Structure

Physi-Chem Properties

Molecular Weight:  294.88
Volume:  180.307
LogP:  2.81
LogD:  2.854
LogS:  -3.892
# Rotatable Bonds:  2
TPSA:  31.23
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.745
Synthetic Accessibility Score:  2.66
Fsp3:  0.286
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.543
MDCK Permeability:  2.338310696359258e-05
Pgp-inhibitor:  0.004
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.132
20% Bioavailability (F20%):  0.037
30% Bioavailability (F30%):  0.937

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.988
Plasma Protein Binding (PPB):  95.23027801513672%
Volume Distribution (VD):  0.595
Pgp-substrate:  8.159441947937012%

ADMET: Metabolism

CYP1A2-inhibitor:  0.983
CYP1A2-substrate:  0.827
CYP2C19-inhibitor:  0.771
CYP2C19-substrate:  0.819
CYP2C9-inhibitor:  0.357
CYP2C9-substrate:  0.77
CYP2D6-inhibitor:  0.025
CYP2D6-substrate:  0.693
CYP3A4-inhibitor:  0.053
CYP3A4-substrate:  0.21

ADMET: Excretion

Clearance (CL):  5.883
Half-life (T1/2):  0.516

ADMET: Toxicity

hERG Blockers:  0.107
Human Hepatotoxicity (H-HT):  0.15
Drug-inuced Liver Injury (DILI):  0.294
AMES Toxicity:  0.045
Rat Oral Acute Toxicity:  0.312
Maximum Recommended Daily Dose:  0.307
Skin Sensitization:  0.455
Carcinogencity:  0.683
Eye Corrosion:  0.033
Eye Irritation:  0.808
Respiratory Toxicity:  0.325

Download Data

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

  Natural Product: NPC298288

Natural Product ID:  NPC298288
Common Name*:   Methyl 4,5-Dibromo-1-Methylpyrrole-2-Carboxylate
IUPAC Name:   methyl 4,5-dibromo-1-methylpyrrole-2-carboxylate
Synonyms:   Methyl-4,5-Dibromocarboxylic Acid Methyl Ester
Standard InCHIKey:  UTOZAUBXQWRZIF-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C7H7Br2NO2/c1-10-5(7(11)12-2)3-4(8)6(10)9/h3H,1-2H3
SMILES:  Cn1c(cc(c1Br)Br)C(=O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL598919
PubChem CID:   360185
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000090] Pyrroles
        • [CHEMONTID:0002554] Pyrrole carboxylic acids and derivatives

*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
NPO22974 Hosta plantaginea Species Asparagaceae Eukaryota n.a. n.a. n.a. PMID[17822295]
NPO33334 agelas sponges Species Agelasidae Eukaryota n.a. Indonesian n.a. PMID[20061160]
NPO10441 Euphorbia salicifolia Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[21612217]
NPO21846 Aster georgianus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22974 Hosta plantaginea Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18417 Streptomyces misakiensis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO10441 Euphorbia salicifolia Species Euphorbiaceae 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
NPT1864 Cell Line L5178Y Mus musculus GI = 83.4 % PMID[473754]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 70307.23 nM PMID[473755]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT572 Cell Line DMS-273 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 33884.42 nM PMID[473755]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT573 Cell Line M19-MEL Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 39445.73 nM PMID[473755]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT574 Cell Line XF498 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 42657.95 nM PMID[473755]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT731 Cell Line LXFL 529 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT576 Cell Line DMS-114 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT577 Cell Line RXF 631 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT578 Cell Line SNB-78 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT579 Cell Line DLD-1 Homo sapiens GI50 n.a. 81846.48 nM PMID[473755]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT732 Cell Line HOP-18 Homo sapiens GI50 n.a. 100000.0 nM PMID[473755]
NPT17 Organism Staphylococcus epidermidis Staphylococcus epidermidis MIC > 67000.0 nM PMID[473754]

