Structure

Physi-Chem Properties

Molecular Weight:  318.22
Volume:  359.108
LogP:  3.574
LogD:  3.01
LogS:  -3.43
# Rotatable Bonds:  13
TPSA:  49.83
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.22
Synthetic Accessibility Score:  3.789
Fsp3:  0.55
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.885
MDCK Permeability:  4.300757063901983e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.029
20% Bioavailability (F20%):  0.999
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.016
Plasma Protein Binding (PPB):  96.72037506103516%
Volume Distribution (VD):  0.296
Pgp-substrate:  2.7150142192840576%

ADMET: Metabolism

CYP1A2-inhibitor:  0.118
CYP1A2-substrate:  0.427
CYP2C19-inhibitor:  0.231
CYP2C19-substrate:  0.51
CYP2C9-inhibitor:  0.321
CYP2C9-substrate:  0.99
CYP2D6-inhibitor:  0.482
CYP2D6-substrate:  0.893
CYP3A4-inhibitor:  0.542
CYP3A4-substrate:  0.102

ADMET: Excretion

Clearance (CL):  3.859
Half-life (T1/2):  0.85

ADMET: Toxicity

hERG Blockers:  0.112
Human Hepatotoxicity (H-HT):  0.624
Drug-inuced Liver Injury (DILI):  0.152
AMES Toxicity:  0.497
Rat Oral Acute Toxicity:  0.241
Maximum Recommended Daily Dose:  0.78
Skin Sensitization:  0.941
Carcinogencity:  0.674
Eye Corrosion:  0.546
Eye Irritation:  0.671
Respiratory Toxicity:  0.941

Download Data

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

  Natural Product: NPC92558

Natural Product ID:  NPC92558
Common Name*:   Leukotriene A4
IUPAC Name:   4-[(2S,3S)-3-[(1E,3E,5Z,8Z)-tetradeca-1,3,5,8-tetraenyl]oxiran-2-yl]butanoic acid
Synonyms:   Leukotriene A4
Standard InCHIKey:  UFPQIRYSPUYQHK-WAQVJNLQSA-N
Standard InCHI:  InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18-19(23-18)16-14-17-20(21)22/h6-7,9-13,15,18-19H,2-5,8,14,16-17H2,1H3,(H,21,22)/b7-6-,10-9-,12-11+,15-13+/t18-,19-/m0/s1
SMILES:  CCCCC/C=CC/C=CC=CC=C[C@@H]1O[C@H]1CCCC(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL69439
PubChem CID:   5280383
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0003909] Fatty Acyls
        • [CHEMONTID:0000262] Fatty acids and conjugates
          • [CHEMONTID:0001989] Heterocyclic fatty acids
            • [CHEMONTID:0001537] Epoxy fatty acids

*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
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]
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]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[1175644]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[12391014]
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]
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]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[15314235]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[16112079]
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]
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]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[17875433]
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]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[19425150]
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. bile 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. n.a. n.a. PMID[20876113]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[21798258]
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]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[23315938]
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]
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]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[24816727]
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]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[25644343]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[26236990]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[27471436]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[3179836]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[347637]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[4696527]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[5432584]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[6121420]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[6780563]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[8600370]
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]
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]

☑ 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
NPT2520 Individual Protein Leukotriene A4 hydrolase Homo sapiens Km = 7600.0 nM PMID[465823]
NPT2520 Individual Protein Leukotriene A4 hydrolase Homo sapiens k cat = 6.8 s-1 PMID[465823]
NPT2520 Individual Protein Leukotriene A4 hydrolase Homo sapiens Vmax = 572.0 nM min-1 mg-1 PMID[465823]
NPT2520 Individual Protein Leukotriene A4 hydrolase Homo sapiens Km = 7600.0 nM PMID[465824]
NPT2520 Individual Protein Leukotriene A4 hydrolase Homo sapiens Vmax = 572.0 nM min-1 mg-1 PMID[465824]
NPT570 Individual Protein Arachidonate 5-lipoxygenase Homo sapiens Inhibition = 78.0 % PMID[465825]
NPT570 Individual Protein Arachidonate 5-lipoxygenase Homo sapiens IC50 = 2000.0 nM PMID[465825]
NPT2 Others Unspecified Ratio = 0.0009 n.a. PMID[465823]
NPT2 Others Unspecified k cat/Km = 90000.0 M-1 s-1 PMID[465824]

