Structure

Physi-Chem Properties

Molecular Weight:  151.06
Volume:  156.399
LogP:  1.817
LogD:  1.528
LogS:  -2.073
# Rotatable Bonds:  2
TPSA:  52.32
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  1
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.482
Synthetic Accessibility Score:  1.514
Fsp3:  0.125
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.481
MDCK Permeability:  5.0898961490020156e-05
Pgp-inhibitor:  0.0
Pgp-substrate:  0.947
Human Intestinal Absorption (HIA):  0.004
20% Bioavailability (F20%):  0.005
30% Bioavailability (F30%):  0.953

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.988
Plasma Protein Binding (PPB):  57.577659606933594%
Volume Distribution (VD):  1.02
Pgp-substrate:  44.459293365478516%

ADMET: Metabolism

CYP1A2-inhibitor:  0.948
CYP1A2-substrate:  0.749
CYP2C19-inhibitor:  0.675
CYP2C19-substrate:  0.683
CYP2C9-inhibitor:  0.253
CYP2C9-substrate:  0.566
CYP2D6-inhibitor:  0.064
CYP2D6-substrate:  0.745
CYP3A4-inhibitor:  0.135
CYP3A4-substrate:  0.219

ADMET: Excretion

Clearance (CL):  8.392
Half-life (T1/2):  0.704

ADMET: Toxicity

hERG Blockers:  0.056
Human Hepatotoxicity (H-HT):  0.074
Drug-inuced Liver Injury (DILI):  0.32
AMES Toxicity:  0.063
Rat Oral Acute Toxicity:  0.034
Maximum Recommended Daily Dose:  0.016
Skin Sensitization:  0.42
Carcinogencity:  0.096
Eye Corrosion:  0.079
Eye Irritation:  0.991
Respiratory Toxicity:  0.844

Download Data

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

  Natural Product: NPC226794

Natural Product ID:  NPC226794
Common Name*:   Methyl Anthranilate
IUPAC Name:   methyl 2-aminobenzoate
Synonyms:  
Standard InCHIKey:  VAMXMNNIEUEQDV-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C8H9NO2/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5H,9H2,1H3
SMILES:  COC(=O)c1ccccc1N
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1493986
PubChem CID:   8635
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000176] Benzoic acids and derivatives
          • [CHEMONTID:0001350] Benzoic acid esters

