Structure

Physi-Chem Properties

Molecular Weight:  132.04
Volume:  119.004
LogP:  -0.938
LogD:  -0.799
LogS:  0.571
# Rotatable Bonds:  1
TPSA:  66.76
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  1
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.433
Synthetic Accessibility Score:  3.471
Fsp3:  0.8
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.132
MDCK Permeability:  0.0007758949650451541
Pgp-inhibitor:  0.001
Pgp-substrate:  0.033
Human Intestinal Absorption (HIA):  0.016
20% Bioavailability (F20%):  0.005
30% Bioavailability (F30%):  0.709

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.403
Plasma Protein Binding (PPB):  12.631021499633789%
Volume Distribution (VD):  0.576
Pgp-substrate:  81.15999603271484%

ADMET: Metabolism

CYP1A2-inhibitor:  0.02
CYP1A2-substrate:  0.063
CYP2C19-inhibitor:  0.014
CYP2C19-substrate:  0.138
CYP2C9-inhibitor:  0.002
CYP2C9-substrate:  0.102
CYP2D6-inhibitor:  0.004
CYP2D6-substrate:  0.143
CYP3A4-inhibitor:  0.009
CYP3A4-substrate:  0.09

ADMET: Excretion

Clearance (CL):  4.803
Half-life (T1/2):  0.899

ADMET: Toxicity

hERG Blockers:  0.032
Human Hepatotoxicity (H-HT):  0.08
Drug-inuced Liver Injury (DILI):  0.249
AMES Toxicity:  0.1
Rat Oral Acute Toxicity:  0.013
Maximum Recommended Daily Dose:  0.014
Skin Sensitization:  0.178
Carcinogencity:  0.343
Eye Corrosion:  0.184
Eye Irritation:  0.956
Respiratory Toxicity:  0.03

Download Data

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

  Natural Product: NPC46254

Natural Product ID:  NPC46254
Common Name*:   2-Deoxy-D-Ribono-1,4-Lactone
IUPAC Name:   (4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-one
Synonyms:  
Standard InCHIKey:  YIXDEYPPAGPYDP-IUYQGCFVSA-N
Standard InCHI:  InChI=1S/C5H8O4/c6-2-4-3(7)1-5(8)9-4/h3-4,6-7H,1-2H2/t3-,4+/m0/s1
SMILES:  C1[C@@H]([C@@H](CO)OC1=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL98888
PubChem CID:   161815
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000050] Lactones
        • [CHEMONTID:0001245] Gamma butyrolactones

