Structure

Physi-Chem Properties

Molecular Weight:  669.14
Volume:  618.507
LogP:  1.516
LogD:  0.147
LogS:  -3.729
# Rotatable Bonds:  9
TPSA:  287.58
# H-Bond Aceptor:  18
# H-Bond Donor:  9
# Rings:  4
# Heavy Atoms:  18

MedChem Properties

QED Drug-Likeness Score:  0.089
Synthetic Accessibility Score:  4.332
Fsp3:  0.2
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  2
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.704
MDCK Permeability:  4.158818228461314e-06
Pgp-inhibitor:  0.113
Pgp-substrate:  0.875
Human Intestinal Absorption (HIA):  0.02
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.104
Plasma Protein Binding (PPB):  95.7286148071289%
Volume Distribution (VD):  0.346
Pgp-substrate:  17.36634063720703%

ADMET: Metabolism

CYP1A2-inhibitor:  0.008
CYP1A2-substrate:  0.003
CYP2C19-inhibitor:  0.055
CYP2C19-substrate:  0.021
CYP2C9-inhibitor:  0.587
CYP2C9-substrate:  0.238
CYP2D6-inhibitor:  0.006
CYP2D6-substrate:  0.147
CYP3A4-inhibitor:  0.441
CYP3A4-substrate:  0.03

ADMET: Excretion

Clearance (CL):  3.109
Half-life (T1/2):  0.953

ADMET: Toxicity

hERG Blockers:  0.077
Human Hepatotoxicity (H-HT):  0.037
Drug-inuced Liver Injury (DILI):  0.719
AMES Toxicity:  0.662
Rat Oral Acute Toxicity:  0.001
Maximum Recommended Daily Dose:  0.002
Skin Sensitization:  0.911
Carcinogencity:  0.136
Eye Corrosion:  0.003
Eye Irritation:  0.371
Respiratory Toxicity:  0.014

Download Data

Data Type Select
General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC106183

Natural Product ID:  NPC106183
Common Name*:   Enterobactin
IUPAC Name:   N-[(3S,7S,11S)-7,11-bis[(2,3-dihydroxybenzoyl)amino]-2,6,10-trioxo-1,5,9-trioxacyclododec-3-yl]-2,3-dihydroxybenzamide
Synonyms:   Enterobactin
Standard InCHIKey:  SERBHKJMVBATSJ-BZSNNMDCSA-N
Standard InCHI:  InChI=1S/C30H27N3O15/c34-19-7-1-4-13(22(19)37)25(40)31-16-10-46-29(44)18(33-27(42)15-6-3-9-21(36)24(15)39)12-48-30(45)17(11-47-28(16)43)32-26(41)14-5-2-8-20(35)23(14)38/h1-9,16-18,34-39H,10-12H2,(H,31,40)(H,32,41)(H,33,42)/t16-,17-,18-/m0/s1
SMILES:  c1cc(c(c(c1)O)O)C(=N[C@H]1COC(=O)[C@H](COC(=O)[C@H](COC1=O)N=C(c1cccc(c1O)O)O)N=C(c1cccc(c1O)O)O)O
Synthetic Gene Cluster:   BGC0000343;
ChEMBL Identifier:   CHEMBL432995
PubChem CID:   34231
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000264] Organic acids and derivatives
      • [CHEMONTID:0001813] Peptidomimetics
        • [CHEMONTID:0001961] Depsipeptides
          • [CHEMONTID:0001994] Cyclic depsipeptides