*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
NPO17494 Prunella vulgaris Species Lamiaceae Eukaryota n.a. stem n.a. DOI[10.1016/0031-9422(86)88033-5]
NPO17494 Prunella vulgaris Species Lamiaceae Eukaryota n.a. leaf n.a. DOI[10.1016/0031-9422(86)88033-5]
NPO17494 Prunella vulgaris Species Lamiaceae Eukaryota whole plant n.a. n.a. DOI[10.1016/j.tetlet.2016.12.029]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[1402962]
NPO19592 Michelia alba Species Magnoliaceae Eukaryota leaves n.a. n.a. PMID[20584613]
NPO17072 Lonicera macranthoides Species Caprifoliaceae Eukaryota n.a. flower bud n.a. PMID[22822669]
NPO2715 Murraya paniculata Species Rutaceae Eukaryota n.a. leaf n.a. PMID[24354205]
NPO2715 Murraya paniculata Species Rutaceae Eukaryota n.a. twig n.a. PMID[24354205]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota Flower Buds n.a. n.a. PMID[26977531]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[8904847]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota Essential Oil n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota Bark n.a. n.a. Database[FooDB]
NPO2715 Murraya paniculata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2476 Lonicera fulvotomentosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19592 Michelia alba Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30045 Citrus grandis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17494 Prunella vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23768 Camellia saluenensis Species Theaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2476 Lonicera fulvotomentosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17072 Lonicera macranthoides Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19592 Michelia alba Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21345 Lonicera hypoglauca Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4596 Lonicera confusa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2715 Murraya paniculata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17494 Prunella vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2715 Murraya paniculata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30045 Citrus grandis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19592 Michelia alba Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7317.2 Citrus aurantium var. amara engl. Varieties Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2476 Lonicera fulvotomentosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21345 Lonicera hypoglauca Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17494 Prunella vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30045 Citrus grandis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[Title]
NPO4596 Lonicera confusa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2715 Murraya paniculata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21345 Lonicera hypoglauca Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2476 Lonicera fulvotomentosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO17072 Lonicera macranthoides Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO17494 Prunella vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17072 Lonicera macranthoides Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19592 Michelia alba Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21345 Lonicera hypoglauca Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2476 Lonicera fulvotomentosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23768 Camellia saluenensis Species Theaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17494 Prunella vulgaris Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2715 Murraya paniculata Species Rutaceae 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
NPT149 Individual Protein Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Homo sapiens Potency = 31622.8 nM PMID[545548]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 34376.2 nM PMID[545548]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 28183.8 nM PMID[545548]
NPT1280 Organism Thrips tabaci Thrips tabaci Ratio = 3.5 n.a. PMID[545549]
NPT1281 Organism Thrips obscuratus Thrips obscuratus Ratio = 22.1 n.a. PMID[545549]
NPT1281 Organism Thrips obscuratus Thrips obscuratus Ratio = 28.3 n.a. PMID[545549]
NPT21 Organism Aspergillus niger Aspergillus niger -logMIC = 1.08 n.a. PMID[545550]
NPT20 Organism Candida albicans Candida albicans -logMIC = 1.08 n.a. PMID[545550]
NPT19 Organism Escherichia coli Escherichia coli -logMIC = 1.69 n.a. PMID[545550]
NPT79 Organism Bacillus subtilis Bacillus subtilis -logMIC = 1.99 n.a. PMID[545550]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus -logMIC = 1.08 n.a. PMID[545550]
NPT29 Organism Rattus norvegicus Rattus norvegicus pLD50 = 7.98 n.a. PMID[545551]
NPT2 Others Unspecified Potency n.a. 21872.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 21119.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 15355.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 52604.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 27535.7 nM PubChem BioAssay data set

