798704]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[8852895]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[8971708]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. PMID[9748245]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO4582 Baphicacanthus cusia Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4593 Lagerstroemia indica Species Lythraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO433 Geranium sibiricum Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. Database[MetaboLights]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO4593 Lagerstroemia indica Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO433 Geranium sibiricum Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4582 Baphicacanthus cusia Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4593 Lagerstroemia indica Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4582 Baphicacanthus cusia Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7639 Senecio isatideus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO433 Geranium sibiricum Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2263 Croton megistocarpus Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21658 Saccharomyces cerevisiae Species Saccharomycetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14100 Persea kusanoi Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8075 Cacospongia scalaris Species Thorectidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4582 Baphicacanthus cusia Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4593 Lagerstroemia indica Species Lythraceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT1061 Individual Protein Carbonic anhydrase XIII Mus musculus KA = 0.09 uM PMID[515401]
NPT233 Individual Protein Carbonic anhydrase II Homo sapiens KA = 43.0 uM PMID[515401]
NPT233 Individual Protein Carbonic anhydrase II Homo sapiens KA = 43.0 uM PMID[515402]
NPT1143 Individual Protein Carbonic anhydrase VA Homo sapiens KA = 0.12 uM PMID[515403]
NPT1144 Individual Protein Carbonic anhydrase VB Homo sapiens KA = 4.38 uM PMID[515403]
NPT233 Individual Protein Carbonic anhydrase II Homo sapiens Ka = 43.0 uM PMID[515404]
NPT1063 Individual Protein Carbonic anhydrase VI Homo sapiens Ka = 13.0 uM PMID[515404]
NPT233 Individual Protein Carbonic anhydrase II Homo sapiens KA = 43.0 uM PMID[515405]
NPT233 Individual Protein Carbonic anhydrase II Homo sapiens Ka = 43.0 uM PMID[515406]
NPT1145 Individual Protein Carbonic anhydrase Saccharomyces cerevisiae S288c Ka = 85.0 uM PMID[515406]
NPT233 Individual Protein Carbonic anhydrase II Homo sapiens Kcat = 2.7 10'6/s PMID[515407]
NPT1146 Individual Protein Carbonic anhydrase III Homo sapiens Kcat = 16.9 10'4/s PMID[515407]
NPT1062 Individual Protein Carbonic anhydrase IV Homo sapiens Kcat = 3.8 10'6/s PMID[515407]
NPT233 Individual Protein Carbonic anhydrase II Homo sapiens Ka = 43.0 uM PMID[515407]
NPT1146 Individual Protein Carbonic anhydrase III Homo sapiens Ka = 1.12 uM PMID[515407]
NPT1062 Individual Protein Carbonic anhydrase IV Homo sapiens Ka = 12.3 uM PMID[515407]
NPT233 Individual Protein Carbonic anhydrase II Homo sapiens KA = 43.0 uM PMID[515408]
NPT1146 Individual Protein Carbonic anhydrase III Homo sapiens KA = 1.12 uM PMID[515408]
NPT1062 Individual Protein Carbonic anhydrase IV Homo sapiens Kcat = 3.8 10'6/s PMID[515409]
NPT1147 Individual Protein Carbonic anhydrase 15 Mus musculus Kcat = 15.0 10'5/s PMID[515409]