*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]
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]
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]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[12369847]
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]
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]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[15292242]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[15610037]
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]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[170247]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[17765195]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[179975]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[19026742]
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]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[21437340]
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]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[22855027]
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]
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]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[24783849]
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]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[2543976]
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]
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]
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]
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]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[398096]
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]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[6102982]
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]
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]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[8852895]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[9470222]
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
NPT4213 Individual Protein Serotransferrin Homo sapiens Fe removed = 6.0 % PMID[575610]
NPT1549 Organism Vibrio cholerae Vibrio cholerae Growth zone = 28.0 mM PMID[575608]
NPT1549 Organism Vibrio cholerae Vibrio cholerae Growth zone = 0.0 mM PMID[575608]
NPT19 Organism Escherichia coli Escherichia coli Growth zone = 0.0 mM PMID[575608]
NPT1549 Organism Vibrio cholerae Vibrio cholerae Growth zone = 22.0 mM PMID[575608]
NPT19 Organism Escherichia coli Escherichia coli Growth zone = 40.0 mM PMID[575608]
NPT19 Organism Escherichia coli Escherichia coli Growth zone = 28.0 mM PMID[575608]
NPT19 Organism Escherichia coli Escherichia coli Inhibitory diameter = 25.0 mM PMID[575609]
NPT2 Others Unspecified Ratio = 120.0 n.a. PMID[575610]
NPT19 Organism Escherichia coli Escherichia coli Inhibitory diameter = 25.0 mM PMID[575611]
NPT19 Organism Escherichia coli Escherichia coli Zone of stimulation = 40.0 mM PMID[575612]
NPT19 Organism Escherichia coli Escherichia coli Zone of stimulation = 30.0 mM PMID[575612]
NPT19 Organism Escherichia coli Escherichia coli Zone of stimulation = 38.0 mM PMID[575613]
NPT19 Organism Escherichia coli Escherichia coli Zone of stimulation = 24.0 mM PMID[575613]
NPT2 Others Unspecified pM = 35.5 n.a. PMID[575614]
NPT2 Others Unspecified Kd = 0.5 nM PMID[575615]