*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]
NPO30270 Cordyceps sinensis Species Cordycipitaceae Eukaryota n.a. mycelium n.a. PMID[10423860]
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 underground 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 dried aerial organs n.a. n.a. PMID[14738379]
NPO21334 Artemisia dracunculus Species Asteraceae Eukaryota dried aerial organs n.a. n.a. PMID[14738379]
NPO6583 Clematis chinensis Species Ranunculaceae Eukaryota roots n.a. n.a. PMID[15387651]
NPO30270 Cordyceps sinensis Species Cordycipitaceae Eukaryota n.a. n.a. n.a. PMID[15863936]
NPO21023 Astilbe koreana Species Saxifragaceae Eukaryota n.a. n.a. n.a. PMID[16580200]
NPO6583 Clematis chinensis Species Ranunculaceae Eukaryota roots and rhizomes Shaoguan, Guangdong Province, China 2007-Dec PMID[20540535]
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]
NPO30270 Cordyceps sinensis Species Cordycipitaceae Eukaryota n.a. mycelium n.a. PMID[21848266]
NPO30270 Cordyceps sinensis Species Cordycipitaceae Eukaryota n.a. n.a. n.a. PMID[21848266]
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]
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 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]
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]
NPO19953 Lupinus formosus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
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]
NPO21460 Anethum graveolens Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21334 Artemisia dracunculus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13106 Rhodomyrtus tomentosa Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22104 Trifolium pratense Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6583 Clematis chinensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30270 Cordyceps sinensis Species Cordycipitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21460 Anethum graveolens Species Apiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO19953 Lupinus formosus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13106 Rhodomyrtus tomentosa Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22104 Trifolium pratense Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6583 Clematis chinensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21587 Hypericum papuanum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18141 Solanum torvum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21334 Artemisia dracunculus Species Asteraceae 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]
NPO4785 Persicaria thunbergii Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20134 Dicliptera riparia Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20508 Ilex kaushue Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22104 Trifolium pratense Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30270 Cordyceps sinensis Species Cordycipitaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18141 Solanum torvum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO6583 Clematis chinensis Species Ranunculaceae 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]
NPO21460 Anethum graveolens Species Apiaceae 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]
NPO6583 Clematis chinensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20635 Dalbergia frutescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22104 Trifolium pratense Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20827 Boronia muelleri Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19953 Lupinus formosus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20045 Burkholderia cepacia Species Burkholderiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO22227 Sambucus ebulus Species Adoxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22880 Aspergillus caespitosus Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21587 Hypericum papuanum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20012 Wunderlichia mirabilis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17581 Streptomyces fulvoviridis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO20696 Colchicum macedonicum Species Colchicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4785 Persicaria thunbergii Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18141 Solanum torvum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20134 Dicliptera riparia Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21775 Zilla spinosa Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21470 Conoideocrella tenuis Species Clavicipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21079 Actinomadura hibisca Species Thermomonosporaceae Bacteria 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]
NPO22490 Limeum pterocarpum Species Limeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6583 Clematis chinensis Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19880 Palicourea alpina Species Rubiaceae 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]
NPO19799 Erwinia rhapontici Species Erwiniaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO6873 Salvia xalapensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20316 Hypselodoris cantabrica Species Chromodorididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21270 Nerita albicilla Species Neritidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20190 Oxandra xylopioides Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22298 Inula thapsoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20889 Anastrepha suspensa Species Tephritidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22746 Salix sieboldiana Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4771 Tanacetum santolinoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20953 Coprosma acerosa Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22362 Tylophora flava Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8570 Ficus elastica Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21400 Macrocystidia cucumis Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20077 Posoqueria latifolia Species Rubiaceae 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]
NPO22689 Cassia carnaval Species Fabaceae 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]
NPO22551 Trifolium alexandrium Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20508 Ilex kaushue Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21460 Anethum graveolens Species Apiaceae 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]
NPO21023 Astilbe koreana Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20764 Euphorbia caducifolia Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29262 Cranfillia vulcanica Species Blechnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15871 Parmelia enteromorpha Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21334 Artemisia dracunculus 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
NPT2766 Individual Protein Prostanoid EP2 receptor Homo sapiens Decrease = 33.0 % PMID[486746]
NPT2766 Individual Protein Prostanoid EP2 receptor Homo sapiens Decrease = 78.0 % PMID[486746]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 6.43 ug.mL-1 PMID[486747]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 = 6.83 ug.mL-1 PMID[486747]

