Structure

Physi-Chem Properties

Molecular Weight:  323.05
Volume:  262.337
LogP:  -3.0
LogD:  -2.015
LogS:  -0.226
# Rotatable Bonds:  4
TPSA:  174.93
# H-Bond Aceptor:  11
# H-Bond Donor:  5
# Rings:  2
# Heavy Atoms:  12

MedChem Properties

QED Drug-Likeness Score:  0.379
Synthetic Accessibility Score:  5.196
Fsp3:  0.556
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:  -6.405
MDCK Permeability:  0.000527976721059531
Pgp-inhibitor:  0.0
Pgp-substrate:  0.03
Human Intestinal Absorption (HIA):  0.924
20% Bioavailability (F20%):  0.986
30% Bioavailability (F30%):  0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.557
Plasma Protein Binding (PPB):  14.63010025024414%
Volume Distribution (VD):  0.39
Pgp-substrate:  82.43101501464844%

ADMET: Metabolism

CYP1A2-inhibitor:  0.009
CYP1A2-substrate:  0.067
CYP2C19-inhibitor:  0.104
CYP2C19-substrate:  0.039
CYP2C9-inhibitor:  0.008
CYP2C9-substrate:  0.093
CYP2D6-inhibitor:  0.025
CYP2D6-substrate:  0.105
CYP3A4-inhibitor:  0.005
CYP3A4-substrate:  0.012

ADMET: Excretion

Clearance (CL):  1.523
Half-life (T1/2):  0.896

ADMET: Toxicity

hERG Blockers:  0.01
Human Hepatotoxicity (H-HT):  0.84
Drug-inuced Liver Injury (DILI):  0.976
AMES Toxicity:  0.023
Rat Oral Acute Toxicity:  0.003
Maximum Recommended Daily Dose:  0.389
Skin Sensitization:  0.251
Carcinogencity:  0.046
Eye Corrosion:  0.003
Eye Irritation:  0.024
Respiratory Toxicity:  0.132

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC6166

Natural Product ID:  NPC6166
Common Name*:   [(2R,3S,4R,5R)-5-(4-Amino-2-Oxopyrimidin-1-Yl)-4-Hydroxy-2-(Hydroxymethyl)Oxolan-3-Yl] Dihydrogen Phosphate
IUPAC Name:   [(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] dihydrogen phosphate
Synonyms:   Cytidine 3'-Phosphate
Standard InCHIKey:  UOOOPKANIPLQPU-XVFCMESISA-N
Standard InCHI:  InChI=1S/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-6(14)7(4(3-13)19-8)20-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1
SMILES:  c1cn([C@H]2[C@@H]([C@@H]([C@@H](CO)O2)OP(=O)(O)O)O)c(nc1=N)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL258728
PubChem CID:   66535
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates
          • [CHEMONTID:0001540] Monosaccharides
            • [CHEMONTID:0001497] Pentoses
              • [CHEMONTID:0002259] Pentose phosphates

