Structure

Physi-Chem Properties

Molecular Weight:  137.05
Volume:  139.103
LogP:  -1.936
LogD:  -2.155
LogS:  0.568
# Rotatable Bonds:  1
TPSA:  44.01
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.46
Synthetic Accessibility Score:  3.449
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:  -5.222
MDCK Permeability:  3.299874879303388e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.996
Human Intestinal Absorption (HIA):  0.947
20% Bioavailability (F20%):  0.91
30% Bioavailability (F30%):  0.965

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.524
Plasma Protein Binding (PPB):  8.958044052124023%
Volume Distribution (VD):  0.688
Pgp-substrate:  95.79496765136719%

ADMET: Metabolism

CYP1A2-inhibitor:  0.026
CYP1A2-substrate:  0.72
CYP2C19-inhibitor:  0.016
CYP2C19-substrate:  0.114
CYP2C9-inhibitor:  0.005
CYP2C9-substrate:  0.05
CYP2D6-inhibitor:  0.017
CYP2D6-substrate:  0.078
CYP3A4-inhibitor:  0.004
CYP3A4-substrate:  0.079

ADMET: Excretion

Clearance (CL):  3.669
Half-life (T1/2):  0.872

ADMET: Toxicity

hERG Blockers:  0.015
Human Hepatotoxicity (H-HT):  0.759
Drug-inuced Liver Injury (DILI):  0.087
AMES Toxicity:  0.006
Rat Oral Acute Toxicity:  0.197
Maximum Recommended Daily Dose:  0.012
Skin Sensitization:  0.199
Carcinogencity:  0.606
Eye Corrosion:  0.118
Eye Irritation:  0.993
Respiratory Toxicity:  0.102

Download Data

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

  Natural Product: NPC230085

Natural Product ID:  NPC230085
Common Name*:   Trigonelline
IUPAC Name:   1-methylpyridin-1-ium-3-carboxylate
Synonyms:   1-Methyl-Nicotinic Acid Anion(Trigonelline)
Standard InCHIKey:  WWNNZCOKKKDOPX-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C7H7NO2/c1-8-4-2-3-6(5-8)7(9)10/h2-5H,1H3
SMILES:  C[n+]1cccc(c1)C(=O)[O-]
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL350675
PubChem CID:   5570
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000279] Alkaloids 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
NPO11043 NPC230085 Raw Fruit 10.45 0.6 20.3 mg/100g Database [DUKE]
NPO11043 NPC230085 Raw Leaf 4.85 0.9 8.8 mg/100g Database [DUKE]
NPO11043 NPC230085 Raw Root 3.8 0.1 7.5 mg/100g Database [DUKE]
NPO31303 NPC230085 Raw Root 4.15 1.4 6.9 mg/100g Database [DUKE]
NPO9788 NPC230085 Other Seed 800 300 1300 mg/100g Database [DUKE]
NPO22132 NPC230085 Other Seed 0.89 0.89 0.89 mg/100g Database [DUKE]
NPO8210 NPC230085 Other (raw) Seed 130 130 130 mg/100g Database [DUKE]
NPO23230 NPC230085 Raw Seed 1.3 1.3 1.3 mg/100g Database [DUKE]
NPO16501 NPC230085 Raw Seed 0.06 0.06 0.06 mg/100g Database [DUKE]
NPO11043 NPC230085 Raw Seed 17.75 12.8 22.7 mg/100g Database [DUKE]
NPO15810 NPC230085 Raw Seed 0.4 0.4 0.4 mg/100g Database [DUKE]
NPO13450 NPC230085 Raw Seed 0.4 0.2 0.6 mg/100g Database [DUKE]
NPO11043 NPC230085 Raw Shoot 5.5 5.5 5.5 mg/100g Database [DUKE]
NPO11043 NPC230085 Raw Sprout Seedling 9.1 9.1 9.1 mg/100g Database [DUKE]
NPO11043 NPC230085 Raw Stem 1.25 0.1 2.4 mg/100g Database [DUKE]