NPT1062 Individual Protein Carbonic anhydrase IV Homo sapiens KA = 12.3 uM PMID[515409]
NPT1147 Individual Protein Carbonic anhydrase 15 Mus musculus KA = 14.1 uM PMID[515409]
NPT3157 Individual Protein Carbonic anhydrase 2 Cryptococcus neoformans var. grubii KA = 47.2 uM PMID[515410]
NPT1148 Individual Protein Carbonic anhydrase Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast) KA = 19.5 uM PMID[515410]
NPT1063 Individual Protein Carbonic anhydrase VI Homo sapiens KA = 13.0 uM PMID[515411]
NPT233 Individual Protein Carbonic anhydrase II Homo sapiens KA = 43.0 uM PMID[515411]
NPT233 Individual Protein Carbonic anhydrase II Homo sapiens Ka = 43.0 uM PMID[515412]
NPT1150 Individual Protein Carbonic anhydrase Methanobacterium thermoautotrophicum Ka = 57.0 uM PMID[515412]
NPT1145 Individual Protein Carbonic anhydrase Saccharomyces cerevisiae S288c Ka = 85.0 uM PMID[515412]
NPT1151 Individual Protein Carbonic anhydrase Candida glabrata CBS 138 Ka = 21.2 uM PMID[515412]
NPT233 Individual Protein Carbonic anhydrase II Homo sapiens KA = 43.0 uM PMID[515415]
NPT233 Individual Protein Carbonic anhydrase II Homo sapiens KA = 43.0 uM PMID[515416]
NPT233 Individual Protein Carbonic anhydrase II Homo sapiens KA = 43.0 uM PMID[515418]
NPT4793 Individual Protein Carbonic anhydrase Methanosarcina thermophila KA = 46.0 uM PMID[515418]
NPT233 Individual Protein Carbonic anhydrase II Homo sapiens KA = 43.0 uM PMID[515419]
NPT1157 Individual Protein L-type amino acid transporter 1 Homo sapiens IC50 = 460000.0 nM PMID[515420]
NPT1157 Individual Protein L-type amino acid transporter 1 Homo sapiens Inhibition = 33.0 % PMID[515420]
NPT1157 Individual Protein L-type amino acid transporter 1 Homo sapiens Activity = 78.0 % PMID[515420]
NPT21975 NUCLEIC-ACID Hairpin ribozyme RNA n.a. K obs = 0.0085 n.a. PMID[515400]
NPT21975 NUCLEIC-ACID Hairpin ribozyme RNA n.a. K obs = 0.026 n.a. PMID[515400]
NPT947 Individual Protein Carbonic anhydrase I Homo sapiens KA = 0.09 uM PMID[515401]
NPT947 Individual Protein Carbonic anhydrase I Homo sapiens KA = 0.09 uM PMID[515402]
NPT955 Individual Protein Carbonic anhydrase VII Homo sapiens KA = 0.71 uM PMID[515402]
NPT954 Individual Protein Carbonic anhydrase XIV Homo sapiens KA = 2.37 uM PMID[515402]
NPT947 Individual Protein Carbonic anhydrase I Homo sapiens Ka = 0.09 uM PMID[515404]
NPT947 Individual Protein Carbonic anhydrase I Homo sapiens KA = 0.09 uM PMID[515405]
NPT948 Individual Protein Carbonic anhydrase IX Homo sapiens KA = 12.5 uM PMID[515405]
NPT949 Individual Protein Carbonic anhydrase XII Homo sapiens KA = 24.7 uM PMID[515405]
NPT2 Others Unspecified Ka = 57.0 uM PMID[515406]
NPT947 Individual Protein Carbonic anhydrase I Homo sapiens Kcat = 9.1 10'5/s PMID[515407]
NPT947 Individual Protein Carbonic anhydrase I Homo sapiens Ka = 0.09 uM PMID[515407]
NPT947 Individual Protein Carbonic anhydrase I Homo sapiens KA = 0.09 uM PMID[515408]
NPT2 Others Unspecified KA = 57.0 uM PMID[515408]
NPT2 Others Unspecified KA = 46.0 uM PMID[515408]
NPT2 Others Unspecified KA = 73.0 uM PMID[515408]
NPT2 Others Unspecified KA = 26.0 uM PMID[515411]
NPT947 Individual Protein Carbonic anhydrase I Homo sapiens KA = 0.09 uM PMID[515411]
NPT197 Protein-Protein Interaction Menin/Histone-lysine N-methyltransferase MLL Homo sapiens Potency = 39810.7 nM PMID[515413]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 14125.4 nM PMID[515414]
NPT947 Individual Protein Carbonic anhydrase I Homo sapiens KA = 0.09 uM PMID[515415]
