Structure

Physi-Chem Properties

Molecular Weight:  137.05
Volume:  139.103
LogP:  -0.086
LogD:  -1.07
LogS:  0.63
# Rotatable Bonds:  2
TPSA:  50.19
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.653
Synthetic Accessibility Score:  1.7
Fsp3:  0.143
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:  -5.201
MDCK Permeability:  3.5056789783993736e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.013
20% Bioavailability (F20%):  0.009
30% Bioavailability (F30%):  0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.159
Plasma Protein Binding (PPB):  25.198089599609375%
Volume Distribution (VD):  0.414
Pgp-substrate:  73.51781463623047%

ADMET: Metabolism

CYP1A2-inhibitor:  0.021
CYP1A2-substrate:  0.393
CYP2C19-inhibitor:  0.028
CYP2C19-substrate:  0.13
CYP2C9-inhibitor:  0.015
CYP2C9-substrate:  0.941
CYP2D6-inhibitor:  0.005
CYP2D6-substrate:  0.226
CYP3A4-inhibitor:  0.018
CYP3A4-substrate:  0.182

ADMET: Excretion

Clearance (CL):  7.084
Half-life (T1/2):  0.831

ADMET: Toxicity

hERG Blockers:  0.026
Human Hepatotoxicity (H-HT):  0.092
Drug-inuced Liver Injury (DILI):  0.958
AMES Toxicity:  0.019
Rat Oral Acute Toxicity:  0.171
Maximum Recommended Daily Dose:  0.018
Skin Sensitization:  0.798
Carcinogencity:  0.335
Eye Corrosion:  0.873
Eye Irritation:  0.984
Respiratory Toxicity:  0.053

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Structure MOL file  
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Similar NPs/Drugs  

  Natural Product: NPC322488

Natural Product ID:  NPC322488
Common Name*:   2-Pyridin-3-Ylacetic Acid
IUPAC Name:   2-pyridin-3-ylacetic acid
Synonyms:  
Standard InCHIKey:  WGNUNYPERJMVRM-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C7H7NO2/c9-7(10)4-6-2-1-3-8-5-6/h1-3,5H,4H2,(H,9,10)
SMILES:  OC(=O)Cc1cccnc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1741437
PubChem CID:   108
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000089] Pyridines 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

☑ 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
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[510291]
NPT2 Others Unspecified Ki = 301995.17 nM PMID[510290]
NPT22586 SINGLE PROTEIN Nicotinate phosphoribosyltransferase Homo sapiens Ki = 1.28 nM PMID[510292]

