Structure

Physi-Chem Properties

Molecular Weight:  748.27
Volume:  714.166
LogP:  3.409
LogD:  1.393
LogS:  -4.59
# Rotatable Bonds:  1
TPSA:  201.42
# H-Bond Aceptor:  14
# H-Bond Donor:  3
# Rings:  10
# Heavy Atoms:  14

MedChem Properties

QED Drug-Likeness Score:  0.199
Synthetic Accessibility Score:  7.045
Fsp3:  0.675
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.314
MDCK Permeability:  9.976323053706437e-05
Pgp-inhibitor:  0.999
Pgp-substrate:  0.999
Human Intestinal Absorption (HIA):  0.696
20% Bioavailability (F20%):  1.0
30% Bioavailability (F30%):  0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.292
Plasma Protein Binding (PPB):  47.7874870300293%
Volume Distribution (VD):  0.555
Pgp-substrate:  48.20100784301758%

ADMET: Metabolism

CYP1A2-inhibitor:  0.003
CYP1A2-substrate:  0.78
CYP2C19-inhibitor:  0.017
CYP2C19-substrate:  0.139
CYP2C9-inhibitor:  0.008
CYP2C9-substrate:  0.002
CYP2D6-inhibitor:  0.001
CYP2D6-substrate:  0.015
CYP3A4-inhibitor:  0.715
CYP3A4-substrate:  0.735

ADMET: Excretion

Clearance (CL):  2.499
Half-life (T1/2):  0.191

ADMET: Toxicity

hERG Blockers:  0.151
Human Hepatotoxicity (H-HT):  0.099
Drug-inuced Liver Injury (DILI):  0.422
AMES Toxicity:  0.074
Rat Oral Acute Toxicity:  0.298
Maximum Recommended Daily Dose:  0.972
Skin Sensitization:  0.388
Carcinogencity:  0.158
Eye Corrosion:  0.003
Eye Irritation:  0.007
Respiratory Toxicity:  0.911

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  Natural Product: NPC60120

Natural Product ID:  NPC60120
Common Name*:   Jasmonic Acid
IUPAC Name:   2-[(1R,2R)-3-oxo-2-[(Z)-pent-2-enyl]cyclopentyl]acetic acid
Synonyms:   Jasmonic Acid
Standard InCHIKey:  ZNJFBWYDHIGLCU-HWKXXFMVSA-N
Standard InCHI:  InChI=1S/C12H18O3/c1-2-3-4-5-10-9(8-12(14)15)6-7-11(10)13/h3-4,9-10H,2,5-8H2,1H3,(H,14,15)/b4-3-/t9-,10-/m1/s1
SMILES:  CC/C=CC[C@@H]1[C@H](CCC1=O)CC(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL449572
PubChem CID:   5281166
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0003909] Fatty Acyls
        • [CHEMONTID:0000504] Lineolic acids and derivatives
          • [CHEMONTID:0000512] Jasmonic acids