☑ 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 NPC106183 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
0.8603 High Similarity NPC477839
0.8082 Intermediate Similarity NPC477838
0.8082 Intermediate Similarity NPC477837
0.7808 Intermediate Similarity NPC6913
0.7744 Intermediate Similarity NPC227553
0.7744 Intermediate Similarity NPC163674
0.7554 Intermediate Similarity NPC70084
0.7483 Intermediate Similarity NPC4974
0.7483 Intermediate Similarity NPC244866
0.7482 Intermediate Similarity NPC86198
0.745 Intermediate Similarity NPC6570
0.7447 Intermediate Similarity NPC284078
0.7429 Intermediate Similarity NPC109371
0.7429 Intermediate Similarity NPC470215
0.7429 Intermediate Similarity NPC268572
0.7429 Intermediate Similarity NPC470214
0.7415 Intermediate Similarity NPC45191
0.741 Intermediate Similarity NPC200988
0.741 Intermediate Similarity NPC610
0.741 Intermediate Similarity NPC145023
0.741 Intermediate Similarity NPC175799
0.7379 Intermediate Similarity NPC210950
0.7379 Intermediate Similarity NPC199738
0.7357 Intermediate Similarity NPC5932
0.7357 Intermediate Similarity NPC122009
0.7312 Intermediate Similarity NPC56635
0.7305 Intermediate Similarity NPC141791
0.7305 Intermediate Similarity NPC263386
0.7297 Intermediate Similarity NPC32626
0.7297 Intermediate Similarity NPC329344
0.7297 Intermediate Similarity NPC275538
0.7297 Intermediate Similarity NPC217052
0.7297 Intermediate Similarity NPC237506
0.7286 Intermediate Similarity NPC283468
0.7278 Intermediate Similarity NPC182119
0.7273 Intermediate Similarity NPC472271
0.7273 Intermediate Similarity NPC222039
0.7273 Intermediate Similarity NPC100478
0.726 Intermediate Similarity NPC118584
0.7254 Intermediate Similarity NPC252817
0.7234 Intermediate Similarity NPC275519
0.7219 Intermediate Similarity NPC106406
0.7211 Intermediate Similarity NPC186898
0.7203 Intermediate Similarity NPC470848
0.7203 Intermediate Similarity NPC470849
0.7192 Intermediate Similarity NPC67951
0.719 Intermediate Similarity NPC197921
0.7183 Intermediate Similarity NPC160235
0.7172 Intermediate Similarity NPC285345
0.7172 Intermediate Similarity NPC306100
0.7162 Intermediate Similarity NPC325651
0.7153 Intermediate Similarity NPC474862
0.7153 Intermediate Similarity NPC147654
0.7152 Intermediate Similarity NPC289572
0.7152 Intermediate Similarity NPC295406
0.7152 Intermediate Similarity NPC200422
0.7152 Intermediate Similarity NPC157478
0.7143 Intermediate Similarity NPC469360
0.7143 Intermediate Similarity NPC91953
0.7134 Intermediate Similarity NPC5462
0.7133 Intermediate Similarity NPC88667
0.7123 Intermediate Similarity NPC85565
0.7107 Intermediate Similarity NPC471032
0.7107 Intermediate Similarity NPC470935
0.7101 Intermediate Similarity NPC158277
0.7097 Intermediate Similarity NPC471875
0.7095 Intermediate Similarity NPC251571
0.7095 Intermediate Similarity NPC296712
0.7083 Intermediate Similarity NPC98305
0.7081 Intermediate Similarity NPC127402
0.7078 Intermediate Similarity NPC279676
0.7078 Intermediate Similarity NPC299583
0.7078 Intermediate Similarity NPC67349
0.7067 Intermediate Similarity NPC326966
0.7067 Intermediate Similarity NPC114102
0.7063 Intermediate Similarity NPC241634
0.7059 Intermediate Similarity NPC158325
0.7059 Intermediate Similarity NPC103398
0.7059 Intermediate Similarity NPC254832
0.7059 Intermediate Similarity NPC204257
0.7059 Intermediate Similarity NPC311742
0.7059 Intermediate Similarity NPC180171
0.7059 Intermediate Similarity NPC71108
0.7059 Intermediate Similarity NPC29317
0.7059 Intermediate Similarity NPC229638
0.7059 Intermediate Similarity NPC267539
0.7059 Intermediate Similarity NPC176102
0.7059 Intermediate Similarity NPC123988
0.7051 Intermediate Similarity NPC38473
0.7047 Intermediate Similarity NPC271808
0.7044 Intermediate Similarity NPC277857
0.7044 Intermediate Similarity NPC40222
0.7044 Intermediate Similarity NPC115144