☑ 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 NPC298288 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
0.932 High Similarity NPC109158
0.9133 High Similarity NPC142688
0.8377 Intermediate Similarity NPC52110
0.7669 Intermediate Similarity NPC27296
0.7556 Intermediate Similarity NPC77061
0.7547 Intermediate Similarity NPC260041
0.7546 Intermediate Similarity NPC474236
0.7439 Intermediate Similarity NPC33229
0.7355 Intermediate Similarity NPC150592
0.7337 Intermediate Similarity NPC474383
0.7179 Intermediate Similarity NPC20021
0.7178 Intermediate Similarity NPC302159
0.7125 Intermediate Similarity NPC85443
0.7097 Intermediate Similarity NPC71236
0.7091 Intermediate Similarity NPC13432
0.7076 Intermediate Similarity NPC476418
0.7076 Intermediate Similarity NPC306160
0.7059 Intermediate Similarity NPC473706
0.7052 Intermediate Similarity NPC470894
0.703 Intermediate Similarity NPC112741
0.6961 Remote Similarity NPC476423
0.6932 Remote Similarity NPC80528
0.6906 Remote Similarity NPC469814
0.6894 Remote Similarity NPC472288
0.6864 Remote Similarity NPC107287
0.6864 Remote Similarity NPC312860
0.6848 Remote Similarity NPC159630
0.6848 Remote Similarity NPC230085
0.6828 Remote Similarity NPC476413
0.6798 Remote Similarity NPC97106
0.6791 Remote Similarity NPC476414
0.678 Remote Similarity NPC226835
0.678 Remote Similarity NPC273532
0.6725 Remote Similarity NPC263455
0.6705 Remote Similarity NPC41717
0.6702 Remote Similarity NPC123395
0.6702 Remote Similarity NPC192306
0.6685 Remote Similarity NPC249614
0.6685 Remote Similarity NPC227489
0.6685 Remote Similarity NPC28096
0.6685 Remote Similarity NPC241025
0.6685 Remote Similarity NPC476421
0.6667 Remote Similarity NPC136441
0.6649 Remote Similarity NPC112489
0.6631 Remote Similarity NPC469489
0.6628 Remote Similarity NPC75135
0.6591 Remote Similarity NPC206148
0.6582 Remote Similarity NPC472286
0.6582 Remote Similarity NPC82053
0.6582 Remote Similarity NPC472287
0.6579 Remote Similarity NPC46811
0.6575 Remote Similarity NPC286195
0.6575 Remote Similarity NPC476419
0.6567 Remote Similarity NPC50562
0.6564 Remote Similarity NPC291517
0.6564 Remote Similarity NPC23215
0.6559 Remote Similarity NPC46022
0.6535 Remote Similarity NPC67658
0.6528 Remote Similarity NPC103361
0.6509 Remote Similarity NPC167400
0.6492 Remote Similarity NPC135950
0.6477 Remote Similarity NPC322644
0.6468 Remote Similarity NPC118940
0.6461 Remote Similarity NPC2414
0.6452 Remote Similarity NPC207851
0.6447 Remote Similarity NPC132539
0.6429 Remote Similarity NPC57398
0.6429 Remote Similarity NPC37268
0.6424 Remote Similarity NPC328029
0.6418 Remote Similarity NPC146418
0.6417 Remote Similarity NPC282103
0.6409 Remote Similarity NPC54214
0.6409 Remote Similarity NPC253810
0.6398 Remote Similarity NPC313823
0.6383 Remote Similarity NPC160381
0.6378 Remote Similarity NPC317010
0.6346 Remote Similarity NPC243633
0.6346 Remote Similarity NPC175150
0.6344 Remote Similarity NPC184932
0.6344 Remote Similarity NPC472861
0.6329 Remote Similarity NPC54066
0.6325 Remote Similarity NPC138596
0.6325 Remote Similarity NPC195704
0.6325 Remote Similarity NPC98156
0.6325 Remote Similarity NPC167200
0.6325 Remote Similarity NPC200397
0.6325 Remote Similarity NPC64661
0.6325 Remote Similarity NPC292434
0.6325 Remote Similarity NPC14448
0.6322 Remote Similarity NPC472260
0.6319 Remote Similarity NPC302647
0.6316 Remote Similarity NPC75544
0.6311 Remote Similarity NPC174576
0.6311 Remote Similarity NPC469717
0.6308 Remote Similarity NPC472284
0.6304 Remote Similarity NPC84347
0.63 Remote Similarity NPC321428