*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
NPO12929 Polianthes tuberosa Species Asparagaceae Eukaryota aerial parts n.a. n.a. PMID[11087596]
NPO12929 Polianthes tuberosa Species Asparagaceae Eukaryota underground parts n.a. n.a. PMID[12398537]
NPO12929 Polianthes tuberosa Species Asparagaceae Eukaryota fresh tubers n.a. n.a. PMID[14738376]
NPO23510 Vicia faba Species Fabaceae Eukaryota flowers n.a. n.a. PMID[16180811]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. PMID[18270436]
NPO9060 Sinularia granosa Species Alcyoniidae Eukaryota n.a. n.a. n.a. PMID[18831569]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. branch n.a. PMID[22014228]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. leaf n.a. PMID[22014228]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[22014228]
NPO9060 Sinularia granosa Species Alcyoniidae Eukaryota n.a. n.a. n.a. PMID[22672798]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. PMID[23793896]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. seed n.a. PMID[24967651]
NPO16831 Hypericum patulum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[31999455]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO23510 Vicia faba Species Fabaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Sprout Seedling n.a. n.a. Database[FooDB]
NPO23510 Vicia faba Species Fabaceae Eukaryota Sprout Seedling n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO23510 Vicia faba Species Fabaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO14149 Saccharina japonica Species Laminariaceae Eukaryota n.a. n.a. Database[FooDB]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. Database[FooDB]
NPO14149 Saccharina japonica Species Laminariaceae Eukaryota n.a. n.a. Database[FooDB]
NPO23510 Vicia faba Species Fabaceae Eukaryota Flower n.a. n.a. Database[FooDB]
NPO23510 Vicia faba Species Fabaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO23510 Vicia faba Species Fabaceae Eukaryota Oil n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO12929 Polianthes tuberosa Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14012 Libanotis condensata Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20824 Ecklonia kurome Species Lessoniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16831 Hypericum patulum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8650.1 Perilla frutescens var. arguta Varieties Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8650.1 Perilla frutescens var. arguta Varieties Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20824 Ecklonia kurome Species Lessoniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12929 Polianthes tuberosa Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15843 Dalbergia retusa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14149 Saccharina japonica Species Laminariaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14012 Libanotis condensata Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16831 Hypericum patulum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16865.1 Prunus serrulata var. spontanea Varieties Rosaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20824 Ecklonia kurome Species Lessoniaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14149 Saccharina japonica Species Laminariaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8288 Vitis cinerea Species Vitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12929 Polianthes tuberosa Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7540 Eucalyptus consideniana Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15615 Petunia hybrid Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22329 Dolomedes okefinokensis Species Pisauridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15843 Dalbergia retusa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15232 Absidia repens Species Cunninghamellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14346 Pterocarpus indica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12106 Aristeomorpha foliacea Species Aristeidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2991 Duboisia leichhardtii Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15742 Euphorbia laurifolia Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13354 Euryspongia arenaria Species Dysideidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16338 Virola calophylloidea Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11547 Lobelia cardinalis Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16150 Nepeta argolica Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20824 Ecklonia kurome Species Lessoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13502 Senecio algens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16260 Stevia yaconensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16498 Adoxophyes orana Species Tortricidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7342 Bostrychia scorpioides Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23510 Vicia faba Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14012 Libanotis condensata Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13841 Allium minutiflorum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22132 Hordeum vulgare Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14968 Mucuna membranacea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8650.1 Perilla frutescens var. arguta Varieties Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16574 Heywoodiella oligocephala n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO12655 Tephrosia virginiana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15121 Solanum habrochaites Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16865.1 Prunus serrulata var. spontanea Varieties Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16417 Elaeocarpus ganitrus Species Elaeocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4167 Oxalis repens Species Oxalidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16885 Phonus arborescens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2295 Cydonia vulgaris Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2725 Casuarina glauca Species Casuarinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10741 Eucalyptus grossa Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16537 Lonicera racemosa Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9060 Sinularia granosa Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14531 Dalbergia inundata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9540 Curvularia falcata Species Pleosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16053 Allium aflatunense Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3247 Orchis fusca Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16831 Hypericum patulum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11780 Alpinia rafflesiana Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14149 Saccharina japonica Species Laminariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1337 Sphyraena japonica Species Sphyraenidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14704 Ephedra frustillata Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15838 Psorospermum molluscum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13204 Mallotus metcalfianus Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5115 Abuta panurensis Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15377 Calea clematidea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4793 Discoglossus pictus Species Alytidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24523 Senecio anteuphorbium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13686 Lepraria lobificans Species Stereocaulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1069 Meum athamanticum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6380 Hydrocotyle vulgaris Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14167 Ambrosia artemisioides Species Asteraceae 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
NPT3504 Individual Protein Aldo-keto-reductase family 1 member C3 Homo sapiens Ki = 162000.0 nM PMID[525783]
NPT3505 Individual Protein Aldo-keto reductase family 1 member C1 Homo sapiens Ki = 106000.0 nM PMID[525783]
NPT3506 Individual Protein Aldo-keto reductase family 1 member C4 Homo sapiens Ki = 37000.0 nM PMID[525783]
NPT3507 Individual Protein Aldo-keto reductase family 1 member C2 Homo sapiens Ki = 18000.0 nM PMID[525783]
NPT3504 Individual Protein Aldo-keto-reductase family 1 member C3 Homo sapiens Ki = 21000.0 nM PMID[525785]
NPT3507 Individual Protein Aldo-keto reductase family 1 member C2 Homo sapiens Ki = 15000.0 nM PMID[525785]
NPT3505 Individual Protein Aldo-keto reductase family 1 member C1 Homo sapiens Ki = 106000.0 nM PMID[525785]
NPT3504 Individual Protein Aldo-keto-reductase family 1 member C3 Homo sapiens Ki = 24000.0 nM PMID[525786]
NPT3130 Organism Lepidium sativum Lepidium sativum Inhibition = 50.0 % PMID[525782]

