Structure

Physi-Chem Properties

Molecular Weight:  268.12
Volume:  244.381
LogP:  -1.557
LogD:  -0.771
LogS:  -1.232
# Rotatable Bonds:  2
TPSA:  112.13
# H-Bond Aceptor:  8
# H-Bond Donor:  4
# Rings:  3
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.537
Synthetic Accessibility Score:  4.72
Fsp3:  0.636
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.381
MDCK Permeability:  6.024963568052044e-06
Pgp-inhibitor:  0.001
Pgp-substrate:  0.998
Human Intestinal Absorption (HIA):  0.35
20% Bioavailability (F20%):  0.988
30% Bioavailability (F30%):  0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.406
Plasma Protein Binding (PPB):  13.603092193603516%
Volume Distribution (VD):  1.638
Pgp-substrate:  86.97960662841797%

ADMET: Metabolism

CYP1A2-inhibitor:  0.018
CYP1A2-substrate:  0.047
CYP2C19-inhibitor:  0.022
CYP2C19-substrate:  0.431
CYP2C9-inhibitor:  0.002
CYP2C9-substrate:  0.488
CYP2D6-inhibitor:  0.005
CYP2D6-substrate:  0.174
CYP3A4-inhibitor:  0.008
CYP3A4-substrate:  0.095

ADMET: Excretion

Clearance (CL):  2.556
Half-life (T1/2):  0.467

ADMET: Toxicity

hERG Blockers:  0.014
Human Hepatotoxicity (H-HT):  0.913
Drug-inuced Liver Injury (DILI):  0.965
AMES Toxicity:  0.943
Rat Oral Acute Toxicity:  0.088
Maximum Recommended Daily Dose:  0.967
Skin Sensitization:  0.111
Carcinogencity:  0.906
Eye Corrosion:  0.003
Eye Irritation:  0.013
Respiratory Toxicity:  0.487

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General Info & Identifiers & Properties  
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Similar NPs/Drugs  

  Natural Product: NPC74306

Natural Product ID:  NPC74306
Common Name*:   Pentostatin
IUPAC Name:   (8R)-3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7,8-dihydro-4H-imidazo[4,5-d][1,3]diazepin-8-ol
Synonyms:   CI-825; Nipent; PD-81565; Pentostatin
Standard InCHIKey:  FPVKHBSQESCIEP-JQCXWYLXSA-N
Standard InCHI:  InChI=1S/C11H16N4O4/c16-3-8-6(17)1-9(19-8)15-5-14-10-7(18)2-12-4-13-11(10)15/h4-9,16-18H,1-3H2,(H,12,13)/t6-,7+,8+,9+/m0/s1
SMILES:  C1[C@@H]([C@@H](CO)O[C@H]1n1cnc2[C@@H](CN=CNc12)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1580
PubChem CID:   439693
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0001979] Imidazodiazepines