☑ 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 NPC92558 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
0.8857 High Similarity NPC317583
0.8243 Intermediate Similarity NPC325627
0.8143 Intermediate Similarity NPC68343
0.8143 Intermediate Similarity NPC328089
0.8056 Intermediate Similarity NPC49863
0.8049 Intermediate Similarity NPC122502
0.8028 Intermediate Similarity NPC323045
0.8028 Intermediate Similarity NPC320642
0.8028 Intermediate Similarity NPC323477
0.8028 Intermediate Similarity NPC317881
0.7975 Intermediate Similarity NPC474510
0.7922 Intermediate Similarity NPC188860
0.7917 Intermediate Similarity NPC328653
0.7857 Intermediate Similarity NPC320305
0.7857 Intermediate Similarity NPC328776
0.7821 Intermediate Similarity NPC233071
0.7778 Intermediate Similarity NPC326268
0.7778 Intermediate Similarity NPC255863
0.7778 Intermediate Similarity NPC318420
0.7778 Intermediate Similarity NPC136164
0.7778 Intermediate Similarity NPC245947
0.7763 Intermediate Similarity NPC326024
0.7763 Intermediate Similarity NPC329914
0.7733 Intermediate Similarity NPC476012
0.7683 Intermediate Similarity NPC170377
0.7647 Intermediate Similarity NPC327388
0.7606 Intermediate Similarity NPC201939
0.7571 Intermediate Similarity NPC478095
0.7536 Intermediate Similarity NPC211752
0.7536 Intermediate Similarity NPC323597
0.7536 Intermediate Similarity NPC323498
0.7532 Intermediate Similarity NPC329890
0.7529 Intermediate Similarity NPC477959
0.7528 Intermediate Similarity NPC107476
0.75 Intermediate Similarity NPC476037
0.747 Intermediate Similarity NPC250315
0.7465 Intermediate Similarity NPC328311
0.7465 Intermediate Similarity NPC327112
0.7465 Intermediate Similarity NPC243532
0.7429 Intermediate Similarity NPC478096
0.7412 Intermediate Similarity NPC309211
0.7412 Intermediate Similarity NPC164393
0.7403 Intermediate Similarity NPC320119
0.7397 Intermediate Similarity NPC470320
0.7381 Intermediate Similarity NPC474251
0.7368 Intermediate Similarity NPC143396
0.7368 Intermediate Similarity NPC475004
0.7342 Intermediate Similarity NPC260396
0.7333 Intermediate Similarity NPC99619
0.7333 Intermediate Similarity NPC26500
0.7326 Intermediate Similarity NPC474765
0.7326 Intermediate Similarity NPC86005
0.7324 Intermediate Similarity NPC329249
0.7324 Intermediate Similarity NPC222852
0.7308 Intermediate Similarity NPC185186
0.7308 Intermediate Similarity NPC327383
0.7303 Intermediate Similarity NPC476049
0.7294 Intermediate Similarity NPC477018
0.7294 Intermediate Similarity NPC21469
0.7294 Intermediate Similarity NPC100921
0.7294 Intermediate Similarity NPC474547
0.7284 Intermediate Similarity NPC267231
0.7273 Intermediate Similarity NPC476660
0.7273 Intermediate Similarity NPC313670