☑ 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
NPT55 Individual Protein Putative fructose-1,6-bisphosphate aldolase Giardia intestinalis Potency = 35397.3 nM PMID[459862]
NPT56 Individual Protein Beta-lactamase AmpC Escherichia coli K-12 Potency = 5623.4 nM PMID[459863]
NPT45 Individual Protein Ubiquitin carboxyl-terminal hydrolase 2 Homo sapiens Potency = 12589.3 nM PMID[459862]
NPT135 Individual Protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 89125.1 nM PMID[459863]
NPT136 Cell Line SK-N-SH Homo sapiens Activity = 15.0 % PMID[459867]
NPT32 Organism Mus musculus Mus musculus Concentration = 2.2 ug (g of wet tissue)-1 PMID[459861]
NPT32 Organism Mus musculus Mus musculus Concentration = 2.1 ug (g of wet tissue)-1 PMID[459861]
NPT32 Organism Mus musculus Mus musculus Concentration = 2.4 ug (g of wet tissue)-1 PMID[459861]
NPT32 Organism Mus musculus Mus musculus Concentration = 1.9 ug (g of wet tissue)-1 PMID[459861]
NPT32 Organism Mus musculus Mus musculus Concentration = 0.9 ug (g of wet tissue)-1 PMID[459861]
NPT861 Individual Protein Isocitrate dehydrogenase [NADP] cytoplasmic Homo sapiens Potency n.a. 3662.6 nM PMID[459863]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 111.59 % PMID[459864]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 98.34 % PMID[459864]
NPT2 Others Unspecified Potency n.a. 12589.3 nM PMID[459862]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM PMID[459866]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM PMID[459866]
NPT23748 PROTEIN COMPLEX GABA-A receptor alpha-1/beta-1 Bos taurus Ki = 13.0 nM PMID[459867]
NPT914 Individual Protein Acetylcholinesterase Bos taurus IC50 = 233000.0 nM PMID[459867]
NPT2 Others Unspecified Activity = 136.0 % PMID[459867]