☑ 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 NPC322488 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
0.8815 High Similarity NPC114310
0.8507 High Similarity NPC315320
0.838 Intermediate Similarity NPC167400
0.8333 Intermediate Similarity NPC29702
0.8069 Intermediate Similarity NPC302159
0.8056 Intermediate Similarity NPC159630
0.8056 Intermediate Similarity NPC230085
0.8043 Intermediate Similarity NPC324611
0.8039 Intermediate Similarity NPC41717
0.8015 Intermediate Similarity NPC471311
0.8015 Intermediate Similarity NPC306397
0.8015 Intermediate Similarity NPC471313
0.8015 Intermediate Similarity NPC165370
0.8015 Intermediate Similarity NPC212125
0.7953 Intermediate Similarity NPC27802
0.7943 Intermediate Similarity NPC328029
0.7919 Intermediate Similarity NPC312860
0.7891 Intermediate Similarity NPC112741
0.7885 Intermediate Similarity NPC273532
0.7867 Intermediate Similarity NPC263455
0.7857 Intermediate Similarity NPC76540
0.7829 Intermediate Similarity NPC113812
0.7826 Intermediate Similarity NPC471589
0.7762 Intermediate Similarity NPC65408
0.7688 Intermediate Similarity NPC111275
0.7682 Intermediate Similarity NPC107287
0.7606 Intermediate Similarity NPC330326
0.7557 Intermediate Similarity NPC235843
0.7537 Intermediate Similarity NPC240136
0.7537 Intermediate Similarity NPC297486
0.7537 Intermediate Similarity NPC471402
0.752 Intermediate Similarity NPC83987
0.7517 Intermediate Similarity NPC471312
0.75 Intermediate Similarity NPC477976
0.7482 Intermediate Similarity NPC151489
0.7481 Intermediate Similarity NPC143603
0.7481 Intermediate Similarity NPC91958
0.7464 Intermediate Similarity NPC290094
0.7455 Intermediate Similarity NPC207851
0.745 Intermediate Similarity NPC471323
0.7447 Intermediate Similarity NPC313823
0.7421 Intermediate Similarity NPC78020
0.7413 Intermediate Similarity NPC256893
0.7394 Intermediate Similarity NPC322043
0.7378 Intermediate Similarity NPC471997
0.7329 Intermediate Similarity NPC253810
0.7329 Intermediate Similarity NPC249614
0.7321 Intermediate Similarity NPC278434
0.7319 Intermediate Similarity NPC48564
0.7319 Intermediate Similarity NPC182570
0.7319 Intermediate Similarity NPC265605
0.7317 Intermediate Similarity NPC164340
0.7317 Intermediate Similarity NPC55772
0.7308 Intermediate Similarity NPC231655
0.7305 Intermediate Similarity NPC202957
0.7305 Intermediate Similarity NPC169625
0.7303 Intermediate Similarity NPC105811
0.7273 Intermediate Similarity NPC70406
0.7273 Intermediate Similarity NPC317010
0.7262 Intermediate Similarity NPC62749
0.7239 Intermediate Similarity NPC110500
0.7239 Intermediate Similarity NPC203468
0.7239 Intermediate Similarity NPC149155
0.7229 Intermediate Similarity NPC71037
0.7219 Intermediate Similarity NPC325775
0.7214 Intermediate Similarity NPC46358
0.7208 Intermediate Similarity NPC313889
0.7203 Intermediate Similarity NPC89490
0.7197 Intermediate Similarity NPC213914
0.7195 Intermediate Similarity NPC476419
0.7195 Intermediate Similarity NPC267885
0.719 Intermediate Similarity NPC477974
0.7188 Intermediate Similarity NPC477975
0.7186 Intermediate Similarity NPC327373
0.7186 Intermediate Similarity NPC325093
0.7181 Intermediate Similarity NPC85443
0.7179 Intermediate Similarity NPC209362
0.7172 Intermediate Similarity NPC471322
0.7172 Intermediate Similarity NPC174421
0.7171 Intermediate Similarity NPC467188
0.7168 Intermediate Similarity NPC146724
0.7163 Intermediate Similarity NPC27740
0.7163 Intermediate Similarity NPC476322
0.716 Intermediate Similarity NPC315555
0.7153 Intermediate Similarity NPC329896
0.7153 Intermediate Similarity NPC475090
0.7153 Intermediate Similarity NPC475105
0.7134 Intermediate Similarity NPC469938
0.7134 Intermediate Similarity NPC139763
0.7126 Intermediate Similarity NPC109922
0.7115 Intermediate Similarity NPC251391
0.7113 Intermediate Similarity NPC166424