NPT2 Others Unspecified KA = 0.012 uM PMID[515415]
NPT2 Others Unspecified KA = 0.09 uM PMID[515416]
NPT2 Others Unspecified KA = 0.012 uM PMID[515416]
NPT947 Individual Protein Carbonic anhydrase I Homo sapiens KA = 0.09 uM PMID[515416]
NPT2 Others Unspecified KA = 18.1 uM PMID[515417]
NPT947 Individual Protein Carbonic anhydrase I Homo sapiens KA = 0.09 uM PMID[515418]
NPT2 Others Unspecified KA = 0.086 uM PMID[515418]
NPT2 Others Unspecified Kcat = 2.16 10'6/s PMID[515418]
NPT947 Individual Protein Carbonic anhydrase I Homo sapiens KA = 0.09 uM PMID[515419]
NPT2 Others Unspecified KA = 4.13 uM PMID[515419]
NPT21652 SINGLE PROTEIN Carbonic anhydrase-like protein, putative Trypanosoma cruzi (strain CL Brener) KA = 7.54 uM PMID[515419]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 5.32 % PMID[515421]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 11.9 % PMID[515422]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 0.7 % PMID[515423]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM PMID[515424]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM PMID[515424]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC18223 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC237812
0.9766 High Similarity NPC185903
0.9766 High Similarity NPC286696
0.96 High Similarity NPC235501
0.9398 High Similarity NPC327477
0.9375 High Similarity NPC126634
0.9141 High Similarity NPC25465
0.9091 High Similarity NPC210947
0.8846 High Similarity NPC470138
0.8828 High Similarity NPC180462
0.8759 High Similarity NPC174020
0.8582 High Similarity NPC470140
0.8472 Intermediate Similarity NPC60537
0.8394 Intermediate Similarity NPC470139
0.8385 Intermediate Similarity NPC15566
0.7891 Intermediate Similarity NPC327613
0.7612 Intermediate Similarity NPC470142
0.76 Intermediate Similarity NPC111132
0.7483 Intermediate Similarity NPC470141
0.748 Intermediate Similarity NPC155498
0.7052 Intermediate Similarity NPC313504
0.7031 Intermediate Similarity NPC187191
0.7031 Intermediate Similarity NPC326248
0.6944 Remote Similarity NPC243319
0.6905 Remote Similarity NPC9639
0.6846 Remote Similarity NPC273327
0.65 Remote Similarity NPC282531
0.6389 Remote Similarity NPC201900
0.6242 Remote Similarity NPC8590
0.6173 Remote Similarity NPC238945
0.6159 Remote Similarity NPC246193
0.6145 Remote Similarity NPC477118
0.6139 Remote Similarity NPC74306
0.6139 Remote Similarity NPC323244
0.6139 Remote Similarity NPC315642
0.6127 Remote Similarity NPC313547
0.6125 Remote Similarity NPC197068
0.6111 Remote Similarity NPC477120
0.608 Remote Similarity NPC477119
0.6074 Remote Similarity NPC293163
0.6071 Remote Similarity NPC124276
0.6019 Remote Similarity NPC328924
0.6 Remote Similarity NPC477417
0.6 Remote Similarity NPC473646
0.6 Remote Similarity NPC477419
0.5965 Remote Similarity NPC472790
0.596 Remote Similarity NPC144223
0.5942 Remote Similarity NPC59314
0.5939 Remote Similarity NPC282247
0.5892 Remote Similarity NPC210123
0.589 Remote Similarity NPC68938
0.589 Remote Similarity NPC278549
0.5845 Remote Similarity NPC69843
0.5838 Remote Similarity NPC54981
0.5833 Remote Similarity NPC41958
0.5794 Remote Similarity NPC171393
0.5794 Remote Similarity NPC295452
0.5765 Remote Similarity NPC33229
0.5753 Remote Similarity NPC63433
0.5739 Remote Similarity NPC290959
0.5714 Remote Similarity NPC237936
0.5705 Remote Similarity NPC252603
0.5699 Remote Similarity NPC54537
0.5698 Remote Similarity NPC110500
0.5698 Remote Similarity NPC149155
