Structure

Physi-Chem Properties

Molecular Weight:  286.11
Volume:  269.914
LogP:  -0.985
LogD:  -0.725
LogS:  -1.132
# Rotatable Bonds:  4
TPSA:  119.61
# H-Bond Aceptor:  7
# H-Bond Donor:  5
# Rings:  2
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.45
Synthetic Accessibility Score:  3.321
Fsp3:  0.538
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.506
MDCK Permeability:  7.034446753095835e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.016
Human Intestinal Absorption (HIA):  0.575
20% Bioavailability (F20%):  0.005
30% Bioavailability (F30%):  0.958

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.324
Plasma Protein Binding (PPB):  31.933658599853516%
Volume Distribution (VD):  0.386
Pgp-substrate:  50.373291015625%

ADMET: Metabolism

CYP1A2-inhibitor:  0.092
CYP1A2-substrate:  0.041
CYP2C19-inhibitor:  0.019
CYP2C19-substrate:  0.405
CYP2C9-inhibitor:  0.001
CYP2C9-substrate:  0.107
CYP2D6-inhibitor:  0.01
CYP2D6-substrate:  0.332
CYP3A4-inhibitor:  0.005
CYP3A4-substrate:  0.052

ADMET: Excretion

Clearance (CL):  1.487
Half-life (T1/2):  0.803

ADMET: Toxicity

hERG Blockers:  0.12
Human Hepatotoxicity (H-HT):  0.029
Drug-inuced Liver Injury (DILI):  0.162
AMES Toxicity:  0.19
Rat Oral Acute Toxicity:  0.02
Maximum Recommended Daily Dose:  0.002
Skin Sensitization:  0.356
Carcinogencity:  0.538
Eye Corrosion:  0.003
Eye Irritation:  0.529
Respiratory Toxicity:  0.021

Download Data

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

  Natural Product: NPC269242

Natural Product ID:  NPC269242
Common Name*:   Gastrodin
IUPAC Name:   (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(hydroxymethyl)phenoxy]oxane-3,4,5-triol
Synonyms:  
Standard InCHIKey:  PUQSUZTXKPLAPR-UJPOAAIJSA-N
Standard InCHI:  InChI=1S/C13H18O7/c14-5-7-1-3-8(4-2-7)19-13-12(18)11(17)10(16)9(6-15)20-13/h1-4,9-18H,5-6H2/t9-,10-,11+,12-,13-/m1/s1
SMILES:  c1cc(ccc1CO)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL274739
PubChem CID:   115067
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates
          • [CHEMONTID:0002105] Glycosyl compounds
            • [CHEMONTID:0004165] Phenolic glycosides

