Structure

Physi-Chem Properties

Molecular Weight:  320.24
Volume:  367.665
LogP:  2.641
LogD:  2.077
LogS:  -3.587
# Rotatable Bonds:  14
TPSA:  57.53
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  0
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.263
Synthetic Accessibility Score:  3.345
Fsp3:  0.55
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.222
MDCK Permeability:  9.300654346588999e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.093
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.003
Plasma Protein Binding (PPB):  97.39692687988281%
Volume Distribution (VD):  0.242
Pgp-substrate:  1.2178376913070679%

ADMET: Metabolism

CYP1A2-inhibitor:  0.204
CYP1A2-substrate:  0.731
CYP2C19-inhibitor:  0.068
CYP2C19-substrate:  0.599
CYP2C9-inhibitor:  0.128
CYP2C9-substrate:  0.991
CYP2D6-inhibitor:  0.087
CYP2D6-substrate:  0.891
CYP3A4-inhibitor:  0.129
CYP3A4-substrate:  0.077

ADMET: Excretion

Clearance (CL):  4.436
Half-life (T1/2):  0.914

ADMET: Toxicity

hERG Blockers:  0.036
Human Hepatotoxicity (H-HT):  0.705
Drug-inuced Liver Injury (DILI):  0.029
AMES Toxicity:  0.314
Rat Oral Acute Toxicity:  0.02
Maximum Recommended Daily Dose:  0.815
Skin Sensitization:  0.937
Carcinogencity:  0.696
Eye Corrosion:  0.009
Eye Irritation:  0.143
Respiratory Toxicity:  0.941

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Structure MOL file  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC317881

Natural Product ID:  NPC317881
Common Name*:   5-Hydroxy-Icosa-6,8,11,14-Tetraenoic Acid
IUPAC Name:   (6E,8Z,11Z,14Z)-5-hydroxyicosa-6,8,11,14-tetraenoic acid
Synonyms:  
Standard InCHIKey:  KGIJOOYOSFUGPC-XTDASVJISA-N
Standard InCHI:  InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h6-7,9-10,12-14,16,19,21H,2-5,8,11,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,13-12-,16-14+
SMILES:  CCCCC/C=CC/C=CC/C=CC=CC(CCCC(=O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL17695
PubChem CID:   9862886
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0003909] Fatty Acyls
        • [CHEMONTID:0000513] Eicosanoids
          • [CHEMONTID:0000046] Hydroxyeicosatetraenoic 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
NPT858 Cell Line LNCaP Homo sapiens Control = 116.0 % PMID[538871]
NPT183 Individual Protein Arachidonate 5-lipoxygenase Rattus norvegicus IC50 = 77000.0 nM PMID[538872]
NPT183 Individual Protein Arachidonate 5-lipoxygenase Rattus norvegicus IC50 = 77000.0 nM PMID[538873]

