Structure

Physi-Chem Properties

Molecular Weight:  216.0
Volume:  165.253
LogP:  -2.529
LogD:  -1.358
LogS:  -0.091
# Rotatable Bonds:  5
TPSA:  141.36
# H-Bond Aceptor:  8
# H-Bond Donor:  4
# Rings:  0
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.292
Synthetic Accessibility Score:  5.275
Fsp3:  0.75
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.89
MDCK Permeability:  0.004166102968156338
Pgp-inhibitor:  0.001
Pgp-substrate:  0.227
Human Intestinal Absorption (HIA):  0.209
20% Bioavailability (F20%):  0.955
30% Bioavailability (F30%):  0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.625
Plasma Protein Binding (PPB):  8.962472915649414%
Volume Distribution (VD):  0.343
Pgp-substrate:  85.69876098632812%

ADMET: Metabolism

CYP1A2-inhibitor:  0.002
CYP1A2-substrate:  0.042
CYP2C19-inhibitor:  0.03
CYP2C19-substrate:  0.043
CYP2C9-inhibitor:  0.005
CYP2C9-substrate:  0.306
CYP2D6-inhibitor:  0.016
CYP2D6-substrate:  0.117
CYP3A4-inhibitor:  0.004
CYP3A4-substrate:  0.004

ADMET: Excretion

Clearance (CL):  1.345
Half-life (T1/2):  0.869

ADMET: Toxicity

hERG Blockers:  0.009
Human Hepatotoxicity (H-HT):  0.071
Drug-inuced Liver Injury (DILI):  0.157
AMES Toxicity:  0.037
Rat Oral Acute Toxicity:  0.005
Maximum Recommended Daily Dose:  0.916
Skin Sensitization:  0.42
Carcinogencity:  0.078
Eye Corrosion:  0.011
Eye Irritation:  0.81
Respiratory Toxicity:  0.619

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  Natural Product: NPC328954

Natural Product ID:  NPC328954
Common Name*:   4-Phospho-D-Erythronate
IUPAC Name:   (2R,3R)-2,3-dihydroxy-4-phosphonooxybutanoic acid
Synonyms:  
Standard InCHIKey:  ZCZXOHUILRHRQJ-PWNYCUMCSA-N
Standard InCHI:  InChI=1S/C4H9O8P/c5-2(3(6)4(7)8)1-12-13(9,10)11/h2-3,5-6H,1H2,(H,7,8)(H2,9,10,11)/t2-,3-/m1/s1
SMILES:  O[C@@H]([C@H](C(=O)O)O)COP(=O)(O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1160945
PubChem CID:   449304
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:0001541] Monosaccharide 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. 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. faeces 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]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. Database[MetaboLights]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria 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
NPT1336 Individual Protein 6-phosphogluconate dehydrogenase Homo sapiens Ki = 130.0 nM PMID[491588]
NPT1336 Individual Protein 6-phosphogluconate dehydrogenase Homo sapiens Ki = 10700.0 nM PMID[491588]
NPT6196 Individual Protein 6-phosphogluconate dehydrogenase, decarboxylating Ovis aries Ki = 10790.0 nM PMID[491589]
NPT2 Others Unspecified Ratio = 83.0 n.a. PMID[491588]
NPT2 Others Unspecified Ki = 130.0 nM PMID[491589]
NPT2 Others Unspecified IC50 = 220000.0 nM PMID[491590]

☑ 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 NPC328954 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
0.8478 Intermediate Similarity NPC320624
0.8478 Intermediate Similarity NPC318951
0.8444 Intermediate Similarity NPC35661
0.8444 Intermediate Similarity NPC322956
0.8444 Intermediate Similarity NPC325307
0.8182 Intermediate Similarity NPC323945
0.8043 Intermediate Similarity NPC24751
0.8043 Intermediate Similarity NPC100742
0.8043 Intermediate Similarity NPC97444
0.8043 Intermediate Similarity NPC19044
0.8043 Intermediate Similarity NPC121018
0.8043 Intermediate Similarity NPC192402
0.8036 Intermediate Similarity NPC320296
0.7636 Intermediate Similarity NPC3547
0.7143 Intermediate Similarity NPC259982
0.7143 Intermediate Similarity NPC313565
0.7143 Intermediate Similarity NPC228782
0.7091 Intermediate Similarity NPC196612
0.7021 Intermediate Similarity NPC328950
0.6964 Remote Similarity NPC6883
0.6957 Remote Similarity NPC159089
0.6957 Remote Similarity NPC5505
0.6909 Remote Similarity NPC277878
0.6863 Remote Similarity NPC270088
0.6863 Remote Similarity NPC242655
0.6863 Remote Similarity NPC38891
0.6786 Remote Similarity NPC323401
0.6786 Remote Similarity NPC19676
0.6739 Remote Similarity NPC191084
0.6739 Remote Similarity NPC168052
0.6739 Remote Similarity NPC250870
0.6735 Remote Similarity NPC320331
0.6607 Remote Similarity NPC317680
0.6531 Remote Similarity NPC316217
0.6531 Remote Similarity NPC222792
0.6481 Remote Similarity NPC247546
0.6481 Remote Similarity NPC172086
0.6444 Remote Similarity NPC266566
0.6444 Remote Similarity NPC31433
0.6444 Remote Similarity NPC321170
0.6444 Remote Similarity NPC329270
0.6364 Remote Similarity NPC46254
0.6333 Remote Similarity NPC293692
0.6333 Remote Similarity NPC220922
0.625 Remote Similarity NPC1037
0.6222 Remote Similarity NPC198126
0.6087 Remote Similarity NPC307739
0.6087 Remote Similarity NPC76217
0.6071 Remote Similarity NPC293378
0.6066 Remote Similarity NPC93861
0.6066 Remote Similarity NPC43169
0.6066 Remote Similarity NPC112224
0.6066 Remote Similarity NPC327895
0.6042 Remote Similarity NPC325165
0.6038 Remote Similarity NPC319680
0.5965 Remote Similarity NPC322158
0.5965 Remote Similarity NPC329128
0.5932 Remote Similarity NPC65985
0.5918 Remote Similarity NPC103612
0.5918 Remote Similarity NPC24967
0.5902 Remote Similarity NPC198377
0.5862 Remote Similarity NPC329095
0.5846 Remote Similarity NPC317651
0.5846 Remote Similarity NPC258690
0.5806 Remote Similarity NPC61567
0.5789 Remote Similarity NPC325822
0.5789 Remote Similarity NPC61270
0.5778 Remote Similarity NPC301586
0.5778 Remote Similarity NPC33415
0.5763 Remote Similarity NPC103672
0.5763 Remote Similarity NPC320043
0.5745 Remote Similarity NPC261351
0.5738 Remote Similarity NPC68743
0.5738 Remote Similarity NPC60830
0.5735 Remote Similarity NPC32148
0.5714 Remote Similarity NPC321873
0.5714 Remote Similarity NPC316685
0.5714 Remote Similarity NPC179624
0.5667 Remote Similarity NPC317501
0.5667 Remote Similarity NPC314821
0.5667 Remote Similarity NPC317626
0.5625 Remote Similarity NPC17935
0.5606 Remote Similarity NPC268243

