Structure

Physi-Chem Properties

Molecular Weight:  174.07
Volume:  197.938
LogP:  2.869
LogD:  1.661
LogS:  -2.881
# Rotatable Bonds:  2
TPSA:  26.3
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  0
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.34
Synthetic Accessibility Score:  3.747
Fsp3:  0.182
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:  -4.272
MDCK Permeability:  8.979089034255594e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.49
20% Bioavailability (F20%):  0.637
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.005
Plasma Protein Binding (PPB):  100.24313354492188%
Volume Distribution (VD):  0.895
Pgp-substrate:  2.9865458011627197%

ADMET: Metabolism

CYP1A2-inhibitor:  0.988
CYP1A2-substrate:  0.61
CYP2C19-inhibitor:  0.957
CYP2C19-substrate:  0.723
CYP2C9-inhibitor:  0.905
CYP2C9-substrate:  0.031
CYP2D6-inhibitor:  0.578
CYP2D6-substrate:  0.051
CYP3A4-inhibitor:  0.903
CYP3A4-substrate:  0.341

ADMET: Excretion

Clearance (CL):  11.082
Half-life (T1/2):  0.656

ADMET: Toxicity

hERG Blockers:  0.0
Human Hepatotoxicity (H-HT):  0.927
Drug-inuced Liver Injury (DILI):  0.983
AMES Toxicity:  0.683
Rat Oral Acute Toxicity:  0.874
Maximum Recommended Daily Dose:  0.449
Skin Sensitization:  0.948
Carcinogencity:  0.607
Eye Corrosion:  0.955
Eye Irritation:  0.976
Respiratory Toxicity:  0.689

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General Info & Identifiers & Properties  
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Similar NPs/Drugs  

  Natural Product: NPC297608

Natural Product ID:  NPC297608
Common Name*:   (2Z,8Z)-Matricaria Acid Methyl Ester
IUPAC Name:   methyl (2Z,8Z)-deca-2,8-dien-4,6-diynoate
Synonyms:  
Standard InCHIKey:  GXPDZHWFJLUFGY-RTAKVZRXSA-N
Standard InCHI:  InChI=1S/C11H10O2/c1-3-4-5-6-7-8-9-10-11(12)13-2/h3-4,9-10H,1-2H3/b4-3-,10-9-
SMILES:  C/C=CC#CC#C/C=CC(=O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2229362
PubChem CID:   5319306
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0003909] Fatty Acyls
        • [CHEMONTID:0000324] Fatty 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
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. DOI[10.1016/0006-291X(79)91731-5]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. DOI[10.1093/emboj/18.8.2021]
NPO2022 Ephemerantha lonchophylla n.a. n.a. n.a. n.a. n.a. n.a. PMID[10514302]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[1091286]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[10977898]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. PMID[11000050]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[1100617]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. PMID[11374973]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[11745165]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[11750815]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. Einan Reservoir in Israel n.a. PMID[12141855]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. PMID[12141855]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[12369847]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[12467448]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[12805358]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. ChEBI[131529]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[13610867]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[13831814]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[14973046]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[15031653]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[15292242]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[15610037]
NPO14305 Moricandia arvensis Species Brassicaceae Eukaryota n.a. n.a. n.a. PMID[15844940]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[1644759]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[16630633]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[170247]
NPO7125 Hintonia latiflora Species Rubiaceae Eukaryota stem bark n.a. n.a. PMID[17067158]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[17765195]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[179975]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. PMID[18163584]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. PMID[18558743]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. PMID[18973386]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[19026742]
NPO7125 Hintonia latiflora Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[19140696]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[19514719]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[19561621]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria water bloom of the cyanobacterium Microcystis aeruginosa n.a. n.a. PMID[19650639]
NPO12088 Conyza canadensis Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[20121251]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[21437340]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[21988831]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria bloom material Lake Kinneret, Israel n.a. PMID[22280481]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[22289691]
NPO12088 Conyza canadensis Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[22612410]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[22855027]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. Kibbutz Geva, Israel n.a. PMID[23153007]