*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
NPO22104 Trifolium pratense Species Fabaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0031-9422(00)94679-X]
NPO21079 Actinomadura hibisca Species Thermomonosporaceae Bacteria n.a. n.a. n.a. DOI[10.1021/jo00272a013]
NPO21587 Hypericum papuanum Species Hypericaceae Eukaryota aerial parts n.a. n.a. PMID[10650088]
NPO20889 Anastrepha suspensa Species Tephritidae Eukaryota n.a. n.a. n.a. PMID[10706642]
NPO20635 Dalbergia frutescens Species Fabaceae Eukaryota bark n.a. n.a. PMID[11076565]
NPO21587 Hypericum papuanum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[11421727]
NPO18141 Solanum torvum Species Solanaceae Eukaryota n.a. fruit n.a. PMID[11830167]
NPO21334 Artemisia dracunculus Species Asteraceae Eukaryota dried aerial organs n.a. n.a. PMID[14738379]
NPO21334 Artemisia dracunculus Species Asteraceae Eukaryota roots and stolons n.a. n.a. PMID[14738379]
NPO21334 Artemisia dracunculus Species Asteraceae Eukaryota leaves n.a. n.a. PMID[14738379]
NPO21334 Artemisia dracunculus Species Asteraceae Eukaryota underground organs n.a. n.a. PMID[14738379]
NPO21334 Artemisia dracunculus Species Asteraceae Eukaryota dried aerial organs n.a. n.a. PMID[14738379]
NPO1756 Cremastra appendiculata Species Orchidaceae Eukaryota n.a. bulb n.a. PMID[14994197]
NPO22309 Gastrodia elata Species Orchidaceae Eukaryota n.a. tuber n.a. PMID[15180301]
NPO1756 Cremastra appendiculata Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[15844951]
NPO21023 Astilbe koreana Species Saxifragaceae Eukaryota n.a. n.a. n.a. PMID[16580200]
NPO1756 Cremastra appendiculata Species Orchidaceae Eukaryota tubers n.a. n.a. PMID[16792409]
NPO22309 Gastrodia elata Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[17381154]
NPO21460 Anethum graveolens Species Apiaceae Eukaryota n.a. seed n.a. PMID[21049975]
NPO21079 Actinomadura hibisca Species Thermomonosporaceae Bacteria n.a. n.a. n.a. PMID[21119678]
NPO21470 Conoideocrella tenuis Species Clavicipitaceae Eukaryota n.a. mycelium n.a. PMID[21473608]
NPO21470 Conoideocrella tenuis Species Clavicipitaceae Eukaryota n.a. n.a. n.a. PMID[21473608]
NPO17553 Pleione bulbocodioides Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[23627123]
NPO21460 Anethum graveolens Species Apiaceae Eukaryota n.a. aerial part n.a. PMID[25154406]
NPO13106 Rhodomyrtus tomentosa Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[25466012]
NPO22309 Gastrodia elata Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[25843525]
NPO13106 Rhodomyrtus tomentosa Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[28245113]
NPO22104 Trifolium pratense Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[30199256]
NPO21334 Artemisia dracunculus Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[31815461]
NPO20045 Burkholderia cepacia Species Burkholderiaceae Bacteria n.a. n.a. n.a. PMID[3839140]
NPO20045 Burkholderia cepacia Species Burkholderiaceae Bacteria n.a. n.a. n.a. PMID[7684040]
NPO24658 Dillenia papuana Species Dilleniaceae Eukaryota n.a. n.a. n.a. PMID[7798959]
NPO21334 Artemisia dracunculus Species Asteraceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO21460 Anethum graveolens Species Apiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO21334 Artemisia dracunculus Species Asteraceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO21460 Anethum graveolens Species Apiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO21460 Anethum graveolens Species Apiaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO21334 Artemisia dracunculus Species Asteraceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO21460 Anethum graveolens Species Apiaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO21334 Artemisia dracunculus Species Asteraceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO21334 Artemisia dracunculus Species Asteraceae Eukaryota n.a. n.a. Database[FooDB]
NPO21460 Anethum graveolens Species Apiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO21460 Anethum graveolens Species Apiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO18141 Solanum torvum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22622 Coptis deltoidea Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13106 Rhodomyrtus tomentosa Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21460 Anethum graveolens Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19953 Lupinus formosus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22309 Gastrodia elata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22104 Trifolium pratense Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21334 Artemisia dracunculus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21460 Anethum graveolens Species Apiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO1756 Cremastra appendiculata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13106 Rhodomyrtus tomentosa Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19953 Lupinus formosus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22104 Trifolium pratense Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21334 Artemisia dracunculus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18141 Solanum torvum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21587 Hypericum papuanum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22309 Gastrodia elata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21460 Anethum graveolens Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22622 Coptis deltoidea Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20134 Dicliptera riparia Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4785 Persicaria thunbergii Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20508 Ilex