0.7113 Intermediate Similarity NPC146373
0.7113 Intermediate Similarity NPC245244
0.7108 Intermediate Similarity NPC213468
0.7108 Intermediate Similarity NPC248041
0.7108 Intermediate Similarity NPC283219
0.7108 Intermediate Similarity NPC126709
0.7107 Intermediate Similarity NPC322644
0.7101 Intermediate Similarity NPC282103
0.7101 Intermediate Similarity NPC318020
0.7086 Intermediate Similarity NPC90229
0.707 Intermediate Similarity NPC229055
0.7035 Intermediate Similarity NPC83111
0.7025 Intermediate Similarity NPC74357
0.702 Intermediate Similarity NPC318935
0.7019 Intermediate Similarity NPC473057
0.7018 Intermediate Similarity NPC328798
0.7014 Intermediate Similarity NPC278451
0.7013 Intermediate Similarity NPC220523
0.7006 Intermediate Similarity NPC248462
0.6994 Remote Similarity NPC114974
0.6981 Remote Similarity NPC138018
0.6977 Remote Similarity NPC182814
0.6977 Remote Similarity NPC44354
0.6975 Remote Similarity NPC471178
0.6971 Remote Similarity NPC20593
0.6962 Remote Similarity NPC33229
0.6957 Remote Similarity NPC59779
0.6957 Remote Similarity NPC124542
0.6957 Remote Similarity NPC71079
0.6957 Remote Similarity NPC471177
0.6949 Remote Similarity NPC474916
0.6946 Remote Similarity NPC64436
0.6937 Remote Similarity NPC80681
0.6937 Remote Similarity NPC230869
0.6936 Remote Similarity NPC154339
0.6928 Remote Similarity NPC303225
0.6923 Remote Similarity NPC123906
0.6918 Remote Similarity NPC476131
0.6914 Remote Similarity NPC474217
0.6914 Remote Similarity NPC265100
0.6914 Remote Similarity NPC97367
0.6909 Remote Similarity NPC302647
0.6901 Remote Similarity NPC329825
0.6897 Remote Similarity NPC127647
0.6897 Remote Similarity NPC138370
0.6894 Remote Similarity NPC131718
0.6882 Remote Similarity NPC469358
0.6875 Remote Similarity NPC135950
0.6875 Remote Similarity NPC129721
0.6872 Remote Similarity NPC213308
0.6871 Remote Similarity NPC85918
0.6871 Remote Similarity NPC69914
0.6871 Remote Similarity NPC282398
0.6861 Remote Similarity NPC473901
0.686 Remote Similarity NPC118084
0.686 Remote Similarity NPC235684
0.6852 Remote Similarity NPC242116
0.6845 Remote Similarity NPC14113
0.6845 Remote Similarity NPC84827
0.6845 Remote Similarity NPC145885
0.6845 Remote Similarity NPC219848
0.6845 Remote Similarity NPC157583
0.6835 Remote Similarity NPC472260
0.6831 Remote Similarity NPC193238
0.6829 Remote Similarity NPC127730
0.6829 Remote Similarity NPC108469
0.6829 Remote Similarity NPC278366
0.6824 Remote Similarity NPC101165
0.6818 Remote Similarity NPC267343
0.6818 Remote Similarity NPC88315
0.681 Remote Similarity NPC102423
0.6805 Remote Similarity NPC256268
0.6802 Remote Similarity NPC311282
0.6802 Remote Similarity NPC295158
0.6796 Remote Similarity NPC57398
0.6792 Remote Similarity NPC73952
0.6792 Remote Similarity NPC259644
0.6792 Remote Similarity NPC25008
0.6792 Remote Similarity NPC469786
0.6792 Remote Similarity NPC469760
0.6792 Remote Similarity NPC469763
0.6792 Remote Similarity NPC469765
0.6788 Remote Similarity NPC70949
0.6782 Remote Similarity NPC321708
0.6778 Remote Similarity NPC470279
0.6772 Remote Similarity NPC473878
0.677 Remote Similarity NPC469762
0.6765 Remote Similarity NPC52831
0.6765 Remote Similarity NPC325705
0.6765 Remote Similarity NPC61011
0.6763 Remote Similarity NPC84268
0.676 Remote Similarity NPC317672
0.675 Remote Similarity NPC211572
0.675 Remote Similarity NPC75540
0.675 Remote Similarity NPC63562
0.675 Remote Similarity NPC80597
0.675 Remote Similarity NPC212376
0.675 Remote Similarity NPC70922
0.6747 Remote Similarity NPC314940
0.6747 Remote Similarity NPC473764
0.6744 Remote Similarity NPC46895
0.6743 Remote Similarity NPC469489
0.674 Remote Similarity NPC328559
0.6731 Remote Similarity NPC314372
0.673 Remote Similarity NPC217021
0.673 Remote Similarity NPC470679
0.6727 Remote Similarity NPC98187
0.6727 Remote Similarity NPC56233

