Structure

Physi-Chem Properties

Molecular Weight:  350.12
Volume:  351.849
LogP:  4.243
LogD:  2.201
LogS:  -5.28
# Rotatable Bonds:  1
TPSA:  83.83
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.824
Synthetic Accessibility Score:  3.94
Fsp3:  0.333
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.057
MDCK Permeability:  1.6630408936180174e-05
Pgp-inhibitor:  0.235
Pgp-substrate:  0.998
Human Intestinal Absorption (HIA):  0.537
20% Bioavailability (F20%):  0.976
30% Bioavailability (F30%):  0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.056
Plasma Protein Binding (PPB):  94.90923309326172%
Volume Distribution (VD):  1.036
Pgp-substrate:  2.6641697883605957%

ADMET: Metabolism

CYP1A2-inhibitor:  0.105
CYP1A2-substrate:  0.892
CYP2C19-inhibitor:  0.079
CYP2C19-substrate:  0.624
CYP2C9-inhibitor:  0.569
CYP2C9-substrate:  0.961
CYP2D6-inhibitor:  0.289
CYP2D6-substrate:  0.295
CYP3A4-inhibitor:  0.248
CYP3A4-substrate:  0.547

ADMET: Excretion

Clearance (CL):  2.845
Half-life (T1/2):  0.062

ADMET: Toxicity

hERG Blockers:  0.261
Human Hepatotoxicity (H-HT):  0.794
Drug-inuced Liver Injury (DILI):  0.828
AMES Toxicity:  0.854
Rat Oral Acute Toxicity:  0.914
Maximum Recommended Daily Dose:  0.971
Skin Sensitization:  0.666
Carcinogencity:  0.102
Eye Corrosion:  0.003
Eye Irritation:  0.159
Respiratory Toxicity:  0.952