☑ 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 NPC226794 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
0.9504 High Similarity NPC122235
0.9206 High Similarity NPC173295
0.9 High Similarity NPC130931
0.8538 High Similarity NPC253476
0.8284 Intermediate Similarity NPC181527
0.8226 Intermediate Similarity NPC229353
0.8148 Intermediate Similarity NPC319645
0.8095 Intermediate Similarity NPC150323
0.8067 Intermediate Similarity NPC172170
0.8029 Intermediate Similarity NPC43477
0.7941 Intermediate Similarity NPC159722
0.7872 Intermediate Similarity NPC259678
0.782 Intermediate Similarity NPC477432
0.7803 Intermediate Similarity NPC72473
0.7803 Intermediate Similarity NPC58827
0.7803 Intermediate Similarity NPC307437
0.7786 Intermediate Similarity NPC205946
0.7586 Intermediate Similarity NPC130398
0.7554 Intermediate Similarity NPC43218
0.75 Intermediate Similarity NPC314098
0.7458 Intermediate Similarity NPC249912
0.7458 Intermediate Similarity NPC276775
0.7458 Intermediate Similarity NPC92754
0.7395 Intermediate Similarity NPC78701
0.7395 Intermediate Similarity NPC225060
0.7395 Intermediate Similarity NPC35448
0.7333 Intermediate Similarity NPC146351
0.7333 Intermediate Similarity NPC314278
0.7333 Intermediate Similarity NPC203925
0.7324 Intermediate Similarity NPC242933
0.7299 Intermediate Similarity NPC194562
0.7273 Intermediate Similarity NPC70624
0.7273 Intermediate Similarity NPC179605
0.7273 Intermediate Similarity NPC279385
0.7236 Intermediate Similarity NPC38262
0.723 Intermediate Similarity NPC241392
0.7218 Intermediate Similarity NPC103292
0.7213 Intermediate Similarity NPC188895
0.7208 Intermediate Similarity NPC189116
0.7206 Intermediate Similarity NPC250476
0.719 Intermediate Similarity NPC118343
0.719 Intermediate Similarity NPC325497
0.7183 Intermediate Similarity NPC316574
0.7154 Intermediate Similarity NPC301943
0.7154 Intermediate Similarity NPC474365
0.7131 Intermediate Similarity NPC42211
0.7123 Intermediate Similarity NPC190945
0.7115 Intermediate Similarity NPC182131
0.7103 Intermediate Similarity NPC301702
0.7097 Intermediate Similarity NPC31786
0.7083 Intermediate Similarity NPC181526
0.7083 Intermediate Similarity NPC314252
0.7078 Intermediate Similarity NPC93653
0.7063 Intermediate Similarity NPC37584
0.7037 Intermediate Similarity NPC268534
0.7037 Intermediate Similarity NPC26285
0.7034 Intermediate Similarity NPC316202
0.7032 Intermediate Similarity NPC257763
0.7019 Intermediate Similarity NPC9475
0.7 Intermediate Similarity NPC316746
0.7 Intermediate Similarity NPC231382
0.6985 Remote Similarity NPC254698
0.6984 Remote Similarity NPC119271
0.6968 Remote Similarity NPC27904
0.6962 Remote Similarity NPC470971
0.6954 Remote Similarity NPC314223
0.695 Remote Similarity NPC23908
0.6943 Remote Similarity NPC299582
0.694 Remote Similarity NPC177684
0.694 Remote Similarity NPC291962
0.6939 Remote Similarity NPC314287
0.6939 Remote Similarity NPC308197
0.6933 Remote Similarity NPC300596
0.6933 Remote Similarity NPC237649
0.6929 Remote Similarity NPC56493
0.6912 Remote Similarity NPC39818
0.6905 Remote Similarity NPC269457
0.6905 Remote Similarity NPC209632
0.6897 Remote Similarity NPC318107
0.6892 Remote Similarity NPC323798
0.6889 Remote Similarity NPC258531
0.6889 Remote Similarity NPC161956
0.6889 Remote Similarity NPC112373
0.688 Remote Similarity NPC89886
0.688 Remote Similarity NPC60679
0.6875 Remote Similarity NPC85493
0.6875 Remote Similarity NPC83628
0.6875 Remote Similarity NPC17417
0.6875 Remote Similarity NPC469636
0.6875 Remote Similarity NPC265407
0.6875 Remote Similarity NPC474364
0.6875 Remote Similarity NPC10251
0.6864 Remote Similarity NPC173443
0.6864 Remote Similarity NPC138370