0.6293 Remote Similarity NPC36405
0.6289 Remote Similarity NPC109922
0.6287 Remote Similarity NPC114310
0.628 Remote Similarity NPC168209
0.6271 Remote Similarity NPC116573
0.6269 Remote Similarity NPC476525
0.6269 Remote Similarity NPC266249
0.6269 Remote Similarity NPC230403
0.625 Remote Similarity NPC138370
0.6243 Remote Similarity NPC295158
0.6237 Remote Similarity NPC276540
0.6237 Remote Similarity NPC233050
0.6207 Remote Similarity NPC123839
0.62 Remote Similarity NPC473239
0.6195 Remote Similarity NPC89508
0.6186 Remote Similarity NPC88315
0.6173 Remote Similarity NPC141454
0.617 Remote Similarity NPC275292
0.617 Remote Similarity NPC243381
0.6165 Remote Similarity NPC477979
0.6158 Remote Similarity NPC311282
0.6154 Remote Similarity NPC474696
0.6145 Remote Similarity NPC113812
0.614 Remote Similarity NPC58268
0.614 Remote Similarity NPC114033
0.614 Remote Similarity NPC129412
0.614 Remote Similarity NPC101130
0.6134 Remote Similarity NPC469961
0.6129 Remote Similarity NPC134586
0.6126 Remote Similarity NPC63571
0.6126 Remote Similarity NPC111566
0.6122 Remote Similarity NPC179701
0.6122 Remote Similarity NPC472116
0.6111 Remote Similarity NPC220408
0.6108 Remote Similarity NPC191310
0.6106 Remote Similarity NPC312645
0.6096 Remote Similarity NPC211997
0.6094 Remote Similarity NPC310633
0.6091 Remote Similarity NPC262898
0.6082 Remote Similarity NPC59839
0.6082 Remote Similarity NPC302717
0.6082 Remote Similarity NPC3698
0.6082 Remote Similarity NPC205604
0.6082 Remote Similarity NPC129753
0.6082 Remote Similarity NPC12831
0.6082 Remote Similarity NPC244087
0.6082 Remote Similarity NPC97230
0.6082 Remote Similarity NPC209281
0.6082 Remote Similarity NPC48171
0.6082 Remote Similarity NPC74928
0.6082 Remote Similarity NPC169308
0.6082 Remote Similarity NPC77582
0.6082 Remote Similarity NPC286529
0.607 Remote Similarity NPC165599
0.6065 Remote Similarity NPC315062
0.6057 Remote Similarity NPC100726
0.6053 Remote Similarity NPC159125
0.6053 Remote Similarity NPC143533
0.605 Remote Similarity NPC9635
0.6044 Remote Similarity NPC73687
0.6036 Remote Similarity NPC29702
0.6034 Remote Similarity NPC74357
0.6031 Remote Similarity NPC83111
0.6029 Remote Similarity NPC470280
0.6029 Remote Similarity NPC476524
0.6022 Remote Similarity NPC271927
0.6 Remote Similarity NPC192712
0.5982 Remote Similarity NPC316411
0.5962 Remote Similarity NPC39500
0.5959 Remote Similarity NPC194040
0.5952 Remote Similarity NPC223189
0.5944 Remote Similarity NPC169586
0.5939 Remote Similarity NPC19342
0.5917 Remote Similarity NPC267853
0.5904 Remote Similarity NPC186068
0.5902 Remote Similarity NPC244741
0.5899 Remote Similarity NPC473878
0.5897 Remote Similarity NPC209917
0.5892 Remote Similarity NPC470509
0.589 Remote Similarity NPC244897
0.5882 Remote Similarity NPC472259
0.5879 Remote Similarity NPC245916
0.5871 Remote Similarity NPC19696
0.5871 Remote Similarity NPC136957
0.5866 Remote Similarity NPC217021
0.5866 Remote Similarity NPC470679
0.5865 Remote Similarity NPC82370
0.5864 Remote Similarity NPC469896
0.5864 Remote Similarity NPC314281
0.5864 Remote Similarity NPC61011
0.5864 Remote Similarity NPC40530
0.5859 Remote Similarity NPC247735
0.5859 Remote Similarity NPC198673
0.5859 Remote Similarity NPC472295
0.5859 Remote Similarity NPC472210
0.5859 Remote Similarity NPC81802
0.5859 Remote Similarity NPC269886
0.5857 Remote Similarity NPC118228
0.5854 Remote Similarity NPC300156
0.5849 Remote Similarity NPC184408
0.5846 Remote Similarity NPC278434
0.5846 Remote Similarity NPC473946
0.5845 Remote Similarity NPC260434

