Structure

Physi-Chem Properties

Molecular Weight:  125.1
Volume:  131.493
LogP:  -0.998
LogD:  -1.578
LogS:  1.06
# Rotatable Bonds:  2
TPSA:  43.84
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  1
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.601
Synthetic Accessibility Score:  2.697
Fsp3:  0.5
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
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:  -5.636
MDCK Permeability:  4.009205895272316e-06
Pgp-inhibitor:  0.0
Pgp-substrate:  0.442
Human Intestinal Absorption (HIA):  0.015
20% Bioavailability (F20%):  0.019
30% Bioavailability (F30%):  0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.568
Plasma Protein Binding (PPB):  7.556064605712891%
Volume Distribution (VD):  1.209
Pgp-substrate:  91.36456298828125%

ADMET: Metabolism

CYP1A2-inhibitor:  0.049
CYP1A2-substrate:  0.638
CYP2C19-inhibitor:  0.027
CYP2C19-substrate:  0.064
CYP2C9-inhibitor:  0.004
CYP2C9-substrate:  0.186
CYP2D6-inhibitor:  0.006
CYP2D6-substrate:  0.476
CYP3A4-inhibitor:  0.008
CYP3A4-substrate:  0.233

ADMET: Excretion

Clearance (CL):  5.458
Half-life (T1/2):  0.848

ADMET: Toxicity

hERG Blockers:  0.024
Human Hepatotoxicity (H-HT):  0.613
Drug-inuced Liver Injury (DILI):  0.135
AMES Toxicity:  0.097
Rat Oral Acute Toxicity:  0.191
Maximum Recommended Daily Dose:  0.833
Skin Sensitization:  0.824
Carcinogencity:  0.841
Eye Corrosion:  0.761
Eye Irritation:  0.194
Respiratory Toxicity:  0.452

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

  Natural Product: NPC326248

Natural Product ID:  NPC326248
Common Name*:   N-Methylhistamine
IUPAC Name:   2-(1-methylimidazol-4-yl)ethanamine
Synonyms:   N-Methylhistamine
Standard InCHIKey:  FHQDWPCFSJMNCT-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C6H11N3/c1-9-4-6(2-3-7)8-5-9/h4-5H,2-3,7H2,1H3
SMILES:  Cn1cc(nc1)CCN
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL507
PubChem CID:   3614
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004707] Organic nitrogen compounds
      • [CHEMONTID:0000278] Organonitrogen compounds
        • [CHEMONTID:0002449] Amines
          • [CHEMONTID:0002450] Primary amines
            • [CHEMONTID:0004253] 2-arylethylamines

*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
NPT4288 Individual Protein Histamine H1 receptor Cavia porcellus Activity < 0.01 n.a. PMID[556160]
NPT4289 Individual Protein Histamine H2 receptor Cavia porcellus Activity < 0.1 n.a. PMID[556160]
NPT210 Individual Protein Thyroid stimulating hormone receptor Homo sapiens Potency = 6309.6 nM PMID[556162]
NPT213 Individual Protein Cytochrome P450 2C19 Homo sapiens Potency = 39810.7 nM PMID[556162]
NPT212 Individual Protein Cytochrome P450 2C9 Homo sapiens Potency = 39810.7 nM PMID[556162]
NPT5 Individual Protein Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Homo sapiens Potency n.a. 7943.3 nM PMID[556163]
NPT62 Individual Protein 6-phospho-1-fructokinase Trypanosoma brucei Potency n.a. 5.4 nM PMID[556163]
NPT2 Others Unspecified C20 = 0.7 uM l-1 PMID[556159]
NPT938 Organism Cavia porcellus Cavia porcellus EC50 = 3300.0 nM PMID[556159]
NPT938 Organism Cavia porcellus Cavia porcellus EC50 = 13800.0 nM PMID[556159]
NPT29 Organism Rattus norvegicus Rattus norvegicus Ratio_EC50 < 4.0 n.a. PMID[556160]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 > 500000.0 nM PMID[556161]
NPT940 Individual Protein Serine/threonine-protein kinase mTOR Homo sapiens Potency = 3288.5 nM PMID[556163]
NPT7 Individual Protein Thioredoxin reductase 1, cytoplasmic Rattus norvegicus Potency n.a. 446.7 nM PMID[556163]
NPT987 Individual Protein Histamine H3 receptor Homo sapiens Ki = 20000.0 nM PMID[556164]
NPT988 Individual Protein Histamine H4 receptor Homo sapiens Ki = 11000.0 nM PMID[556164]
NPT20556 SINGLE PROTEIN Replicase polyprotein 1ab Severe acute respiratory syndrome coronavirus 2 Inhibition = 27.43 % PMID[556165]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 Inhibition = 0.08 % PMID[556166]