☑ 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 NPC230085 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC159630
0.95 High Similarity NPC112741
0.9496 High Similarity NPC167400
0.9371 High Similarity NPC312860
0.9306 High Similarity NPC263455
0.9236 High Similarity NPC107287
0.8859 High Similarity NPC113812
0.8592 High Similarity NPC114310
0.8481 Intermediate Similarity NPC476419
0.8417 Intermediate Similarity NPC471589
0.8408 Intermediate Similarity NPC273532
0.8323 Intermediate Similarity NPC317010
0.8291 Intermediate Similarity NPC249614
0.8264 Intermediate Similarity NPC29702
0.8085 Intermediate Similarity NPC212125
0.8056 Intermediate Similarity NPC322488
0.7958 Intermediate Similarity NPC306397
0.7958 Intermediate Similarity NPC165370
0.7895 Intermediate Similarity NPC302159
0.7875 Intermediate Similarity NPC41717
0.7818 Intermediate Similarity NPC164340
0.7613 Intermediate Similarity NPC105811
0.7597 Intermediate Similarity NPC467188
0.7558 Intermediate Similarity NPC44354
0.7532 Intermediate Similarity NPC471323
0.7529 Intermediate Similarity NPC207851
0.7485 Intermediate Similarity NPC282103
0.7468 Intermediate Similarity NPC70406
0.7458 Intermediate Similarity NPC329024
0.745 Intermediate Similarity NPC330326
0.7443 Intermediate Similarity NPC135950
0.7416 Intermediate Similarity NPC324245
0.7416 Intermediate Similarity NPC320748
0.7407 Intermediate Similarity NPC76540
0.7405 Intermediate Similarity NPC313889
0.7375 Intermediate Similarity NPC33229
0.7375 Intermediate Similarity NPC229055
0.7375 Intermediate Similarity NPC209362
0.7374 Intermediate Similarity NPC103361
0.7333 Intermediate Similarity NPC79223
0.7329 Intermediate Similarity NPC74357
0.7318 Intermediate Similarity NPC474916
0.7318 Intermediate Similarity NPC317672
0.7318 Intermediate Similarity NPC59033
0.7312 Intermediate Similarity NPC251391
0.7303 Intermediate Similarity NPC328029
0.7299 Intermediate Similarity NPC278434
0.7297 Intermediate Similarity NPC313823
0.7293 Intermediate Similarity NPC328559
0.7293 Intermediate Similarity NPC32451
0.7273 Intermediate Similarity NPC138370
0.7268 Intermediate Similarity NPC289086
0.725 Intermediate Similarity NPC472260
0.7248 Intermediate Similarity NPC71236
0.7246 Intermediate Similarity NPC27802
0.7216 Intermediate Similarity NPC469489
0.7211 Intermediate Similarity NPC151489
0.7207 Intermediate Similarity NPC109922
0.7182 Intermediate Similarity NPC123395
0.7178 Intermediate Similarity NPC213914
0.7174 Intermediate Similarity NPC12944
0.7174 Intermediate Similarity NPC25442
0.7167 Intermediate Similarity NPC90229
0.7158 Intermediate Similarity NPC57398
0.7151 Intermediate Similarity NPC63041
0.7151 Intermediate Similarity NPC470190
0.7151 Intermediate Similarity NPC146724
0.7135 Intermediate Similarity NPC309498
0.7125 Intermediate Similarity NPC123906
0.7119 Intermediate Similarity NPC83111
0.7112 Intermediate Similarity NPC472752
0.7112 Intermediate Similarity NPC472550
0.7112 Intermediate Similarity NPC304179
0.7112 Intermediate Similarity NPC48042
0.7108 Intermediate Similarity NPC265100
0.7105 Intermediate Similarity NPC194541
0.7097 Intermediate Similarity NPC156044
0.7086 Intermediate Similarity NPC295158
0.7086 Intermediate Similarity NPC315320
0.7083 Intermediate Similarity NPC70949
0.7083 Intermediate Similarity NPC470894
0.7079 Intermediate Similarity NPC114974
0.7073 Intermediate Similarity NPC138018
0.7051 Intermediate Similarity NPC85443
0.7037 Intermediate Similarity NPC470189
0.7037 Intermediate Similarity NPC40919
0.7032 Intermediate Similarity NPC472288
0.7032 Intermediate Similarity NPC65408
0.7024 Intermediate Similarity NPC114637
0.7014 Intermediate Similarity NPC240136
0.7014 Intermediate Similarity NPC471402
0.7014 Intermediate Similarity NPC297486