*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
NPO24105 Artemisia iwayomogi Species Asteraceae Eukaryota n.a. aerial part n.a. DOI[10.1002/hlca.201300170.]
NPO22210 Allium ampeloprasum Species Amaryllidaceae Eukaryota n.a. n.a. 1996-Sep PMID[10352947]
NPO17888 Myxococcus xanthus Species Myxococcaceae Bacteria n.a. n.a. n.a. PMID[12141877]
NPO24105 Artemisia iwayomogi Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[12735688]
NPO17888 Myxococcus xanthus Species Myxococcaceae Bacteria n.a. n.a. n.a. PMID[14575429]
NPO22210 Allium ampeloprasum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. PMID[15877880]
NPO23720 Taxus wallichiana Species Taxaceae Eukaryota needles Himalayan n.a. PMID[16480866]
NPO22210 Allium ampeloprasum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. PMID[18460139]
NPO22210 Allium ampeloprasum Species Amaryllidaceae Eukaryota n.a. Northeastern Regional Plant Introduction Station at Geneva 1966, 1967, and 1968 crop seasons PMID[18460139]
NPO24105 Artemisia iwayomogi Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23510022]
NPO23720 Taxus wallichiana Species Taxaceae Eukaryota Stem Bark n.a. n.a. PMID[28240909]
NPO23720 Taxus wallichiana Species Taxaceae Eukaryota Roots n.a. n.a. PMID[28581744]
NPO17888 Myxococcus xanthus Species Myxococcaceae Bacteria n.a. n.a. n.a. PMID[31465225]
NPO23720 Taxus wallichiana Species Taxaceae Eukaryota n.a. n.a. n.a. PMID[7264680]
NPO22210 Allium ampeloprasum Species Amaryllidaceae Eukaryota n.a. n.a. Database[FooDB]
NPO22210 Allium ampeloprasum Species Amaryllidaceae Eukaryota Flower n.a. n.a. Database[FooDB]
NPO22210 Allium ampeloprasum Species Amaryllidaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO22210 Allium ampeloprasum Species Amaryllidaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO22210 Allium ampeloprasum Species Amaryllidaceae Eukaryota n.a. n.a. Database[FooDB]
NPO23720 Taxus wallichiana Species Taxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19994 Scutellaria viscidula Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22210 Allium ampeloprasum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18919 Helenium amarum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21175 Senecio retrorsus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17801 Drimia altissima Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18919 Helenium amarum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23431 Aconitum umbrosum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23720 Taxus wallichiana Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22210 Allium ampeloprasum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19994 Scutellaria viscidula Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21175 Senecio retrorsus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19994 Scutellaria viscidula Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23720 Taxus wallichiana Species Taxaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18919 Helenium amarum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24105 Artemisia iwayomogi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO19994 Scutellaria viscidula Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17801 Drimia altissima Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6439 Lithospermum carolinense Species Boraginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26544 Bolboschoenus maritimus Species Cyperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23981 Maytenus disticha Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24063 Evasterias retifera Species Asteriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23431 Aconitum umbrosum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23175 Streptomyces antibioticus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO19539 Uperoleia rugosa Species Myobatrachidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23686 Selinum tenuifolium Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9228.2 Narcissus