☑ 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 NPC326248 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 NPC187191
0.9388 High Similarity NPC155498
0.9184 High Similarity NPC111132
0.87 High Similarity NPC273327
0.8469 Intermediate Similarity NPC9639
0.8411 Intermediate Similarity NPC327613
0.7563 Intermediate Similarity NPC180462
0.7561 Intermediate Similarity NPC126634
0.7323 Intermediate Similarity NPC210947
0.725 Intermediate Similarity NPC15566
0.7177 Intermediate Similarity NPC25465
0.704 Intermediate Similarity NPC235501
0.7031 Intermediate Similarity NPC237812
0.7031 Intermediate Similarity NPC18223
0.6953 Remote Similarity NPC470140
0.6905 Remote Similarity NPC470138
0.687 Remote Similarity NPC286696
0.687 Remote Similarity NPC185903
0.6807 Remote Similarity NPC68938
0.6794 Remote Similarity NPC470139
0.6768 Remote Similarity NPC237936
0.6741 Remote Similarity NPC197068
0.6618 Remote Similarity NPC327477
0.6562 Remote Similarity NPC243319
0.646 Remote Similarity NPC174114
0.646 Remote Similarity NPC87981
0.6435 Remote Similarity NPC476099
0.6429 Remote Similarity NPC204104
0.6423 Remote Similarity NPC174020
0.6415 Remote Similarity NPC277608
0.6381 Remote Similarity NPC76536
0.6364 Remote Similarity NPC270637
0.6364 Remote Similarity NPC51000
0.6364 Remote Similarity NPC60537
0.6338 Remote Similarity NPC282531
0.6263 Remote Similarity NPC100312
0.6262 Remote Similarity NPC262236
0.6204 Remote Similarity NPC326364
0.6168 Remote Similarity NPC190949
0.6121 Remote Similarity NPC476561
0.6087 Remote Similarity NPC293163
0.6017 Remote Similarity NPC18335
0.6016 Remote Similarity NPC313547
0.5968 Remote Similarity NPC63433
0.5966 Remote Similarity NPC119133
0.5965 Remote Similarity NPC476128
0.5932 Remote Similarity NPC59314
0.5929 Remote Similarity NPC74306
0.5929 Remote Similarity NPC315642
0.5912 Remote Similarity NPC470141
0.5902 Remote Similarity NPC47936
0.5882 Remote Similarity NPC476564
0.584 Remote Similarity NPC148385
0.5821 Remote Similarity NPC104011
0.5816 Remote Similarity NPC8590
0.5812 Remote Similarity NPC332382
0.5806 Remote Similarity NPC256849
0.5806 Remote Similarity NPC41958
0.5786 Remote Similarity NPC477119
0.5781 Remote Similarity NPC252603
0.575 Remote Similarity NPC476562
0.5748 Remote Similarity NPC240084
0.5748 Remote Similarity NPC278549
0.5735 Remote Similarity NPC57279
0.5714 Remote Similarity NPC296437
0.5692 Remote Similarity NPC470142
0.5674 Remote Similarity NPC470266
0.5667 Remote Similarity NPC10466
0.566 Remote Similarity NPC317054
0.5659 Remote Similarity NPC327579
0.5658 Remote Similarity NPC124276
0.5645 Remote Similarity NPC312187
0.5645 Remote Similarity NPC4837
0.5625 Remote Similarity NPC14223
0.5621 Remote Similarity NPC300238
0.5616 Remote Similarity NPC244700
0.561 Remote Similarity NPC75131
0.5606 Remote Similarity NPC109322

