Structure

Physi-Chem Properties

Molecular Weight:  172.05
Volume:  183.461
LogP:  3.075
LogD:  2.567
LogS:  -3.451
# Rotatable Bonds:  1
TPSA:  37.3
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.717
Synthetic Accessibility Score:  1.35
Fsp3:  0.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.683
MDCK Permeability:  1.6304516975651495e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.011
20% Bioavailability (F20%):  0.011
30% Bioavailability (F30%):  0.109

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.431
Plasma Protein Binding (PPB):  92.63919830322266%
Volume Distribution (VD):  0.217
Pgp-substrate:  5.870748043060303%

ADMET: Metabolism

CYP1A2-inhibitor:  0.219
CYP1A2-substrate:  0.11
CYP2C19-inhibitor:  0.069
CYP2C19-substrate:  0.055
CYP2C9-inhibitor:  0.13
CYP2C9-substrate:  0.088
CYP2D6-inhibitor:  0.026
CYP2D6-substrate:  0.083
CYP3A4-inhibitor:  0.023
CYP3A4-substrate:  0.086

ADMET: Excretion

Clearance (CL):  1.66
Half-life (T1/2):  0.85

ADMET: Toxicity

hERG Blockers:  0.07
Human Hepatotoxicity (H-HT):  0.653
Drug-inuced Liver Injury (DILI):  0.973
AMES Toxicity:  0.011
Rat Oral Acute Toxicity:  0.124
Maximum Recommended Daily Dose:  0.014
Skin Sensitization:  0.455
Carcinogencity:  0.099
Eye Corrosion:  0.028
Eye Irritation:  0.99
Respiratory Toxicity:  0.231

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

  Natural Product: NPC318327

Natural Product ID:  NPC318327
Common Name*:   Beta-Naphtoic Acid
IUPAC Name:   naphthalene-2-carboxylic acid
Synonyms:   Naphthalene-2-Carboxylic Acid
Standard InCHIKey:  UOBYKYZJUGYBDK-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C11H8O2/c12-11(13)10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,(H,12,13)
SMILES:  C1=CC=C2C=C(C=CC2=C1)C(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL114648
PubChem CID:   7123
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000023] Naphthalenes
        • [CHEMONTID:0001871] Naphthalenecarboxylic acids and derivatives
          • [CHEMONTID:0002421] Naphthalenecarboxylic 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. urine 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. bile 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
NPT183 Individual Protein Arachidonate 5-lipoxygenase Rattus norvegicus Inhibition = 0.0 % PMID[456033]
NPT2794 Individual Protein Quinolone resistance protein norA Staphylococcus aureus Activity > 128.0 ug ml-1 PMID[456037]
NPT35 Others n.a. LogD = 2.78 n.a. PMID[456032]
NPT27 Others Unspecified Log LD50 = -1.92 n.a. PMID[456032]
NPT450 Organism Meloidogyne incognita Meloidogyne incognita EC50 > 1000.0 ug.mL-1 PMID[456034]
NPT35 Others n.a. pKa = 4.45 n.a. PMID[456035]
NPT2 Others Unspecified Inhibition = 96.4 % PMID[456035]
NPT2 Others Unspecified IC50 = 61400.0 nM PMID[456035]
NPT35 Others n.a. pKa n.a. 4.18 n.a. PMID[456036]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC > 128.0 ug.mL-1 PMID[456037]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC >= 64.0 ug.mL-1 PMID[456037]
NPT29 Organism Rattus norvegicus Rattus norvegicus T/C = 1.13 n.a. PMID[456038]
NPT2 Others Unspecified log1/Ki = 3.86 n.a. PMID[456039]