0.7262 Intermediate Similarity NPC272814
0.7253 Intermediate Similarity NPC473291
0.7246 Intermediate Similarity NPC52264
0.7241 Intermediate Similarity NPC281516
0.7237 Intermediate Similarity NPC474823
0.7237 Intermediate Similarity NPC218477
0.7222 Intermediate Similarity NPC474035
0.7222 Intermediate Similarity NPC81386
0.7209 Intermediate Similarity NPC116575
0.7209 Intermediate Similarity NPC112685
0.7209 Intermediate Similarity NPC477010
0.7204 Intermediate Similarity NPC475053
0.7195 Intermediate Similarity NPC469747
0.7195 Intermediate Similarity NPC263574
0.7179 Intermediate Similarity NPC477086
0.7179 Intermediate Similarity NPC477087
0.7176 Intermediate Similarity NPC474776
0.7162 Intermediate Similarity NPC226592
0.716 Intermediate Similarity NPC7563
0.716 Intermediate Similarity NPC84360
0.716 Intermediate Similarity NPC116177
0.716 Intermediate Similarity NPC320630
0.7159 Intermediate Similarity NPC106040
0.7159 Intermediate Similarity NPC474032
0.7159 Intermediate Similarity NPC295312
0.7159 Intermediate Similarity NPC115179
0.7159 Intermediate Similarity NPC477011
0.7143 Intermediate Similarity NPC14961
0.7143 Intermediate Similarity NPC473772
0.7143 Intermediate Similarity NPC475659
0.7143 Intermediate Similarity NPC270013
0.7143 Intermediate Similarity NPC272050
0.7143 Intermediate Similarity NPC18951
0.7126 Intermediate Similarity NPC154097
0.7126 Intermediate Similarity NPC473649
0.7126 Intermediate Similarity NPC159750
0.7126 Intermediate Similarity NPC470401
0.7126 Intermediate Similarity NPC231889
0.7126 Intermediate Similarity NPC475703
0.7126 Intermediate Similarity NPC160138
0.7125 Intermediate Similarity NPC327041
0.7125 Intermediate Similarity NPC285840
0.7125 Intermediate Similarity NPC473948
0.7123 Intermediate Similarity NPC113293
0.7123 Intermediate Similarity NPC477829
0.7111 Intermediate Similarity NPC212486
0.7105 Intermediate Similarity NPC104537
0.7105 Intermediate Similarity NPC127091
0.7105 Intermediate Similarity NPC271921
0.7105 Intermediate Similarity NPC478097
0.7105 Intermediate Similarity NPC478100
0.7105 Intermediate Similarity NPC148192
0.7105 Intermediate Similarity NPC330426
0.7105 Intermediate Similarity NPC22101
0.7101 Intermediate Similarity NPC137538
0.7097 Intermediate Similarity NPC161855
0.7093 Intermediate Similarity NPC197903
0.7093 Intermediate Similarity NPC322529
0.7093 Intermediate Similarity NPC99395
0.7093 Intermediate Similarity NPC137033
0.7093 Intermediate Similarity NPC474369
0.7089 Intermediate Similarity NPC477085
0.7079 Intermediate Similarity NPC474761
0.7079 Intermediate Similarity NPC473619
0.7079 Intermediate Similarity NPC316228
0.7079 Intermediate Similarity NPC476004
0.7079 Intermediate Similarity NPC51004