Download Data

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

  Natural Product: NPC52110

Natural Product ID:  NPC52110
Common Name*:   4,5-Dibromo-2-Pyrrolic Acid
IUPAC Name:   4,5-dibromo-1H-pyrrole-2-carboxylic acid
Synonyms:  
Standard InCHIKey:  ZUROCNHARMFRKA-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C5H3Br2NO2/c6-2-1-3(5(9)10)8-4(2)7/h1,8H,(H,9,10)
SMILES:  Brc1[nH]c(cc1Br)C(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL397590
PubChem CID:   161830
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000090] Pyrroles
        • [CHEMONTID:0002554] Pyrrole carboxylic acids and derivatives
          • [CHEMONTID:0002555] Pyrrole carboxylic acids
            • [CHEMONTID:0002557] Pyrrole 2-carboxylic 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
NPO27323 Cestrum nocturnum Species Solanaceae Eukaryota leaves n.a. n.a. PMID[11170659]
NPO27012 Laurencia pannosa Species Rhodomelaceae Eukaryota n.a. Malaysian n.a. PMID[11374951]
NPO27323 Cestrum nocturnum Species Solanaceae Eukaryota leaves n.a. n.a. PMID[12502329]
NPO27072 Monochaetum vulcanicum Species Melastomataceae Eukaryota n.a. n.a. n.a. PMID[15165161]
NPO40426 Agelas oroides enoyl Strain Agelasidae Eukaryota Tubers n.a. n.a. PMID[17765547]
NPO8720 Agelas flabelliformis Species Agelasidae Eukaryota n.a. n.a. n.a. PMID[2530314]
NPO17223 Agelas oroides Species Agelasidae Eukaryota n.a. n.a. n.a. PMID[32072810]
NPO27323 Cestrum nocturnum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27725 Artemisia vestita Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27323 Cestrum nocturnum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27725 Artemisia vestita Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27773 Rhododendron ovatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27323 Cestrum nocturnum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27725 Artemisia vestita Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO27323 Cestrum nocturnum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27773 Rhododendron ovatum Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27262 Dryopteris inaequalis Species Dryopteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27191 Schistochila appendiculata Species Schistochilaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27725 Artemisia vestita Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27740 Alcantara ekmaniana n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO7497 Guatteria blepharophylla Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26895 Baccharis bigelovii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11140 Coprinopsis cinerea Species Psathyrellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22488 Leptosphaeria oraemaris Species Leptosphaeriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27012 Laurencia pannosa Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27569 Archangelica officinalis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8720 Agelas flabelliformis Species Agelasidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27648 Cereus aethiops Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27707 Soja hispida Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27688 Aeonium goochiae Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20208 Rhinogobius brunneus Species Gobiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17223 Agelas oroides Species Agelasidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16500 Byssochlamys spectabilis Species Thermoascaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27072 Monochaetum vulcanicum Species Melastomataceae 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
NPT1333 Individual Protein Enoyl-acyl-carrier protein reductase Plasmodium falciparum IC50 > 100.0 ug.mL-1 PMID[521579]
NPT839 Cell Line L6 Rattus norvegicus IC50 > 90.0 ug.mL-1 PMID[521579]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 > 50.0 ug.mL-1 PMID[521579]
NPT844 Organism Trypanosoma brucei rhodesiense Trypanosoma brucei rhodesiense IC50 = 20.9 ug.mL-1 PMID[521579]
NPT580 Organism Trypanosoma cruzi Trypanosoma cruzi IC50 > 30.0 ug.mL-1 PMID[521579]
NPT633 Organism Leishmania donovani Leishmania donovani IC50 = 7.9 ug.mL-1 PMID[521579]
NPT2 Others Unspecified Activity = 100.0 % PMID[521580]
NPT2 Others Unspecified Activity = 40.0 % PMID[521580]
NPT2 Others Unspecified Activity = 59.0 % PMID[521580]
NPT2 Others Unspecified Activity = 31.0 % PMID[521580]
NPT2 Others Unspecified Activity = 13.0 % PMID[521580]
NPT2 Others Unspecified Activity = 0.0 % PMID[521580]
NPT27 Others Unspecified Activity = 10.0 % PMID[521580]
NPT27 Others Unspecified Activity = 0.0 % PMID[521580]
NPT27 Others Unspecified Activity = 12.0 % PMID[521580]
NPT27 Others Unspecified Activity = 27.0 % PMID[521580]
NPT27 Others Unspecified Activity = 66.0 % PMID[521580]
NPT27 Others Unspecified Activity = 99.0 % PMID[521580]
NPT27 Others Unspecified Activity = 80.0 % PMID[521580]
NPT27 Others Unspecified Activity = 95.0 % PMID[521580]
NPT27 Others Unspecified Activity = 113.0 % PMID[521580]
NPT2 Others Unspecified Activity = 83.0 % PMID[521580]
NPT2 Others Unspecified Activity = 99.0 % PMID[521580]
NPT2 Others Unspecified Activity = 84.0 % PMID[521580]
NPT2 Others Unspecified Activity = 64.0 % PMID[521580]
NPT2 Others Unspecified Activity = 70.0 % PMID[521580]
NPT2 Others Unspecified Activity = 29.0 % PMID[521580]
NPT2 Others Unspecified Activity = 43.0 % PMID[521580]
NPT2 Others Unspecified Activity = 39.0 % PMID[521580]
NPT2 Others Unspecified Activity = 50.0 % PMID[521580]
NPT27 Others Unspecified Activity = 100.0 % PMID[521580]