0.5698 Remote Similarity NPC203468
0.5697 Remote Similarity NPC42483
0.5696 Remote Similarity NPC262926
0.5692 Remote Similarity NPC473376
0.5685 Remote Similarity NPC476524
0.5685 Remote Similarity NPC71238
0.5676 Remote Similarity NPC62749
0.5674 Remote Similarity NPC476099
0.5667 Remote Similarity NPC267885
0.566 Remote Similarity NPC61198
0.566 Remote Similarity NPC320818
0.5659 Remote Similarity NPC40530
0.5659 Remote Similarity NPC314281
0.5646 Remote Similarity NPC148385
0.5644 Remote Similarity NPC177996
0.5644 Remote Similarity NPC147983
0.5621 Remote Similarity NPC321052
0.5621 Remote Similarity NPC207633
0.5604 Remote Similarity NPC248041
0.5604 Remote Similarity NPC283219
0.5604 Remote Similarity NPC126709

  Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC18223 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
1.0 High Similarity NPD9133 Approved
0.9531 High Similarity NPD9628 Approved
0.9466 High Similarity NPD9183 Clinical (unspecified phase)
0.9318 High Similarity NPD1451 Approved
0.9037 High Similarity NPD9627 Approved
0.8828 High Similarity NPD300 Approved
0.8472 Intermediate Similarity NPD2180 Approved
0.8403 Intermediate Similarity NPD1731 Clinical (unspecified phase)
0.8356 Intermediate Similarity NPD3697 Discontinued
0.8356 Intermediate Similarity NPD2604 Approved
0.8333 Intermediate Similarity NPD875 Clinical (unspecified phase)
0.8133 Intermediate Similarity NPD3130 Discontinued
0.8028 Intermediate Similarity NPD5342 Clinical (unspecified phase)
0.7785 Intermediate Similarity NPD3108 Clinical (unspecified phase)
0.7769 Intermediate Similarity NPD9132 Discontinued
0.7658 Intermediate Similarity NPD3105 Discontinued
0.76 Intermediate Similarity NPD8862 Approved
0.76 Intermediate Similarity NPD8861 Approved
0.76 Intermediate Similarity NPD8859 Approved
0.7436 Intermediate Similarity NPD5768 Phase 2
0.7181 Intermediate Similarity NPD566 Approved
0.7181 Intermediate Similarity NPD568 Approved
0.7181 Intermediate Similarity NPD567 Approved
0.7067 Intermediate Similarity NPD3706 Clinical (unspecified phase)
0.695 Remote Similarity NPD1389 Clinical (unspecified phase)
0.695 Remote Similarity NPD1388 Phase 1
0.695 Remote Similarity NPD1390 Phase 1
0.6944 Remote Similarity NPD9081 Clinical (unspecified phase)
0.6875 Remote Similarity NPD1807 Clinical (unspecified phase)
0.6631 Remote Similarity NPD8261 Discontinued
0.6612 Remote Similarity NPD3497 Clinical (unspecified phase)
0.6543 Remote Similarity NPD7465 Suspended
0.649 Remote Similarity NPD576 Discontinued
0.6478 Remote Similarity NPD3708 Phase 2
0.6409 Remote Similarity NPD8641 Approved
0.623 Remote Similarity NPD8113 Phase 2
0.6221 Remote Similarity NPD3347 Clinical (unspecified phase)
0.6194 Remote Similarity NPD1808 Phase 1
0.6185 Remote Similarity NPD1037 Clinical (unspecified phase)
0.6173 Remote Similarity NPD8271 Discontinued
0.6139 Remote Similarity NPD582 Approved
0.6139 Remote Similarity NPD1117 Clinical (unspecified phase)
0.6139 Remote Similarity NPD8292 Phase 2
0.6129 Remote Similarity NPD1249 Clinical (unspecified phase)
0.6066 Remote Similarity NPD459 Clinical (unspecified phase)
0.6065 Remote Similarity NPD1120 Approved
0.6065 Remote Similarity NPD1121 Approved
0.6056 Remote Similarity NPD7245 Approved
0.6056 Remote Similarity NPD7246 Clinical (unspecified phase)
0.6039 Remote Similarity NPD209 Clinical (unspecified phase)
0.6037 Remote Similarity NPD7842 Phase 2
0.6032 Remote Similarity NPD8629 Discontinued