  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 NPC322488 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
0.8889 High Similarity NPD2896 Discontinued
0.875 High Similarity NPD203 Clinical (unspecified phase)
0.8507 High Similarity NPD9207 Approved
0.8507 High Similarity NPD9206 Approved
0.838 Intermediate Similarity NPD9075 Approved
0.838 Intermediate Similarity NPD9074 Approved
0.8227 Intermediate Similarity NPD107 Approved
0.8182 Intermediate Similarity NPD751 Clinical (unspecified phase)
0.8015 Intermediate Similarity NPD9284 Approved
0.8015 Intermediate Similarity NPD9080 Approved
0.7986 Intermediate Similarity NPD1627 Clinical (unspecified phase)
0.7908 Intermediate Similarity NPD5088 Discontinued
0.7895 Intermediate Similarity NPD2511 Approved
0.7891 Intermediate Similarity NPD9271 Approved
0.7867 Intermediate Similarity NPD2809 Approved
0.7793 Intermediate Similarity NPD4805 Approved
0.7762 Intermediate Similarity NPD201 Phase 2
0.7762 Intermediate Similarity NPD200 Phase 2
0.7733 Intermediate Similarity NPD510 Phase 1
0.7655 Intermediate Similarity NPD4804 Approved
0.7639 Intermediate Similarity NPD9506 Approved
0.7606 Intermediate Similarity NPD9100 Approved
0.7533 Intermediate Similarity NPD4703 Approved
0.7533 Intermediate Similarity NPD4702 Approved
0.7532 Intermediate Similarity NPD820 Phase 3
0.75 Intermediate Similarity NPD5965 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD272 Approved
0.75 Intermediate Similarity NPD3717 Discontinued
0.7483 Intermediate Similarity NPD1649 Discontinued
0.7468 Intermediate Similarity NPD5611 Phase 2
0.7468 Intermediate Similarity NPD276 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD5322 Clinical (unspecified phase)
0.7451 Intermediate Similarity NPD180 Clinical (unspecified phase)
0.745 Intermediate Similarity NPD3813 Approved
0.7447 Intermediate Similarity NPD1095 Clinical (unspecified phase)
0.7417 Intermediate Similarity NPD1270 Approved
0.7403 Intermediate Similarity NPD5257 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD2061 Approved
0.7388 Intermediate Similarity NPD269 Clinical (unspecified phase)
0.7351 Intermediate Similarity NPD6148 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD1352 Discontinued
0.7319 Intermediate Similarity NPD271 Approved
0.7319 Intermediate Similarity NPD268 Approved
0.7319 Intermediate Similarity NPD270 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD9098 Phase 3
0.7308 Intermediate Similarity NPD9099 Clinical (unspecified phase)
0.7284 Intermediate Similarity NPD750 Phase 2
0.7273 Intermediate Similarity NPD3262 Approved
0.7267 Intermediate Similarity NPD1575 Approved
0.7267 Intermediate Similarity NPD1573 Approved
0.725 Intermediate Similarity NPD4174 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD9599 Approved
0.7239 Intermediate Similarity NPD482 Approved
0.7229 Intermediate Similarity NPD1783 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD485 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD8304 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD749 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD1661 Suspended
0.7186 Intermediate Similarity NPD5213 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD5728 Clinical (unspecified phase)
0.7163 Intermediate Similarity NPD9357 Approved
0.7152 Intermediate Similarity NPD5255 Approved