☑ 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 NPC52110 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
0.9189 High Similarity NPC142688
0.8986 High Similarity NPC109158
0.8377 Intermediate Similarity NPC298288
0.8377 Intermediate Similarity NPC33229
0.8235 Intermediate Similarity NPC13432
0.8219 Intermediate Similarity NPC150592
0.8027 Intermediate Similarity NPC20021
0.7812 Intermediate Similarity NPC27296
0.7806 Intermediate Similarity NPC260041
0.7684 Intermediate Similarity NPC77061
0.7665 Intermediate Similarity NPC80528
0.7597 Intermediate Similarity NPC85443
0.7578 Intermediate Similarity NPC474236
0.7576 Intermediate Similarity NPC474383
0.7312 Intermediate Similarity NPC302159
0.7209 Intermediate Similarity NPC37268
0.7119 Intermediate Similarity NPC469814
0.7102 Intermediate Similarity NPC184932
0.7102 Intermediate Similarity NPC472861
0.7101 Intermediate Similarity NPC206148
0.7101 Intermediate Similarity NPC476418
0.7083 Intermediate Similarity NPC473706
0.7079 Intermediate Similarity NPC476423
0.7 Intermediate Similarity NPC306160
0.6994 Remote Similarity NPC302647
0.699 Remote Similarity NPC469717
0.6973 Remote Similarity NPC141454
0.6959 Remote Similarity NPC2414
0.6919 Remote Similarity NPC474696
0.6899 Remote Similarity NPC23215
0.6899 Remote Similarity NPC291517
0.6882 Remote Similarity NPC322644
0.6855 Remote Similarity NPC64661
0.6855 Remote Similarity NPC200397
0.6855 Remote Similarity NPC195704
0.6855 Remote Similarity NPC98156
0.6855 Remote Similarity NPC167200
0.6855 Remote Similarity NPC292434
0.6855 Remote Similarity NPC14448
0.6855 Remote Similarity NPC138596
0.6848 Remote Similarity NPC476413
0.6818 Remote Similarity NPC97106
0.6811 Remote Similarity NPC476414
0.68 Remote Similarity NPC273532
0.678 Remote Similarity NPC136441
0.6761 Remote Similarity NPC271927
0.6758 Remote Similarity NPC46022
0.6758 Remote Similarity NPC112489
0.6754 Remote Similarity NPC165599
0.6724 Remote Similarity NPC41717
0.6687 Remote Similarity NPC169308
0.6687 Remote Similarity NPC74928
0.6687 Remote Similarity NPC302717
0.6687 Remote Similarity NPC12831
0.6687 Remote Similarity NPC286529
0.6687 Remote Similarity NPC205604
0.6687 Remote Similarity NPC97230
0.6687 Remote Similarity NPC209281
0.6687 Remote Similarity NPC129753
0.6687 Remote Similarity NPC244087
0.6687 Remote Similarity NPC59839
0.6687 Remote Similarity NPC3698
0.6687 Remote Similarity NPC48171
0.6687 Remote Similarity NPC77582
0.6685 Remote Similarity NPC221873
0.6649 Remote Similarity NPC9635
0.6649 Remote Similarity NPC83111
0.6649 Remote Similarity NPC321428
0.6649 Remote Similarity NPC244741
0.6646 Remote Similarity NPC114033
0.6646 Remote Similarity NPC101130
0.6646 Remote Similarity NPC129412
0.6646 Remote Similarity NPC58268
0.6612 Remote Similarity NPC311282
0.661 Remote Similarity NPC227489
0.661 Remote Similarity NPC28096
0.661 Remote Similarity NPC476421
0.661 Remote Similarity NPC226835
0.661 Remote Similarity NPC54214
0.6596 Remote Similarity NPC46811
0.6592 Remote Similarity NPC476419
0.6582 Remote Similarity NPC325297
0.6576 Remote Similarity NPC63571
0.6576 Remote Similarity NPC111566
0.655 Remote Similarity NPC75135
0.6543 Remote Similarity NPC328029
0.6541 Remote Similarity NPC278434
0.6541 Remote Similarity NPC310633
0.6531 Remote Similarity NPC476524
0.6527 Remote Similarity NPC167400
0.6517 Remote Similarity NPC253810
0.6514 Remote Similarity NPC73687
0.6491 Remote Similarity NPC312860
0.6477 Remote Similarity NPC471944
0.6474 Remote Similarity NPC179701
0.6474 Remote Similarity NPC475870
0.645 Remote Similarity NPC89508