☑ 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 NPC60120 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
0.9219 High Similarity NPC154728
0.9219 High Similarity NPC304665
0.9219 High Similarity NPC126899
0.8429 Intermediate Similarity NPC321017
0.8382 Intermediate Similarity NPC476614
0.8082 Intermediate Similarity NPC279537
0.803 Intermediate Similarity NPC125312
0.803 Intermediate Similarity NPC174560
0.7821 Intermediate Similarity NPC65350
0.7812 Intermediate Similarity NPC477201
0.7808 Intermediate Similarity NPC55527
0.7778 Intermediate Similarity NPC29328
0.775 Intermediate Similarity NPC6247
0.7742 Intermediate Similarity NPC281245
0.7714 Intermediate Similarity NPC476626
0.7671 Intermediate Similarity NPC300940
0.7625 Intermediate Similarity NPC142649
0.7619 Intermediate Similarity NPC139029
0.7619 Intermediate Similarity NPC36061
0.7619 Intermediate Similarity NPC294548
0.7619 Intermediate Similarity NPC1813
0.7606 Intermediate Similarity NPC476629
0.7571 Intermediate Similarity NPC197089
0.7564 Intermediate Similarity NPC47031
0.7536 Intermediate Similarity NPC234767
0.7534 Intermediate Similarity NPC469737
0.7534 Intermediate Similarity NPC288667
0.7532 Intermediate Similarity NPC201225
0.7532 Intermediate Similarity NPC164308
0.7532 Intermediate Similarity NPC477371
0.75 Intermediate Similarity NPC85813
0.75 Intermediate Similarity NPC424
0.75 Intermediate Similarity NPC25417
0.75 Intermediate Similarity NPC67608
0.75 Intermediate Similarity NPC88966
0.75 Intermediate Similarity NPC87564
0.75 Intermediate Similarity NPC281972
0.75 Intermediate Similarity NPC290563
0.75 Intermediate Similarity NPC32467
0.75 Intermediate Similarity NPC154245
0.75 Intermediate Similarity NPC6095
0.75 Intermediate Similarity NPC261831
0.7468 Intermediate Similarity NPC238991
0.7468 Intermediate Similarity NPC7414
0.7468 Intermediate Similarity NPC302661
0.7463 Intermediate Similarity NPC274927
0.7463 Intermediate Similarity NPC106851
0.7436 Intermediate Similarity NPC26139
0.7436 Intermediate Similarity NPC115418
0.7436 Intermediate Similarity NPC164218
0.7432 Intermediate Similarity NPC177826
0.7403 Intermediate Similarity NPC192006
0.7397 Intermediate Similarity NPC18543
0.7368 Intermediate Similarity NPC469646
0.7361 Intermediate Similarity NPC53302
0.7353 Intermediate Similarity NPC174447
0.7353 Intermediate Similarity NPC122521
0.7353 Intermediate Similarity NPC235242
0.7353 Intermediate Similarity NPC251042
0.7344 Intermediate Similarity NPC321062
0.7344 Intermediate Similarity NPC70387
0.7342 Intermediate Similarity NPC38350
0.7342 Intermediate Similarity NPC147066
0.7342 Intermediate Similarity NPC477372
0.7342 Intermediate Similarity NPC201912
0.7342 Intermediate Similarity NPC191711
0.7342 Intermediate Similarity NPC88735
0.7333 Intermediate Similarity NPC472966
0.7313 Intermediate Similarity NPC329819
0.7302 Intermediate Similarity NPC48162
0.7273 Intermediate Similarity NPC187777
0.7273 Intermediate Similarity NPC472014
0.7273 Intermediate Similarity NPC74685
0.7273 Intermediate Similarity NPC18951
0.7273 Intermediate Similarity NPC179764
0.726 Intermediate Similarity NPC144511
0.726 Intermediate Similarity NPC296522
0.726 Intermediate Similarity NPC199557
0.725 Intermediate Similarity NPC133391
0.725 Intermediate Similarity NPC260956
0.725 Intermediate Similarity NPC320514
0.7246 Intermediate Similarity NPC40082
0.7237 Intermediate Similarity NPC251435
0.7237 Intermediate Similarity NPC77501
0.7231 Intermediate Similarity NPC319589
0.7206 Intermediate Similarity NPC329550
0.7195 Intermediate Similarity NPC28887
0.7195 Intermediate Similarity NPC29447
0.7195 Intermediate Similarity NPC311702
0.7195 Intermediate Similarity NPC94531
0.7195 Intermediate Similarity NPC123319
0.7188 Intermediate Similarity NPC92114
0.7183 Intermediate Similarity NPC474329
0.7183 Intermediate Similarity NPC474304
0.7179 Intermediate Similarity NPC260814
0.7179 Intermediate Similarity NPC39547
