Structure

Physi-Chem Properties

Molecular Weight:  82.05
Volume:  85.905
LogP:  0.171
LogD:  -0.135
LogS:  0.91
# Rotatable Bonds:  0
TPSA:  28.68
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.49
Synthetic Accessibility Score:  3.322
Fsp3:  0.25
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:  -4.334
MDCK Permeability:  6.467567345680436e-06
Pgp-inhibitor:  0.0
Pgp-substrate:  0.215
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.2
30% Bioavailability (F30%):  0.58

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.661
Plasma Protein Binding (PPB):  13.679222106933594%
Volume Distribution (VD):  1.212
Pgp-substrate:  83.42948150634766%

ADMET: Metabolism

CYP1A2-inhibitor:  0.566
CYP1A2-substrate:  0.212
CYP2C19-inhibitor:  0.208
CYP2C19-substrate:  0.466
CYP2C9-inhibitor:  0.015
CYP2C9-substrate:  0.324
CYP2D6-inhibitor:  0.432
CYP2D6-substrate:  0.034
CYP3A4-inhibitor:  0.399
CYP3A4-substrate:  0.223

ADMET: Excretion

Clearance (CL):  11.677
Half-life (T1/2):  0.892

ADMET: Toxicity

hERG Blockers:  0.053
Human Hepatotoxicity (H-HT):  0.655
Drug-inuced Liver Injury (DILI):  0.51
AMES Toxicity:  0.037
Rat Oral Acute Toxicity:  0.822
Maximum Recommended Daily Dose:  0.078
Skin Sensitization:  0.92
Carcinogencity:  0.019
Eye Corrosion:  0.922
Eye Irritation:  0.993
Respiratory Toxicity:  0.68

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Similar NPs/Drugs  

  Natural Product: NPC9639

Natural Product ID:  NPC9639
Common Name*:   5-Methyl-1H-Imidazole
IUPAC Name:   5-methyl-1H-imidazole
Synonyms:  
Standard InCHIKey:  XLSZMDLNRCVEIJ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C4H6N2/c1-4-2-5-3-6-4/h2-3H,1H3,(H,5,6)
SMILES:  Cc1cnc[nH]1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1230309
PubChem CID:   13195
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000436] Azoles
        • [CHEMONTID:0000078] Imidazoles