0.7073 Intermediate Similarity NPC182292
0.7073 Intermediate Similarity NPC127526
0.7073 Intermediate Similarity NPC474341
0.7073 Intermediate Similarity NPC108816
0.7073 Intermediate Similarity NPC93763
0.7067 Intermediate Similarity NPC478099
0.7067 Intermediate Similarity NPC478098
0.7065 Intermediate Similarity NPC476315
0.7065 Intermediate Similarity NPC473859
0.7059 Intermediate Similarity NPC11620
0.7059 Intermediate Similarity NPC475842
0.7059 Intermediate Similarity NPC253801
0.7059 Intermediate Similarity NPC52923
0.7051 Intermediate Similarity NPC475310
0.7045 Intermediate Similarity NPC89001
0.7045 Intermediate Similarity NPC474471
0.7045 Intermediate Similarity NPC153805
0.7045 Intermediate Similarity NPC227379
0.7045 Intermediate Similarity NPC202672
0.7045 Intermediate Similarity NPC473715
0.7042 Intermediate Similarity NPC225929
0.7037 Intermediate Similarity NPC49392
0.7037 Intermediate Similarity NPC190400
0.7037 Intermediate Similarity NPC271070
0.7033 Intermediate Similarity NPC57405
0.7033 Intermediate Similarity NPC303942
0.7024 Intermediate Similarity NPC184208
0.7024 Intermediate Similarity NPC325031
0.7024 Intermediate Similarity NPC297440
0.7024 Intermediate Similarity NPC8538
0.7013 Intermediate Similarity NPC48218
0.7013 Intermediate Similarity NPC324981
0.7013 Intermediate Similarity NPC141481
0.7013 Intermediate Similarity NPC473559
0.7011 Intermediate Similarity NPC107717
0.7011 Intermediate Similarity NPC142117
0.7011 Intermediate Similarity NPC114694
0.7011 Intermediate Similarity NPC232555
0.7011 Intermediate Similarity NPC171174
0.7011 Intermediate Similarity NPC62118
0.7011 Intermediate Similarity NPC69082
0.7011 Intermediate Similarity NPC47937
0.7011 Intermediate Similarity NPC284902
0.7011 Intermediate Similarity NPC61527
0.7011 Intermediate Similarity NPC279267
0.7011 Intermediate Similarity NPC240695
0.7011 Intermediate Similarity NPC475581
0.7011 Intermediate Similarity NPC231096
0.7 Intermediate Similarity NPC474321
0.7 Intermediate Similarity NPC128061
0.7 Intermediate Similarity NPC28779
0.7 Intermediate Similarity NPC228473
0.7 Intermediate Similarity NPC227396
0.7 Intermediate Similarity NPC473321
0.7 Intermediate Similarity NPC10316
0.7 Intermediate Similarity NPC200845
0.7 Intermediate Similarity NPC30515
0.7 Intermediate Similarity NPC223677
0.6988 Remote Similarity NPC1180
0.6988 Remote Similarity NPC471537
0.6986 Remote Similarity NPC174447
0.6986 Remote Similarity NPC251042
0.6986 Remote Similarity NPC122521
0.6977 Remote Similarity NPC14575
0.6977 Remote Similarity NPC72464
0.6977 Remote Similarity NPC156804
0.6977 Remote Similarity NPC196487
0.6974 Remote Similarity NPC478101
0.6974 Remote Similarity NPC146811