0.7179 Intermediate Similarity NPC27949
0.7179 Intermediate Similarity NPC323249
0.7164 Intermediate Similarity NPC225929
0.7162 Intermediate Similarity NPC318766
0.716 Intermediate Similarity NPC477852
0.716 Intermediate Similarity NPC477373
0.716 Intermediate Similarity NPC83569
0.716 Intermediate Similarity NPC69279
0.716 Intermediate Similarity NPC102197
0.7143 Intermediate Similarity NPC180886
0.7143 Intermediate Similarity NPC322457
0.7143 Intermediate Similarity NPC224227
0.7121 Intermediate Similarity NPC54766
0.7121 Intermediate Similarity NPC473863
0.7121 Intermediate Similarity NPC274290
0.7105 Intermediate Similarity NPC283908
0.7105 Intermediate Similarity NPC251970
0.7105 Intermediate Similarity NPC241854
0.7105 Intermediate Similarity NPC206875
0.7105 Intermediate Similarity NPC3753
0.7105 Intermediate Similarity NPC183503
0.7105 Intermediate Similarity NPC161923
0.7105 Intermediate Similarity NPC103958
0.7105 Intermediate Similarity NPC237591
0.7105 Intermediate Similarity NPC476046
0.7101 Intermediate Similarity NPC243532
0.7097 Intermediate Similarity NPC180534
0.7089 Intermediate Similarity NPC84185
0.7089 Intermediate Similarity NPC476624
0.7089 Intermediate Similarity NPC158846
0.7089 Intermediate Similarity NPC196827
0.7089 Intermediate Similarity NPC471890
0.7089 Intermediate Similarity NPC469690
0.7089 Intermediate Similarity NPC66677
0.7089 Intermediate Similarity NPC274996
0.7089 Intermediate Similarity NPC472013
0.7083 Intermediate Similarity NPC18252
0.7073 Intermediate Similarity NPC7927
0.7073 Intermediate Similarity NPC238197
0.7073 Intermediate Similarity NPC230527
0.7067 Intermediate Similarity NPC319163
0.7067 Intermediate Similarity NPC67076
0.7067 Intermediate Similarity NPC160817
0.7051 Intermediate Similarity NPC240170
0.7051 Intermediate Similarity NPC276769
0.7051 Intermediate Similarity NPC120776
0.7051 Intermediate Similarity NPC97377
0.7051 Intermediate Similarity NPC165711
0.7051 Intermediate Similarity NPC107668
0.7042 Intermediate Similarity NPC473902
0.7037 Intermediate Similarity NPC129080
0.7037 Intermediate Similarity NPC477269
0.7037 Intermediate Similarity NPC477271
0.7037 Intermediate Similarity NPC477270
0.7031 Intermediate Similarity NPC262968
0.7027 Intermediate Similarity NPC10758
0.7027 Intermediate Similarity NPC469914
0.7027 Intermediate Similarity NPC250928
0.7013 Intermediate Similarity NPC279666
0.7013 Intermediate Similarity NPC474011
0.7013 Intermediate Similarity NPC192540
0.7013 Intermediate Similarity NPC201027
0.7013 Intermediate Similarity NPC476844
0.7 Intermediate Similarity NPC30675
0.7 Intermediate Similarity NPC201939
0.7 Intermediate Similarity NPC200446
0.7 Intermediate Similarity NPC475795
0.6988 Remote Similarity NPC473038
0.6988 Remote Similarity NPC476628
0.6988 Remote Similarity NPC269638
0.6988 Remote Similarity NPC11711
0.6986 Remote Similarity NPC278895
0.6986 Remote Similarity NPC472875
0.6984 Remote Similarity NPC5413
0.6984 Remote Similarity NPC149821
0.6974 Remote Similarity NPC470237
0.6974 Remote Similarity NPC35656
0.6974 Remote Similarity NPC472956
0.6962 Remote Similarity NPC169095
0.6962 Remote Similarity NPC218817
0.6962 Remote Similarity NPC476627
0.6962 Remote Similarity NPC469495
0.6962 Remote Similarity NPC74410
0.6962 Remote Similarity NPC11796
0.6962 Remote Similarity NPC179028
0.6957 Remote Similarity NPC259261
0.6951 Remote Similarity NPC310470
0.6951 Remote Similarity NPC168188
0.6951 Remote Similarity NPC167103
0.6951 Remote Similarity NPC470015
0.6933 Remote Similarity NPC472955
0.6933 Remote Similarity NPC67183
0.6923 Remote Similarity NPC110461
0.6923 Remote Similarity NPC216407
0.6923 Remote Similarity NPC266159
0.6923 Remote Similarity NPC61863
0.6923 Remote Similarity NPC69143
0.6923 Remote Similarity NPC469514
0.6923 Remote Similarity NPC215481
0.6923 Remote Similarity NPC12740
0.6923 Remote Similarity NPC20466
0.6923 Remote Similarity NPC472967
0.6914 Remote Similarity NPC470241
0.6914 Remote Similarity NPC316844