kaushue Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18141 Solanum torvum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22104 Trifolium pratense Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17553 Pleione bulbocodioides Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12875 Pleione yunnanensis Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21460 Anethum graveolens Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO13106 Rhodomyrtus tomentosa Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1756 Cremastra appendiculata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22309 Gastrodia elata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21460 Anethum graveolens Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1756 Cremastra appendiculata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22622 Coptis deltoidea Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12875 Pleione yunnanensis Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO17553 Pleione bulbocodioides Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22309 Gastrodia elata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20045 Burkholderia cepacia Species Burkholderiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO21334 Artemisia dracunculus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19953 Lupinus formosus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22227 Sambucus ebulus Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22104 Trifolium pratense Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21587 Hypericum papuanum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20696 Colchicum macedonicum Species Colchicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20012 Wunderlichia mirabilis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22880 Aspergillus caespitosus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17581 Streptomyces fulvoviridis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO20134 Dicliptera riparia Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4785 Persicaria thunbergii Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12875 Pleione yunnanensis Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21079 Actinomadura hibisca Species Thermomonosporaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO21775 Zilla spinosa Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19799 Erwinia rhapontici Species Erwiniaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO19880 Palicourea alpina Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6873 Salvia xalapensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22622 Coptis deltoidea Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21212 Scrophularia smithii Species Scrophulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18141 Solanum torvum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22490 Limeum pterocarpum Species Limeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10757 Cyanospira rippkae Species Aphanizomenonaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO13106 Rhodomyrtus tomentosa Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21470 Conoideocrella tenuis Species Clavicipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21270 Nerita albicilla Species Neritidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17553 Pleione bulbocodioides Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22309 Gastrodia elata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22746 Salix sieboldiana Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8570 Ficus elastica Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22298 Inula thapsoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20190 Oxandra xylopioides Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20953 Coprosma acerosa Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20316 Hypselodoris cantabrica Species Chromodorididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21839 Cymathere triplicata n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO20889 Anastrepha suspensa Species Tephritidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20508 Ilex kaushue Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21905 Helianthopsis bishopii n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO4771 Tanacetum santolinoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21023 Astilbe koreana Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15871 Parmelia enteromorpha Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21400 Macrocystidia cucumis Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22551 Trifolium alexandrium Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22362 Tylophora flava Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20077 Posoqueria latifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20635 Dalbergia frutescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22689 Cassia carnaval Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24658 Dillenia papuana Species Dilleniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22042 Kaunia arbuscularis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21460 Anethum graveolens Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20764 Euphorbia caducifolia Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1756 Cremastra appendiculata Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29262 Cranfillia vulcanica Species Blechnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20827 Boronia muelleri 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
NPT675 Individual Protein Succinate semialdehyde dehydrogenase Homo sapiens IC50 > 1000000.0 nM PMID[494914]
NPT674 Individual Protein Gamma-amino-N-butyrate transaminase Homo sapiens IC50 > 1000000.0 nM PMID[494914]