0.644 Remote Similarity NPC262898
0.6432 Remote Similarity NPC241025
0.6432 Remote Similarity NPC82370
0.6432 Remote Similarity NPC474258
0.6429 Remote Similarity NPC82053
0.6418 Remote Similarity NPC50562
0.6404 Remote Similarity NPC470894
0.6402 Remote Similarity NPC114310
0.6402 Remote Similarity NPC472288
0.6398 Remote Similarity NPC160381
0.6386 Remote Similarity NPC67658
0.6379 Remote Similarity NPC212742
0.6378 Remote Similarity NPC132539
0.6378 Remote Similarity NPC207851
0.6375 Remote Similarity NPC71236
0.6368 Remote Similarity NPC19342
0.6364 Remote Similarity NPC473946
0.6355 Remote Similarity NPC312645
0.6354 Remote Similarity NPC186068
0.633 Remote Similarity NPC209917
0.6322 Remote Similarity NPC141353
0.6319 Remote Similarity NPC286195
0.6286 Remote Similarity NPC116573
0.6281 Remote Similarity NPC476525
0.6264 Remote Similarity NPC263455
0.6257 Remote Similarity NPC109447
0.6243 Remote Similarity NPC469976
0.6237 Remote Similarity NPC248782
0.6236 Remote Similarity NPC162268
0.6224 Remote Similarity NPC98864
0.6209 Remote Similarity NPC247980
0.6205 Remote Similarity NPC19696
0.6205 Remote Similarity NPC136957
0.6198 Remote Similarity NPC88315
0.6198 Remote Similarity NPC473821
0.6196 Remote Similarity NPC15573
0.6196 Remote Similarity NPC217372
0.6196 Remote Similarity NPC183662
0.6193 Remote Similarity NPC57398
0.6193 Remote Similarity NPC469716
0.6186 Remote Similarity NPC74153
0.618 Remote Similarity NPC26491
0.6178 Remote Similarity NPC210123
0.6176 Remote Similarity NPC118228
0.6176 Remote Similarity NPC159630
0.6176 Remote Similarity NPC230085
0.6172 Remote Similarity NPC229893
0.6166 Remote Similarity NPC202812
0.6162 Remote Similarity NPC248041
0.6162 Remote Similarity NPC219336
0.6162 Remote Similarity NPC276540
0.6162 Remote Similarity NPC126709
0.6162 Remote Similarity NPC283219
0.6162 Remote Similarity NPC233050
0.6159 Remote Similarity NPC194541
0.6158 Remote Similarity NPC207020
0.6158 Remote Similarity NPC118940
0.6158 Remote Similarity NPC113812
0.615 Remote Similarity NPC283117
0.6146 Remote Similarity NPC74969
0.6134 Remote Similarity NPC48117
0.6134 Remote Similarity NPC476526
0.6134 Remote Similarity NPC329765
0.6126 Remote Similarity NPC144381
0.6124 Remote Similarity NPC243633
0.6124 Remote Similarity NPC175150
0.612 Remote Similarity NPC64055
0.6119 Remote Similarity NPC39679
0.6117 Remote Similarity NPC472285
0.6117 Remote Similarity NPC223189
0.6111 Remote Similarity NPC233380
0.6111 Remote Similarity NPC115232
0.6108 Remote Similarity NPC111275
0.6103 Remote Similarity NPC174281
0.6103 Remote Similarity NPC475286
0.6096 Remote Similarity NPC275292
0.6096 Remote Similarity NPC243381
0.6094 Remote Similarity NPC138370
0.6087 Remote Similarity NPC110500
0.6087 Remote Similarity NPC149155
0.6087 Remote Similarity NPC303225
0.6087 Remote Similarity NPC184408
0.6087 Remote Similarity NPC203468
0.6087 Remote Similarity NPC174576
0.6085 Remote Similarity NPC295158
0.6082 Remote Similarity NPC276517
0.608 Remote Similarity NPC476098
0.6071 Remote Similarity NPC306376
0.6071 Remote Similarity NPC472284
0.607 Remote Similarity NPC270918
0.6069 Remote Similarity NPC112741
0.6069 Remote Similarity NPC257142
0.6065 Remote Similarity NPC174489
0.6058 Remote Similarity NPC168209
0.6054 Remote Similarity NPC267885
0.6048 Remote Similarity NPC29702
0.6047 Remote Similarity NPC200553
0.6047 Remote Similarity NPC279189
0.6044 Remote Similarity NPC78020
0.6043 Remote Similarity NPC317010
0.604 Remote Similarity NPC266249
0.6038 Remote Similarity NPC214142
0.6037 Remote Similarity NPC162002