0.7044 Intermediate Similarity NPC268515
0.7042 Intermediate Similarity NPC311737
0.7042 Intermediate Similarity NPC278652
0.7042 Intermediate Similarity NPC38458
0.7027 Intermediate Similarity NPC476353
0.7027 Intermediate Similarity NPC475695
0.7024 Intermediate Similarity NPC90984
0.702 Intermediate Similarity NPC214869
0.7014 Intermediate Similarity NPC476183
0.7014 Intermediate Similarity NPC34634
0.7014 Intermediate Similarity NPC265454
0.7013 Intermediate Similarity NPC120852
0.7013 Intermediate Similarity NPC160607
0.7013 Intermediate Similarity NPC312770
0.7013 Intermediate Similarity NPC204848
0.7013 Intermediate Similarity NPC471283
0.7013 Intermediate Similarity NPC41473
0.7013 Intermediate Similarity NPC14600
0.7012 Intermediate Similarity NPC62903
0.7012 Intermediate Similarity NPC7178
0.7007 Intermediate Similarity NPC469568
0.7007 Intermediate Similarity NPC288945
0.7 Intermediate Similarity NPC195749
0.7 Intermediate Similarity NPC264558
0.7 Intermediate Similarity NPC477300
0.7 Intermediate Similarity NPC52029
0.7 Intermediate Similarity NPC35961
0.6994 Remote Similarity NPC212699
0.6994 Remote Similarity NPC207675
0.6993 Remote Similarity NPC886
0.6993 Remote Similarity NPC287597
0.6993 Remote Similarity NPC309434
0.6993 Remote Similarity NPC34293
0.6993 Remote Similarity NPC203124
0.6987 Remote Similarity NPC156709
0.6987 Remote Similarity NPC179505
0.6986 Remote Similarity NPC327070
0.6982 Remote Similarity NPC83241
0.698 Remote Similarity NPC161593
0.698 Remote Similarity NPC145888
0.698 Remote Similarity NPC16031
0.6978 Remote Similarity NPC179002
0.6978 Remote Similarity NPC187583
0.6978 Remote Similarity NPC257430
0.6972 Remote Similarity NPC281277
0.6972 Remote Similarity NPC82963
0.697 Remote Similarity NPC155015
0.697 Remote Similarity NPC142479
0.6968 Remote Similarity NPC310252
0.6968 Remote Similarity NPC302583
0.6968 Remote Similarity NPC100558
0.6968 Remote Similarity NPC84789
0.6968 Remote Similarity NPC308976
0.6966 Remote Similarity NPC476281
0.6966 Remote Similarity NPC476184
0.6959 Remote Similarity NPC197832
0.6959 Remote Similarity NPC132921
0.6959 Remote Similarity NPC289459
0.6957 Remote Similarity NPC28776
0.6957 Remote Similarity NPC473138
0.6951 Remote Similarity NPC107602
0.695 Remote Similarity NPC328593
0.695 Remote Similarity NPC261453
0.695 Remote Similarity NPC33749
0.6946 Remote Similarity NPC179250
0.6946 Remote Similarity NPC50380
0.6939 Remote Similarity NPC476241
0.6939 Remote Similarity NPC212541
0.6939 Remote Similarity NPC476260
0.6933 Remote Similarity NPC155838
0.6932 Remote Similarity NPC276120
0.6928 Remote Similarity NPC284855
0.6928 Remote Similarity NPC282477
0.6918 Remote Similarity NPC292443
0.6918 Remote Similarity NPC470130
0.6918 Remote Similarity NPC183824
0.6913 Remote Similarity NPC251407
0.6913 Remote Similarity NPC213552
0.6913 Remote Similarity NPC120225
0.6913 Remote Similarity NPC168653
0.6913 Remote Similarity NPC94179
0.6906 Remote Similarity NPC147634
0.6906 Remote Similarity NPC226401
0.6906 Remote Similarity NPC79793
0.6906 Remote Similarity NPC120982
0.6906 Remote Similarity NPC174096
0.6901 Remote Similarity NPC474967
0.6901 Remote Similarity NPC37302
0.6901 Remote Similarity NPC233669
0.6901 Remote Similarity NPC95412
0.6899 Remote Similarity NPC13818
0.6899 Remote Similarity NPC35702
0.6899 Remote Similarity NPC471027
0.6899 Remote Similarity NPC224389
0.6899 Remote Similarity NPC297517
0.6899 Remote Similarity NPC477335
0.6899 Remote Similarity NPC206095
0.6899 Remote Similarity NPC67467
0.6897 Remote Similarity NPC328485
0.6897 Remote Similarity NPC477061
0.6897 Remote Similarity NPC45777
0.6897 Remote Similarity NPC260837
0.6894 Remote Similarity NPC322660
0.6892 Remote Similarity NPC246704
0.6892 Remote Similarity NPC476179
0.6892 Remote Similarity NPC476125
0.6887 Remote Similarity NPC241354