pseudonarcissus subsp. radinganorum Subspecies Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18919 Helenium amarum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23781 Lemaireocereus stellatus Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21915 Diospyros chloroxylon Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23688 Lonicera nitida Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22028 Ligularia lankongensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24105 Artemisia iwayomogi Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23363 0dulisporium hinnuleum Species Xylariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23113 Garcinia neglecta Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23268 Xanthorrhoea reflexa Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21747 Sideritis glacialis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23720 Taxus wallichiana Species Taxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20290 Vernonia arkansana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16976 Phebalium rotundifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17888 Myxococcus xanthus Species Myxococcaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO21175 Senecio retrorsus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22210 Allium ampeloprasum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23611 Conyza pallidiflora Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13151.1 Pulsatilla vulgaris subsp. grandis Subspecies Ranunculaceae 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
NPT1754 Individual Protein Adenosine deaminase Bos taurus Ki = 0.0025 nM PMID[545987]
NPT3838 Individual Protein Adenosine deaminase Homo sapiens Ki = 0.1 nM PMID[545988]
NPT1754 Individual Protein Adenosine deaminase Bos taurus Ki = 0.001 nM PMID[545989]
NPT3838 Individual Protein Adenosine deaminase Homo sapiens Ki = 0.033 nM PMID[545990]
NPT1754 Individual Protein Adenosine deaminase Bos taurus REA = 2800000.0 n.a. PMID[545991]
NPT3838 Individual Protein Adenosine deaminase Homo sapiens Ki = 0.0025 nM PMID[545992]
NPT1754 Individual Protein Adenosine deaminase Bos taurus Ki = 0.001 nM PMID[545995]
NPT1754 Individual Protein Adenosine deaminase Bos taurus Ki = 0.01 nM PMID[545996]
NPT137 Cell Line L1210 Mus musculus IC50 = 1900.0 nM PMID[545997]
NPT137 Cell Line L1210 Mus musculus IC50 = 250.0 nM PMID[545997]
NPT3838 Individual Protein Adenosine deaminase Homo sapiens Ki = 0.0001 nM PMID[546003]
NPT3838 Individual Protein Adenosine deaminase Homo sapiens Ki = 0.5 nM PMID[546011]
NPT3838 Individual Protein Adenosine deaminase Homo sapiens Ki = 0.026 nM PMID[546011]
NPT2 Others Unspecified Potency n.a. 33491.5 nM PubChem BioAssay data set
NPT32 Organism Mus musculus Mus musculus Cmax = 12.2 ug.mL-1 PMID[545990]
NPT32 Organism Mus musculus Mus musculus AUC = 9500.0 ng.hr.mL-1 PMID[545990]
NPT32 Organism Mus musculus Mus musculus MST = 28.5 day PMID[545993]
NPT32 Organism Mus musculus Mus musculus MST = 34.0 day PMID[545993]
NPT32 Organism Mus musculus Mus musculus MST = 42.5 day PMID[545993]
NPT32 Organism Mus musculus Mus musculus MST = 34.0 day PMID[545998]
NPT32 Organism Mus musculus Mus musculus MST = 42.5 day PMID[545998]
NPT35 Others n.a. LogP = -1.1 n.a. PMID[546000]
NPT20596 PHENOTYPE Hepatotoxicity n.a. Composite Activity - Active = 0.0 n.a. PMID[546001]
NPT20596 PHENOTYPE Hepatotoxicity n.a. Composite Activity - Marginal = 0.0 n.a. PMID[546001]
NPT20596 PHENOTYPE Hepatotoxicity n.a. Alkaline Phosphatase Increase - Index Value = 0.0 n.a. PMID[546001]
NPT20596 PHENOTYPE Hepatotoxicity n.a. Alkaline Phosphatase Increase - Number of Reports < 4.0 n.a. PMID[546001]
NPT20596 PHENOTYPE Hepatotoxicity n.a. SGOT Increase - Index Value = 0.0 n.a. PMID[546001]
NPT20596 PHENOTYPE Hepatotoxicity n.a. SGOT Increase - Number of Reports < 4.0 n.a. PMID[546001]
NPT20596 PHENOTYPE Hepatotoxicity n.a. SGPT Increase - Index Value = 0.0 n.a. PMID[546001]
NPT20596 PHENOTYPE Hepatotoxicity n.a. SGPT Increase - Number of Reports < 4.0 n.a. PMID[546001]