*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
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[10654410]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[10843587]
NPO20142 Embelia schimperi Species Primulaceae Eukaryota n.a. n.a. n.a. PMID[11054840]
NPO18668 Asimina parviflora Species Annonaceae Eukaryota twigs n.a. n.a. PMID[1453182]
NPO19667 Hypericum styphelioides Species Hypericaceae Eukaryota leaves n.a. n.a. PMID[15165152]
NPO19667 Hypericum styphelioides Species Hypericaceae Eukaryota n.a. leaf n.a. PMID[15165152]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota Roots n.a. n.a. PMID[15568770]
NPO18286 Lycogala epidendrum Species Enteridiidae Eukaryota n.a. n.a. n.a. PMID[15911254]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[16392664]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota roots Hualien Hsien, Taiwan 2003-JUL PMID[16933887]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[16933887]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[17951038]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[18175961]
NPO20879 Clerodendrum bungei Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[18348535]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. root n.a. PMID[18975262]
NPO3152 Morella rubra Species Myricaceae Eukaryota n.a. n.a. n.a. PMID[19407970]
NPO3152 Morella rubra Species Myricaceae Eukaryota n.a. bark n.a. PMID[21553897]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[24295087]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. PMID[24333010]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. PMID[24459770]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[27575476]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota Roots n.a. n.a. PMID[30298740]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota Roots n.a. n.a. PMID[9868163]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. Database[Article]
NPO12056 Chondrodendron tomentosum Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21375 Euphorbia nematocypha Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18286 Lycogala epidendrum Species Enteridiidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17334 Onopordum acanthium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21170 Embelia parviflora Species Primulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18668 Asimina parviflora Species Annonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20879 Clerodendrum bungei Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3152 Morella rubra Species Myricaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18286 Lycogala epidendrum Species Enteridiidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21170 Embelia parviflora Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17334 Onopordum acanthium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20142 Embelia schimperi Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20680 Erythrina melanacantha Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21375 Euphorbia nematocypha Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20489 Epilobium hirsutum Species Onagraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12056 Chondrodendron tomentosum Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20680 Erythrina melanacantha Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21170 Embelia parviflora Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21375 Euphorbia nematocypha Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17334 Onopordum acanthium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18286 Lycogala epidendrum Species Enteridiidae Eukaryota n.a. n.a. n.a. Database[Title]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18143 Dendronephthya griffini Species Nephtheidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20142 Embelia schimperi Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19912 Vellozia nanuzae Species Velloziaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20084 Atraphaxis spinosa Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19995 Baccharis neglecta Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20421 Aplophyllum alberti-regelii n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO16569 Gymnocalycium schickendantzii Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11523 Erysimum leptophyllum Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21375 Euphorbia nematocypha Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20489 Epilobium hirsutum Species Onagraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28072 Theonella conica Species Theonellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17849 Centaurea maculosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20598 Lythrum salicaria Species Lythraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20680 Erythrina melanacantha Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4051 Tricholoma columbetta Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21243 Siphonaria capensis Species Siphonariidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12313 Haplophyllum obtusifolium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13449 Syzygium polycephaloides Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21108 Eria anomala Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21562 Diospyros assimilis Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14241 Planchonia grandis Species Asterolecaniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16141 Piper regnellii Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18286 Lycogala epidendrum Species Enteridiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18866 Pteridium esculentum Species Dennstaedtiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17560 Pancratium sickenbergeri Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9968 Shigella dysenteriae Species Enterobacteriaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO19810 Myxococcus stipitatus Species Myxococcaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO21495 Abelia chinensis Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12056 Chondrodendron tomentosum Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18668 Asimina parviflora Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17334 Onopordum acanthium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17258 Rhinella marina Species Bufonidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27367 Latrunculia magnifica Species Latrunculiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20843 Monsonia senegalensis Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19511 Dolabella californica Species Aplysiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22961 Cordia leucocephala Species Cordiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18473 Plathymenia reticulata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19036 Esenbeckia leiocarpa Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5903 Conus mus Species Conidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22937 Vernonia fagifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21631 Faramea salicifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21038 Lemaireocereus longispinus Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28202 Helichrysum tenuifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3152 Morella rubra Species Myricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20624 Simarouba glauca Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21170 Embelia parviflora Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19667 Hypericum styphelioides Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20879 Clerodendrum bungei Species Lamiaceae 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
NPT347 Cell Line Lymphoblastoid cells Homo sapiens Potency = 79432.8 nM PMID[458305]
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 35481.3 nM PMID[458305]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 36.6 nM PMID[458306]
NPT4170 Individual Protein Peptidyl-prolyl cis-trans isomerase FKBP5 Homo sapiens Kd = 2900000.0 nM PMID[458307]
NPT2 Others Unspecified Potency n.a. 47067.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 5232.9 nM PubChem BioAssay data set
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 281.8 nM PMID[458305]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 16511.3 nM PMID[458306]