  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 NPC60120 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
0.7895 Intermediate Similarity NPD5368 Approved
0.7692 Intermediate Similarity NPD6435 Approved
0.7632 Intermediate Similarity NPD5784 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD3172 Approved
0.7564 Intermediate Similarity NPD5369 Approved
0.75 Intermediate Similarity NPD3194 Approved
0.75 Intermediate Similarity NPD3196 Approved
0.75 Intermediate Similarity NPD4266 Approved
0.75 Intermediate Similarity NPD3195 Phase 2
0.7468 Intermediate Similarity NPD4270 Approved
0.7468 Intermediate Similarity NPD4269 Approved
0.7436 Intermediate Similarity NPD4252 Approved
0.7317 Intermediate Similarity NPD5786 Approved
0.7195 Intermediate Similarity NPD5363 Approved
0.7179 Intermediate Similarity NPD4271 Approved
0.7179 Intermediate Similarity NPD4268 Approved
0.716 Intermediate Similarity NPD5362 Discontinued
0.7097 Intermediate Similarity NPD622 Approved
0.7083 Intermediate Similarity NPD7331 Phase 2
0.7031 Intermediate Similarity NPD28 Approved
0.7031 Intermediate Similarity NPD29 Approved
0.7 Intermediate Similarity NPD4821 Approved
0.7 Intermediate Similarity NPD5790 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD4822 Approved
0.7 Intermediate Similarity NPD4819 Approved
0.7 Intermediate Similarity NPD4820 Approved
0.6984 Remote Similarity NPD3173 Approved
0.6806 Remote Similarity NPD3197 Phase 1
0.6782 Remote Similarity NPD5785 Approved
0.6747 Remote Similarity NPD5332 Approved
0.6747 Remote Similarity NPD7154 Phase 3
0.6747 Remote Similarity NPD5331 Approved
0.6712 Remote Similarity NPD7341 Phase 2
0.6707 Remote Similarity NPD4790 Discontinued
0.6705 Remote Similarity NPD5284 Approved
0.6705 Remote Similarity NPD5281 Approved
0.6627 Remote Similarity NPD3667 Approved
0.6627 Remote Similarity NPD4223 Phase 3
0.6627 Remote Similarity NPD4221 Approved
0.6512 Remote Similarity NPD5690 Phase 2
0.6512 Remote Similarity NPD4249 Approved
0.6508 Remote Similarity NPD4222 Approved
0.6508 Remote Similarity NPD3174 Discontinued
0.6508 Remote Similarity NPD634 Phase 3
0.6506 Remote Similarity NPD857 Phase 3
0.6479 Remote Similarity NPD3198 Approved
0.6471 Remote Similarity NPD4786 Approved
0.6471 Remote Similarity NPD3133 Approved
0.6471 Remote Similarity NPD3665 Phase 1
0.6471 Remote Similarity NPD4197 Approved
0.6471 Remote Similarity NPD3666 Approved
0.6471 Remote Similarity NPD9298 Approved
0.6452 Remote Similarity NPD5696 Approved
0.6444 Remote Similarity NPD6399 Phase 3
0.6437 Remote Similarity NPD4250 Approved
0.6437 Remote Similarity NPD4251 Approved
0.6395 Remote Similarity NPD5329 Approved
0.6364 Remote Similarity NPD4518 Approved
0.6341 Remote Similarity NPD3617 Approved
0.6333 Remote Similarity NPD6079 Approved
0.6322 Remote Similarity NPD7521 Approved
0.6322 Remote Similarity NPD6098 Approved
0.6322 Remote Similarity NPD5330 Approved
0.6322 Remote Similarity NPD4694 Approved
0.6322 Remote Similarity NPD4689 Approved
0.6322 Remote Similarity NPD7334 Approved