  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 NPC298288 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
0.703 Intermediate Similarity NPD9271 Approved
0.6802 Remote Similarity NPD1630 Approved
0.6796 Remote Similarity NPD3178 Discontinued
0.6744 Remote Similarity NPD820 Phase 3
0.6686 Remote Similarity NPD1631 Approved
0.6667 Remote Similarity NPD107 Approved
0.6646 Remote Similarity NPD9076 Clinical (unspecified phase)
0.6569 Remote Similarity NPD1996 Discontinued
0.6509 Remote Similarity NPD9075 Approved
0.6509 Remote Similarity NPD9074 Approved
0.6444 Remote Similarity NPD1575 Approved
0.6444 Remote Similarity NPD1573 Approved
0.6429 Remote Similarity NPD1586 Approved
0.6407 Remote Similarity NPD569 Clinical (unspecified phase)
0.6402 Remote Similarity NPD5891 Approved
0.6392 Remote Similarity NPD772 Phase 3
0.6392 Remote Similarity NPD4987 Clinical (unspecified phase)
0.639 Remote Similarity NPD1623 Approved
0.6379 Remote Similarity NPD180 Clinical (unspecified phase)
0.6364 Remote Similarity NPD1096 Discontinued
0.6339 Remote Similarity NPD4736 Clinical (unspecified phase)
0.6324 Remote Similarity NPD1587 Approved
0.6305 Remote Similarity NPD5866 Approved
0.629 Remote Similarity NPD1643 Phase 3
0.6281 Remote Similarity NPD3947 Discontinued
0.6278 Remote Similarity NPD2915 Discontinued
0.6237 Remote Similarity NPD8304 Clinical (unspecified phase)
0.6188 Remote Similarity NPD1568 Clinical (unspecified phase)
0.617 Remote Similarity NPD1783 Clinical (unspecified phase)
0.615 Remote Similarity NPD2121 Clinical (unspecified phase)
0.6134 Remote Similarity NPD9243 Approved
0.6119 Remote Similarity NPD3360 Clinical (unspecified phase)
0.6094 Remote Similarity NPD6393 Clinical (unspecified phase)
0.6066 Remote Similarity NPD4174 Clinical (unspecified phase)
0.6054 Remote Similarity NPD485 Clinical (unspecified phase)
0.6043 Remote Similarity NPD5104 Approved
0.6041 Remote Similarity NPD2289 Phase 3
0.6041 Remote Similarity NPD2290 Phase 3
0.6032 Remote Similarity NPD6452 Discontinued
0.6029 Remote Similarity NPD1591 Approved
0.6023 Remote Similarity NPD4804 Approved
0.6019 Remote Similarity NPD7180 Phase 3
0.601 Remote Similarity NPD4948 Discontinued
0.6 Remote Similarity NPD4520 Approved
0.5972 Remote Similarity NPD6770 Approved
0.5965 Remote Similarity NPD203 Clinical (unspecified phase)
0.5963 Remote Similarity NPD6263 Clinical (unspecified phase)
0.5955 Remote Similarity NPD9596 Approved
0.5955 Remote Similarity NPD9595 Approved
0.5954 Remote Similarity NPD4805 Approved
0.5954 Remote Similarity NPD5020 Approved
0.595 Remote Similarity NPD2778 Approved
0.5942 Remote Similarity NPD5475 Discontinued
0.5926 Remote Similarity NPD3259 Approved
0.5917 Remote Similarity NPD7688 Phase 1
0.5914 Remote Similarity NPD565 Phase 2
0.5912 Remote Similarity NPD2582 Approved
0.5912 Remote Similarity NPD2581 Approved
0.5904 Remote Similarity NPD1031 Discontinued
0.5902 Remote Similarity NPD3371 Approved
0.5882 Remote Similarity NPD2130 Discontinued
0.5874 Remote Similarity NPD2510 Approved
0.5874 Remote Similarity NPD2509 Approved
0.5862 Remote Similarity NPD2779 Approved
0.5854 Remote Similarity NPD4862 Clinical (unspecified phase)
0.5851 Remote Similarity NPD750 Phase 2
0.585 Remote Similarity NPD5003 Discontinued
0.5849 Remote Similarity NPD5632 Approved
0.5829 Remote Similarity NPD2433 Clinical (unspecified phase)
0.5825 Remote Similarity NPD5075 Discontinued
0.5819 Remote Similarity NPD1801 Approved
0.5819 Remote Similarity NPD1802 Approved
0.5817 Remote Similarity NPD1166 Clinical (unspecified phase)
0.5817 Remote Similarity NPD4900 Clinical (unspecified phase)
0.5789 Remote Similarity NPD7470 Discontinued
0.5787 Remote Similarity NPD2564 Approved
0.5787 Remote Similarity NPD2565 Phase 2