NPT20596 PHENOTYPE Hepatotoxicity n.a. LDH Increase - Index Value = 0.0 n.a. PMID[546001]
NPT20596 PHENOTYPE Hepatotoxicity n.a. LDH Increase - Number of Reports < 4.0 n.a. PMID[546001]
NPT20596 PHENOTYPE Hepatotoxicity n.a. GGT Increase - Index Value = 0.0 n.a. PMID[546001]
NPT20596 PHENOTYPE Hepatotoxicity n.a. GGT Increase - Number of Reports < 4.0 n.a. PMID[546001]
NPT20596 PHENOTYPE Hepatotoxicity n.a. HepSE_bilirubinemia = 0.0 n.a. PMID[546002]
NPT20596 PHENOTYPE Hepatotoxicity n.a. HepSE_cholecystitis = 0.0 n.a. PMID[546002]
NPT20596 PHENOTYPE Hepatotoxicity n.a. HepSE_cholelithiasis = 0.0 n.a. PMID[546002]
NPT20596 PHENOTYPE Hepatotoxicity n.a. HepSE_cirrhosis = 0.0 n.a. PMID[546002]
NPT20596 PHENOTYPE Hepatotoxicity n.a. HepSE_elevated liver function tests = 1.0 n.a. PMID[546002]
NPT20596 PHENOTYPE Hepatotoxicity n.a. HepSE_hepatic failure = 0.0 n.a. PMID[546002]
NPT20596 PHENOTYPE Hepatotoxicity n.a. HepSE_hepatic necrosis = 0.0 n.a. PMID[546002]
NPT20596 PHENOTYPE Hepatotoxicity n.a. HepSE_hepatitis = 0.0 n.a. PMID[546002]
NPT20596 PHENOTYPE Hepatotoxicity n.a. HepSE_hepatomegaly = 0.0 n.a. PMID[546002]
NPT20596 PHENOTYPE Hepatotoxicity n.a. HepSE_jaundice = 0.0 n.a. PMID[546002]
NPT20596 PHENOTYPE Hepatotoxicity n.a. HepSE_liver disease = 1.0 n.a. PMID[546002]
NPT20596 PHENOTYPE Hepatotoxicity n.a. HepSE_liver fatty = 0.0 n.a. PMID[546002]
NPT20596 PHENOTYPE Hepatotoxicity n.a. HepSE_liver function tests abnormal = 1.0 n.a. PMID[546002]
NPT20596 PHENOTYPE Hepatotoxicity n.a. HepSE_Combined Scores = 3.0 n.a. PMID[546002]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Hepatotoxicity (moderate) = 16.0 n.a. PMID[546004]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Hepatotoxicity (moderate) = 81.3 % PMID[546004]
NPT2 Others Unspecified Hepatotoxicity (acute) = 1.0 n.a. PMID[546004]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Hepatotoxicity (acute) = 0.0 % PMID[546004]
NPT2 Others Unspecified Hepatotoxicity (cytolytic) = 1.0 n.a. PMID[546004]
NPT2 Others Unspecified Hepatotoxicity (choleostasis) = 0.0 n.a. PMID[546004]
NPT2 Others Unspecified Hepatotoxicity (severe hepatitis) = 2.0 n.a. PMID[546004]
NPT2 Others Unspecified Hepatotoxicity (chronic liver disease) = 0.0 n.a. PMID[546004]
NPT2 Others Unspecified Hepatotoxicity (cirrhosis) = 0.0 n.a. PMID[546004]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Hepatotoxicity (granulomatous hepatitis) = 0.0 n.a. PMID[546004]
NPT2 Others Unspecified Hepatotoxicity (association with vascular disease) = 0.0 n.a. PMID[546004]
NPT2 Others Unspecified Hepatotoxicity (steatosis) = 1.0 n.a. PMID[546004]
NPT2 Others Unspecified Hepatotoxicity (malignant tumour) = 0.0 n.a. PMID[546004]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Hepatotoxicity (benign tumour) = 0.0 n.a. PMID[546004]
NPT2 Others Unspecified AC50 n.a. 1000.0 nM PMID[546006]
NPT2 Others Unspecified Ac50 n.a. 1.0 uM PMID[546006]
NPT2 Others Unspecified AC50 n.a. 3548.1 nM PMID[546006]
NPT2 Others Unspecified Ac50 n.a. 3.548 uM PMID[546006]
NPT713 Individual Protein Bile salt export pump Homo sapiens IC50 > 133000.0 nM PMID[546007]
NPT605 Organism Homo sapiens Homo sapiens DILI_severity_class = 3.0 n.a. PMID[546008]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 3.17 % PMID[546009]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Hit score = 0.0932 n.a. PMID[546010]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 10.69 % PMID[546012]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 13.02 % PMID[546013]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -0.02 % PMID[546014]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = -0.07 % PMID[546015]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM PMID[546016]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM PMID[546016]
NPT27704 SINGLE PROTEIN Adenosine deaminase Plasmodium falciparum Ki = 8.2 nM PMID[546011]
NPT27704 SINGLE PROTEIN Adenosine deaminase Plasmodium falciparum Ki = 0.038 nM PMID[546011]