0.7 Intermediate Similarity NPC323551
0.7 Intermediate Similarity NPC280473
0.7 Intermediate Similarity NPC471313
0.7 Intermediate Similarity NPC472553
0.7 Intermediate Similarity NPC476467
0.7 Intermediate Similarity NPC253810
0.7 Intermediate Similarity NPC471311
0.6989 Remote Similarity NPC311282
0.6963 Remote Similarity NPC83987
0.6963 Remote Similarity NPC165837
0.6963 Remote Similarity NPC41724
0.6963 Remote Similarity NPC51008
0.6959 Remote Similarity NPC191310
0.6954 Remote Similarity NPC61011
0.6946 Remote Similarity NPC242116
0.6944 Remote Similarity NPC56170
0.6933 Remote Similarity NPC470679
0.6933 Remote Similarity NPC217021
0.6933 Remote Similarity NPC109158
0.6932 Remote Similarity NPC285923
0.6928 Remote Similarity NPC80681
0.6927 Remote Similarity NPC264674
0.6927 Remote Similarity NPC319128
0.6927 Remote Similarity NPC228331
0.6927 Remote Similarity NPC4421
0.6919 Remote Similarity NPC469529
0.6906 Remote Similarity NPC103230
0.6901 Remote Similarity NPC235843
0.6895 Remote Similarity NPC309845
0.6891 Remote Similarity NPC477909
0.6891 Remote Similarity NPC62844
0.6891 Remote Similarity NPC42678
0.6891 Remote Similarity NPC477907
0.6891 Remote Similarity NPC477910
0.6891 Remote Similarity NPC207531
0.6891 Remote Similarity NPC193361
0.6891 Remote Similarity NPC470306
0.6886 Remote Similarity NPC322644
0.6875 Remote Similarity NPC327373
0.6868 Remote Similarity NPC202812
0.6857 Remote Similarity NPC73994
0.6856 Remote Similarity NPC471014
0.6856 Remote Similarity NPC475408
0.6856 Remote Similarity NPC206343
0.6856 Remote Similarity NPC6981
0.6856 Remote Similarity NPC477908
0.6856 Remote Similarity NPC471016
0.6854 Remote Similarity NPC118084
0.6852 Remote Similarity NPC477974
0.6848 Remote Similarity NPC298288
0.6839 Remote Similarity NPC219848
0.6839 Remote Similarity NPC83774
0.6836 Remote Similarity NPC46895
0.6824 Remote Similarity NPC182570
0.6824 Remote Similarity NPC48564
0.6824 Remote Similarity NPC265605
0.6823 Remote Similarity NPC111732
0.6821 Remote Similarity NPC62367
0.6821 Remote Similarity NPC144779
0.6821 Remote Similarity NPC6576
0.6821 Remote Similarity NPC187494
0.6821 Remote Similarity NPC473115
0.6821 Remote Similarity NPC158020
0.6821 Remote Similarity NPC75600
0.6821 Remote Similarity NPC294579
0.6821 Remote Similarity NPC473089
0.6821 Remote Similarity NPC319556
0.6821 Remote Similarity NPC212768
0.6809 Remote Similarity NPC472259
0.6802 Remote Similarity NPC302647
0.68 Remote Similarity NPC256268
0.6795 Remote Similarity NPC291517
0.6789 Remote Similarity NPC266249
0.6786 Remote Similarity NPC84815
0.6786 Remote Similarity NPC231655
0.6786 Remote Similarity NPC301368
0.6786 Remote Similarity NPC472555
0.6786 Remote Similarity NPC216428
0.6784 Remote Similarity NPC319456
0.6782 Remote Similarity NPC84347
0.678 Remote Similarity NPC243058
0.6774 Remote Similarity NPC470279
0.6772 Remote Similarity NPC82053
0.6768 Remote Similarity NPC473878
0.6765 Remote Similarity NPC471178
0.6761 Remote Similarity NPC52831
0.6761 Remote Similarity NPC325705
0.6751 Remote Similarity NPC477901
0.6748 Remote Similarity NPC100726
0.6742 Remote Similarity NPC203635
0.6735 Remote Similarity NPC91958
0.6735 Remote Similarity NPC143603
0.6733 Remote Similarity NPC290094
0.6725 Remote Similarity NPC98187
0.672 Remote Similarity NPC81535
0.6719 Remote Similarity NPC123839
0.6717 Remote Similarity NPC477903
0.6717 Remote Similarity NPC477912
0.671 Remote Similarity NPC174421
0.671 Remote Similarity NPC324611
0.671 Remote Similarity NPC256893
0.6706 Remote Similarity NPC473057
0.6689 Remote Similarity NPC476322
0.6688 Remote Similarity NPC23215
0.6687 Remote Similarity NPC318935
0.6685 Remote Similarity NPC322043
0.6685 Remote Similarity NPC325093
0.6683 Remote Similarity NPC235364