  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 NPC92558 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
0.8056 Intermediate Similarity NPD4247 Clinical (unspecified phase)
0.7465 Intermediate Similarity NPD4246 Clinical (unspecified phase)
0.7191 Intermediate Similarity NPD7983 Approved
0.7079 Intermediate Similarity NPD6698 Approved
0.7079 Intermediate Similarity NPD46 Approved
0.6957 Remote Similarity NPD3172 Approved
0.6933 Remote Similarity NPD3197 Phase 1
0.6923 Remote Similarity NPD5779 Approved
0.6923 Remote Similarity NPD5778 Approved
0.6897 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6889 Remote Similarity NPD7838 Discovery
0.6857 Remote Similarity NPD3194 Approved
0.6857 Remote Similarity NPD3196 Approved
0.6857 Remote Similarity NPD4266 Approved
0.6857 Remote Similarity NPD3195 Phase 2
0.6707 Remote Similarity NPD8039 Approved
0.6702 Remote Similarity NPD7839 Suspended
0.6618 Remote Similarity NPD3173 Approved
0.6548 Remote Similarity NPD4756 Discovery
0.6477 Remote Similarity NPD7154 Phase 3
0.6444 Remote Similarity NPD4249 Approved
0.6444 Remote Similarity NPD5786 Approved
0.6429 Remote Similarity NPD29 Approved
0.6429 Remote Similarity NPD28 Approved
0.6413 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6413 Remote Similarity NPD6101 Approved
0.641 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6374 Remote Similarity NPD4250 Approved
0.6374 Remote Similarity NPD4251 Approved
0.6364 Remote Similarity NPD6435 Approved
0.6322 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6292 Remote Similarity NPD5362 Discontinued
0.6277 Remote Similarity NPD6411 Approved
0.6267 Remote Similarity NPD6109 Phase 1
0.6237 Remote Similarity NPD1695 Approved
0.6232 Remote Similarity NPD622 Approved
0.6232 Remote Similarity NPD5343 Approved
0.6224 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6197 Remote Similarity NPD6927 Phase 3
0.618 Remote Similarity NPD5209 Approved
0.618 Remote Similarity NPD4270 Approved
0.618 Remote Similarity NPD4269 Approved
0.6176 Remote Similarity NPD3174 Discontinued
0.6176 Remote Similarity NPD4222 Approved
0.617 Remote Similarity NPD5785 Approved
0.6136 Remote Similarity NPD5368 Approved
0.6136 Remote Similarity NPD4252 Approved
0.6092 Remote Similarity NPD4271 Approved
0.6092 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6092 Remote Similarity NPD4268 Approved
0.6082 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6067 Remote Similarity NPD5369 Approved
0.6018 Remote Similarity NPD7829 Approved
0.6018 Remote Similarity NPD7830 Approved
0.6 Remote Similarity NPD6648 Approved
0.5978 Remote Similarity NPD5363 Approved
0.5955 Remote Similarity NPD4822 Approved
0.5955 Remote Similarity NPD4820 Approved
0.5955 Remote Similarity NPD4821 Approved
0.5955 Remote Similarity NPD4819 Approved
0.5942 Remote Similarity NPD39 Approved
0.5938 Remote Similarity NPD7637 Suspended
0.5914 Remote Similarity NPD6422 Discontinued
0.5844 Remote Similarity NPD585 Clinical (unspecified phase)
0.5841 Remote Similarity NPD8513 Phase 3
0.5841 Remote Similarity NPD8517 Approved
0.5841 Remote Similarity NPD8444 Approved
0.5841 Remote Similarity NPD8515 Approved
0.5841 Remote Similarity NPD8516 Approved
0.5833 Remote Similarity NPD6053 Discontinued
0.581 Remote Similarity NPD7899 Clinical (unspecified phase)
0.5806 Remote Similarity NPD6082 Clinical (unspecified phase)
0.5797 Remote Similarity NPD6096 Approved
0.5797 Remote Similarity NPD6097 Approved
0.5794 Remote Similarity NPD6371 Approved
0.5784 Remote Similarity NPD5344 Discontinued
0.5761 Remote Similarity NPD5332 Approved
0.5761 Remote Similarity NPD5331 Approved
0.5743 Remote Similarity NPD7638 Approved
0.5741 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5732 Remote Similarity NPD7331 Phase 2
0.5729 Remote Similarity NPD5370 Suspended
0.5714 Remote Similarity NPD5048 Discontinued
0.5714 Remote Similarity NPD4790 Discontinued
0.5686 Remote Similarity NPD7640 Approved
0.5686 Remote Similarity NPD7639 Approved
0.5679 Remote Similarity NPD5325 Clinical (unspecified phase)
0.5652 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5652 Remote Similarity NPD5326 Phase 3
0.5641 Remote Similarity NPD8451 Approved
0.5641 Remote Similarity NPD8273 Phase 1
0.5638 Remote Similarity NPD1694 Approved
0.5612 Remote Similarity NPD4810 Clinical (unspecified phase)
0.5607 Remote Similarity NPD6686 Approved
0.5603 Remote Similarity NPD7642 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