☑ 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 NPC74306 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 NPC315642
0.8741 High Similarity NPC262926
0.8676 High Similarity NPC61198
0.8456 Intermediate Similarity NPC324009
0.8417 Intermediate Similarity NPC30326
0.8394 Intermediate Similarity NPC319221
0.8369 Intermediate Similarity NPC186619
0.8322 Intermediate Similarity NPC317746
0.8264 Intermediate Similarity NPC64705
0.8264 Intermediate Similarity NPC232408
0.8252 Intermediate Similarity NPC211820
0.8252 Intermediate Similarity NPC251233
0.8252 Intermediate Similarity NPC318590
0.8194 Intermediate Similarity NPC177169
0.8194 Intermediate Similarity NPC89147
0.8194 Intermediate Similarity NPC274384
0.8143 Intermediate Similarity NPC320818
0.7704 Intermediate Similarity NPC327579
0.7703 Intermediate Similarity NPC107374
0.7703 Intermediate Similarity NPC21448
0.7703 Intermediate Similarity NPC156461
0.7651 Intermediate Similarity NPC164665
0.7651 Intermediate Similarity NPC189068
0.76 Intermediate Similarity NPC309832
0.76 Intermediate Similarity NPC269827
0.76 Intermediate Similarity NPC219313
0.7568 Intermediate Similarity NPC229974
0.7551 Intermediate Similarity NPC209525
0.7551 Intermediate Similarity NPC161659
0.7532 Intermediate Similarity NPC14590
0.75 Intermediate Similarity NPC239737
0.7468 Intermediate Similarity NPC321052
0.7451 Intermediate Similarity NPC326694
0.7451 Intermediate Similarity NPC150853
0.745 Intermediate Similarity NPC314152
0.7436 Intermediate Similarity NPC52238
0.7432 Intermediate Similarity NPC317821
0.7403 Intermediate Similarity NPC185991
0.7403 Intermediate Similarity NPC85689
0.7403 Intermediate Similarity NPC211025
0.7389 Intermediate Similarity NPC54320
0.7389 Intermediate Similarity NPC311197
0.7389 Intermediate Similarity NPC313754
0.7372 Intermediate Similarity NPC174802
0.7355 Intermediate Similarity NPC321814
0.7355 Intermediate Similarity NPC472816
0.732 Intermediate Similarity NPC121222
0.7308 Intermediate Similarity NPC130586
0.7308 Intermediate Similarity NPC212551
0.7308 Intermediate Similarity NPC164952
0.7308 Intermediate Similarity NPC302778
0.729 Intermediate Similarity NPC161224
0.7278 Intermediate Similarity NPC226245
0.7244 Intermediate Similarity NPC207633
0.7215 Intermediate Similarity NPC224076
0.7206 Intermediate Similarity NPC313547
0.717 Intermediate Similarity NPC316618
0.7134 Intermediate Similarity NPC328479
0.7073 Intermediate Similarity NPC261595