*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
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. DOI[10.1016/0006-291X(79)91731-5]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. DOI[10.1093/emboj/18.8.2021]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. DOI[10.1172/JCI16309]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. DOI[10.1371/journal.pone.0115359]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[10557354]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[1091286]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[10977898]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[1100617]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[11034610]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[11419736]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[11530998]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[11745165]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[11750815]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[1175644]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[12369847]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[12391014]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[12467448]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[12805358]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[12812989]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[12840027]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[12878451]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. ChEBI[131529]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[13610867]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[13831814]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[14973046]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[15031653]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[15084647]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[1521032]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[15230696]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[15292242]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[15314235]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[15610037]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[16112079]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[1644759]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[16630633]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[16770722]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[1687010]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[170247]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[17116739]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[17190852]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[17765195]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[17875433]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[179975]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[18311922]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[18544912]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[18799520]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[19026742]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[19425150]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[19514719]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[19561621]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[19961175]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[20506249]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[20601097]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. faeces n.a. PMID[20708442]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. urine n.a. PMID[20708442]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. bile n.a. PMID[20708442]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[20876113]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[21437340]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[21798258]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[21988831]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[22289691]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[2268561]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[22711758]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[22855027]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[23315938]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[23537328]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[23676670]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[23717534]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[23752203]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[23810710]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[23811455]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[23868375]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[23919613]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[24101735]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[241475]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[24206068]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[24399466]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[24494566]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[24558969]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[24783849]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[24816727]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[24831709]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[24939187]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[24966042]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[24967680]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[25114169]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[25181601]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[25293588]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[2543976]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[25644343]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[25867074]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[26195826]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[26236990]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[26337258]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[26670289]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[26826371]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[27471436]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[29897754]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[30302998]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[3179836]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[318639]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[3283102]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[347637]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[398096]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[4696527]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[4877125]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[4879561]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[4908789]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[5332408]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[5432584]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[6102982]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[6121420]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[6284709]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[6338507]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[6780563]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[7042909]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[7601837]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[8600370]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[8852895]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[8987136]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[9192820]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[9470222]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[9800648]
NPO146 Heliotropium indicum Species Heliotropiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. Database[MetaboLights]
NPO146 Heliotropium indicum Species Heliotropiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO146 Heliotropium indicum Species Heliotropiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11677 Lactobacillus acidophilus Species Lactobacillaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO146 Heliotropium indicum Species Heliotropiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3230 Clitocybe truncicola Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9659 Codium divaricatum Species Codiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3574.1 Pinus parviflora var. pentaphylla Varieties Pinaceae 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
NPT46 Individual Protein Thyroid hormone receptor beta-1 Homo sapiens Potency = 70794.6 nM PMID[451265]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Potency = 7943.3 nM PMID[451265]
NPT907 Individual Protein Ribonuclease pancreatic Homo sapiens Inhibition = 24.0 % PMID[451260]
NPT907 Individual Protein Ribonuclease pancreatic Homo sapiens IC50 = 312000.0 nM PMID[451260]
NPT907 Individual Protein Ribonuclease pancreatic Homo sapiens Ki = 103000.0 nM PMID[451260]
NPT908 Individual Protein Ribonuclease pancreatic Bos taurus Ki = 103000.0 nM PMID[451261]
NPT908 Individual Protein Ribonuclease pancreatic Bos taurus Ki = 103000.0 nM PMID[451262]
NPT909 Individual Protein Seminal ribonuclease Bos taurus Ki = 27900.0 nM PMID[451263]
NPT908 Individual Protein Ribonuclease pancreatic Bos taurus Ki = 20100.0 nM PMID[451263]
NPT907 Individual Protein Ribonuclease pancreatic Homo sapiens Ratio = 0.7099 n.a. PMID[451264]
NPT197 Protein-Protein Interaction Menin/Histone-lysine N-methyltransferase MLL Homo sapiens Potency = 39810.7 nM PMID[451265]