NPO452 Arnica acaulis Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23501116]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[23537328]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[23676670]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. Water Reservoir near Kibbutz Hafetz Haim, Israel n.a. PMID[23718637]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[241475]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[24206068]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria Bloom n.a. n.a. PMID[24261937]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. PMID[24642434]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[24783849]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[24831709]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. PMID[24868986]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[24939187]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[24966042]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[24967680]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[2543976]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[25867074]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[26195826]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[26337258]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[26670289]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[26826371]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. PMID[29405714]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria Bloom n.a. n.a. PMID[29847132]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[29897754]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[30302998]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[318639]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[3283102]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[398096]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[4877125]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[4879561]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[4908789]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[5332408]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[6102982]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[6284709]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[6338507]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[7042909]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[7601837]
NPO9993 Streptomyces aurantiogriseus Species Streptomycetaceae Bacteria n.a. n.a. n.a. PMID[8784436]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[8852895]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. PMID[9249979]
NPO2022 Ephemerantha lonchophylla n.a. n.a. n.a. n.a. n.a. n.a. PMID[9461658]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria n.a. n.a. n.a. PMID[9470222]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. PMID[9842728]
NPO11170 Akebia trifoliata Species Lardizabalaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12088 Conyza canadensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11170 Akebia trifoliata Species Lardizabalaceae Eukaryota n.a. pericarp n.a. PMID[p25172756]
NPO169 Ruta tuberculata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11170 Akebia trifoliata Species Lardizabalaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12088 Conyza canadensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6202 Aglaomorpha coronans Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21831.2 Solidago virgaurea l. var. leiocarpa (benth.) a. gray Varieties Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11170 Akebia trifoliata Species Lardizabalaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12088 Conyza canadensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. Database[Title]
NPO11170 Akebia trifoliata Species Lardizabalaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO2380 Solidago decurrens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16926 Thymbra capitata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14305 Moricandia arvensis Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12129 Fagara mantchurica n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO9993 Streptomyces aurantiogriseus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO9371 Pilocarpus organensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17138 Lethasterias nanimensis Species Asteriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27862 Chelonanthus alatus Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2022 Ephemerantha lonchophylla n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO9043 Salvia breviflora Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6202 Aglaomorpha coronans Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3288 Microcystis aeruginosa Species Microcystaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO12360 Pithecellobium jiringa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2493 Parmelia reptans Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10576 Forsythia europaea Species Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7125 Hintonia latiflora Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11170 Akebia trifoliata Species Lardizabalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11419 Pityrodia jamesii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9790 Anthemis austriaca Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10329 Stachys tomentosa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9665 Dehaasia longipedicellata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25641 Peltophorum vogelianum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12088 Conyza canadensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15632 Podopetalum ormondi n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO169 Ruta tuberculata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2380 Solidago decurrens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7658 Chrysanthemum caucasicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO452 Arnica acaulis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8425 Gymnosporia rothiana Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO730 Escherichia coli Species Enterobacteriaceae Bacteria 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
NPT5140 Organism Planorbella trivolvis Planorbella trivolvis LC50 = 24000.0 nM PMID[485979]