  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 NPC230085 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
0.9778 High Similarity NPD107 Approved
0.95 High Similarity NPD9271 Approved
0.9496 High Similarity NPD9075 Approved
0.9496 High Similarity NPD9074 Approved
0.9048 High Similarity NPD820 Phase 3
0.8403 Intermediate Similarity NPD203 Clinical (unspecified phase)
0.8322 Intermediate Similarity NPD272 Approved
0.8261 Intermediate Similarity NPD8304 Clinical (unspecified phase)
0.8085 Intermediate Similarity NPD9284 Approved
0.7958 Intermediate Similarity NPD9080 Approved
0.784 Intermediate Similarity NPD485 Clinical (unspecified phase)
0.7712 Intermediate Similarity NPD175 Clinical (unspecified phase)
0.7644 Intermediate Similarity NPD5975 Clinical (unspecified phase)
0.7613 Intermediate Similarity NPD1270 Approved
0.76 Intermediate Similarity NPD9506 Approved
0.7586 Intermediate Similarity NPD1173 Approved
0.7568 Intermediate Similarity NPD1627 Clinical (unspecified phase)
0.7566 Intermediate Similarity NPD1649 Discontinued
0.745 Intermediate Similarity NPD9100 Approved
0.7434 Intermediate Similarity NPD2896 Discontinued
0.7419 Intermediate Similarity NPD1352 Discontinued
0.7412 Intermediate Similarity NPD1783 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD510 Phase 1
0.7358 Intermediate Similarity NPD5965 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD5088 Discontinued
0.7308 Intermediate Similarity NPD751 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD2336 Approved
0.7268 Intermediate Similarity NPD944 Approved
0.7268 Intermediate Similarity NPD2831 Approved
0.7239 Intermediate Similarity NPD1630 Approved
0.7232 Intermediate Similarity NPD981 Phase 2
0.7226 Intermediate Similarity NPD9599 Approved
0.7225 Intermediate Similarity NPD1096 Discontinued
0.7197 Intermediate Similarity NPD3813 Approved
0.7189 Intermediate Similarity NPD3371 Approved
0.7174 Intermediate Similarity NPD3947 Discontinued
0.7174 Intermediate Similarity NPD7396 Approved
0.7161 Intermediate Similarity NPD4804 Approved
0.7111 Intermediate Similarity NPD2307 Discontinued
0.711 Intermediate Similarity NPD3178 Discontinued
0.7108 Intermediate Similarity NPD1631 Approved
0.7099 Intermediate Similarity NPD180 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD9206 Approved
0.7086 Intermediate Similarity NPD9207 Approved
0.707 Intermediate Similarity NPD4805 Approved
0.7049 Intermediate Similarity NPD4491 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD4376 Phase 3
0.7037 Intermediate Similarity NPD4417 Approved
0.7033 Intermediate Similarity NPD4987 Clinical (unspecified phase)
0.7032 Intermediate Similarity NPD200 Phase 2
0.7032 Intermediate Similarity NPD201 Phase 2
0.7027 Intermediate Similarity NPD2121 Clinical (unspecified phase)
0.7024 Intermediate Similarity NPD4174 Clinical (unspecified phase)
0.6995 Remote Similarity NPD1623 Approved
0.6993 Remote Similarity NPD269 Clinical (unspecified phase)
0.6988 Remote Similarity NPD2511 Approved
0.6979 Remote Similarity NPD5490 Discontinued
0.6968 Remote Similarity NPD2509 Approved
0.6968 Remote Similarity NPD2510 Approved
0.6951 Remote Similarity NPD2061 Approved
0.6943 Remote Similarity NPD569 Clinical (unspecified phase)
0.6941 Remote Similarity NPD1573 Approved