  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 NPC106183 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
0.7451 Intermediate Similarity NPD3400 Discontinued
0.7357 Intermediate Similarity NPD1759 Phase 1
0.7317 Intermediate Similarity NPD6746 Phase 2
0.7297 Intermediate Similarity NPD1048 Approved
0.7296 Intermediate Similarity NPD3111 Phase 1
0.7286 Intermediate Similarity NPD1758 Phase 1
0.7267 Intermediate Similarity NPD555 Phase 2
0.719 Intermediate Similarity NPD9570 Approved
0.7143 Intermediate Similarity NPD7978 Discontinued
0.7133 Intermediate Similarity NPD259 Phase 1
0.7123 Intermediate Similarity NPD2922 Phase 1
0.7114 Intermediate Similarity NPD3136 Phase 2
0.7103 Intermediate Similarity NPD2337 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD825 Approved
0.7086 Intermediate Similarity NPD826 Approved
0.7086 Intermediate Similarity NPD6346 Approved
0.7081 Intermediate Similarity NPD3455 Phase 2
0.702 Intermediate Similarity NPD5729 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD5563 Clinical (unspecified phase)
0.698 Remote Similarity NPD9569 Approved
0.6968 Remote Similarity NPD6032 Approved
0.6937 Remote Similarity NPD4123 Phase 3
0.6933 Remote Similarity NPD4675 Approved
0.6933 Remote Similarity NPD4678 Approved
0.6923 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6908 Remote Similarity NPD520 Approved
0.6906 Remote Similarity NPD9280 Clinical (unspecified phase)
0.6886 Remote Similarity NPD7975 Clinical (unspecified phase)
0.6879 Remote Similarity NPD7596 Clinical (unspecified phase)
0.6855 Remote Similarity NPD6190 Approved
0.6853 Remote Similarity NPD5291 Approved
0.6853 Remote Similarity NPD5292 Approved
0.6848 Remote Similarity NPD8019 Approved
0.6829 Remote Similarity NPD6502 Phase 2
0.6815 Remote Similarity NPD7266 Discontinued
0.6807 Remote Similarity NPD7089 Clinical (unspecified phase)
0.68 Remote Similarity NPD7451 Discontinued
0.68 Remote Similarity NPD6584 Phase 3
0.6797 Remote Similarity NPD7477 Discontinued
0.6795 Remote Similarity NPD6866 Clinical (unspecified phase)
0.6795 Remote Similarity NPD6867 Clinical (unspecified phase)
0.6776 Remote Similarity NPD9536 Phase 1
0.6776 Remote Similarity NPD9537 Phase 1
0.6774 Remote Similarity NPD5314 Approved
0.6753 Remote Similarity NPD3061 Approved
0.6753 Remote Similarity NPD3062 Approved
0.6753 Remote Similarity NPD3059 Approved
0.6752 Remote Similarity NPD7450 Phase 2
0.675 Remote Similarity NPD3692 Discontinued
0.675 Remote Similarity NPD2219 Phase 1
0.6735 Remote Similarity NPD3421 Phase 3
0.6733 Remote Similarity NPD3055 Approved
0.6733 Remote Similarity NPD3053 Approved
0.6731 Remote Similarity NPD3553 Approved
0.6731 Remote Similarity NPD3554 Approved
0.6731 Remote Similarity NPD3552 Approved
0.6731 Remote Similarity NPD3555 Approved
0.6714 Remote Similarity NPD3021 Approved
0.6714 Remote Similarity NPD3022 Approved
0.6689 Remote Similarity NPD258 Approved
0.6689 Remote Similarity NPD257 Approved
0.6687 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4005 Discontinued
0.6667 Remote Similarity NPD5310 Approved
0.6667 Remote Similarity NPD5311 Approved
0.6647 Remote Similarity NPD7945 Clinical (unspecified phase)
0.6646 Remote Similarity NPD302 Approved
0.6646 Remote Similarity NPD2122 Discontinued
0.6645 Remote Similarity NPD468 Phase 1
0.6645 Remote Similarity NPD2203 Discontinued
0.6644 Remote Similarity NPD6624 Discontinued
0.6629 Remote Similarity NPD5035 Approved
0.6627 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6626 Remote Similarity NPD2504 Approved
0.6626 Remote Similarity NPD4160 Clinical (unspecified phase)
0.6626 Remote Similarity NPD2505 Approved
0.6626 Remote Similarity NPD4739 Approved
0.6626 Remote Similarity NPD7446 Clinical (unspecified phase)
0.6607 Remote Similarity NPD7972 Discontinued
0.66 Remote Similarity NPD9622 Approved
0.66 Remote Similarity NPD6582 Phase 2
0.66 Remote Similarity NPD6583 Phase 3
0.6593 Remote Similarity NPD9273 Approved
0.6581 Remote Similarity NPD2674 Phase 3
0.6581 Remote Similarity NPD839 Approved
0.6581 Remote Similarity NPD840 Approved
0.6573 Remote Similarity NPD36 Approved
0.6573 Remote Similarity NPD4954 Approved
0.6573 Remote Similarity NPD4955 Approved
0.6573 Remote Similarity NPD5028 Approved
0.6573 Remote Similarity NPD5026 Approved
0.6573 Remote Similarity NPD5034 Approved
0.6568 Remote Similarity NPD7737 Approved
0.6568 Remote Similarity NPD7738 Approved
0.6562 Remote Similarity NPD8151 Discontinued
0.6554 Remote Similarity NPD9381 Approved
0.6554 Remote Similarity NPD9384 Approved
0.6552 Remote Similarity NPD5822 Clinical (unspecified phase)
0.6545 Remote Similarity NPD7131 Phase 3
0.6544 Remote Similarity NPD9712 Approved