  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 NPC52110 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
0.75 Intermediate Similarity NPD3178 Discontinued
0.6667 Remote Similarity NPD9076 Clinical (unspecified phase)
0.6598 Remote Similarity NPD2715 Clinical (unspecified phase)
0.6546 Remote Similarity NPD2721 Clinical (unspecified phase)
0.6527 Remote Similarity NPD9075 Approved
0.6527 Remote Similarity NPD9074 Approved
0.642 Remote Similarity NPD1631 Approved
0.6404 Remote Similarity NPD2844 Phase 3
0.6378 Remote Similarity NPD1096 Discontinued
0.6287 Remote Similarity NPD107 Approved
0.6278 Remote Similarity NPD1573 Approved
0.6278 Remote Similarity NPD1575 Approved
0.627 Remote Similarity NPD1783 Clinical (unspecified phase)
0.625 Remote Similarity NPD1630 Approved
0.6212 Remote Similarity NPD5901 Discontinued
0.6184 Remote Similarity NPD1996 Discontinued
0.6175 Remote Similarity NPD4736 Clinical (unspecified phase)
0.6154 Remote Similarity NPD1592 Phase 3
0.6136 Remote Similarity NPD276 Clinical (unspecified phase)
0.6087 Remote Similarity NPD482 Approved
0.6075 Remote Similarity NPD1587 Approved
0.6069 Remote Similarity NPD9271 Approved
0.6054 Remote Similarity NPD749 Clinical (unspecified phase)
0.6021 Remote Similarity NPD4948 Discontinued
0.602 Remote Similarity NPD5003 Discontinued
0.6019 Remote Similarity NPD3757 Clinical (unspecified phase)
0.601 Remote Similarity NPD484 Approved
0.6 Remote Similarity NPD8096 Phase 3
0.6 Remote Similarity NPD8097 Phase 3
0.5976 Remote Similarity NPD203 Clinical (unspecified phase)
0.5957 Remote Similarity NPD1643 Phase 3
0.5941 Remote Similarity NPD569 Clinical (unspecified phase)
0.5938 Remote Similarity NPD6141 Clinical (unspecified phase)
0.5934 Remote Similarity NPD1568 Clinical (unspecified phase)
0.5928 Remote Similarity NPD5592 Clinical (unspecified phase)
0.592 Remote Similarity NPD2121 Clinical (unspecified phase)
0.5914 Remote Similarity NPD1586 Approved
0.5897 Remote Similarity NPD9243 Approved
0.5895 Remote Similarity NPD2094 Phase 2
0.5895 Remote Similarity NPD2095 Phase 2
0.5895 Remote Similarity NPD2092 Phase 2
0.5891 Remote Similarity NPD8098 Approved
0.5888 Remote Similarity NPD2289 Phase 3
0.5888 Remote Similarity NPD2290 Phase 3
0.5876 Remote Similarity NPD2564 Approved
0.5876 Remote Similarity NPD2565 Phase 2
0.5873 Remote Similarity NPD6452 Discontinued
0.5872 Remote Similarity NPD5020 Approved
0.5867 Remote Similarity NPD1173 Approved
0.5864 Remote Similarity NPD2091 Phase 2
0.5864 Remote Similarity NPD2096 Phase 2
0.5843 Remote Similarity NPD180 Clinical (unspecified phase)
0.5833 Remote Similarity NPD820 Phase 3
0.5829 Remote Similarity NPD7946 Pre-registration
0.5829 Remote Similarity NPD772 Phase 3
0.5825 Remote Similarity NPD1534 Approved