0.6857 Remote Similarity NPC209389
0.6852 Remote Similarity NPC8467
0.685 Remote Similarity NPC37622
0.685 Remote Similarity NPC30594
0.6838 Remote Similarity NPC257490
0.6829 Remote Similarity NPC98416
0.6829 Remote Similarity NPC283810
0.6825 Remote Similarity NPC114594
0.6822 Remote Similarity NPC214067
0.6822 Remote Similarity NPC196246
0.6822 Remote Similarity NPC174099
0.6822 Remote Similarity NPC251854
0.6822 Remote Similarity NPC93084
0.68 Remote Similarity NPC45613
0.6777 Remote Similarity NPC261181
0.6776 Remote Similarity NPC144691
0.6769 Remote Similarity NPC210089
0.6769 Remote Similarity NPC305912
0.6769 Remote Similarity NPC474157
0.6769 Remote Similarity NPC260818
0.6769 Remote Similarity NPC476003
0.6769 Remote Similarity NPC1082
0.6766 Remote Similarity NPC282103
0.6763 Remote Similarity NPC472244
0.6763 Remote Similarity NPC470343
0.6763 Remote Similarity NPC325013
0.6757 Remote Similarity NPC472241
0.6755 Remote Similarity NPC315829
0.6748 Remote Similarity NPC253423
0.6744 Remote Similarity NPC476206
0.6744 Remote Similarity NPC259791
0.6744 Remote Similarity NPC476212
0.6744 Remote Similarity NPC476256
0.6744 Remote Similarity NPC99846
0.6744 Remote Similarity NPC476257
0.6744 Remote Similarity NPC21483
0.6744 Remote Similarity NPC269023
0.6744 Remote Similarity NPC476129
0.6744 Remote Similarity NPC476205
0.6744 Remote Similarity NPC198205
0.6744 Remote Similarity NPC476207
0.6742 Remote Similarity NPC57051
0.6735 Remote Similarity NPC472243
0.6718 Remote Similarity NPC321852
0.6718 Remote Similarity NPC270699
0.6718 Remote Similarity NPC82899
0.6714 Remote Similarity NPC322433
0.6712 Remote Similarity NPC287358
0.6711 Remote Similarity NPC242000
0.671 Remote Similarity NPC114808
0.6707 Remote Similarity NPC471742
0.6705 Remote Similarity NPC476218
0.6705 Remote Similarity NPC108804
0.6695 Remote Similarity NPC89377
0.6694 Remote Similarity NPC229242
0.6691 Remote Similarity NPC317758
0.6687 Remote Similarity NPC28368
0.6667 Remote Similarity NPC128368
0.6667 Remote Similarity NPC62765
0.6667 Remote Similarity NPC272524
0.6667 Remote Similarity NPC161611
0.6667 Remote Similarity NPC130797
0.6667 Remote Similarity NPC198390
0.6647 Remote Similarity NPC470317
0.6646 Remote Similarity NPC84347
0.6641 Remote Similarity NPC167504
0.664 Remote Similarity NPC217621
0.6629 Remote Similarity NPC112752
0.6629 Remote Similarity NPC311054
0.6627 Remote Similarity NPC160381
0.6627 Remote Similarity NPC85613
0.6627 Remote Similarity NPC475685
0.6626 Remote Similarity NPC177261
0.6624 Remote Similarity NPC123241
0.6624 Remote Similarity NPC61013
0.6623 Remote Similarity NPC472242
0.6621 Remote Similarity NPC316104
0.6621 Remote Similarity NPC162417
0.6617 Remote Similarity NPC307651
0.6617 Remote Similarity NPC474363
0.6617 Remote Similarity NPC308744
0.6617 Remote Similarity NPC153053
0.6604 Remote Similarity NPC293458
0.6591 Remote Similarity NPC107828
0.6591 Remote Similarity NPC79496
0.6591 Remote Similarity NPC158282
0.6591 Remote Similarity NPC90358
0.6591 Remote Similarity NPC474314
0.6583 Remote Similarity NPC220893
0.6582 Remote Similarity NPC193410
0.6571 Remote Similarity NPC192533
0.6568 Remote Similarity NPC49184
0.6567 Remote Similarity NPC81808
0.6567 Remote Similarity NPC474685
0.6567 Remote Similarity NPC210092
0.6562 Remote Similarity NPC204867
0.6543 Remote Similarity NPC470894
0.6541 Remote Similarity NPC248117
0.6541 Remote Similarity NPC474176
0.6535 Remote Similarity NPC304873
0.6535 Remote Similarity NPC25458
0.6532 Remote Similarity NPC61944
0.6527 Remote Similarity NPC5167
0.6525 Remote Similarity NPC58616
0.6524 Remote Similarity NPC73280
0.6524 Remote Similarity NPC191310