  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 NPC328954 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
0.8043 Intermediate Similarity NPD8603 Approved
0.8043 Intermediate Similarity NPD8600 Approved
0.8043 Intermediate Similarity NPD8599 Approved
0.8043 Intermediate Similarity NPD8601 Approved
0.8043 Intermediate Similarity NPD8602 Approved
0.8043 Intermediate Similarity NPD8598 Approved
0.8043 Intermediate Similarity NPD8604 Approved
0.8043 Intermediate Similarity NPD8605 Approved
0.6909 Remote Similarity NPD9007 Approved
0.6909 Remote Similarity NPD9011 Approved
0.6909 Remote Similarity NPD8960 Approved
0.6909 Remote Similarity NPD64 Approved
0.6909 Remote Similarity NPD66 Approved
0.6909 Remote Similarity NPD72 Approved
0.6909 Remote Similarity NPD9010 Approved
0.6909 Remote Similarity NPD9009 Approved
0.6909 Remote Similarity NPD9008 Approved
0.6909 Remote Similarity NPD65 Approved
0.6724 Remote Similarity NPD73 Approved
0.6481 Remote Similarity NPD9003 Clinical (unspecified phase)
0.6481 Remote Similarity NPD9005 Phase 3
0.6481 Remote Similarity NPD9004 Approved
0.6444 Remote Similarity NPD8237 Approved
0.6333 Remote Similarity NPD8959 Approved
0.6222 Remote Similarity NPD8618 Approved
0.6222 Remote Similarity NPD8236 Phase 1
0.6222 Remote Similarity NPD8234 Approved
0.6222 Remote Similarity NPD8235 Approved
0.614 Remote Similarity NPD9002 Approved
0.614 Remote Similarity NPD9001 Clinical (unspecified phase)
0.6094 Remote Similarity NPD1151 Approved
0.6087 Remote Similarity NPD8205 Approved
0.6087 Remote Similarity NPD8202 Approved
0.6071 Remote Similarity NPD9126 Approved
0.6071 Remote Similarity NPD71 Approved
0.6071 Remote Similarity NPD9129 Approved
0.6 Remote Similarity NPD8617 Approved
0.6 Remote Similarity NPD8619 Approved
0.5893 Remote Similarity NPD70 Approved
0.5893 Remote Similarity NPD9123 Approved
0.5893 Remote Similarity NPD9130 Phase 3
0.5893 Remote Similarity NPD9121 Approved
0.5893 Remote Similarity NPD9127 Approved
0.5893 Remote Similarity NPD9125 Approved
0.5893 Remote Similarity NPD109 Approved
0.5893 Remote Similarity NPD9122 Approved
0.5893 Remote Similarity NPD9124 Approved
0.5893 Remote Similarity NPD9128 Approved
0.5893 Remote Similarity NPD108 Approved
0.587 Remote Similarity NPD8203 Approved
0.587 Remote Similarity NPD8206 Approved
0.587 Remote Similarity NPD55 Approved
0.587 Remote Similarity NPD54 Approved
0.587 Remote Similarity NPD8204 Approved
0.5846 Remote Similarity NPD8961 Approved
0.5789 Remote Similarity NPD8964 Approved
0.5789 Remote Similarity NPD9061 Clinical (unspecified phase)
0.5778 Remote Similarity NPD8549 Clinical (unspecified phase)
0.5763 Remote Similarity NPD9049 Discontinued
0.5763 Remote Similarity NPD9050 Approved
0.5735 Remote Similarity NPD897 Approved
0.5735 Remote Similarity NPD898 Approved
0.5735 Remote Similarity NPD896 Approved
0.5667 Remote Similarity NPD9035 Clinical (unspecified phase)
0.5667 Remote Similarity NPD9036 Phase 3

  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