0.6941 Remote Similarity NPD1575 Approved
0.6932 Remote Similarity NPD721 Approved
0.6919 Remote Similarity NPD5322 Clinical (unspecified phase)
0.691 Remote Similarity NPD4948 Discontinued
0.6864 Remote Similarity NPD1568 Clinical (unspecified phase)
0.6859 Remote Similarity NPD206 Clinical (unspecified phase)
0.6851 Remote Similarity NPD6665 Discontinued
0.6848 Remote Similarity NPD2809 Approved
0.6824 Remote Similarity NPD271 Approved
0.6824 Remote Similarity NPD270 Clinical (unspecified phase)
0.6824 Remote Similarity NPD268 Approved
0.6821 Remote Similarity NPD1586 Approved
0.6809 Remote Similarity NPD6987 Phase 1
0.6786 Remote Similarity NPD9099 Clinical (unspecified phase)
0.6786 Remote Similarity NPD9098 Phase 3
0.6784 Remote Similarity NPD1343 Approved
0.6783 Remote Similarity NPD4823 Approved
0.6783 Remote Similarity NPD4824 Approved
0.6771 Remote Similarity NPD5475 Discontinued
0.6763 Remote Similarity NPD750 Phase 2
0.6761 Remote Similarity NPD1643 Phase 3
0.6761 Remote Similarity NPD9510 Approved
0.6758 Remote Similarity NPD3406 Suspended
0.675 Remote Similarity NPD5020 Approved
0.6727 Remote Similarity NPD9595 Approved
0.6727 Remote Similarity NPD9596 Approved
0.6723 Remote Similarity NPD9362 Approved
0.6723 Remote Similarity NPD4011 Clinical (unspecified phase)
0.672 Remote Similarity NPD5901 Discontinued
0.6705 Remote Similarity NPD1587 Approved
0.6686 Remote Similarity NPD1292 Clinical (unspecified phase)
0.6684 Remote Similarity NPD7010 Phase 3
0.6667 Remote Similarity NPD1291 Clinical (unspecified phase)
0.6667 Remote Similarity NPD2581 Approved
0.6667 Remote Similarity NPD2582 Approved
0.6648 Remote Similarity NPD3569 Discontinued
0.6646 Remote Similarity NPD4702 Approved
0.6646 Remote Similarity NPD4703 Approved
0.6633 Remote Similarity NPD4301 Approved
0.6633 Remote Similarity NPD3393 Approved
0.6633 Remote Similarity NPD3394 Approved
0.6633 Remote Similarity NPD3389 Approved
0.6631 Remote Similarity NPD6137 Clinical (unspecified phase)
0.663 Remote Similarity NPD4988 Discontinued
0.6629 Remote Similarity NPD4883 Approved
0.6628 Remote Similarity NPD5611 Phase 2
0.6627 Remote Similarity NPD704 Clinical (unspecified phase)
0.6627 Remote Similarity NPD5255 Approved
0.6615 Remote Similarity NPD3795 Approved
0.6615 Remote Similarity NPD3794 Approved
0.6615 Remote Similarity NPD1367 Phase 2
0.6611 Remote Similarity NPD2814 Clinical (unspecified phase)
0.6605 Remote Similarity NPD3717 Discontinued
0.6603 Remote Similarity NPD9726 Discontinued
0.6591 Remote Similarity NPD3238 Discontinued
0.6579 Remote Similarity NPD9357 Approved
0.6573 Remote Similarity NPD2481 Approved
0.6573 Remote Similarity NPD2479 Phase 3
0.6571 Remote Similarity NPD1599 Approved
0.6562 Remote Similarity NPD9076 Clinical (unspecified phase)
0.6562 Remote Similarity NPD1380 Discovery
0.6559 Remote Similarity NPD6226 Phase 3
0.6559 Remote Similarity NPD7061 Clinical (unspecified phase)
0.6558 Remote Similarity NPD2119 Approved
0.6558 Remote Similarity NPD2118 Approved
0.6554 Remote Similarity NPD2753 Discontinued
0.655 Remote Similarity NPD5400 Approved
0.6545 Remote Similarity NPD6323 Clinical (unspecified phase)
0.6543 Remote Similarity NPD7000 Clinical (unspecified phase)
0.6543 Remote Similarity NPD6999 Discontinued