0.6322 Remote Similarity NPD3618 Phase 1
0.6322 Remote Similarity NPD5205 Approved
0.6322 Remote Similarity NPD7146 Approved
0.6322 Remote Similarity NPD4688 Approved
0.6322 Remote Similarity NPD4690 Approved
0.6322 Remote Similarity NPD5279 Phase 3
0.6322 Remote Similarity NPD6409 Approved
0.6322 Remote Similarity NPD4693 Phase 3
0.6322 Remote Similarity NPD4138 Approved
0.6322 Remote Similarity NPD6684 Approved
0.6322 Remote Similarity NPD5280 Approved
0.6304 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6304 Remote Similarity NPD1693 Approved
0.6304 Remote Similarity NPD5695 Phase 3
0.6304 Remote Similarity NPD4629 Approved
0.6304 Remote Similarity NPD5210 Approved
0.6292 Remote Similarity NPD5370 Suspended
0.6292 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6292 Remote Similarity NPD6101 Approved
0.6292 Remote Similarity NPD5328 Approved
0.6279 Remote Similarity NPD5766 Clinical (unspecified phase)
0.625 Remote Similarity NPD39 Approved
0.6232 Remote Similarity NPD615 Clinical (unspecified phase)
0.6222 Remote Similarity NPD5207 Approved
0.6216 Remote Similarity NPD2664 Clinical (unspecified phase)
0.6207 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6203 Remote Similarity NPD6081 Approved
0.619 Remote Similarity NPD4695 Discontinued
0.618 Remote Similarity NPD6903 Approved
0.618 Remote Similarity NPD5208 Approved
0.618 Remote Similarity NPD6672 Approved
0.618 Remote Similarity NPD5737 Approved
0.618 Remote Similarity NPD7513 Clinical (unspecified phase)
0.617 Remote Similarity NPD6084 Phase 2
0.617 Remote Similarity NPD6083 Phase 2
0.6164 Remote Similarity NPD4246 Clinical (unspecified phase)
0.6154 Remote Similarity NPD4810 Clinical (unspecified phase)
0.6154 Remote Similarity NPD4137 Phase 3
0.6154 Remote Similarity NPD6411 Approved
0.6154 Remote Similarity NPD5694 Approved
0.6145 Remote Similarity NPD3732 Approved
0.6136 Remote Similarity NPD4623 Approved
0.6136 Remote Similarity NPD4519 Discontinued
0.6136 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6118 Remote Similarity NPD4692 Approved
0.6118 Remote Similarity NPD4139 Approved
0.6111 Remote Similarity NPD4753 Phase 2
0.6111 Remote Similarity NPD6080 Approved
0.6111 Remote Similarity NPD6673 Approved
0.6111 Remote Similarity NPD6904 Approved
0.6092 Remote Similarity NPD3668 Phase 3
0.6087 Remote Similarity NPD5778 Approved
0.6087 Remote Similarity NPD5779 Approved
0.6076 Remote Similarity NPD4747 Approved
0.6076 Remote Similarity NPD4691 Approved
0.6071 Remote Similarity NPD4195 Approved
0.6067 Remote Similarity NPD3573 Approved
0.6064 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6064 Remote Similarity NPD5222 Approved
0.6064 Remote Similarity NPD5221 Approved
0.6064 Remote Similarity NPD7614 Phase 1
0.6049 Remote Similarity NPD4058 Approved
0.6049 Remote Similarity NPD4687 Approved
0.6044 Remote Similarity NPD5692 Phase 3
0.6044 Remote Similarity NPD4096 Approved
0.6026 Remote Similarity NPD3621 Clinical (unspecified phase)
0.6024 Remote Similarity NPD4756 Discovery