☑ 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 NPC269242 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
0.9825 High Similarity NPC469412
0.9825 High Similarity NPC198734
0.9737 High Similarity NPC60589
0.9737 High Similarity NPC469708
0.9569 High Similarity NPC226712
0.9386 High Similarity NPC175771
0.9328 High Similarity NPC287429
0.9322 High Similarity NPC476142
0.9262 High Similarity NPC166040
0.925 High Similarity NPC470510
0.9211 High Similarity NPC313193
0.9106 High Similarity NPC248355
0.9106 High Similarity NPC270849
0.9106 High Similarity NPC26653
0.9098 High Similarity NPC198798
0.9043 High Similarity NPC157338
0.9032 High Similarity NPC80600
0.9032 High Similarity NPC472024
0.9024 High Similarity NPC146540
0.9024 High Similarity NPC40377
0.9024 High Similarity NPC302378
0.8968 High Similarity NPC25821
0.896 High Similarity NPC9912
0.896 High Similarity NPC121376
0.8952 High Similarity NPC295970
0.8952 High Similarity NPC97326
0.8934 High Similarity NPC12308
0.8889 High Similarity NPC26080
0.8889 High Similarity NPC303422
0.8889 High Similarity NPC299144
0.8889 High Similarity NPC85799
0.8889 High Similarity NPC148055
0.8889 High Similarity NPC165686
0.888 High Similarity NPC474491
0.8879 High Similarity NPC142319
0.8828 High Similarity NPC79957
0.8819 High Similarity NPC49074
0.8819 High Similarity NPC115022
0.8819 High Similarity NPC294166
0.881 High Similarity NPC65942
0.881 High Similarity NPC166168
0.881 High Similarity NPC248307
0.88 High Similarity NPC307110
0.88 High Similarity NPC218003
0.877 High Similarity NPC212176
0.876 High Similarity NPC166180
0.875 High Similarity NPC187194
0.875 High Similarity NPC130496
0.875 High Similarity NPC251981
0.875 High Similarity NPC188555
0.875 High Similarity NPC476411
0.875 High Similarity NPC13745
0.875 High Similarity NPC471029
0.875 High Similarity NPC48863
0.874 High Similarity NPC162093
0.873 High Similarity NPC262606
0.8696 High Similarity NPC46844
0.8692 High Similarity NPC262328
0.8692 High Similarity NPC87777
0.8692 High Similarity NPC470413
0.8692 High Similarity NPC138738
0.8682 High Similarity NPC238243
0.8672 High Similarity NPC215833
0.8672 High Similarity NPC69513
0.8672 High Similarity NPC6836
0.8655 High Similarity NPC9248
0.8632 High Similarity NPC301735
0.8615 High Similarity NPC103409
0.8615 High Similarity NPC242028
0.8615 High Similarity NPC40664
0.8615 High Similarity NPC3293
0.8615 High Similarity NPC186418
0.8615 High Similarity NPC164857
0.8615 High Similarity NPC165482
0.8615 High Similarity NPC37468
0.8615 High Similarity NPC138350
0.8615 High Similarity NPC197723
0.8615 High Similarity NPC203230
0.8607 High Similarity NPC11724
0.8605 High Similarity NPC87696
0.8605 High Similarity NPC35731
0.8605 High Similarity NPC470881
0.8595 High Similarity NPC469702
0.8595 High Similarity NPC282409
0.8594 High Similarity NPC269421
0.8594 High Similarity NPC252833
0.8594 High Similarity NPC470270
0.8584 High Similarity NPC37714
0.8584 High Similarity NPC152384
0.8584 High Similarity NPC8302
0.8561 High Similarity NPC106944
0.855 High Similarity NPC59324
0.855 High Similarity NPC124149
0.855 High Similarity NPC65530
0.8538 High Similarity NPC55040
0.8538 High Similarity NPC470236
0.8538 High Similarity NPC212729
0.8537 High Similarity NPC52097
0.8527 High Similarity NPC132895
0.8525 High Similarity NPC476448
0.8525 High Similarity NPC476872
0.8525 High Similarity NPC201402
0.8525 High Similarity NPC469703
0.8525 High Similarity NPC476445
0.8525 High Similarity NPC160854
0.8525 High Similarity NPC469704
0.8525 High Similarity NPC469548
0.8516 High Similarity NPC475067
0.8496 Intermediate Similarity NPC186406