☑ 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 NPC318327 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
0.9709 High Similarity NPC66208
0.9505 High Similarity NPC105899
0.95 High Similarity NPC255676
0.9083 High Similarity NPC158157
0.9074 High Similarity NPC186933
0.902 High Similarity NPC304873
0.901 High Similarity NPC217621
0.8911 High Similarity NPC229242
0.8835 High Similarity NPC25458
0.8812 High Similarity NPC253423
0.8807 High Similarity NPC196673
0.88 High Similarity NPC172925
0.8713 High Similarity NPC61944
0.8704 High Similarity NPC474057
0.8654 High Similarity NPC284477
0.8598 High Similarity NPC249811
0.8571 High Similarity NPC329556
0.8559 High Similarity NPC476357
0.8558 High Similarity NPC282895
0.8547 High Similarity NPC236189
0.8496 Intermediate Similarity NPC228318
0.8462 Intermediate Similarity NPC228435
0.8455 Intermediate Similarity NPC79496
0.8448 Intermediate Similarity NPC269923
0.8448 Intermediate Similarity NPC167323
0.8411 Intermediate Similarity NPC134120
0.84 Intermediate Similarity NPC62765
0.8393 Intermediate Similarity NPC306740
0.8364 Intermediate Similarity NPC475002
0.8364 Intermediate Similarity NPC95126
0.8333 Intermediate Similarity NPC261181
0.8305 Intermediate Similarity NPC85511
0.8288 Intermediate Similarity NPC186128
0.8261 Intermediate Similarity NPC328694
0.8257 Intermediate Similarity NPC211439
0.8182 Intermediate Similarity NPC85493
0.8165 Intermediate Similarity NPC37914
0.8151 Intermediate Similarity NPC275145
0.8148 Intermediate Similarity NPC249067
0.8148 Intermediate Similarity NPC472221
0.8148 Intermediate Similarity NPC472222
0.8142 Intermediate Similarity NPC471721
0.813 Intermediate Similarity NPC31539
0.8083 Intermediate Similarity NPC164014
0.8073 Intermediate Similarity NPC172483
0.807 Intermediate Similarity NPC274839
0.8058 Intermediate Similarity NPC128645
0.8056 Intermediate Similarity NPC247976
0.8053 Intermediate Similarity NPC93287
0.8051 Intermediate Similarity NPC472981
0.8037 Intermediate Similarity NPC42211
0.8036 Intermediate Similarity NPC133308
0.8036 Intermediate Similarity NPC260818
0.8036 Intermediate Similarity NPC210089
0.8036 Intermediate Similarity NPC167504
0.8033 Intermediate Similarity NPC115797
0.8033 Intermediate Similarity NPC51448
0.802 Intermediate Similarity NPC329064
0.8 Intermediate Similarity NPC318107
0.7982 Intermediate Similarity NPC114594
0.7982 Intermediate Similarity NPC329282
0.7965 Intermediate Similarity NPC321852
0.7965 Intermediate Similarity NPC158282
0.7944 Intermediate Similarity NPC118343
0.7944 Intermediate Similarity NPC203925
0.7934 Intermediate Similarity NPC142956
0.7931 Intermediate Similarity NPC212891
0.7913 Intermediate Similarity NPC93181
0.7913 Intermediate Similarity NPC221275
0.7909 Intermediate Similarity NPC209632
0.7895 Intermediate Similarity NPC272524
0.789 Intermediate Similarity NPC60679
0.789 Intermediate Similarity NPC274443
0.787 Intermediate Similarity NPC136810
0.787 Intermediate Similarity NPC128248
0.787 Intermediate Similarity NPC133809
0.787 Intermediate Similarity NPC225079
0.787 Intermediate Similarity NPC70624
0.787 Intermediate Similarity NPC469481
0.7864 Intermediate Similarity NPC86670
0.7864 Intermediate Similarity NPC277277
0.7864 Intermediate Similarity NPC70940
0.7864 Intermediate Similarity NPC274455
0.7851 Intermediate Similarity NPC318067
0.7851 Intermediate Similarity NPC228739
0.7838 Intermediate Similarity NPC142326
0.7838 Intermediate Similarity NPC94751
0.7838 Intermediate Similarity NPC100767
0.7833 Intermediate Similarity NPC120545
0.7826 Intermediate Similarity NPC153053
0.7823 Intermediate Similarity NPC48248
0.7823 Intermediate Similarity NPC96024
0.7818 Intermediate Similarity NPC31786
0.7815 Intermediate Similarity NPC232958
0.7807 Intermediate Similarity NPC292834
0.7807 Intermediate Similarity NPC471188
0.7805 Intermediate Similarity NPC160499
0.7798 Intermediate Similarity NPC188895
0.7798 Intermediate Similarity NPC45613
0.7798 Intermediate Similarity NPC222390
0.7798 Intermediate Similarity NPC244427