0.7151 Intermediate Similarity NPD6665 Discontinued
0.7143 Intermediate Similarity NPD2091 Phase 2
0.7143 Intermediate Similarity NPD6178 Phase 3
0.7143 Intermediate Similarity NPD2096 Phase 2
0.7143 Intermediate Similarity NPD1096 Discontinued
0.7125 Intermediate Similarity NPD6635 Approved
0.7125 Intermediate Similarity NPD1631 Approved
0.7114 Intermediate Similarity NPD9076 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD206 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD2095 Phase 2
0.7083 Intermediate Similarity NPD2092 Phase 2
0.7083 Intermediate Similarity NPD2094 Phase 2
0.7069 Intermediate Similarity NPD5975 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD9583 Approved
0.7059 Intermediate Similarity NPD175 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD9726 Discontinued
0.7051 Intermediate Similarity NPD9706 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD4824 Approved
0.7037 Intermediate Similarity NPD4823 Approved
0.7025 Intermediate Similarity NPD6026 Approved
0.7024 Intermediate Similarity NPD3178 Discontinued
0.7014 Intermediate Similarity NPD2118 Approved
0.7014 Intermediate Similarity NPD992 Clinical (unspecified phase)
0.7014 Intermediate Similarity NPD1598 Discontinued
0.7014 Intermediate Similarity NPD2119 Approved
0.7014 Intermediate Similarity NPD991 Phase 2
0.7011 Intermediate Similarity NPD4529 Approved
0.7011 Intermediate Similarity NPD4528 Approved
0.7011 Intermediate Similarity NPD4526 Approved
0.7 Intermediate Similarity NPD6454 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD1380 Discovery
0.6994 Remote Similarity NPD2336 Approved
0.6982 Remote Similarity NPD6194 Discontinued
0.6975 Remote Similarity NPD1568 Clinical (unspecified phase)
0.6937 Remote Similarity NPD1630 Approved
0.6932 Remote Similarity NPD7818 Clinical (unspecified phase)
0.6914 Remote Similarity NPD1173 Approved
0.6901 Remote Similarity NPD4336 Clinical (unspecified phase)
0.6899 Remote Similarity NPD2012 Clinical (unspecified phase)
0.689 Remote Similarity NPD5862 Discovery
0.6884 Remote Similarity NPD60 Approved
0.6882 Remote Similarity NPD5092 Clinical (unspecified phase)
0.6879 Remote Similarity NPD7233 Approved
0.6879 Remote Similarity NPD7234 Approved
0.6875 Remote Similarity NPD5541 Clinical (unspecified phase)
0.6871 Remote Similarity NPD926 Approved
0.6871 Remote Similarity NPD925 Approved
0.6871 Remote Similarity NPD3475 Approved
0.6871 Remote Similarity NPD3476 Approved
0.6867 Remote Similarity NPD1037 Clinical (unspecified phase)
0.6863 Remote Similarity NPD1383 Phase 3
0.6863 Remote Similarity NPD5020 Approved
0.6863 Remote Similarity NPD1382 Phase 2
0.6857 Remote Similarity NPD5505 Discontinued
0.6855 Remote Similarity NPD5358 Clinical (unspecified phase)
0.6852 Remote Similarity NPD5400 Approved
0.6852 Remote Similarity NPD8026 Phase 1
0.6836 Remote Similarity NPD2307 Discontinued
0.6832 Remote Similarity NPD704 Clinical (unspecified phase)
0.6829 Remote Similarity NPD424 Approved
0.6829 Remote Similarity NPD425 Approved
0.6826 Remote Similarity NPD4883 Approved
0.6818 Remote Similarity NPD1427 Clinical (unspecified phase)
0.6816 Remote Similarity NPD6999 Discontinued
0.6816 Remote Similarity NPD7000 Clinical (unspecified phase)
0.6805 Remote Similarity NPD5398 Clinical (unspecified phase)
0.6795 Remote Similarity NPD7469 Discontinued