0.8496 Intermediate Similarity NPC210192
0.8496 Intermediate Similarity NPC469661
0.8485 Intermediate Similarity NPC212770
0.8485 Intermediate Similarity NPC100389
0.8485 Intermediate Similarity NPC98777
0.848 Intermediate Similarity NPC167571
0.848 Intermediate Similarity NPC207179
0.848 Intermediate Similarity NPC278552
0.8473 Intermediate Similarity NPC172818
0.8473 Intermediate Similarity NPC294470
0.8473 Intermediate Similarity NPC52277
0.8473 Intermediate Similarity NPC25695
0.8473 Intermediate Similarity NPC104167
0.8473 Intermediate Similarity NPC177035
0.8473 Intermediate Similarity NPC469383
0.8473 Intermediate Similarity NPC475628
0.8473 Intermediate Similarity NPC199459
0.8462 Intermediate Similarity NPC34456
0.8462 Intermediate Similarity NPC107478
0.8455 Intermediate Similarity NPC55608
0.8455 Intermediate Similarity NPC469686
0.8455 Intermediate Similarity NPC266045
0.8435 Intermediate Similarity NPC251306
0.8433 Intermediate Similarity NPC469559
0.8433 Intermediate Similarity NPC189115
0.8433 Intermediate Similarity NPC128337
0.8433 Intermediate Similarity NPC84207
0.8433 Intermediate Similarity NPC5253
0.8433 Intermediate Similarity NPC49542
0.8433 Intermediate Similarity NPC139976
0.8433 Intermediate Similarity NPC475084
0.8433 Intermediate Similarity NPC230718
0.8433 Intermediate Similarity NPC145319
0.8433 Intermediate Similarity NPC472353
0.8433 Intermediate Similarity NPC60249
0.843 Intermediate Similarity NPC228907
0.8425 Intermediate Similarity NPC72529
0.8421 Intermediate Similarity NPC195814
0.8421 Intermediate Similarity NPC202700
0.8417 Intermediate Similarity NPC301651
0.8417 Intermediate Similarity NPC473556
0.8409 Intermediate Similarity NPC36434
0.8409 Intermediate Similarity NPC304152
0.8409 Intermediate Similarity NPC134260
0.84 Intermediate Similarity NPC94276
0.84 Intermediate Similarity NPC109822
0.8397 Intermediate Similarity NPC185778
0.839 Intermediate Similarity NPC115379
0.8387 Intermediate Similarity NPC471067
0.8385 Intermediate Similarity NPC215037
0.837 Intermediate Similarity NPC185307
0.837 Intermediate Similarity NPC478239
0.837 Intermediate Similarity NPC116922
0.837 Intermediate Similarity NPC46092
0.837 Intermediate Similarity NPC473044
0.837 Intermediate Similarity NPC252169
0.837 Intermediate Similarity NPC470950
0.8361 Intermediate Similarity NPC135961
0.8359 Intermediate Similarity NPC86030
0.8359 Intermediate Similarity NPC5851
0.8358 Intermediate Similarity NPC273932
0.8358 Intermediate Similarity NPC476442
0.8358 Intermediate Similarity NPC215512
0.8358 Intermediate Similarity NPC89686
0.8358 Intermediate Similarity NPC108674
0.8358 Intermediate Similarity NPC257095
0.8358 Intermediate Similarity NPC76871
0.8358 Intermediate Similarity NPC80098
0.8346 Intermediate Similarity NPC147821
0.8346 Intermediate Similarity NPC298821
0.8346 Intermediate Similarity NPC118787
0.8346 Intermediate Similarity NPC183181
0.8346 Intermediate Similarity NPC288416
0.8346 Intermediate Similarity NPC111247
0.8346 Intermediate Similarity NPC163332
0.8346 Intermediate Similarity NPC292056
0.8346 Intermediate Similarity NPC319625
0.8346 Intermediate Similarity NPC41706
0.8333 Intermediate Similarity NPC157554
0.8333 Intermediate Similarity NPC83218
0.8333 Intermediate Similarity NPC126991
0.832 Intermediate Similarity NPC232454
0.832 Intermediate Similarity NPC470907
0.832 Intermediate Similarity NPC178449
0.8309 Intermediate Similarity NPC225445
0.8309 Intermediate Similarity NPC473045
0.8309 Intermediate Similarity NPC168579
0.8309 Intermediate Similarity NPC470235
0.8309 Intermediate Similarity NPC25292
0.8309 Intermediate Similarity NPC469313
0.8309 Intermediate Similarity NPC177597