0.582 Remote Similarity NPD5398 Clinical (unspecified phase)
0.5816 Remote Similarity NPD6665 Discontinued
0.5792 Remote Similarity NPD5140 Approved
0.5792 Remote Similarity NPD5138 Approved
0.5789 Remote Similarity NPD2323 Clinical (unspecified phase)
0.5787 Remote Similarity NPD510 Phase 1
0.5775 Remote Similarity NPD750 Phase 2
0.5769 Remote Similarity NPD6657 Clinical (unspecified phase)
0.5767 Remote Similarity NPD7865 Approved
0.5758 Remote Similarity NPD9080 Approved
0.5753 Remote Similarity NPD1326 Approved
0.5753 Remote Similarity NPD1325 Approved
0.575 Remote Similarity NPD7459 Phase 2
0.5749 Remote Similarity NPD7998 Clinical (unspecified phase)
0.5742 Remote Similarity NPD3243 Approved
0.573 Remote Similarity NPD4554 Clinical (unspecified phase)
0.5729 Remote Similarity NPD6449 Clinical (unspecified phase)
0.5729 Remote Similarity NPD5728 Clinical (unspecified phase)
0.5728 Remote Similarity NPD6376 Discontinued
0.5723 Remote Similarity NPD5352 Clinical (unspecified phase)
0.5722 Remote Similarity NPD3315 Phase 3
0.5721 Remote Similarity NPD7470 Discontinued
0.5714 Remote Similarity NPD2779 Approved
0.5714 Remote Similarity NPD1554 Clinical (unspecified phase)
0.5707 Remote Similarity NPD4862 Clinical (unspecified phase)
0.57 Remote Similarity NPD4506 Discontinued
0.5698 Remote Similarity NPD9343 Clinical (unspecified phase)
0.5687 Remote Similarity NPD8160 Phase 2
0.5682 Remote Similarity NPD6263 Clinical (unspecified phase)
0.5681 Remote Similarity NPD6770 Approved
0.5678 Remote Similarity NPD5975 Clinical (unspecified phase)
0.5674 Remote Similarity NPD6160 Clinical (unspecified phase)
0.5661 Remote Similarity NPD158 Discontinued
0.5659 Remote Similarity NPD3947 Discontinued
0.5659 Remote Similarity NPD6323 Clinical (unspecified phase)
0.5652 Remote Similarity NPD2510 Approved
0.5652 Remote Similarity NPD2509 Approved
0.5648 Remote Similarity NPD7547 Clinical (unspecified phase)
0.5646 Remote Similarity NPD5416 Discontinued
0.564 Remote Similarity NPD5417 Clinical (unspecified phase)
0.5634 Remote Similarity NPD5632 Approved
0.5628 Remote Similarity NPD604 Clinical (unspecified phase)
0.5622 Remote Similarity NPD863 Approved
0.5622 Remote Similarity NPD862 Approved
0.5622 Remote Similarity NPD861 Approved
0.5619 Remote Similarity NPD3918 Approved
0.5619 Remote Similarity NPD5866 Approved
0.5619 Remote Similarity NPD3917 Approved
0.5619 Remote Similarity NPD3916 Clinical (unspecified phase)
0.5615 Remote Similarity NPD7866 Approved
0.5613 Remote Similarity NPD3393 Approved
0.5613 Remote Similarity NPD3389 Approved
0.5613 Remote Similarity NPD2433 Clinical (unspecified phase)
0.5613 Remote Similarity NPD3394 Approved
0.56 Remote Similarity NPD3834 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