☑ 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 NPC9639 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
0.9072 High Similarity NPC155498
0.9062 High Similarity NPC111132
0.8469 Intermediate Similarity NPC187191
0.8469 Intermediate Similarity NPC326248
0.8286 Intermediate Similarity NPC327613
0.809 Intermediate Similarity NPC237936
0.7727 Intermediate Similarity NPC68938
0.7565 Intermediate Similarity NPC15566
0.75 Intermediate Similarity NPC273327
0.75 Intermediate Similarity NPC51000
0.7436 Intermediate Similarity NPC180462
0.7333 Intermediate Similarity NPC25465
0.732 Intermediate Similarity NPC190949
0.725 Intermediate Similarity NPC243319
0.719 Intermediate Similarity NPC235501
0.7143 Intermediate Similarity NPC293163
0.7037 Intermediate Similarity NPC476099
0.6944 Remote Similarity NPC59314
0.6905 Remote Similarity NPC18223
0.6905 Remote Similarity NPC237812
0.6881 Remote Similarity NPC18335
0.6842 Remote Similarity NPC313547
0.6744 Remote Similarity NPC185903
0.6744 Remote Similarity NPC286696
0.6609 Remote Similarity NPC41958
0.6596 Remote Similarity NPC100312
0.6596 Remote Similarity NPC204104
0.6541 Remote Similarity NPC174020
0.6526 Remote Similarity NPC270637
0.6496 Remote Similarity NPC148385
0.6496 Remote Similarity NPC63433
0.6493 Remote Similarity NPC327477
0.6493 Remote Similarity NPC197068
0.6484 Remote Similarity NPC126634
0.6435 Remote Similarity NPC4837
0.6435 Remote Similarity NPC312187
0.6387 Remote Similarity NPC278549
0.6346 Remote Similarity NPC326364
0.6328 Remote Similarity NPC57279
0.6306 Remote Similarity NPC174114
0.6306 Remote Similarity NPC87981
0.6288 Remote Similarity NPC210947
0.6283 Remote Similarity NPC476562
0.6281 Remote Similarity NPC252603
0.625 Remote Similarity NPC240084
0.625 Remote Similarity NPC189314
0.6214 Remote Similarity NPC282531
0.6127 Remote Similarity NPC60537
0.6106 Remote Similarity NPC476561
0.6091 Remote Similarity NPC476128
0.6047 Remote Similarity NPC246193
0.6036 Remote Similarity NPC320256
0.6 Remote Similarity NPC470138
0.594 Remote Similarity NPC470140
0.5912 Remote Similarity NPC8590
0.5868 Remote Similarity NPC199790
0.5814 Remote Similarity NPC144223
0.5812 Remote Similarity NPC119133
0.5809 Remote Similarity NPC470139
0.5794 Remote Similarity NPC277608
0.576 Remote Similarity NPC327579
0.5755 Remote Similarity NPC76536
0.5726 Remote Similarity NPC476564
0.5725 Remote Similarity NPC14330
0.5682 Remote Similarity NPC287876
0.5682 Remote Similarity NPC104011
0.568 Remote Similarity NPC158847
0.5652 Remote Similarity NPC332382
0.5648 Remote Similarity NPC262236
0.562 Remote Similarity NPC47936
0.56 Remote Similarity NPC300238