  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 NPC269242 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
0.9569 High Similarity NPD1091 Approved
0.8276 Intermediate Similarity NPD290 Approved
0.8205 Intermediate Similarity NPD2684 Approved
0.8083 Intermediate Similarity NPD7843 Approved
0.803 Intermediate Similarity NPD1613 Approved
0.803 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8014 Intermediate Similarity NPD1653 Approved
0.792 Intermediate Similarity NPD1357 Approved
0.7914 Intermediate Similarity NPD5058 Phase 3
0.7886 Intermediate Similarity NPD7157 Approved
0.7881 Intermediate Similarity NPD968 Approved
0.784 Intermediate Similarity NPD1548 Phase 1
0.7803 Intermediate Similarity NPD3027 Phase 3
0.7734 Intermediate Similarity NPD3705 Approved
0.7734 Intermediate Similarity NPD1610 Phase 2
0.7727 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7721 Intermediate Similarity NPD4536 Approved
0.7721 Intermediate Similarity NPD4538 Approved
0.7721 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7698 Intermediate Similarity NPD1652 Phase 2
0.7698 Intermediate Similarity NPD6674 Discontinued
0.7681 Intermediate Similarity NPD7266 Discontinued
0.7664 Intermediate Similarity NPD5960 Phase 3
0.7664 Intermediate Similarity NPD5588 Approved
0.7652 Intermediate Similarity NPD2861 Phase 2
0.7652 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD8455 Phase 2
0.7615 Intermediate Similarity NPD3685 Discontinued
0.7594 Intermediate Similarity NPD4908 Phase 1
0.7584 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7578 Intermediate Similarity NPD5846 Approved
0.7578 Intermediate Similarity NPD6516 Phase 2
0.7557 Intermediate Similarity NPD8651 Approved
0.7556 Intermediate Similarity NPD6233 Phase 2
0.7542 Intermediate Similarity NPD291 Approved
0.7537 Intermediate Similarity NPD3179 Approved
0.7537 Intermediate Similarity NPD3180 Approved
0.7522 Intermediate Similarity NPD9365 Approved
0.7521 Intermediate Similarity NPD1358 Approved
0.75 Intermediate Similarity NPD821 Approved
0.7481 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7464 Intermediate Similarity NPD7097 Phase 1
0.7462 Intermediate Similarity NPD422 Phase 1
0.7447 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7445 Intermediate Similarity NPD4340 Discontinued
0.7419 Intermediate Similarity NPD228 Approved
0.7398 Intermediate Similarity NPD556 Approved
0.7394 Intermediate Similarity NPD4628 Phase 3
0.7353 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7353 Intermediate Similarity NPD6798 Discontinued
0.7323 Intermediate Similarity NPD6671 Approved
0.7319 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7319 Intermediate Similarity NPD5124 Phase 1
0.7308 Intermediate Similarity NPD5125 Phase 3
0.7308 Intermediate Similarity NPD5126 Approved
0.7299 Intermediate Similarity NPD4062 Phase 3
0.728 Intermediate Similarity NPD969 Suspended
0.7273 Intermediate Similarity NPD2231 Phase 2
0.7273 Intermediate Similarity NPD2235 Phase 2
0.7266 Intermediate Similarity NPD6653 Approved
0.7254 Intermediate Similarity NPD2424 Discontinued
0.7246 Intermediate Similarity NPD4060 Phase 1
0.7239 Intermediate Similarity NPD1820 Approved
0.7239 Intermediate Similarity NPD1819 Approved
0.7239 Intermediate Similarity NPD1817 Approved
0.7239 Intermediate Similarity NPD1818 Approved
0.7222 Intermediate Similarity NPD5535 Approved
0.7197 Intermediate Similarity NPD1535 Discovery
0.7194 Intermediate Similarity NPD6355 Discontinued
0.7183 Intermediate Similarity NPD1375 Discontinued
0.7176 Intermediate Similarity NPD1778 Approved
0.7163 Intermediate Similarity NPD7033 Discontinued
0.7154 Intermediate Similarity NPD1894 Discontinued
0.7154 Intermediate Similarity NPD3134 Approved
0.7153 Intermediate Similarity NPD4535 Phase 3
0.7152 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD7054 Approved
0.7143 Intermediate Similarity NPD1481 Phase 2
0.7121 Intermediate Similarity NPD3496 Discontinued
0.7107 Intermediate Similarity NPD7074 Phase 3
0.7107 Intermediate Similarity NPD7472 Approved
0.7103 Intermediate Similarity NPD2677 Approved
0.7101 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD1048 Approved
0.7097 Intermediate Similarity NPD9552 Approved
0.7092 Intermediate Similarity NPD4978 Clinical (unspecified phase)
0.709 Intermediate Similarity NPD6582 Phase 2
0.709 Intermediate Similarity NPD6583 Phase 3
0.709 Intermediate Similarity NPD4749 Approved
0.7089 Intermediate Similarity NPD3818 Discontinued
0.7075 Intermediate Similarity NPD3536 Discontinued
0.7071 Intermediate Similarity NPD5735 Approved
0.7063 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD5762 Approved
0.7063 Intermediate Similarity NPD5763 Approved
0.7063 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD6797 Phase 2