0.6788 Remote Similarity NPD1292 Clinical (unspecified phase)
0.6788 Remote Similarity NPD6872 Clinical (unspecified phase)
0.6786 Remote Similarity NPD8840 Approved
0.6786 Remote Similarity NPD9392 Approved
0.6786 Remote Similarity NPD9396 Approved
0.6783 Remote Similarity NPD748 Clinical (unspecified phase)
0.678 Remote Similarity NPD4427 Phase 2
0.6779 Remote Similarity NPD1995 Approved
0.6779 Remote Similarity NPD1994 Approved
0.6779 Remote Similarity NPD1993 Approved
0.677 Remote Similarity NPD2582 Approved
0.677 Remote Similarity NPD2581 Approved
0.6765 Remote Similarity NPD9510 Approved
0.6761 Remote Similarity NPD4376 Phase 3
0.6757 Remote Similarity NPD715 Phase 3
0.6755 Remote Similarity NPD792 Discontinued
0.6733 Remote Similarity NPD4028 Approved
0.6733 Remote Similarity NPD3942 Approved
0.6733 Remote Similarity NPD4029 Approved
0.6733 Remote Similarity NPD4030 Approved
0.6733 Remote Similarity NPD3944 Approved
0.6732 Remote Similarity NPD569 Clinical (unspecified phase)
0.6727 Remote Similarity NPD6446 Discontinued
0.6727 Remote Similarity NPD5636 Discontinued
0.6726 Remote Similarity NPD158 Discontinued
0.6721 Remote Similarity NPD6987 Phase 1
0.6709 Remote Similarity NPD1183 Approved
0.6707 Remote Similarity NPD5934 Clinical (unspecified phase)
0.6707 Remote Similarity NPD3583 Phase 2
0.6706 Remote Similarity NPD1587 Approved
0.6705 Remote Similarity NPD4949 Discontinued
0.6689 Remote Similarity NPD2142 Approved
0.6689 Remote Similarity NPD2140 Approved
0.6689 Remote Similarity NPD2141 Approved
0.6687 Remote Similarity NPD112 Approved
0.6687 Remote Similarity NPD2781 Approved
0.6687 Remote Similarity NPD9705 Discontinued
0.6687 Remote Similarity NPD1343 Approved
0.6686 Remote Similarity NPD5100 Phase 3
0.6685 Remote Similarity NPD484 Approved
0.6685 Remote Similarity NPD2305 Discontinued
0.6667 Remote Similarity NPD2782 Approved
0.6667 Remote Similarity NPD2780 Approved
0.6667 Remote Similarity NPD2121 Clinical (unspecified phase)
0.6667 Remote Similarity NPD9383 Approved
0.6667 Remote Similarity NPD9382 Approved
0.6648 Remote Similarity NPD4081 Clinical (unspecified phase)
0.6648 Remote Similarity NPD7061 Clinical (unspecified phase)
0.6647 Remote Similarity NPD721 Approved
0.6647 Remote Similarity NPD2620 Phase 2
0.6647 Remote Similarity NPD5751 Clinical (unspecified phase)
0.6647 Remote Similarity NPD2619 Clinical (unspecified phase)
0.6646 Remote Similarity NPD2089 Clinical (unspecified phase)
0.6646 Remote Similarity NPD4239 Clinical (unspecified phase)
0.663 Remote Similarity NPD6137 Clinical (unspecified phase)
0.663 Remote Similarity NPD5426 Phase 3
0.6628 Remote Similarity NPD4383 Clinical (unspecified phase)
0.6627 Remote Similarity NPD9690 Approved
0.6627 Remote Similarity NPD5065 Approved
0.6622 Remote Similarity NPD1031 Discontinued
0.6614 Remote Similarity NPD2847 Phase 2
0.6609 Remote Similarity NPD4889 Approved
0.6608 Remote Similarity NPD1620 Clinical (unspecified phase)
0.66 Remote Similarity NPD803 Phase 1
0.6596 Remote Similarity NPD3779 Clinical (unspecified phase)
0.6594 Remote Similarity NPD181 Approved
0.6593 Remote Similarity NPD4396 Clinical (unspecified phase)
0.6593 Remote Similarity NPD5043 Discontinued
0.659 Remote Similarity NPD4345 Clinical (unspecified phase)
0.6588 Remote Similarity NPD5471 Phase 3
0.6588 Remote Similarity NPD3238 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