☑ 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 NPC6166 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 NPC280946
1.0 High Similarity NPC226769
0.9886 High Similarity NPC120887
0.9775 High Similarity NPC328779
0.9663 High Similarity NPC90240
0.956 High Similarity NPC328914
0.9438 High Similarity NPC329384
0.9195 High Similarity NPC190334
0.9195 High Similarity NPC62927
0.8851 High Similarity NPC229249
0.8261 Intermediate Similarity NPC328806
0.8211 Intermediate Similarity NPC36985
0.8211 Intermediate Similarity NPC17892
0.8125 Intermediate Similarity NPC283698
0.8125 Intermediate Similarity NPC73765
0.7895 Intermediate Similarity NPC324390
0.7812 Intermediate Similarity NPC322594
0.7812 Intermediate Similarity NPC320249
0.7474 Intermediate Similarity NPC89051
0.7474 Intermediate Similarity NPC43246
0.74 Intermediate Similarity NPC317639
0.7358 Intermediate Similarity NPC329277
0.7245 Intermediate Similarity NPC315063
0.7222 Intermediate Similarity NPC155087
0.7222 Intermediate Similarity NPC149843
0.7158 Intermediate Similarity NPC106780
0.7131 Intermediate Similarity NPC318142
0.7111 Intermediate Similarity NPC315806
0.71 Intermediate Similarity NPC327344
0.6961 Remote Similarity NPC318166
0.6961 Remote Similarity NPC324516
0.693 Remote Similarity NPC313813
0.67 Remote Similarity NPC163352
0.67 Remote Similarity NPC210456
0.6667 Remote Similarity NPC325723
0.6526 Remote Similarity NPC329077
0.6421 Remote Similarity NPC469972
0.64 Remote Similarity NPC71339
0.64 Remote Similarity NPC112842
0.6341 Remote Similarity NPC284651
0.6095 Remote Similarity NPC171116
0.596 Remote Similarity NPC325902
0.5797 Remote Similarity NPC211820
0.5797 Remote Similarity NPC251233
0.5781 Remote Similarity NPC315058
0.5755 Remote Similarity NPC177169
0.5714 Remote Similarity NPC245534
0.5714 Remote Similarity NPC232408
0.5714 Remote Similarity NPC64705
0.569 Remote Similarity NPC239705
0.569 Remote Similarity NPC314413
0.569 Remote Similarity NPC314398
0.5683 Remote Similarity NPC318590
0.5652 Remote Similarity NPC186619
0.5649 Remote Similarity NPC313962
0.5643 Remote Similarity NPC274384
0.5643 Remote Similarity NPC89147
0.5643 Remote Similarity NPC317746
0.5641 Remote Similarity NPC322449
0.5641 Remote Similarity NPC189854
0.5641 Remote Similarity NPC92874
0.5641 Remote Similarity NPC62845
0.5641 Remote Similarity NPC166242