0.7055 Intermediate Similarity NPC323091
0.7051 Intermediate Similarity NPC136349
0.703 Intermediate Similarity NPC321458
0.703 Intermediate Similarity NPC324033
0.702 Intermediate Similarity NPC129756
0.7019 Intermediate Similarity NPC195140
0.6882 Remote Similarity NPC189261
0.6807 Remote Similarity NPC324484
0.6786 Remote Similarity NPC290959
0.6766 Remote Similarity NPC325906
0.6735 Remote Similarity NPC180462
0.6732 Remote Similarity NPC33996
0.6725 Remote Similarity NPC326529
0.6686 Remote Similarity NPC324198
0.6686 Remote Similarity NPC319100
0.6686 Remote Similarity NPC326082
0.6647 Remote Similarity NPC222174
0.6629 Remote Similarity NPC313514
0.6628 Remote Similarity NPC313897
0.6581 Remote Similarity NPC210947
0.6545 Remote Similarity NPC93365
0.6529 Remote Similarity NPC168702
0.6529 Remote Similarity NPC125659
0.6524 Remote Similarity NPC60537
0.6471 Remote Similarity NPC33382
0.6444 Remote Similarity NPC293163
0.6375 Remote Similarity NPC174020
0.6369 Remote Similarity NPC470139
0.6364 Remote Similarity NPC327613
0.6335 Remote Similarity NPC327477
0.6329 Remote Similarity NPC286696
0.6329 Remote Similarity NPC185903
0.6323 Remote Similarity NPC126634
0.6304 Remote Similarity NPC59314
0.6282 Remote Similarity NPC470140
0.6214 Remote Similarity NPC119133
0.62 Remote Similarity NPC250178
0.6188 Remote Similarity NPC24589
0.6181 Remote Similarity NPC41958
0.6175 Remote Similarity NPC282458
0.6175 Remote Similarity NPC78941
0.6139 Remote Similarity NPC18223
0.6139 Remote Similarity NPC470141
0.6139 Remote Similarity NPC237812
0.6062 Remote Similarity NPC103388
0.6047 Remote Similarity NPC321393
0.6026 Remote Similarity NPC470138
0.6026 Remote Similarity NPC235501
0.599 Remote Similarity NPC107160
0.5986 Remote Similarity NPC63433
0.5981 Remote Similarity NPC21461
0.5957 Remote Similarity NPC10466
0.5957 Remote Similarity NPC201900
0.5929 Remote Similarity NPC326248
0.5929 Remote Similarity NPC187191
0.5924 Remote Similarity NPC25465
0.5897 Remote Similarity NPC157821
0.5887 Remote Similarity NPC273327
0.5876 Remote Similarity NPC276373
0.5873 Remote Similarity NPC313504
0.5855 Remote Similarity NPC470142
0.5846 Remote Similarity NPC5802
0.5829 Remote Similarity NPC160666
0.5779 Remote Similarity NPC109322
0.5764 Remote Similarity NPC155498
0.5758 Remote Similarity NPC8590
0.5742 Remote Similarity NPC15566
0.5734 Remote Similarity NPC111132
0.5714 Remote Similarity NPC320256
0.5687 Remote Similarity NPC57279
0.5602 Remote Similarity NPC158055