0.6012 Remote Similarity NPD276 Clinical (unspecified phase)
0.6 Remote Similarity NPD536 Clinical (unspecified phase)
0.5976 Remote Similarity NPD1335 Approved
0.5964 Remote Similarity NPD1029 Clinical (unspecified phase)
0.5964 Remote Similarity NPD1030 Approved
0.5964 Remote Similarity NPD1027 Approved
0.5959 Remote Similarity NPD9360 Approved
0.5942 Remote Similarity NPD8837 Clinical (unspecified phase)
0.5915 Remote Similarity NPD8954 Approved
0.5915 Remote Similarity NPD8955 Approved
0.5914 Remote Similarity NPD460 Discontinued
0.5912 Remote Similarity NPD1118 Discontinued
0.5876 Remote Similarity NPD7834 Approved
0.5876 Remote Similarity NPD8410 Clinical (unspecified phase)
0.5875 Remote Similarity NPD1431 Approved
0.5875 Remote Similarity NPD1430 Approved
0.5871 Remote Similarity NPD547 Clinical (unspecified phase)
0.5865 Remote Similarity NPD8119 Discontinued
0.5855 Remote Similarity NPD515 Phase 1
0.5854 Remote Similarity NPD775 Approved
0.5846 Remote Similarity NPD7981 Discontinued
0.5839 Remote Similarity NPD2618 Phase 1
0.5817 Remote Similarity NPD870 Clinical (unspecified phase)
0.5799 Remote Similarity NPD1303 Phase 1
0.5799 Remote Similarity NPD695 Discontinued
0.5769 Remote Similarity NPD2138 Approved
0.5769 Remote Similarity NPD545 Clinical (unspecified phase)
0.5769 Remote Similarity NPD2137 Approved
0.5765 Remote Similarity NPD3405 Phase 3
0.5753 Remote Similarity NPD757 Phase 3
0.5743 Remote Similarity NPD237 Clinical (unspecified phase)
0.574 Remote Similarity NPD510 Phase 1
0.5731 Remote Similarity NPD1290 Phase 2
0.573 Remote Similarity NPD2009 Clinical (unspecified phase)
0.5729 Remote Similarity NPD8458 Clinical (unspecified phase)
0.5724 Remote Similarity NPD579 Clinical (unspecified phase)
0.5714 Remote Similarity NPD340 Approved
0.5714 Remote Similarity NPD8186 Phase 1
0.5714 Remote Similarity NPD8185 Discontinued
0.5714 Remote Similarity NPD341 Approved
0.5705 Remote Similarity NPD76 Approved
0.5705 Remote Similarity NPD9288 Approved
0.5705 Remote Similarity NPD307 Approved
0.5705 Remote Similarity NPD9292 Approved
0.5705 Remote Similarity NPD9289 Approved
0.57 Remote Similarity NPD8488 Clinical (unspecified phase)
0.5698 Remote Similarity NPD482 Approved
0.5697 Remote Similarity NPD9724 Phase 1
0.5696 Remote Similarity NPD194 Clinical (unspecified phase)
0.5686 Remote Similarity NPD245 Suspended
0.5676 Remote Similarity NPD1368 Approved
0.5665 Remote Similarity NPD1042 Clinical (unspecified phase)
0.566 Remote Similarity NPD252 Clinical (unspecified phase)
0.5657 Remote Similarity NPD6545 Clinical (unspecified phase)
0.5652 Remote Similarity NPD2096 Phase 2
0.5652 Remote Similarity NPD2457 Phase 2
0.5652 Remote Similarity NPD2091 Phase 2
0.5652 Remote Similarity NPD2456 Phase 2
0.5644 Remote Similarity NPD3353 Approved
0.5641 Remote Similarity NPD9632 Phase 3
0.5637 Remote Similarity NPD8105 Discontinued
0.5625 Remote Similarity NPD8075 Discontinued
0.5622 Remote Similarity NPD7557 Clinical (unspecified phase)
0.5616 Remote Similarity NPD7980 Clinical (unspecified phase)
0.5613 Remote Similarity NPD1355 Clinical (unspecified phase)
0.5613 Remote Similarity NPD1354 Approved
0.5613 Remote Similarity NPD1356 Approved
0.5608 Remote Similarity NPD996 Phase 2
0.5608 Remote Similarity NPD994 Phase 2
0.5605 Remote Similarity NPD9650 Phase 3
0.5602 Remote Similarity NPD7531 Clinical (unspecified phase)

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data