  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 NPC6166 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
0.956 High Similarity NPD1455 Phase 3
0.956 High Similarity NPD1454 Phase 3
0.9195 High Similarity NPD9602 Phase 3
0.9195 High Similarity NPD9603 Phase 3
0.9195 High Similarity NPD9604 Approved
0.9062 High Similarity NPD6946 Approved
0.8851 High Similarity NPD9601 Approved
0.8791 High Similarity NPD9585 Discontinued
0.8506 High Similarity NPD9600 Approved
0.8462 Intermediate Similarity NPD9553 Approved
0.8462 Intermediate Similarity NPD9554 Approved
0.8462 Intermediate Similarity NPD301 Discontinued
0.8421 Intermediate Similarity NPD514 Clinical (unspecified phase)
0.8315 Intermediate Similarity NPD9572 Clinical (unspecified phase)
0.8286 Intermediate Similarity NPD3138 Phase 3
0.828 Intermediate Similarity NPD267 Discontinued
0.8208 Intermediate Similarity NPD3139 Phase 3
0.8202 Intermediate Similarity NPD9573 Phase 2
0.8191 Intermediate Similarity NPD6943 Clinical (unspecified phase)
0.8125 Intermediate Similarity NPD9639 Clinical (unspecified phase)
0.8021 Intermediate Similarity NPD215 Discontinued
0.7935 Intermediate Similarity NPD9555 Phase 2
0.7865 Intermediate Similarity NPD9427 Approved
0.7755 Intermediate Similarity NPD6948 Phase 3
0.77 Intermediate Similarity NPD192 Phase 2
0.7528 Intermediate Similarity NPD9407 Approved
0.75 Intermediate Similarity NPD4743 Phase 2
0.7476 Intermediate Similarity NPD7651 Approved
0.7474 Intermediate Similarity NPD9580 Clinical (unspecified phase)
0.7474 Intermediate Similarity NPD9581 Clinical (unspecified phase)
0.7473 Intermediate Similarity NPD9403 Discontinued
0.7429 Intermediate Similarity NPD3128 Phase 3
0.7407 Intermediate Similarity NPD1804 Phase 2
0.7407 Intermediate Similarity NPD1805 Phase 2
0.7358 Intermediate Similarity NPD1428 Phase 2
0.7358 Intermediate Similarity NPD3129 Phase 3
0.7273 Intermediate Similarity NPD285 Discontinued
0.7204 Intermediate Similarity NPD9429 Discontinued
0.7191 Intermediate Similarity NPD9405 Approved
0.7184 Intermediate Similarity NPD3121 Phase 2
0.7111 Intermediate Similarity NPD9653 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD6936 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD6935 Phase 3
0.701 Intermediate Similarity NPD9557 Clinical (unspecified phase)
0.699 Remote Similarity NPD762 Discontinued
0.6961 Remote Similarity NPD1706 Clinical (unspecified phase)
0.6916 Remote Similarity NPD1061 Clinical (unspecified phase)
0.6852 Remote Similarity NPD2633 Phase 1
0.6809 Remote Similarity NPD9372 Phase 2
0.6759 Remote Similarity NPD244 Clinical (unspecified phase)
0.67 Remote Similarity NPD1760 Approved
0.6699 Remote Similarity NPD1686 Approved
0.6698 Remote Similarity NPD5789 Clinical (unspecified phase)
0.6667 Remote Similarity NPD9565 Discontinued
0.6607 Remote Similarity NPD6693 Phase 3
0.6598 Remote Similarity NPD9556 Approved
0.6569 Remote Similarity NPD755 Phase 3
0.6538 Remote Similarity NPD279 Clinical (unspecified phase)
0.6531 Remote Similarity NPD9560 Approved
0.6531 Remote Similarity NPD9561 Approved
0.6525 Remote Similarity NPD6918 Phase 1
0.6509 Remote Similarity NPD2621 Clinical (unspecified phase)
0.6481 Remote Similarity NPD223 Clinical (unspecified phase)
0.6465 Remote Similarity NPD9559 Phase 1
0.6465 Remote Similarity NPD9546 Phase 2
0.6449 Remote Similarity NPD502 Approved
0.6429 Remote Similarity NPD9558 Phase 3
0.6421 Remote Similarity NPD9370 Approved
0.64 Remote Similarity NPD9533 Phase 2
0.64 Remote Similarity NPD280 Approved
0.6392 Remote Similarity NPD9369 Clinical (unspecified phase)
0.6379 Remote Similarity NPD7914 Suspended
0.6373 Remote Similarity NPD241 Discontinued
0.6364 Remote Similarity NPD2691 Clinical (unspecified phase)
0.6275 Remote Similarity NPD170 Approved
0.6275 Remote Similarity NPD9562 Discovery
0.6275 Remote Similarity NPD240 Phase 3
0.6261 Remote Similarity NPD284 Phase 1
0.625 Remote Similarity NPD3161 Clinical (unspecified phase)
0.6168 Remote Similarity NPD501 Phase 1
0.6139 Remote Similarity NPD9529 Phase 1
0.6095 Remote Similarity NPD841 Approved
0.6078 Remote Similarity NPD238 Clinical (unspecified phase)
0.6078 Remote Similarity NPD239 Phase 2
0.604 Remote Similarity NPD9534 Phase 2
0.604 Remote Similarity NPD9535 Phase 2
0.6 Remote Similarity NPD1385 Discontinued
0.5981 Remote Similarity NPD251 Approved
0.5926 Remote Similarity NPD7761 Suspended
0.5876 Remote Similarity NPD9347 Approved
0.5876 Remote Similarity NPD9346 Approved
0.5854 Remote Similarity NPD7756 Clinical (unspecified phase)
0.5761 Remote Similarity NPD9211 Clinical (unspecified phase)
0.5714 Remote Similarity NPD9654 Phase 2

  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