0.7797 Intermediate Similarity NPC318173
0.7788 Intermediate Similarity NPC110704
0.7788 Intermediate Similarity NPC103346
0.7787 Intermediate Similarity NPC295664
0.7787 Intermediate Similarity NPC173978
0.7769 Intermediate Similarity NPC244351
0.7769 Intermediate Similarity NPC300274
0.7769 Intermediate Similarity NPC307174
0.7769 Intermediate Similarity NPC223351
0.7769 Intermediate Similarity NPC91478
0.7769 Intermediate Similarity NPC283514
0.7768 Intermediate Similarity NPC141523
0.7768 Intermediate Similarity NPC203732
0.7767 Intermediate Similarity NPC199567
0.775 Intermediate Similarity NPC216216
0.775 Intermediate Similarity NPC144547
0.7745 Intermediate Similarity NPC322387
0.7739 Intermediate Similarity NPC143768
0.7739 Intermediate Similarity NPC128368
0.7736 Intermediate Similarity NPC130398
0.7734 Intermediate Similarity NPC288089
0.7731 Intermediate Similarity NPC472708
0.7727 Intermediate Similarity NPC89886
0.7719 Intermediate Similarity NPC265513
0.7712 Intermediate Similarity NPC160199
0.7712 Intermediate Similarity NPC45794
0.7705 Intermediate Similarity NPC375356
0.77 Intermediate Similarity NPC285773
0.7699 Intermediate Similarity NPC99846
0.7699 Intermediate Similarity NPC269023
0.7699 Intermediate Similarity NPC83628
0.7699 Intermediate Similarity NPC265407
0.7698 Intermediate Similarity NPC55949
0.7698 Intermediate Similarity NPC27659
0.7692 Intermediate Similarity NPC322197
0.7692 Intermediate Similarity NPC62272
0.7692 Intermediate Similarity NPC26224
0.7686 Intermediate Similarity NPC295034
0.7686 Intermediate Similarity NPC198336
0.768 Intermediate Similarity NPC282923
0.7679 Intermediate Similarity NPC37622
0.7679 Intermediate Similarity NPC30594
0.7679 Intermediate Similarity NPC119271
0.7679 Intermediate Similarity NPC83409
0.7679 Intermediate Similarity NPC185763
0.7674 Intermediate Similarity NPC161632
0.7672 Intermediate Similarity NPC211421
0.7672 Intermediate Similarity NPC67377
0.7672 Intermediate Similarity NPC237366
0.7667 Intermediate Similarity NPC988
0.7667 Intermediate Similarity NPC289432
0.7667 Intermediate Similarity NPC234337
0.7667 Intermediate Similarity NPC183339
0.7667 Intermediate Similarity NPC133389
0.7652 Intermediate Similarity NPC280789
0.7642 Intermediate Similarity NPC111088
0.7642 Intermediate Similarity NPC289883
0.7632 Intermediate Similarity NPC273837
0.7623 Intermediate Similarity NPC282577
0.7619 Intermediate Similarity NPC146647
0.7619 Intermediate Similarity NPC117899
0.7619 Intermediate Similarity NPC34414
0.7619 Intermediate Similarity NPC276238
0.7611 Intermediate Similarity NPC112903
0.7611 Intermediate Similarity NPC56493
0.7607 Intermediate Similarity NPC474685
0.7607 Intermediate Similarity NPC474095
0.7603 Intermediate Similarity NPC165197
0.7603 Intermediate Similarity NPC241001
0.7596 Intermediate Similarity NPC418308
0.7596 Intermediate Similarity NPC325709
0.7593 Intermediate Similarity NPC249912
0.7593 Intermediate Similarity NPC156021
0.7593 Intermediate Similarity NPC289201
0.7593 Intermediate Similarity NPC226041
0.7593 Intermediate Similarity NPC92754
0.7593 Intermediate Similarity NPC276775
0.7589 Intermediate Similarity NPC269457
0.7586 Intermediate Similarity NPC13784
0.7586 Intermediate Similarity NPC470253
0.7583 Intermediate Similarity NPC204784
0.7583 Intermediate Similarity NPC233165
0.7583 Intermediate Similarity NPC202015
0.7583 Intermediate Similarity NPC184579
0.7581 Intermediate Similarity NPC103540
0.7581 Intermediate Similarity NPC275576
0.7581 Intermediate Similarity NPC470765
0.7568 Intermediate Similarity NPC291426
0.7565 Intermediate Similarity NPC474157
0.7563 Intermediate Similarity NPC125252
0.7561 Intermediate Similarity NPC328107
0.7559 Intermediate Similarity NPC31799
0.7559 Intermediate Similarity NPC136588
0.7559 Intermediate Similarity NPC199253
0.7545 Intermediate Similarity NPC473325
0.7544 Intermediate Similarity NPC17417
0.7544 Intermediate Similarity NPC17525
0.7544 Intermediate Similarity NPC10251
0.7542 Intermediate Similarity NPC135730