☑ 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 NPC317881 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 NPC323045
0.9677 High Similarity NPC49863
0.9516 High Similarity NPC328653
0.9355 High Similarity NPC320642
0.9355 High Similarity NPC323477
0.9016 High Similarity NPC327112
0.8955 High Similarity NPC325627
0.875 High Similarity NPC245947
0.875 High Similarity NPC255863
0.875 High Similarity NPC136164
0.8548 High Similarity NPC322002
0.8413 Intermediate Similarity NPC328311
0.8254 Intermediate Similarity NPC329249
0.8182 Intermediate Similarity NPC318420
0.8182 Intermediate Similarity NPC326268
0.803 Intermediate Similarity NPC470320
0.8028 Intermediate Similarity NPC92558
0.7971 Intermediate Similarity NPC143396
0.7969 Intermediate Similarity NPC322186
0.7969 Intermediate Similarity NPC318306
0.7941 Intermediate Similarity NPC99619
0.7941 Intermediate Similarity NPC26500
0.7846 Intermediate Similarity NPC243532
0.7778 Intermediate Similarity NPC472808
0.7778 Intermediate Similarity NPC324224
0.7778 Intermediate Similarity NPC227396
0.7761 Intermediate Similarity NPC226592
0.7727 Intermediate Similarity NPC201939
0.7727 Intermediate Similarity NPC113293
0.7727 Intermediate Similarity NPC477829
0.7714 Intermediate Similarity NPC317583
0.7714 Intermediate Similarity NPC236208
0.7656 Intermediate Similarity NPC323436
0.7639 Intermediate Similarity NPC326024
0.7606 Intermediate Similarity NPC476037
0.75 Intermediate Similarity NPC5413
0.75 Intermediate Similarity NPC18951
0.75 Intermediate Similarity NPC149821
0.7463 Intermediate Similarity NPC321838
0.7432 Intermediate Similarity NPC260396
0.7429 Intermediate Similarity NPC478097
0.7424 Intermediate Similarity NPC329550
0.7419 Intermediate Similarity NPC92114
0.7407 Intermediate Similarity NPC86005
0.7407 Intermediate Similarity NPC477959
0.7397 Intermediate Similarity NPC329890
0.7391 Intermediate Similarity NPC476654
0.7391 Intermediate Similarity NPC476657
0.7391 Intermediate Similarity NPC476655
0.7385 Intermediate Similarity NPC211752
0.7385 Intermediate Similarity NPC44542
0.7385 Intermediate Similarity NPC323498
0.7385 Intermediate Similarity NPC472445
0.7385 Intermediate Similarity NPC323597
0.7368 Intermediate Similarity NPC127526
0.7361 Intermediate Similarity NPC476012
0.7361 Intermediate Similarity NPC476660
0.7333 Intermediate Similarity NPC207292
0.7333 Intermediate Similarity NPC91495
0.7313 Intermediate Similarity NPC81896
0.7313 Intermediate Similarity NPC321919
0.7302 Intermediate Similarity NPC70387
0.7302 Intermediate Similarity NPC321062
0.7286 Intermediate Similarity NPC476656
0.7286 Intermediate Similarity NPC476659
0.7286 Intermediate Similarity NPC146811
0.726 Intermediate Similarity NPC320119
0.7246 Intermediate Similarity NPC68343
0.7246 Intermediate Similarity NPC328089
0.7231 Intermediate Similarity NPC327388
0.7231 Intermediate Similarity NPC325977
0.7231 Intermediate Similarity NPC477201
0.7222 Intermediate Similarity NPC473772
0.7222 Intermediate Similarity NPC470436
0.7206 Intermediate Similarity NPC328776
0.7206 Intermediate Similarity NPC320305
0.7206 Intermediate Similarity NPC475984
0.7188 Intermediate Similarity NPC137538
0.7188 Intermediate Similarity NPC25417
0.7188 Intermediate Similarity NPC290563
0.7188 Intermediate Similarity NPC424
0.7188 Intermediate Similarity NPC281972
0.7188 Intermediate Similarity NPC85813
0.7188 Intermediate Similarity NPC87564
0.7188 Intermediate Similarity NPC32467
0.7188 Intermediate Similarity NPC88966
0.7188 Intermediate Similarity NPC154245
0.7188 Intermediate Similarity NPC261831
0.7188 Intermediate Similarity NPC322461
0.7188 Intermediate Similarity NPC6095
0.7188 Intermediate Similarity NPC110732
0.7183 Intermediate Similarity NPC22101
0.7183 Intermediate Similarity NPC104537
0.7183 Intermediate Similarity NPC478100
0.7183 Intermediate Similarity NPC25298