  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 NPC326248 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
0.9184 High Similarity NPD8859 Approved
0.9184 High Similarity NPD8862 Approved
0.9184 High Similarity NPD8861 Approved
0.8257 Intermediate Similarity NPD9132 Discontinued
0.7563 Intermediate Similarity NPD300 Approved
0.7542 Intermediate Similarity NPD1390 Phase 1
0.7542 Intermediate Similarity NPD1388 Phase 1
0.7542 Intermediate Similarity NPD1389 Clinical (unspecified phase)
0.7295 Intermediate Similarity NPD1807 Clinical (unspecified phase)
0.7031 Intermediate Similarity NPD9628 Approved
0.7031 Intermediate Similarity NPD9133 Approved
0.7 Intermediate Similarity NPD875 Clinical (unspecified phase)
0.6923 Remote Similarity NPD757 Phase 3
0.6842 Remote Similarity NPD5342 Clinical (unspecified phase)
0.6786 Remote Similarity NPD341 Approved
0.6786 Remote Similarity NPD340 Approved
0.6772 Remote Similarity NPD9650 Phase 3
0.6768 Remote Similarity NPD8186 Phase 1
0.6768 Remote Similarity NPD8185 Discontinued
0.6767 Remote Similarity NPD1451 Approved
0.6767 Remote Similarity NPD9183 Clinical (unspecified phase)
0.6727 Remote Similarity NPD9194 Approved
0.6727 Remote Similarity NPD9193 Approved
0.67 Remote Similarity NPD8584 Approved
0.6692 Remote Similarity NPD576 Discontinued
0.6667 Remote Similarity NPD9627 Approved
0.6593 Remote Similarity NPD3706 Clinical (unspecified phase)
0.6574 Remote Similarity NPD9210 Phase 2
0.6562 Remote Similarity NPD9081 Clinical (unspecified phase)
0.6471 Remote Similarity NPD174 Discontinued
0.6408 Remote Similarity NPD1731 Clinical (unspecified phase)
0.6389 Remote Similarity NPD2604 Approved
0.6364 Remote Similarity NPD8838 Approved
0.6364 Remote Similarity NPD2180 Approved
0.635 Remote Similarity NPD566 Approved
0.635 Remote Similarity NPD568 Approved
0.635 Remote Similarity NPD567 Approved
0.6311 Remote Similarity NPD163 Approved
0.6294 Remote Similarity NPD1030 Approved
0.6294 Remote Similarity NPD1027 Approved
0.6294 Remote Similarity NPD1029 Clinical (unspecified phase)
0.6293 Remote Similarity NPD9626 Clinical (unspecified phase)
0.6276 Remote Similarity NPD3697 Discontinued
0.627 Remote Similarity NPD306 Approved
0.6222 Remote Similarity NPD799 Phase 1
0.6216 Remote Similarity NPD5768 Phase 2
0.6216 Remote Similarity NPD3130 Discontinued
0.6174 Remote Similarity NPD1015 Phase 2
0.6174 Remote Similarity NPD1016 Phase 2
0.6116 Remote Similarity NPD9412 Discontinued
0.6096 Remote Similarity NPD1303 Phase 1
0.6093 Remote Similarity NPD1333 Phase 3
0.6077 Remote Similarity NPD515 Phase 1
0.605 Remote Similarity NPD1816 Clinical (unspecified phase)
0.6036 Remote Similarity NPD8786 Approved
0.6033 Remote Similarity NPD8955 Approved
0.6033 Remote Similarity NPD8954 Approved
0.6018 Remote Similarity NPD9189 Discontinued
0.6017 Remote Similarity NPD8836 Approved
0.6014 Remote Similarity NPD1290 Phase 2
0.6 Remote Similarity NPD1288 Clinical (unspecified phase)