☑ 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 NPC297608 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
0.9474 High Similarity NPC250954
0.85 High Similarity NPC281043
0.8 Intermediate Similarity NPC90490
0.7826 Intermediate Similarity NPC82446
0.7805 Intermediate Similarity NPC147824
0.7805 Intermediate Similarity NPC298413
0.7674 Intermediate Similarity NPC41409
0.75 Intermediate Similarity NPC65353
0.7436 Intermediate Similarity NPC63354
0.7292 Intermediate Similarity NPC15789
0.7273 Intermediate Similarity NPC57923
0.725 Intermediate Similarity NPC297363
0.725 Intermediate Similarity NPC122676
0.725 Intermediate Similarity NPC60675
0.7174 Intermediate Similarity NPC270706
0.7143 Intermediate Similarity NPC63598
0.7021 Intermediate Similarity NPC128280
0.6939 Remote Similarity NPC236338
0.6939 Remote Similarity NPC275316
0.6889 Remote Similarity NPC102879
0.6875 Remote Similarity NPC128520
0.6842 Remote Similarity NPC323552
0.6818 Remote Similarity NPC8270
0.6731 Remote Similarity NPC151761
0.6731 Remote Similarity NPC159535
0.6667 Remote Similarity NPC159773
0.6667 Remote Similarity NPC308418
0.6667 Remote Similarity NPC106531
0.6667 Remote Similarity NPC221250
0.6585 Remote Similarity NPC224651
0.6585 Remote Similarity NPC98098
0.6512 Remote Similarity NPC107877
0.6481 Remote Similarity NPC150717
0.6481 Remote Similarity NPC245002
0.6458 Remote Similarity NPC26600
0.6458 Remote Similarity NPC47946
0.6444 Remote Similarity NPC203382
0.6415 Remote Similarity NPC269615
0.6415 Remote Similarity NPC478120
0.6364 Remote Similarity NPC129150
0.6364 Remote Similarity NPC294938
0.6364 Remote Similarity NPC226511
0.6346 Remote Similarity NPC191643
0.6327 Remote Similarity NPC197467
0.6296 Remote Similarity NPC474913
0.6279 Remote Similarity NPC9290
0.625 Remote Similarity NPC312547
0.625 Remote Similarity NPC223679
0.625 Remote Similarity NPC254095
0.619 Remote Similarity NPC146507
0.619 Remote Similarity NPC310810
0.6182 Remote Similarity NPC86948
0.6182 Remote Similarity NPC221763
0.614 Remote Similarity NPC97570
0.614 Remote Similarity NPC302564
0.614 Remote Similarity NPC82465
0.614 Remote Similarity NPC159650
0.614 Remote Similarity NPC22897
0.6122 Remote Similarity NPC172042
0.6087 Remote Similarity NPC123357
0.6078 Remote Similarity NPC234084
0.6078 Remote Similarity NPC135698
0.6078 Remote Similarity NPC126184
0.6071 Remote Similarity NPC212730
0.6071 Remote Similarity NPC293437
0.6071 Remote Similarity NPC249850
0.6071 Remote Similarity NPC471279
0.6071 Remote Similarity NPC135863
0.6071 Remote Similarity NPC265551
0.6071 Remote Similarity NPC471277
0.6034 Remote Similarity NPC130953
0.6034 Remote Similarity NPC309408
0.6034 Remote Similarity NPC26223
0.6 Remote Similarity NPC173157
0.6 Remote Similarity NPC478117
0.6 Remote Similarity NPC8466
0.5968 Remote Similarity NPC225272
0.5965 Remote Similarity NPC189700
0.5965 Remote Similarity NPC21946
0.5965 Remote Similarity NPC474084
0.5962 Remote Similarity NPC221467
0.5952 Remote Similarity NPC144407
0.5932 Remote Similarity NPC26810
0.5926 Remote Similarity NPC477781
0.5926 Remote Similarity NPC477780
0.5918 Remote Similarity NPC51329
0.5918 Remote Similarity NPC304079
0.5918 Remote Similarity NPC6963
0.5918 Remote Similarity NPC12907
0.5893 Remote Similarity NPC230296
0.5882 Remote Similarity NPC68577
0.5862 Remote Similarity NPC222852
0.5862 Remote Similarity NPC474267
0.5849 Remote Similarity NPC43053
0.5833 Remote Similarity NPC187922
0.5833 Remote Similarity NPC44343
0.5833 Remote Similarity NPC210303
0.5833 Remote Similarity NPC473737
0.5833 Remote Similarity NPC179087
0.5818 Remote Similarity NPC218486
0.5769 Remote Similarity NPC15912
0.5769 Remote Similarity NPC250919
0.5769 Remote Similarity NPC223675
0.5763 Remote Similarity NPC471278
0.5763 Remote Similarity NPC98519
0.5763 Remote Similarity NPC79756
0.5763 Remote Similarity NPC299730
0.575 Remote Similarity NPC20903
0.5738 Remote Similarity NPC25747
0.5738 Remote Similarity NPC470808
0.5738 Remote Similarity NPC148233
0.5738 Remote Similarity NPC308457
0.5714 Remote Similarity NPC273054
0.5686 Remote Similarity NPC308331
0.5682 Remote Similarity NPC72258
0.5667 Remote Similarity NPC151648
0.5667 Remote Similarity NPC14437
0.5667 Remote Similarity NPC270412
0.566 Remote Similarity NPC27264
0.5645 Remote Similarity NPC96414
0.5645 Remote Similarity NPC273600
0.5645 Remote Similarity NPC19769
0.5614 Remote Similarity NPC51846
0.5614 Remote Similarity NPC472808
0.5614 Remote Similarity NPC324224

  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 NPC297608 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
0.8684 High Similarity NPD9115 Approved
0.6585 Remote Similarity NPD8573 Approved
0.5854 Remote Similarity NPD9114 Clinical (unspecified phase)
0.5849 Remote Similarity NPD6927 Phase 3
0.58 Remote Similarity NPD9378 Approved
0.5769 Remote Similarity NPD4220 Pre-registration
0.575 Remote Similarity NPD8187 Phase 3
0.5745 Remote Similarity NPD8839 Phase 3
0.5667 Remote Similarity NPD9418 Clinical (unspecified phase)
0.566 Remote Similarity NPD9437 Clinical (unspecified phase)
0.56 Remote Similarity NPD6096 Approved
0.56 Remote Similarity NPD6097 Approved

  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