0.6023 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6023 Remote Similarity NPD1694 Approved
0.6022 Remote Similarity NPD5122 Clinical (unspecified phase)
0.6 Remote Similarity NPD5173 Approved
0.6 Remote Similarity NPD5697 Approved
0.6 Remote Similarity NPD5276 Approved
0.5978 Remote Similarity NPD7983 Approved
0.5978 Remote Similarity NPD5693 Phase 1
0.5978 Remote Similarity NPD6050 Approved
0.5978 Remote Similarity NPD7515 Phase 2
0.5976 Remote Similarity NPD8039 Approved
0.5974 Remote Similarity NPD4224 Phase 2
0.5955 Remote Similarity NPD6422 Discontinued
0.5942 Remote Similarity NPD3186 Phase 1
0.5941 Remote Similarity NPD6011 Approved
0.5941 Remote Similarity NPD6899 Approved
0.5941 Remote Similarity NPD6881 Approved
0.5938 Remote Similarity NPD5326 Phase 3
0.5934 Remote Similarity NPD7285 Clinical (unspecified phase)
0.5918 Remote Similarity NPD5091 Approved
0.5914 Remote Similarity NPD4202 Approved
0.59 Remote Similarity NPD7128 Approved
0.59 Remote Similarity NPD5739 Approved
0.59 Remote Similarity NPD6402 Approved
0.59 Remote Similarity NPD6675 Approved
0.5897 Remote Similarity NPD4247 Clinical (unspecified phase)
0.5895 Remote Similarity NPD4697 Phase 3
0.5882 Remote Similarity NPD6013 Approved
0.5882 Remote Similarity NPD6014 Approved
0.5882 Remote Similarity NPD6012 Approved
0.5876 Remote Similarity NPD5286 Approved
0.5876 Remote Similarity NPD4696 Approved
0.5876 Remote Similarity NPD5285 Approved
0.587 Remote Similarity NPD1090 Approved
0.587 Remote Similarity NPD1089 Approved
0.587 Remote Similarity NPD1086 Approved
0.5862 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5862 Remote Similarity NPD5209 Approved
0.5862 Remote Similarity NPD4800 Clinical (unspecified phase)
0.5854 Remote Similarity NPD5733 Approved
0.5851 Remote Similarity NPD7748 Approved
0.5851 Remote Similarity NPD6001 Approved
0.5843 Remote Similarity NPD1733 Clinical (unspecified phase)
0.5842 Remote Similarity NPD5701 Approved
0.5833 Remote Similarity NPD4755 Approved
0.5825 Remote Similarity NPD7102 Approved
0.5825 Remote Similarity NPD6883 Approved
0.5825 Remote Similarity NPD7290 Approved
0.5816 Remote Similarity NPD5223 Approved
0.5806 Remote Similarity NPD9448 Phase 2
0.5806 Remote Similarity NPD7637 Suspended
0.5806 Remote Similarity NPD633 Phase 3
0.5806 Remote Similarity NPD77 Approved
0.5806 Remote Similarity NPD9450 Approved
0.5795 Remote Similarity NPD4788 Approved
0.5789 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5784 Remote Similarity NPD7320 Approved
0.5769 Remote Similarity NPD6869 Approved
0.5769 Remote Similarity NPD6847 Approved
0.5769 Remote Similarity NPD6108 Clinical (unspecified phase)
0.5769 Remote Similarity NPD6650 Approved
0.5769 Remote Similarity NPD6617 Approved
0.5769 Remote Similarity NPD6649 Approved
0.5769 Remote Similarity NPD8130 Phase 1
0.5761 Remote Similarity NPD800 Approved
0.5761 Remote Similarity NPD5346 Phase 2
0.5761 Remote Similarity NPD5347 Phase 2

  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