  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 NPC226794 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
0.8871 High Similarity NPD553 Approved
0.8871 High Similarity NPD9567 Approved
0.8871 High Similarity NPD552 Approved
0.837 Intermediate Similarity NPD6414 Clinical (unspecified phase)
0.8345 Intermediate Similarity NPD2737 Clinical (unspecified phase)
0.8284 Intermediate Similarity NPD3170 Approved
0.8284 Intermediate Similarity NPD1626 Approved
0.8148 Intermediate Similarity NPD1109 Approved
0.8148 Intermediate Similarity NPD1110 Approved
0.8095 Intermediate Similarity NPD9272 Approved
0.8056 Intermediate Similarity NPD2672 Discontinued
0.8043 Intermediate Similarity NPD1625 Approved
0.7971 Intermediate Similarity NPD1189 Approved
0.7931 Intermediate Similarity NPD2836 Approved
0.7836 Intermediate Similarity NPD9471 Clinical (unspecified phase)
0.781 Intermediate Similarity NPD2670 Approved
0.7786 Intermediate Similarity NPD1574 Approved
0.7762 Intermediate Similarity NPD4888 Discontinued
0.7692 Intermediate Similarity NPD1802 Approved
0.7692 Intermediate Similarity NPD1801 Approved
0.7655 Intermediate Similarity NPD1230 Approved
0.7639 Intermediate Similarity NPD7528 Approved
0.7586 Intermediate Similarity NPD9509 Clinical (unspecified phase)
0.745 Intermediate Similarity NPD1208 Approved
0.745 Intermediate Similarity NPD1211 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD3684 Discontinued
0.7383 Intermediate Similarity NPD1093 Approved
0.7383 Intermediate Similarity NPD1092 Approved
0.7381 Intermediate Similarity NPD9508 Approved
0.7338 Intermediate Similarity NPD1531 Approved
0.7333 Intermediate Similarity NPD1593 Approved
0.7329 Intermediate Similarity NPD1340 Discontinued
0.7323 Intermediate Similarity NPD181 Approved
0.7293 Intermediate Similarity NPD518 Clinical (unspecified phase)
0.729 Intermediate Similarity NPD2821 Approved
0.7255 Intermediate Similarity NPD1210 Approved
0.7218 Intermediate Similarity NPD9693 Approved
0.7218 Intermediate Similarity NPD9692 Approved
0.719 Intermediate Similarity NPD1238 Approved
0.7183 Intermediate Similarity NPD1532 Approved
0.7183 Intermediate Similarity NPD9279 Approved
0.7153 Intermediate Similarity NPD9477 Approved
0.7153 Intermediate Similarity NPD9278 Suspended
0.7153 Intermediate Similarity NPD9275 Approved
0.7153 Intermediate Similarity NPD9274 Approved
0.7153 Intermediate Similarity NPD9276 Approved
0.7152 Intermediate Similarity NPD1514 Discontinued
0.7132 Intermediate Similarity NPD2198 Approved
0.7132 Intermediate Similarity NPD2199 Approved
0.7123 Intermediate Similarity NPD2435 Approved
0.7103 Intermediate Similarity NPD75 Approved
0.7103 Intermediate Similarity NPD168 Phase 1
0.7103 Intermediate Similarity NPD167 Phase 2
0.7103 Intermediate Similarity NPD9277 Approved
0.7097 Intermediate Similarity NPD164 Approved
0.7047 Intermediate Similarity NPD4161 Discontinued
0.7027 Intermediate Similarity NPD4041 Approved
0.6987 Remote Similarity NPD955 Approved
0.6986 Remote Similarity NPD2923 Approved
0.6962 Remote Similarity NPD2249 Approved
0.6962 Remote Similarity NPD2681 Approved
0.6962 Remote Similarity NPD2680 Approved