  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 NPC318327 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
0.9252 High Similarity NPD5951 Approved
0.88 High Similarity NPD688 Clinical (unspecified phase)
0.8761 High Similarity NPD7163 Clinical (unspecified phase)
0.8571 High Similarity NPD1931 Clinical (unspecified phase)
0.8571 High Similarity NPD1929 Approved
0.8571 High Similarity NPD1930 Approved
0.8519 High Similarity NPD6831 Clinical (unspecified phase)
0.85 High Similarity NPD1239 Approved
0.8476 Intermediate Similarity NPD1932 Approved
0.84 Intermediate Similarity NPD9258 Approved
0.84 Intermediate Similarity NPD9256 Approved
0.8333 Intermediate Similarity NPD1202 Approved
0.8197 Intermediate Similarity NPD7008 Discontinued
0.8148 Intermediate Similarity NPD1237 Approved
0.8113 Intermediate Similarity NPD2066 Phase 3
0.8095 Intermediate Similarity NPD1564 Approved
0.8095 Intermediate Similarity NPD1566 Phase 3
0.8095 Intermediate Similarity NPD1565 Approved
0.8049 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.8018 Intermediate Similarity NPD2329 Discontinued
0.8 Intermediate Similarity NPD9259 Approved
0.8 Intermediate Similarity NPD9257 Approved
0.8 Intermediate Similarity NPD182 Clinical (unspecified phase)
0.7944 Intermediate Similarity NPD1238 Approved
0.7869 Intermediate Similarity NPD1164 Approved
0.7864 Intermediate Similarity NPD1090 Approved
0.7864 Intermediate Similarity NPD1089 Approved
0.7864 Intermediate Similarity NPD1086 Approved
0.7818 Intermediate Similarity NPD164 Approved
0.781 Intermediate Similarity NPD1563 Approved
0.7807 Intermediate Similarity NPD9508 Approved
0.7767 Intermediate Similarity NPD800 Approved
0.7714 Intermediate Similarity NPD1088 Approved
0.77 Intermediate Similarity NPD9491 Approved
0.7692 Intermediate Similarity NPD5408 Approved
0.7692 Intermediate Similarity NPD5405 Approved
0.7692 Intermediate Similarity NPD5406 Approved
0.7692 Intermediate Similarity NPD5404 Approved
0.7686 Intermediate Similarity NPD1201 Approved
0.7664 Intermediate Similarity NPD1989 Approved
0.7642 Intermediate Similarity NPD1283 Approved
0.7619 Intermediate Similarity NPD6966 Discovery
0.7581 Intermediate Similarity NPD1470 Approved
0.7573 Intermediate Similarity NPD1087 Approved
0.757 Intermediate Similarity NPD1693 Approved
0.7565 Intermediate Similarity NPD4141 Clinical (unspecified phase)
0.7565 Intermediate Similarity NPD2181 Clinical (unspecified phase)
0.7544 Intermediate Similarity NPD2182 Approved
0.7523 Intermediate Similarity NPD9495 Approved
0.75 Intermediate Similarity NPD226 Approved
0.748 Intermediate Similarity NPD4878 Approved
0.7463 Intermediate Similarity NPD7003 Approved
0.7422 Intermediate Similarity NPD3764 Approved
0.7411 Intermediate Similarity NPD5700 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD9260 Approved
0.7398 Intermediate Similarity NPD1281 Approved
0.7381 Intermediate Similarity NPD6007 Clinical (unspecified phase)
0.7377 Intermediate Similarity NPD2345 Approved
0.7368 Intermediate Similarity NPD2346 Discontinued
0.736 Intermediate Similarity NPD1888 Phase 1
0.735 Intermediate Similarity NPD1609 Clinical (unspecified phase)
0.7345 Intermediate Similarity NPD5909 Discontinued