  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 NPC9639 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
0.9062 High Similarity NPD8859 Approved
0.9062 High Similarity NPD8861 Approved
0.9062 High Similarity NPD8862 Approved
0.8131 Intermediate Similarity NPD9132 Discontinued
0.809 Intermediate Similarity NPD8185 Discontinued
0.809 Intermediate Similarity NPD8186 Phase 1
0.7767 Intermediate Similarity NPD340 Approved
0.7767 Intermediate Similarity NPD341 Approved
0.7719 Intermediate Similarity NPD1388 Phase 1
0.7719 Intermediate Similarity NPD1390 Phase 1
0.7719 Intermediate Similarity NPD1389 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD9210 Phase 2
0.75 Intermediate Similarity NPD8838 Approved
0.7436 Intermediate Similarity NPD300 Approved
0.7311 Intermediate Similarity NPD1807 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD9081 Clinical (unspecified phase)
0.6944 Remote Similarity NPD8837 Clinical (unspecified phase)
0.6905 Remote Similarity NPD9133 Approved
0.6905 Remote Similarity NPD9628 Approved
0.6887 Remote Similarity NPD9194 Approved
0.6887 Remote Similarity NPD9193 Approved
0.6881 Remote Similarity NPD8836 Approved
0.6783 Remote Similarity NPD757 Phase 3
0.6726 Remote Similarity NPD8955 Approved
0.6726 Remote Similarity NPD8954 Approved
0.6718 Remote Similarity NPD5342 Clinical (unspecified phase)
0.6701 Remote Similarity NPD8584 Approved
0.6641 Remote Similarity NPD1451 Approved
0.6641 Remote Similarity NPD9183 Clinical (unspecified phase)
0.664 Remote Similarity NPD9650 Phase 3
0.661 Remote Similarity NPD9360 Approved
0.6591 Remote Similarity NPD3706 Clinical (unspecified phase)
0.6541 Remote Similarity NPD9627 Approved
0.629 Remote Similarity NPD579 Clinical (unspecified phase)
0.6286 Remote Similarity NPD1029 Clinical (unspecified phase)
0.6286 Remote Similarity NPD1027 Approved
0.6286 Remote Similarity NPD1030 Approved
0.6281 Remote Similarity NPD9288 Approved
0.6281 Remote Similarity NPD9292 Approved
0.6281 Remote Similarity NPD76 Approved
0.6281 Remote Similarity NPD9289 Approved
0.625 Remote Similarity NPD8833 Approved
0.625 Remote Similarity NPD8831 Approved
0.6241 Remote Similarity NPD875 Clinical (unspecified phase)
0.6197 Remote Similarity NPD1303 Phase 1
0.6174 Remote Similarity NPD1816 Clinical (unspecified phase)
0.617 Remote Similarity NPD1731 Clinical (unspecified phase)
0.6167 Remote Similarity NPD163 Approved
0.6154 Remote Similarity NPD2604 Approved
0.6154 Remote Similarity NPD3697 Discontinued
0.614 Remote Similarity NPD9626 Clinical (unspecified phase)
0.6127 Remote Similarity NPD2180 Approved
0.6111 Remote Similarity NPD1290 Phase 2
0.6102 Remote Similarity NPD9375 Discontinued
0.6084 Remote Similarity NPD695 Discontinued
0.605 Remote Similarity NPD9373 Approved
0.5986 Remote Similarity NPD3130 Discontinued
0.5986 Remote Similarity NPD5768 Phase 2
0.5966 Remote Similarity NPD9412 Discontinued
0.595 Remote Similarity NPD9374 Approved
0.594 Remote Similarity NPD576 Discontinued
0.5938 Remote Similarity NPD515 Phase 1
0.5935 Remote Similarity NPD237 Clinical (unspecified phase)
0.5926 Remote Similarity NPD8787 Clinical (unspecified phase)
0.5918 Remote Similarity NPD1042 Clinical (unspecified phase)
0.5909 Remote Similarity NPD9101 Discontinued
0.5909 Remote Similarity NPD9083 Clinical (unspecified phase)
0.5887 Remote Similarity NPD307 Approved
0.5872 Remote Similarity NPD8786 Approved
0.5856 Remote Similarity NPD9189 Discontinued
0.5854 Remote Similarity NPD1368 Approved
0.5852 Remote Similarity NPD799 Phase 1
0.584 Remote Similarity NPD9409 Discontinued
0.5839 Remote Similarity NPD1122 Clinical (unspecified phase)
0.5812 Remote Similarity NPD9291 Approved
0.5806 Remote Similarity NPD9606 Approved
0.5789 Remote Similarity NPD209 Clinical (unspecified phase)
0.576 Remote Similarity NPD9607 Approved
0.5746 Remote Similarity NPD9484 Clinical (unspecified phase)
0.5726 Remote Similarity NPD9195 Approved
0.5714 Remote Similarity NPD9190 Approved
0.5714 Remote Similarity NPD3347 Clinical (unspecified phase)
0.5714 Remote Similarity NPD3105 Discontinued
0.5691 Remote Similarity NPD9086 Approved
0.5688 Remote Similarity NPD8565 Clinical (unspecified phase)
0.5688 Remote Similarity NPD8835 Approved
0.5682 Remote Similarity NPD8829 Clinical (unspecified phase)
0.5678 Remote Similarity NPD9345 Clinical (unspecified phase)
0.5678 Remote Similarity NPD9371 Clinical (unspecified phase)
0.5678 Remote Similarity NPD9196 Phase 2
0.5672 Remote Similarity NPD1264 Phase 2
0.5652 Remote Similarity NPD9134 Approved
0.5652 Remote Similarity NPD9135 Approved
0.5652 Remote Similarity NPD9255 Phase 2
0.5649 Remote Similarity NPD870 Clinical (unspecified phase)
0.5643 Remote Similarity NPD568 Approved
0.5643 Remote Similarity NPD567 Approved
0.5643 Remote Similarity NPD566 Approved
0.5643 Remote Similarity NPD174 Discontinued
0.5641 Remote Similarity NPD3108 Clinical (unspecified phase)
0.5621 Remote Similarity NPD2478 Clinical (unspecified phase)

  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