0.6962 Remote Similarity NPD2247 Approved
0.695 Remote Similarity NPD3502 Discovery
0.6937 Remote Similarity NPD2248 Approved
0.6937 Remote Similarity NPD2246 Approved
0.6934 Remote Similarity NPD182 Clinical (unspecified phase)
0.6897 Remote Similarity NPD9259 Approved
0.6897 Remote Similarity NPD9257 Approved
0.6883 Remote Similarity NPD2366 Approved
0.6875 Remote Similarity NPD476 Approved
0.6875 Remote Similarity NPD2182 Approved
0.6863 Remote Similarity NPD5086 Approved
0.6853 Remote Similarity NPD5184 Approved
0.6853 Remote Similarity NPD3373 Approved
0.6853 Remote Similarity NPD5182 Approved
0.6853 Remote Similarity NPD5185 Approved
0.6846 Remote Similarity NPD6185 Discontinued
0.6824 Remote Similarity NPD1195 Approved
0.6812 Remote Similarity NPD9541 Approved
0.6812 Remote Similarity NPD9539 Approved
0.6806 Remote Similarity NPD9694 Discovery
0.68 Remote Similarity NPD4607 Approved
0.6797 Remote Similarity NPD3399 Approved
0.6797 Remote Similarity NPD2948 Discontinued
0.6783 Remote Similarity NPD1874 Clinical (unspecified phase)
0.6779 Remote Similarity NPD2387 Approved
0.6779 Remote Similarity NPD1196 Approved
0.6777 Remote Similarity NPD1202 Approved
0.6769 Remote Similarity NPD2181 Clinical (unspecified phase)
0.6761 Remote Similarity NPD486 Clinical (unspecified phase)
0.6759 Remote Similarity NPD3528 Clinical (unspecified phase)
0.6755 Remote Similarity NPD6758 Approved
0.6755 Remote Similarity NPD3352 Approved
0.6731 Remote Similarity NPD212 Discontinued
0.6715 Remote Similarity NPD1079 Discontinued
0.6714 Remote Similarity NPD9540 Approved
0.6714 Remote Similarity NPD797 Clinical (unspecified phase)
0.6708 Remote Similarity NPD5183 Approved
0.6708 Remote Similarity NPD5186 Approved
0.6707 Remote Similarity NPD7546 Discontinued
0.6691 Remote Similarity NPD661 Approved
0.6691 Remote Similarity NPD660 Approved
0.6691 Remote Similarity NPD657 Approved
0.6691 Remote Similarity NPD1640 Clinical (unspecified phase)
0.6691 Remote Similarity NPD655 Approved
0.669 Remote Similarity NPD1228 Phase 2
0.6687 Remote Similarity NPD5919 Clinical (unspecified phase)
0.6667 Remote Similarity NPD9258 Approved
0.6667 Remote Similarity NPD9256 Approved
0.6667 Remote Similarity NPD1655 Clinical (unspecified phase)
0.6667 Remote Similarity NPD1527 Phase 2
0.6667 Remote Similarity NPD4513 Discontinued
0.6646 Remote Similarity NPD2034 Discontinued
0.6645 Remote Similarity NPD1543 Discontinued
0.6645 Remote Similarity NPD2512 Phase 3
0.6644 Remote Similarity NPD1206 Approved
0.6644 Remote Similarity NPD1207 Approved
0.6625 Remote Similarity NPD5430 Discontinued
0.6623 Remote Similarity NPD7670 Clinical (unspecified phase)
0.6617 Remote Similarity NPD1371 Approved
0.6617 Remote Similarity NPD1374 Approved
0.6617 Remote Similarity NPD1373 Approved
0.6617 Remote Similarity NPD1370 Approved
0.6594 Remote Similarity NPD1124 Approved
0.6594 Remote Similarity NPD1123 Approved
0.6584 Remote Similarity NPD1559 Discontinued
0.657 Remote Similarity NPD5042 Phase 1
0.6552 Remote Similarity NPD1541 Approved
0.6549 Remote Similarity NPD698 Approved
0.6549 Remote Similarity NPD701 Approved