0.7333 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7315 Intermediate Similarity NPD5122 Clinical (unspecified phase)
0.7311 Intermediate Similarity NPD2629 Approved
0.7304 Intermediate Similarity NPD9267 Approved
0.7304 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7304 Intermediate Similarity NPD9264 Approved
0.7304 Intermediate Similarity NPD9263 Approved
0.73 Intermediate Similarity NPD9490 Approved
0.7288 Intermediate Similarity NPD5277 Phase 2
0.7273 Intermediate Similarity NPD3495 Discontinued
0.7258 Intermediate Similarity NPD6287 Discontinued
0.7248 Intermediate Similarity NPD6048 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD6049 Phase 2
0.7241 Intermediate Similarity NPD9266 Approved
0.7241 Intermediate Similarity NPD74 Approved
0.7238 Intermediate Similarity NPD650 Approved
0.7236 Intermediate Similarity NPD1362 Clinical (unspecified phase)
0.7236 Intermediate Similarity NPD3412 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD225 Approved
0.72 Intermediate Similarity NPD227 Approved
0.7184 Intermediate Similarity NPD3971 Phase 1
0.7179 Intermediate Similarity NPD1317 Discontinued
0.7167 Intermediate Similarity NPD690 Clinical (unspecified phase)
0.7157 Intermediate Similarity NPD942 Approved
0.7155 Intermediate Similarity NPD2342 Discontinued
0.7154 Intermediate Similarity NPD2313 Discontinued
0.713 Intermediate Similarity NPD7609 Phase 3
0.7109 Intermediate Similarity NPD4980 Approved
0.709 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7075 Intermediate Similarity NPD4793 Discontinued
0.7068 Intermediate Similarity NPD3528 Clinical (unspecified phase)
0.7064 Intermediate Similarity NPD7631 Approved
0.7064 Intermediate Similarity NPD1508 Approved
0.7049 Intermediate Similarity NPD9493 Approved
0.7042 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.704 Intermediate Similarity NPD4879 Approved
0.704 Intermediate Similarity NPD1889 Phase 1
0.7016 Intermediate Similarity NPD1245 Approved
0.7016 Intermediate Similarity NPD1651 Approved
0.7016 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7016 Intermediate Similarity NPD4102 Approved
0.7016 Intermediate Similarity NPD4105 Approved
0.7 Intermediate Similarity NPD7635 Approved
0.6992 Remote Similarity NPD7610 Discontinued
0.6985 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6963 Remote Similarity NPD4308 Phase 3
0.6963 Remote Similarity NPD2799 Discontinued
0.696 Remote Similarity NPD3019 Approved
0.696 Remote Similarity NPD2932 Approved
0.6957 Remote Similarity NPD9261 Approved
0.6953 Remote Similarity NPD1574 Approved
0.6944 Remote Similarity NPD5346 Phase 2
0.6944 Remote Similarity NPD5347 Phase 2
0.6942 Remote Similarity NPD4869 Clinical (unspecified phase)
0.6935 Remote Similarity NPD7009 Phase 2
0.6935 Remote Similarity NPD9545 Approved
0.693 Remote Similarity NPD1616 Discontinued
0.6923 Remote Similarity NPD3226 Approved
0.6923 Remote Similarity NPD6591 Clinical (unspecified phase)
0.6912 Remote Similarity NPD2935 Discontinued
0.6905 Remote Similarity NPD4106 Approved
0.6905 Remote Similarity NPD4135 Approved
0.6905 Remote Similarity NPD4136 Approved
0.69 Remote Similarity NPD9716 Approved
0.6899 Remote Similarity NPD1203 Approved
0.6887 Remote Similarity NPD5734 Clinical (unspecified phase)
0.6885 Remote Similarity NPD1246 Approved
0.6885 Remote Similarity NPD9281 Approved