0.5787 Remote Similarity NPD7547 Clinical (unspecified phase)
0.5782 Remote Similarity NPD1638 Discovery
0.5782 Remote Similarity NPD2547 Discontinued
0.5782 Remote Similarity NPD4667 Clinical (unspecified phase)
0.5782 Remote Similarity NPD3257 Approved
0.578 Remote Similarity NPD7994 Phase 2
0.5778 Remote Similarity NPD510 Phase 1
0.5756 Remote Similarity NPD2670 Approved
0.5755 Remote Similarity NPD3393 Approved
0.5755 Remote Similarity NPD3389 Approved
0.5755 Remote Similarity NPD3394 Approved
0.5753 Remote Similarity NPD1580 Clinical (unspecified phase)
0.575 Remote Similarity NPD5975 Clinical (unspecified phase)
0.5744 Remote Similarity NPD1308 Approved
0.5741 Remote Similarity NPD6160 Clinical (unspecified phase)
0.5741 Remote Similarity NPD6209 Approved
0.5735 Remote Similarity NPD3945 Discontinued
0.5733 Remote Similarity NPD2921 Clinical (unspecified phase)
0.5729 Remote Similarity NPD4376 Phase 3
0.5728 Remote Similarity NPD5901 Discontinued
0.5721 Remote Similarity NPD5850 Phase 3
0.5714 Remote Similarity NPD3315 Phase 3
0.5714 Remote Similarity NPD5809 Phase 3
0.5714 Remote Similarity NPD4417 Approved
0.5708 Remote Similarity NPD3757 Clinical (unspecified phase)
0.5708 Remote Similarity NPD7268 Clinical (unspecified phase)
0.5701 Remote Similarity NPD1867 Approved
0.57 Remote Similarity NPD4529 Approved
0.57 Remote Similarity NPD4528 Approved
0.57 Remote Similarity NPD4526 Approved
0.57 Remote Similarity NPD2715 Clinical (unspecified phase)
0.5698 Remote Similarity NPD272 Approved
0.5694 Remote Similarity NPD4506 Discontinued
0.5688 Remote Similarity NPD6247 Clinical (unspecified phase)
0.5682 Remote Similarity NPD1579 Discontinued
0.5681 Remote Similarity NPD2401 Approved
0.5681 Remote Similarity NPD2402 Approved
0.5674 Remote Similarity NPD3258 Approved
0.5674 Remote Similarity NPD6974 Phase 3
0.5674 Remote Similarity NPD2785 Clinical (unspecified phase)
0.5672 Remote Similarity NPD4418 Discontinued
0.5672 Remote Similarity NPD4602 Approved
0.5667 Remote Similarity NPD3392 Approved
0.5665 Remote Similarity NPD7459 Phase 2
0.5659 Remote Similarity NPD5017 Discontinued
0.5657 Remote Similarity NPD4334 Discontinued
0.5656 Remote Similarity NPD4952 Phase 3
0.5656 Remote Similarity NPD1659 Phase 1
0.5655 Remote Similarity NPD9284 Approved
0.5654 Remote Similarity NPD158 Discontinued
0.5652 Remote Similarity NPD7396 Approved
0.5652 Remote Similarity NPD4326 Phase 2
0.5652 Remote Similarity NPD2721 Clinical (unspecified phase)
0.5652 Remote Similarity NPD3946 Clinical (unspecified phase)
0.565 Remote Similarity NPD6665 Discontinued
0.565 Remote Similarity NPD981 Phase 2
0.5646 Remote Similarity NPD1367 Phase 2
0.5634 Remote Similarity NPD7538 Clinical (unspecified phase)
0.5633 Remote Similarity NPD5483 Clinical (unspecified phase)
0.5631 Remote Similarity NPD1467 Approved
0.5631 Remote Similarity NPD1466 Phase 3
0.5625 Remote Similarity NPD4901 Clinical (unspecified phase)
0.5625 Remote Similarity NPD749 Clinical (unspecified phase)
0.5625 Remote Similarity NPD7001 Phase 3
0.5619 Remote Similarity NPD9510 Approved
0.5619 Remote Similarity NPD5583 Clinical (unspecified phase)
0.5612 Remote Similarity NPD721 Approved
0.5608 Remote Similarity NPD2844 Phase 3
0.5606 Remote Similarity NPD1034 Phase 3
0.5606 Remote Similarity NPD1033 Clinical (unspecified phase)
0.5605 Remote Similarity NPD7031 Phase 1
0.5604 Remote Similarity NPD9343 Clinical (unspecified phase)
0.5604 Remote Similarity NPD6176 Phase 1
0.5602 Remote Similarity NPD2076 Approved
0.5602 Remote Similarity NPD2077 Approved
0.5602 Remote Similarity NPD4524 Discontinued
0.56 Remote Similarity NPD7853 Phase 2
0.56 Remote Similarity NPD2323 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