0.7059 Intermediate Similarity NPD558 Phase 2
0.7059 Intermediate Similarity NPD5647 Approved
0.7054 Intermediate Similarity NPD191 Approved
0.705 Intermediate Similarity NPD1423 Approved
0.7042 Intermediate Similarity NPD4108 Discontinued
0.7037 Intermediate Similarity NPD3225 Approved
0.7031 Intermediate Similarity NPD1241 Discontinued
0.7031 Intermediate Similarity NPD5283 Phase 1
0.7029 Intermediate Similarity NPD3167 Approved
0.7029 Intermediate Similarity NPD3166 Approved
0.7029 Intermediate Similarity NPD3164 Approved
0.7029 Intermediate Similarity NPD7095 Approved
0.7029 Intermediate Similarity NPD3165 Approved
0.7023 Intermediate Similarity NPD1182 Approved
0.7021 Intermediate Similarity NPD3052 Approved
0.7021 Intermediate Similarity NPD3054 Approved
0.7019 Intermediate Similarity NPD7251 Discontinued
0.7019 Intermediate Similarity NPD6559 Discontinued
0.7014 Intermediate Similarity NPD1549 Phase 2
0.7007 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD5837 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD1558 Phase 1
0.6985 Remote Similarity NPD6362 Approved
0.6985 Remote Similarity NPD1794 Approved
0.6975 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6975 Remote Similarity NPD7808 Phase 3
0.6974 Remote Similarity NPD37 Approved
0.6963 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6963 Remote Similarity NPD2983 Phase 2
0.6963 Remote Similarity NPD2982 Phase 2
0.6954 Remote Similarity NPD4380 Phase 2
0.6953 Remote Similarity NPD1138 Approved
0.6948 Remote Similarity NPD4965 Approved
0.6948 Remote Similarity NPD4967 Phase 2
0.6948 Remote Similarity NPD4966 Approved
0.6944 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6944 Remote Similarity NPD6005 Phase 3
0.6944 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6944 Remote Similarity NPD6004 Phase 3
0.6944 Remote Similarity NPD6002 Phase 3
0.6944 Remote Similarity NPD521 Clinical (unspecified phase)
0.6943 Remote Similarity NPD3787 Discontinued
0.694 Remote Similarity NPD776 Approved
0.6939 Remote Similarity NPD5756 Phase 2
0.6935 Remote Similarity NPD9697 Approved
0.6934 Remote Similarity NPD6584 Phase 3
0.6934 Remote Similarity NPD3691 Phase 2
0.6934 Remote Similarity NPD3690 Phase 2
0.6933 Remote Similarity NPD3686 Approved
0.6933 Remote Similarity NPD3687 Approved
0.6929 Remote Similarity NPD1726 Clinical (unspecified phase)
0.6928 Remote Similarity NPD2978 Approved
0.6928 Remote Similarity NPD2977 Approved
0.6906 Remote Similarity NPD4625 Phase 3
0.6894 Remote Similarity NPD9545 Approved
0.6892 Remote Similarity NPD1774 Approved
0.6892 Remote Similarity NPD6799 Approved
0.6892 Remote Similarity NPD7212 Phase 2
0.6892 Remote Similarity NPD7213 Phase 3
0.6891 Remote Similarity NPD2934 Approved
0.6891 Remote Similarity NPD2933 Approved
0.6889 Remote Similarity NPD1608 Approved
0.6889 Remote Similarity NPD2981 Phase 2
0.6884 Remote Similarity NPD3018 Phase 2
0.6879 Remote Similarity NPD4140 Approved
0.6879 Remote Similarity NPD2238 Phase 2
0.6879 Remote Similarity NPD7199 Phase 2
0.6875 Remote Similarity NPD7228 Approved
0.6875 Remote Similarity NPD2239 Approved
0.6875 Remote Similarity NPD2240 Approved
0.6875 Remote Similarity NPD1139 Approved
0.6875 Remote Similarity NPD1137 Approved
0.687 Remote Similarity NPD3596 Phase 2
0.6867 Remote Similarity NPD5403 Approved
0.6866 Remote Similarity NPD3847 Discontinued
0.6863 Remote Similarity NPD1934 Approved
0.6861 Remote Similarity NPD987 Approved
0.6859 Remote Similarity NPD6234 Discontinued
0.6857 Remote Similarity NPD3056 Clinical (unspecified phase)
0.6855 Remote Similarity NPD9501 Approved
0.6852 Remote Similarity NPD7007 Discovery
0.685 Remote Similarity NPD5451 Approved
0.6849 Remote Similarity NPD4236 Phase 3
0.6849 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6849 Remote Similarity NPD4237 Approved
0.6846 Remote Similarity NPD4123 Phase 3
0.6846 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6842 Remote Similarity NPD5585 Approved
0.6842 Remote Similarity NPD6382 Discontinued
0.6839 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6833 Remote Similarity NPD2859 Approved
0.6833 Remote Similarity NPD2860 Approved
0.6829 Remote Similarity NPD846 Approved
0.6829 Remote Similarity NPD940 Approved
0.6818 Remote Similarity NPD5772 Approved
0.6818 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6818 Remote Similarity NPD5773 Approved
0.6818 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6812 Remote Similarity NPD6917 Clinical (unspecified phase)
0.681 Remote Similarity NPD7685 Pre-registration
0.6797 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6795 Remote Similarity NPD7075 Discontinued
0.6786 Remote Similarity NPD5163 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