0.6875 Remote Similarity NPD5206 Clinical (unspecified phase)
0.6875 Remote Similarity NPD5157 Phase 1
0.6875 Remote Similarity NPD5158 Clinical (unspecified phase)
0.6875 Remote Similarity NPD1843 Approved
0.6875 Remote Similarity NPD5159 Phase 2
0.685 Remote Similarity NPD5618 Discontinued
0.6846 Remote Similarity NPD2798 Approved
0.6835 Remote Similarity NPD3750 Approved
0.6835 Remote Similarity NPD4628 Phase 3
0.6825 Remote Similarity NPD5305 Approved
0.6825 Remote Similarity NPD4626 Approved
0.6825 Remote Similarity NPD5306 Approved
0.6825 Remote Similarity NPD1104 Approved
0.6822 Remote Similarity NPD1876 Approved
0.681 Remote Similarity NPD6647 Phase 2
0.6806 Remote Similarity NPD5086 Approved
0.6803 Remote Similarity NPD1280 Clinical (unspecified phase)
0.6797 Remote Similarity NPD3972 Approved
0.6797 Remote Similarity NPD1608 Approved
0.6791 Remote Similarity NPD2979 Phase 3
0.6788 Remote Similarity NPD6897 Clinical (unspecified phase)
0.6769 Remote Similarity NPD2797 Approved
0.6746 Remote Similarity NPD1855 Clinical (unspecified phase)
0.6739 Remote Similarity NPD7702 Clinical (unspecified phase)
0.6731 Remote Similarity NPD1507 Clinical (unspecified phase)
0.6719 Remote Similarity NPD4807 Approved
0.6719 Remote Similarity NPD518 Clinical (unspecified phase)
0.6719 Remote Similarity NPD4806 Approved
0.6716 Remote Similarity NPD6663 Approved
0.6716 Remote Similarity NPD7714 Approved
0.6716 Remote Similarity NPD7715 Approved
0.6713 Remote Similarity NPD6273 Approved
0.6696 Remote Similarity NPD3020 Approved
0.6695 Remote Similarity NPD5048 Discontinued
0.6694 Remote Similarity NPD4198 Discontinued
0.669 Remote Similarity NPD7390 Discontinued
0.669 Remote Similarity NPD7458 Discontinued
0.6667 Remote Similarity NPD3880 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5736 Approved
0.6667 Remote Similarity NPD4307 Phase 2
0.6667 Remote Similarity NPD9717 Approved
0.6667 Remote Similarity NPD1551 Phase 2
0.6643 Remote Similarity NPD1625 Approved
0.6643 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6643 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6642 Remote Similarity NPD5422 Clinical (unspecified phase)
0.6641 Remote Similarity NPD7457 Clinical (unspecified phase)
0.662 Remote Similarity NPD7236 Approved
0.6609 Remote Similarity NPD253 Approved
0.6602 Remote Similarity NPD9294 Approved
0.6594 Remote Similarity NPD3748 Approved
0.6593 Remote Similarity NPD7961 Discontinued
0.6589 Remote Similarity NPD1611 Approved
0.6585 Remote Similarity NPD7094 Approved
0.6585 Remote Similarity NPD6858 Approved
0.6579 Remote Similarity NPD2859 Approved
0.6579 Remote Similarity NPD2860 Approved
0.6577 Remote Similarity NPD3672 Approved
0.6577 Remote Similarity NPD3673 Approved
0.6569 Remote Similarity NPD1607 Approved
0.6569 Remote Similarity NPD6817 Clinical (unspecified phase)
0.6562 Remote Similarity NPD2286 Discontinued
0.6562 Remote Similarity NPD9272 Approved
0.6562 Remote Similarity NPD17 Approved
0.6562 Remote Similarity NPD4199 Phase 3
0.656 Remote Similarity NPD256 Approved
0.656 Remote Similarity NPD255 Approved
0.6557 Remote Similarity NPD3642 Approved
0.6557 Remote Similarity NPD3643 Approved
0.6557 Remote Similarity NPD3644 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