  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 NPC74306 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 NPD582 Approved
0.8864 High Similarity NPD9632 Phase 3
0.8676 High Similarity NPD252 Clinical (unspecified phase)
0.8467 Intermediate Similarity NPD194 Clinical (unspecified phase)
0.8298 Intermediate Similarity NPD549 Approved
0.7987 Intermediate Similarity NPD3086 Phase 3
0.7919 Intermediate Similarity NPD3085 Phase 1
0.7815 Intermediate Similarity NPD536 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD2624 Phase 2
0.7704 Intermediate Similarity NPD9607 Approved
0.7703 Intermediate Similarity NPD249 Approved
0.7703 Intermediate Similarity NPD250 Approved
0.7677 Intermediate Similarity NPD4074 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD1750 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD1369 Phase 2
0.763 Intermediate Similarity NPD9606 Approved
0.7622 Intermediate Similarity NPD209 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD195 Approved
0.76 Intermediate Similarity NPD186 Discovery
0.75 Intermediate Similarity NPD2646 Discontinued
0.75 Intermediate Similarity NPD1732 Phase 3
0.745 Intermediate Similarity NPD185 Approved
0.7419 Intermediate Similarity NPD3107 Discontinued
0.7407 Intermediate Similarity NPD9374 Approved
0.7403 Intermediate Similarity NPD283 Approved
0.7389 Intermediate Similarity NPD217 Approved
0.7389 Intermediate Similarity NPD219 Phase 3
0.7389 Intermediate Similarity NPD218 Approved
0.7389 Intermediate Similarity NPD220 Clinical (unspecified phase)
0.7389 Intermediate Similarity NPD216 Approved
0.7372 Intermediate Similarity NPD339 Approved
0.7351 Intermediate Similarity NPD166 Approved
0.7319 Intermediate Similarity NPD307 Approved
0.7315 Intermediate Similarity NPD193 Suspended
0.731 Intermediate Similarity NPD545 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD214 Approved
0.7308 Intermediate Similarity NPD213 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD242 Approved
0.7308 Intermediate Similarity NPD338 Approved
0.729 Intermediate Similarity NPD353 Discontinued
0.7267 Intermediate Similarity NPD1431 Approved
0.7267 Intermediate Similarity NPD1430 Approved
0.7259 Intermediate Similarity NPD9373 Approved
0.7215 Intermediate Similarity NPD169 Phase 2
0.7208 Intermediate Similarity NPD775 Approved
0.7192 Intermediate Similarity NPD547 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD9605 Phase 3
0.7073 Intermediate Similarity NPD247 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD2152 Clinical (unspecified phase)
0.7051 Intermediate Similarity NPD548 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD2647 Phase 3
0.6959 Remote Similarity NPD4716 Approved
0.6954 Remote Similarity NPD1808 Phase 1
0.6933 Remote Similarity NPD1120 Approved
0.6933 Remote Similarity NPD1121 Approved
0.6923 Remote Similarity NPD5666 Phase 2
0.6919 Remote Similarity NPD4744 Clinical (unspecified phase)
0.6901 Remote Similarity NPD9409 Discontinued
0.6849 Remote Similarity NPD515 Phase 1
0.6812 Remote Similarity NPD9375 Discontinued
0.6766 Remote Similarity NPD7988 Suspended
0.6766 Remote Similarity NPD1777 Approved
0.6766 Remote Similarity NPD1776 Approved
0.6743 Remote Similarity NPD1692 Approved
0.6689 Remote Similarity NPD870 Clinical (unspecified phase)
0.6687 Remote Similarity NPD5768 Phase 2
0.6686 Remote Similarity NPD4171 Clinical (unspecified phase)
0.6647 Remote Similarity NPD1412 Clinical (unspecified phase)
0.6629 Remote Similarity NPD7138 Phase 2
0.6627 Remote Similarity NPD516 Clinical (unspecified phase)
0.6618 Remote Similarity NPD9626 Clinical (unspecified phase)
0.66 Remote Similarity NPD248 Discontinued
0.6587 Remote Similarity NPD3083 Approved
0.6573 Remote Similarity NPD5682 Phase 3
0.6573 Remote Similarity NPD5683 Clinical (unspecified phase)
0.6573 Remote Similarity NPD6417 Clinical (unspecified phase)
0.6573 Remote Similarity NPD5684 Clinical (unspecified phase)
0.6545 Remote Similarity NPD546 Clinical (unspecified phase)
0.6545 Remote Similarity NPD3697 Discontinued
0.6543 Remote Similarity NPD7842 Phase 2