0.5986 Remote Similarity NPD695 Discontinued
0.5966 Remote Similarity NPD9291 Approved
0.596 Remote Similarity NPD1122 Clinical (unspecified phase)
0.5952 Remote Similarity NPD9360 Approved
0.5946 Remote Similarity NPD8787 Clinical (unspecified phase)
0.5935 Remote Similarity NPD9373 Approved
0.5935 Remote Similarity NPD3105 Discontinued
0.5933 Remote Similarity NPD1042 Clinical (unspecified phase)
0.5932 Remote Similarity NPD8837 Clinical (unspecified phase)
0.5929 Remote Similarity NPD582 Approved
0.5918 Remote Similarity NPD1257 Approved
0.5909 Remote Similarity NPD870 Clinical (unspecified phase)
0.5906 Remote Similarity NPD307 Approved
0.5882 Remote Similarity NPD9195 Approved
0.5877 Remote Similarity NPD9190 Approved
0.5873 Remote Similarity NPD1368 Approved
0.586 Remote Similarity NPD3108 Clinical (unspecified phase)
0.584 Remote Similarity NPD9374 Approved
0.584 Remote Similarity NPD9086 Approved
0.5833 Remote Similarity NPD9196 Phase 2
0.5833 Remote Similarity NPD3347 Clinical (unspecified phase)
0.5833 Remote Similarity NPD9371 Clinical (unspecified phase)
0.5833 Remote Similarity NPD9345 Clinical (unspecified phase)
0.5827 Remote Similarity NPD578 Discontinued
0.582 Remote Similarity NPD613 Phase 2
0.5814 Remote Similarity NPD2221 Clinical (unspecified phase)
0.5812 Remote Similarity NPD9134 Approved
0.5812 Remote Similarity NPD9255 Phase 2
0.5812 Remote Similarity NPD9135 Approved
0.5809 Remote Similarity NPD1058 Discontinued
0.5806 Remote Similarity NPD9359 Approved
0.5806 Remote Similarity NPD9358 Approved
0.5802 Remote Similarity NPD579 Clinical (unspecified phase)
0.58 Remote Similarity NPD939 Clinical (unspecified phase)
0.5781 Remote Similarity NPD76 Approved
0.5781 Remote Similarity NPD9288 Approved
0.5781 Remote Similarity NPD580 Discontinued
0.5781 Remote Similarity NPD9292 Approved
0.5781 Remote Similarity NPD9289 Approved
0.5762 Remote Similarity NPD1869 Phase 2
0.5752 Remote Similarity NPD418 Approved
0.575 Remote Similarity NPD3341 Clinical (unspecified phase)
0.5742 Remote Similarity NPD2478 Clinical (unspecified phase)
0.5736 Remote Similarity NPD9409 Discontinued
0.5726 Remote Similarity NPD9375 Discontinued
0.5725 Remote Similarity NPD1734 Clinical (unspecified phase)
0.5714 Remote Similarity NPD9197 Discontinued
0.5706 Remote Similarity NPD2457 Phase 2
0.5706 Remote Similarity NPD2456 Phase 2
0.5703 Remote Similarity NPD9606 Approved
0.5677 Remote Similarity NPD1313 Approved
0.5669 Remote Similarity NPD2875 Clinical (unspecified phase)
0.5659 Remote Similarity NPD9607 Approved
0.5639 Remote Similarity NPD9408 Phase 3
0.5636 Remote Similarity NPD3378 Clinical (unspecified phase)
0.5633 Remote Similarity NPD1567 Clinical (unspecified phase)
0.563 Remote Similarity NPD9633 Phase 3
0.562 Remote Similarity NPD9502 Clinical (unspecified phase)
0.5612 Remote Similarity NPD809 Discontinued

  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