0.7183 Intermediate Similarity NPC148192
0.7183 Intermediate Similarity NPC127091
0.7183 Intermediate Similarity NPC271921
0.7183 Intermediate Similarity NPC330426
0.7164 Intermediate Similarity NPC222852
0.7162 Intermediate Similarity NPC329914
0.7162 Intermediate Similarity NPC284006
0.7143 Intermediate Similarity NPC478099
0.7143 Intermediate Similarity NPC313670
0.7143 Intermediate Similarity NPC478098
0.7125 Intermediate Similarity NPC52923
0.7121 Intermediate Similarity NPC225929
0.7105 Intermediate Similarity NPC279537
0.7105 Intermediate Similarity NPC188860
0.7101 Intermediate Similarity NPC29697
0.7101 Intermediate Similarity NPC470965
0.7097 Intermediate Similarity NPC59051
0.7083 Intermediate Similarity NPC324981
0.7083 Intermediate Similarity NPC141481
0.7083 Intermediate Similarity NPC48218
0.7083 Intermediate Similarity NPC473559
0.7077 Intermediate Similarity NPC228473
0.7077 Intermediate Similarity NPC52264
0.7073 Intermediate Similarity NPC164393
0.7067 Intermediate Similarity NPC474321
0.7059 Intermediate Similarity NPC122521
0.7059 Intermediate Similarity NPC251042
0.7059 Intermediate Similarity NPC174447
0.7051 Intermediate Similarity NPC321728
0.7042 Intermediate Similarity NPC478101
0.7037 Intermediate Similarity NPC219966
0.7031 Intermediate Similarity NPC1813
0.7031 Intermediate Similarity NPC36061
0.7031 Intermediate Similarity NPC294548
0.7031 Intermediate Similarity NPC61177
0.7031 Intermediate Similarity NPC139029
0.7031 Intermediate Similarity NPC217188
0.7027 Intermediate Similarity NPC67076
0.7027 Intermediate Similarity NPC293114
0.7027 Intermediate Similarity NPC319163
0.7013 Intermediate Similarity NPC233071
0.7 Intermediate Similarity NPC476658
0.7 Intermediate Similarity NPC117572
0.6986 Remote Similarity NPC130618
0.6984 Remote Similarity NPC59408
0.6984 Remote Similarity NPC284212
0.6984 Remote Similarity NPC71053
0.6984 Remote Similarity NPC470411
0.6984 Remote Similarity NPC28205
0.6974 Remote Similarity NPC473948
0.6957 Remote Similarity NPC325929
0.6957 Remote Similarity NPC271282
0.6957 Remote Similarity NPC26810
0.6957 Remote Similarity NPC66460
0.6957 Remote Similarity NPC40082
0.6951 Remote Similarity NPC137033
0.6944 Remote Similarity NPC473829
0.6944 Remote Similarity NPC475443
0.6933 Remote Similarity NPC470435
0.6923 Remote Similarity NPC192006
0.6923 Remote Similarity NPC182292
0.6912 Remote Similarity NPC274927
0.6912 Remote Similarity NPC106851
0.6897 Remote Similarity NPC5418
0.6892 Remote Similarity NPC42526
0.6875 Remote Similarity NPC281245
0.6875 Remote Similarity NPC297440
0.6867 Remote Similarity NPC122502
0.6867 Remote Similarity NPC309211
0.6849 Remote Similarity NPC474823
0.6835 Remote Similarity NPC201225
0.6835 Remote Similarity NPC469747
0.6835 Remote Similarity NPC263574
0.6835 Remote Similarity NPC1180
0.6825 Remote Similarity NPC291437
0.6825 Remote Similarity NPC328784
0.6818 Remote Similarity NPC473863
0.6818 Remote Similarity NPC274290
0.6818 Remote Similarity NPC474513
0.6818 Remote Similarity NPC200845
0.6818 Remote Similarity NPC470963
0.6818 Remote Similarity NPC10316
0.6818 Remote Similarity NPC152668
0.6818 Remote Similarity NPC28779
0.6818 Remote Similarity NPC317899
0.6818 Remote Similarity NPC223677
0.6818 Remote Similarity NPC128061
0.6818 Remote Similarity NPC146551
0.6806 Remote Similarity NPC142423
0.6806 Remote Similarity NPC308294
0.68 Remote Similarity NPC477087
0.68 Remote Similarity NPC316185
0.68 Remote Similarity NPC126061
0.68 Remote Similarity NPC477086
0.6795 Remote Similarity NPC110813
0.6795 Remote Similarity NPC120776
0.6795 Remote Similarity NPC240170
0.6786 Remote Similarity NPC179659
0.6769 Remote Similarity NPC309606
0.6769 Remote Similarity NPC139545
0.6769 Remote Similarity NPC474496
0.6769 Remote Similarity NPC39633
0.6769 Remote Similarity NPC284224
0.6765 Remote Similarity NPC34416
0.6757 Remote Similarity NPC475982