0.6538 Remote Similarity NPD5837 Clinical (unspecified phase)
0.6538 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6538 Remote Similarity NPD1613 Approved
0.6536 Remote Similarity NPD4006 Discontinued
0.6536 Remote Similarity NPD4993 Discontinued
0.6532 Remote Similarity NPD7608 Discontinued
0.6524 Remote Similarity NPD1754 Clinical (unspecified phase)
0.6522 Remote Similarity NPD5177 Phase 3
0.6519 Remote Similarity NPD8150 Discontinued
0.6519 Remote Similarity NPD5688 Approved
0.6519 Remote Similarity NPD5689 Approved
0.6517 Remote Similarity NPD5030 Phase 2
0.6516 Remote Similarity NPD601 Approved
0.6516 Remote Similarity NPD598 Approved
0.6516 Remote Similarity NPD3145 Approved
0.6516 Remote Similarity NPD3144 Approved
0.6516 Remote Similarity NPD597 Approved
0.651 Remote Similarity NPD1981 Approved
0.651 Remote Similarity NPD1980 Approved
0.651 Remote Similarity NPD1983 Approved
0.6503 Remote Similarity NPD7554 Discontinued
0.6503 Remote Similarity NPD3300 Phase 2
0.6497 Remote Similarity NPD7695 Clinical (unspecified phase)
0.6497 Remote Similarity NPD275 Approved
0.6497 Remote Similarity NPD274 Approved
0.6494 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6494 Remote Similarity NPD5137 Approved
0.649 Remote Similarity NPD3676 Clinical (unspecified phase)
0.649 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6485 Remote Similarity NPD7526 Approved
0.6485 Remote Similarity NPD4186 Clinical (unspecified phase)
0.6485 Remote Similarity NPD7527 Clinical (unspecified phase)
0.6485 Remote Similarity NPD52 Approved
0.6481 Remote Similarity NPD8166 Discontinued
0.6481 Remote Similarity NPD6658 Clinical (unspecified phase)
0.648 Remote Similarity NPD5032 Approved
0.6477 Remote Similarity NPD7493 Clinical (unspecified phase)
0.6474 Remote Similarity NPD6407 Approved
0.6474 Remote Similarity NPD1136 Approved
0.6474 Remote Similarity NPD1132 Approved
0.6474 Remote Similarity NPD1130 Approved
0.6474 Remote Similarity NPD6405 Approved
0.6471 Remote Similarity NPD7494 Clinical (unspecified phase)
0.6471 Remote Similarity NPD9711 Approved
0.6471 Remote Similarity NPD9710 Approved
0.6467 Remote Similarity NPD4480 Approved
0.6463 Remote Similarity NPD4357 Discontinued
0.6461 Remote Similarity NPD6184 Discontinued
0.646 Remote Similarity NPD4149 Clinical (unspecified phase)
0.6458 Remote Similarity NPD9379 Approved
0.6458 Remote Similarity NPD9377 Approved
0.6456 Remote Similarity NPD817 Approved
0.6456 Remote Similarity NPD2568 Approved
0.6456 Remote Similarity NPD823 Approved
0.6452 Remote Similarity NPD3027 Phase 3
0.6452 Remote Similarity NPD2372 Approved
0.6452 Remote Similarity NPD4738 Phase 2
0.645 Remote Similarity NPD5722 Discontinued
0.6438 Remote Similarity NPD2935 Discontinued
0.6433 Remote Similarity NPD4060 Phase 1
0.6433 Remote Similarity NPD943 Approved
0.6433 Remote Similarity NPD1558 Phase 1
0.6429 Remote Similarity NPD5038 Approved
0.6429 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6429 Remote Similarity NPD5037 Approved
0.6424 Remote Similarity NPD5108 Clinical (unspecified phase)
0.6424 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6419 Remote Similarity NPD2226 Clinical (unspecified phase)
0.6412 Remote Similarity NPD2393 Clinical (unspecified phase)
0.641 Remote Similarity NPD6798 Discontinued
0.6407 Remote Similarity NPD1653 Approved
0.64 Remote Similarity NPD4135 Approved
0.64 Remote Similarity NPD4136 Approved
0.64 Remote Similarity NPD4106 Approved
0.6398 Remote Similarity NPD3656 Approved
0.6395 Remote Similarity NPD9568 Approved
0.6393 Remote Similarity NPD4435 Approved
0.6392 Remote Similarity NPD4618 Approved
0.6392 Remote Similarity NPD230 Phase 1
0.6392 Remote Similarity NPD447 Suspended
0.6392 Remote Similarity NPD4622 Approved
0.6389 Remote Similarity NPD3936 Clinical (unspecified phase)
0.6387 Remote Similarity NPD5202 Clinical (unspecified phase)
0.6386 Remote Similarity NPD6390 Discontinued
0.6386 Remote Similarity NPD5261 Clinical (unspecified phase)
0.638 Remote Similarity NPD6331 Phase 2
0.6375 Remote Similarity NPD1753 Discontinued
0.6374 Remote Similarity NPD2379 Clinical (unspecified phase)
0.6374 Remote Similarity NPD5036 Approved
0.6374 Remote Similarity NPD3817 Phase 2
0.637 Remote Similarity NPD9618 Approved
0.637 Remote Similarity NPD9614 Approved
0.6369 Remote Similarity NPD6233 Phase 2
0.6369 Remote Similarity NPD5745 Approved
0.6369 Remote Similarity NPD7959 Clinical (unspecified phase)
0.6369 Remote Similarity NPD1726 Clinical (unspecified phase)
0.6364 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6364 Remote Similarity NPD2421 Approved
0.6364 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6364 Remote Similarity NPD2420 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