0.6528 Remote Similarity NPD9360 Approved
0.6524 Remote Similarity NPD2180 Approved
0.6508 Remote Similarity NPD2877 Clinical (unspecified phase)
0.6508 Remote Similarity NPD2876 Phase 3
0.65 Remote Similarity NPD2631 Clinical (unspecified phase)
0.65 Remote Similarity NPD2632 Approved
0.65 Remote Similarity NPD2630 Approved
0.6463 Remote Similarity NPD1731 Clinical (unspecified phase)
0.644 Remote Similarity NPD2824 Phase 2
0.6434 Remote Similarity NPD9584 Phase 2
0.6419 Remote Similarity NPD798 Discontinued
0.6368 Remote Similarity NPD2965 Clinical (unspecified phase)
0.6352 Remote Similarity NPD1451 Approved
0.6347 Remote Similarity NPD2604 Approved
0.6323 Remote Similarity NPD1119 Phase 2
0.6312 Remote Similarity NPD5342 Clinical (unspecified phase)
0.6304 Remote Similarity NPD8837 Clinical (unspecified phase)
0.6301 Remote Similarity NPD237 Clinical (unspecified phase)
0.6296 Remote Similarity NPD7531 Clinical (unspecified phase)
0.6294 Remote Similarity NPD3130 Discontinued
0.6286 Remote Similarity NPD1816 Clinical (unspecified phase)
0.6241 Remote Similarity NPD9416 Phase 3
0.6241 Remote Similarity NPD9417 Phase 3
0.6236 Remote Similarity NPD1046 Clinical (unspecified phase)
0.6234 Remote Similarity NPD282 Approved
0.6214 Remote Similarity NPD9291 Approved
0.6196 Remote Similarity NPD4054 Clinical (unspecified phase)
0.6188 Remote Similarity NPD2253 Discontinued
0.6184 Remote Similarity NPD300 Approved
0.6182 Remote Similarity NPD3708 Phase 2
0.6139 Remote Similarity NPD9628 Approved
0.6139 Remote Similarity NPD9133 Approved
0.6139 Remote Similarity NPD6381 Phase 2
0.6125 Remote Similarity NPD875 Clinical (unspecified phase)
0.6105 Remote Similarity NPD5665 Clinical (unspecified phase)
0.6074 Remote Similarity NPD7158 Phase 1
0.6069 Remote Similarity NPD527 Clinical (unspecified phase)
0.6041 Remote Similarity NPD4495 Phase 1
0.6039 Remote Similarity NPD1355 Clinical (unspecified phase)
0.6039 Remote Similarity NPD1127 Approved
0.6039 Remote Similarity NPD1356 Approved
0.6039 Remote Similarity NPD1128 Approved
0.6039 Remote Similarity NPD1354 Approved
0.6033 Remote Similarity NPD1063 Phase 2
0.6025 Remote Similarity NPD1118 Discontinued
0.6014 Remote Similarity NPD1368 Approved
0.6012 Remote Similarity NPD231 Clinical (unspecified phase)
0.6 Remote Similarity NPD9633 Phase 3
0.5986 Remote Similarity NPD9406 Approved
0.5976 Remote Similarity NPD9627 Approved
0.5955 Remote Similarity NPD3105 Discontinued
0.5951 Remote Similarity NPD1117 Clinical (unspecified phase)
0.5951 Remote Similarity NPD6036 Suspended
0.5951 Remote Similarity NPD9183 Clinical (unspecified phase)
0.5915 Remote Similarity NPD566 Approved
0.5915 Remote Similarity NPD567 Approved
0.5915 Remote Similarity NPD568 Approved
0.5909 Remote Similarity NPD9408 Phase 3
0.5909 Remote Similarity NPD281 Approved
0.5907 Remote Similarity NPD4599 Clinical (unspecified phase)
0.59 Remote Similarity NPD2902 Phase 2
0.59 Remote Similarity NPD2903 Clinical (unspecified phase)
0.5876 Remote Similarity NPD4459 Clinical (unspecified phase)
0.5876 Remote Similarity NPD4458 Phase 2
0.5843 Remote Similarity NPD1730 Discontinued
0.5823 Remote Similarity NPD9650 Phase 3
0.5808 Remote Similarity NPD796 Phase 2
0.5801 Remote Similarity NPD3108 Clinical (unspecified phase)
0.5776 Remote Similarity NPD535 Approved
0.5751 Remote Similarity NPD691 Discontinued
0.5734 Remote Similarity NPD8862 Approved
0.5734 Remote Similarity NPD8859 Approved
0.5734 Remote Similarity NPD8861 Approved
0.5707 Remote Similarity NPD5080 Phase 2
0.5659 Remote Similarity NPD5079 Phase 2
0.5655 Remote Similarity NPD9196 Phase 2
0.5655 Remote Similarity NPD9415 Clinical (unspecified phase)
0.5652 Remote Similarity NPD9083 Clinical (unspecified phase)
0.5652 Remote Similarity NPD4555 Clinical (unspecified phase)
0.5646 Remote Similarity NPD613 Phase 2
0.5636 Remote Similarity NPD3695 Approved
0.5636 Remote Similarity NPD3696 Approved
0.5632 Remote Similarity NPD207 Discontinued
0.5625 Remote Similarity NPD245 Suspended
0.5602 Remote Similarity NPD6840 Approved

  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