0.6547 Remote Similarity NPD6287 Discontinued
0.6541 Remote Similarity NPD4311 Approved
0.6533 Remote Similarity NPD2365 Approved
0.6524 Remote Similarity NPD5997 Discontinued
0.6519 Remote Similarity NPD3812 Clinical (unspecified phase)
0.651 Remote Similarity NPD1209 Approved
0.651 Remote Similarity NPD1205 Approved
0.6503 Remote Similarity NPD663 Approved
0.6503 Remote Similarity NPD658 Approved
0.6503 Remote Similarity NPD662 Approved
0.6503 Remote Similarity NPD656 Approved
0.6503 Remote Similarity NPD659 Approved
0.6493 Remote Similarity NPD1175 Approved
0.649 Remote Similarity NPD2820 Phase 3
0.6486 Remote Similarity NPD2567 Approved
0.6486 Remote Similarity NPD2569 Approved
0.6485 Remote Similarity NPD5466 Approved
0.6478 Remote Similarity NPD7114 Clinical (unspecified phase)
0.6471 Remote Similarity NPD9493 Approved
0.6463 Remote Similarity NPD2791 Discontinued
0.6463 Remote Similarity NPD1165 Clinical (unspecified phase)
0.6456 Remote Similarity NPD6570 Approved
0.6456 Remote Similarity NPD6571 Approved
0.6452 Remote Similarity NPD9260 Approved
0.6438 Remote Similarity NPD441 Approved
0.6438 Remote Similarity NPD7244 Discontinued
0.6437 Remote Similarity NPD7570 Approved
0.6437 Remote Similarity NPD7569 Approved
0.642 Remote Similarity NPD3252 Approved
0.6418 Remote Similarity NPD2607 Approved
0.6414 Remote Similarity NPD1190 Approved
0.6408 Remote Similarity NPD196 Phase 1
0.6408 Remote Similarity NPD1036 Approved
0.6407 Remote Similarity NPD3965 Phase 1
0.6397 Remote Similarity NPD256 Approved
0.6397 Remote Similarity NPD255 Approved
0.6389 Remote Similarity NPD1781 Discontinued
0.6386 Remote Similarity NPD2359 Approved
0.6383 Remote Similarity NPD6637 Approved
0.6377 Remote Similarity NPD9545 Approved
0.6376 Remote Similarity NPD4077 Clinical (unspecified phase)
0.637 Remote Similarity NPD1920 Approved
0.637 Remote Similarity NPD1680 Approved
0.637 Remote Similarity NPD1919 Approved
0.637 Remote Similarity NPD1681 Approved
0.637 Remote Similarity NPD14 Approved
0.637 Remote Similarity NPD731 Approved
0.637 Remote Similarity NPD1682 Approved
0.6354 Remote Similarity NPD2121 Clinical (unspecified phase)
0.6353 Remote Similarity NPD3253 Clinical (unspecified phase)
0.6349 Remote Similarity NPD9566 Approved
0.6347 Remote Similarity NPD2361 Approved
0.6345 Remote Similarity NPD2919 Clinical (unspecified phase)
0.6345 Remote Similarity NPD2918 Clinical (unspecified phase)
0.6343 Remote Similarity NPD4302 Clinical (unspecified phase)
0.6327 Remote Similarity NPD2950 Approved
0.6327 Remote Similarity NPD2949 Approved
0.6323 Remote Similarity NPD1553 Approved
0.6309 Remote Similarity NPD1654 Clinical (unspecified phase)
0.6304 Remote Similarity NPD2509 Approved
0.6304 Remote Similarity NPD2510 Approved
0.6303 Remote Similarity NPD1839 Phase 1
0.6301 Remote Similarity NPD1619 Phase 3
0.6301 Remote Similarity NPD1069 Approved
0.6301 Remote Similarity NPD6039 Approved
0.6301 Remote Similarity NPD1070 Approved
0.6294 Remote Similarity NPD9587 Clinical (unspecified phase)
0.6282 Remote Similarity NPD9271 Approved
0.628 Remote Similarity NPD8003 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