0.6538 Remote Similarity NPD9364 Phase 2
0.6538 Remote Similarity NPD9363 Approved
0.6533 Remote Similarity NPD7404 Approved
0.6532 Remote Similarity NPD6446 Discontinued
0.6512 Remote Similarity NPD6635 Approved
0.6508 Remote Similarity NPD5228 Phase 3
0.6497 Remote Similarity NPD5100 Phase 3
0.6497 Remote Similarity NPD749 Clinical (unspecified phase)
0.6495 Remote Similarity NPD6529 Discontinued
0.6494 Remote Similarity NPD9583 Approved
0.6492 Remote Similarity NPD5513 Phase 2
0.649 Remote Similarity NPD5891 Approved
0.648 Remote Similarity NPD1618 Phase 2
0.6474 Remote Similarity NPD925 Approved
0.6474 Remote Similarity NPD926 Approved
0.6461 Remote Similarity NPD5751 Clinical (unspecified phase)
0.6455 Remote Similarity NPD7049 Clinical (unspecified phase)
0.6452 Remote Similarity NPD4526 Approved
0.6452 Remote Similarity NPD4528 Approved
0.6452 Remote Similarity NPD4529 Approved
0.6448 Remote Similarity NPD2770 Discontinued
0.6442 Remote Similarity NPD1383 Phase 3
0.6442 Remote Similarity NPD1382 Phase 2
0.6441 Remote Similarity NPD482 Approved
0.6433 Remote Similarity NPD3475 Approved
0.6433 Remote Similarity NPD3476 Approved
0.6432 Remote Similarity NPD3805 Clinical (unspecified phase)
0.6429 Remote Similarity NPD4889 Approved
0.6429 Remote Similarity NPD9343 Clinical (unspecified phase)
0.6425 Remote Similarity NPD4559 Clinical (unspecified phase)
0.6425 Remote Similarity NPD5398 Clinical (unspecified phase)
0.6421 Remote Similarity NPD4396 Clinical (unspecified phase)
0.6421 Remote Similarity NPD8248 Clinical (unspecified phase)
0.6419 Remote Similarity NPD60 Approved
0.6418 Remote Similarity NPD3280 Approved
0.6412 Remote Similarity NPD276 Clinical (unspecified phase)
0.641 Remote Similarity NPD5583 Clinical (unspecified phase)
0.641 Remote Similarity NPD1095 Clinical (unspecified phase)
0.641 Remote Similarity NPD1031 Discontinued
0.6402 Remote Similarity NPD1427 Clinical (unspecified phase)
0.64 Remote Similarity NPD6872 Clinical (unspecified phase)
0.6398 Remote Similarity NPD5505 Discontinued
0.6398 Remote Similarity NPD7098 Clinical (unspecified phase)
0.6395 Remote Similarity NPD687 Clinical (unspecified phase)
0.6395 Remote Similarity NPD112 Approved
0.6395 Remote Similarity NPD9705 Discontinued
0.6393 Remote Similarity NPD3315 Phase 3
0.6392 Remote Similarity NPD6135 Phase 1
0.6389 Remote Similarity NPD3927 Phase 2
0.6387 Remote Similarity NPD5017 Discontinued
0.6386 Remote Similarity NPD7469 Discontinued
0.6386 Remote Similarity NPD6148 Clinical (unspecified phase)
0.6383 Remote Similarity NPD2290 Phase 3
0.6383 Remote Similarity NPD2289 Phase 3
0.638 Remote Similarity NPD1395 Clinical (unspecified phase)
0.6379 Remote Similarity NPD2780 Approved
0.6379 Remote Similarity NPD2782 Approved
0.6378 Remote Similarity NPD3321 Discontinued
0.6374 Remote Similarity NPD9382 Approved
0.6374 Remote Similarity NPD9383 Approved
0.6368 Remote Similarity NPD6661 Clinical (unspecified phase)
0.6364 Remote Similarity NPD8823 Approved
0.6359 Remote Similarity NPD7467 Discontinued
0.6359 Remote Similarity NPD6791 Phase 2
0.6352 Remote Similarity NPD1993 Approved
0.6352 Remote Similarity NPD1994 Approved
0.6352 Remote Similarity NPD1995 Approved
0.6348 Remote Similarity NPD4736 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