  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 NPC317881 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
0.9677 High Similarity NPD4247 Clinical (unspecified phase)
0.9016 High Similarity NPD4246 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD3173 Approved
0.75 Intermediate Similarity NPD3197 Phase 1
0.7188 Intermediate Similarity NPD3195 Phase 2
0.7188 Intermediate Similarity NPD3194 Approved
0.7188 Intermediate Similarity NPD3196 Approved
0.7188 Intermediate Similarity NPD4266 Approved
0.7059 Intermediate Similarity NPD7983 Approved
0.7031 Intermediate Similarity NPD3172 Approved
0.7 Intermediate Similarity NPD4222 Approved
0.7 Intermediate Similarity NPD39 Approved
0.7 Intermediate Similarity NPD3174 Discontinued
0.6977 Remote Similarity NPD5778 Approved
0.6977 Remote Similarity NPD5779 Approved
0.6923 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6774 Remote Similarity NPD5343 Approved
0.6765 Remote Similarity NPD6109 Phase 1
0.675 Remote Similarity NPD4252 Approved
0.6742 Remote Similarity NPD7839 Suspended
0.6719 Remote Similarity NPD29 Approved
0.6719 Remote Similarity NPD28 Approved
0.6709 Remote Similarity NPD4271 Approved
0.6709 Remote Similarity NPD4268 Approved
0.6667 Remote Similarity NPD5326 Phase 3
0.6667 Remote Similarity NPD5786 Approved
0.6585 Remote Similarity NPD4269 Approved
0.6585 Remote Similarity NPD4270 Approved
0.6543 Remote Similarity NPD4822 Approved
0.6543 Remote Similarity NPD5368 Approved
0.6543 Remote Similarity NPD4820 Approved
0.6543 Remote Similarity NPD4819 Approved
0.6543 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6543 Remote Similarity NPD4821 Approved
0.6506 Remote Similarity NPD5362 Discontinued
0.6506 Remote Similarity NPD7154 Phase 3
0.6452 Remote Similarity NPD4265 Approved
0.6406 Remote Similarity NPD4220 Pre-registration
0.6395 Remote Similarity NPD4250 Approved
0.6395 Remote Similarity NPD4251 Approved
0.6386 Remote Similarity NPD6435 Approved
0.6375 Remote Similarity NPD4756 Discovery
0.6353 Remote Similarity NPD5363 Approved
0.631 Remote Similarity NPD5331 Approved
0.631 Remote Similarity NPD5332 Approved
0.6292 Remote Similarity NPD7637 Suspended
0.629 Remote Similarity NPD6097 Approved
0.629 Remote Similarity NPD6096 Approved
0.6279 Remote Similarity NPD4249 Approved
0.6265 Remote Similarity NPD4790 Discontinued
0.625 Remote Similarity NPD5764 Clinical (unspecified phase)
0.625 Remote Similarity NPD622 Approved
0.625 Remote Similarity NPD6101 Approved
0.6212 Remote Similarity NPD6927 Phase 3
0.6125 Remote Similarity NPD8039 Approved
0.6118 Remote Similarity NPD6110 Phase 1
0.6111 Remote Similarity NPD6411 Approved
0.6076 Remote Similarity NPD4732 Discontinued
0.6071 Remote Similarity NPD5369 Approved
0.6067 Remote Similarity NPD5370 Suspended
0.602 Remote Similarity NPD5048 Discontinued
0.6 Remote Similarity NPD5785 Approved
0.6 Remote Similarity NPD6698 Approved
0.6 Remote Similarity NPD7838 Discovery
0.6 Remote Similarity NPD46 Approved
0.5934 Remote Similarity NPD4810 Clinical (unspecified phase)
0.5921 Remote Similarity NPD7331 Phase 2
0.5904 Remote Similarity NPD3732 Approved
0.5895 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5765 Remote Similarity NPD8259 Clinical (unspecified phase)
0.5765 Remote Similarity NPD7514 Phase 3
0.5765 Remote Similarity NPD7332 Phase 2
0.5733 Remote Similarity NPD3210 Clinical (unspecified phase)
0.5732 Remote Similarity NPD8264 Approved
0.5714 Remote Similarity NPD7145 Approved
0.5698 Remote Similarity NPD6902 Approved
0.5632 Remote Similarity NPD5209 Approved
0.5618 Remote Similarity NPD6082 Clinical (unspecified phase)
0.56 Remote Similarity NPD4192 Approved
0.56 Remote Similarity NPD4193 Approved
0.56 Remote Similarity NPD368 Approved
0.56 Remote Similarity NPD4191 Approved
0.56 Remote Similarity NPD4194 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