☑ 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 NPC46254 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
0.8491 Intermediate Similarity NPC293692
0.7818 Intermediate Similarity NPC220922
0.7818 Intermediate Similarity NPC61567
0.7551 Intermediate Similarity NPC242655
0.7551 Intermediate Similarity NPC38891
0.7547 Intermediate Similarity NPC277878
0.7407 Intermediate Similarity NPC19676
0.7407 Intermediate Similarity NPC323401
0.7407 Intermediate Similarity NPC196612
0.7321 Intermediate Similarity NPC198377
0.7292 Intermediate Similarity NPC35661
0.7273 Intermediate Similarity NPC6883
0.72 Intermediate Similarity NPC270088
0.7167 Intermediate Similarity NPC268243
0.7167 Intermediate Similarity NPC317651
0.7167 Intermediate Similarity NPC258690
0.7143 Intermediate Similarity NPC313565
0.7143 Intermediate Similarity NPC228782
0.7143 Intermediate Similarity NPC259982
0.7115 Intermediate Similarity NPC247546
0.7115 Intermediate Similarity NPC172086
0.7091 Intermediate Similarity NPC65985
0.7069 Intermediate Similarity NPC179624
0.6957 Remote Similarity NPC321699
0.6939 Remote Similarity NPC192402
0.6939 Remote Similarity NPC121018
0.6939 Remote Similarity NPC24751
0.6939 Remote Similarity NPC97444
0.6939 Remote Similarity NPC19044
0.6939 Remote Similarity NPC100742
0.6889 Remote Similarity NPC227267
0.6842 Remote Similarity NPC60830
0.6842 Remote Similarity NPC68743
0.68 Remote Similarity NPC320189
0.6739 Remote Similarity NPC191084
0.6739 Remote Similarity NPC250870
0.6739 Remote Similarity NPC168052
0.6735 Remote Similarity NPC320331
0.6731 Remote Similarity NPC133771
0.6719 Remote Similarity NPC469925
0.6719 Remote Similarity NPC32148
0.6667 Remote Similarity NPC469937
0.6667 Remote Similarity NPC320588
0.6667 Remote Similarity NPC293378
0.6667 Remote Similarity NPC29721
0.6667 Remote Similarity NPC323945
0.6667 Remote Similarity NPC23155
0.6667 Remote Similarity NPC53463
0.6618 Remote Similarity NPC125164
0.6557 Remote Similarity NPC320296
0.6531 Remote Similarity NPC94368
0.65 Remote Similarity NPC320032
0.6471 Remote Similarity NPC310220
0.6458 Remote Similarity NPC206924
0.6364 Remote Similarity NPC82315
0.6364 Remote Similarity NPC328954
0.6346 Remote Similarity NPC319680
0.6304 Remote Similarity NPC125575
0.6296 Remote Similarity NPC252918
0.6296 Remote Similarity NPC230789
0.6286 Remote Similarity NPC228411
0.625 Remote Similarity NPC103612
0.625 Remote Similarity NPC24967
0.625 Remote Similarity NPC159089
0.625 Remote Similarity NPC5505
0.623 Remote Similarity NPC322855
0.619 Remote Similarity NPC10659
0.6182 Remote Similarity NPC200618
0.6182 Remote Similarity NPC131770
0.6167 Remote Similarity NPC3547
0.6154 Remote Similarity NPC317182
0.6154 Remote Similarity NPC176500
0.6154 Remote Similarity NPC291502
0.6154 Remote Similarity NPC298699
0.6154 Remote Similarity NPC134252
0.6154 Remote Similarity NPC213159
0.6154 Remote Similarity NPC86191
0.6129 Remote Similarity NPC17935
0.6129 Remote Similarity NPC470363
0.6094 Remote Similarity NPC325773
0.6087 Remote Similarity NPC187058
0.6087 Remote Similarity NPC182541
0.6087 Remote Similarity NPC127074
0.6087 Remote Similarity NPC197207
0.6087 Remote Similarity NPC149070
0.6078 Remote Similarity NPC266553
0.6071 Remote Similarity NPC82512
0.6056 Remote Similarity NPC161038
0.6042 Remote Similarity NPC317203
0.6042 Remote Similarity NPC325165
0.6038 Remote Similarity NPC320240
0.6038 Remote Similarity NPC70756
0.6034 Remote Similarity NPC317680
0.6032 Remote Similarity NPC81896
0.6032 Remote Similarity NPC321919
0.6029 Remote Similarity NPC28526
0.6 Remote Similarity NPC475232
0.6 Remote Similarity NPC474100
0.6 Remote Similarity NPC473775
0.6 Remote Similarity NPC314103
0.6 Remote Similarity NPC51249
0.6 Remote Similarity NPC297440
0.6 Remote Similarity NPC128713
0.6 Remote Similarity NPC473699
0.6 Remote Similarity NPC475260
0.5965 Remote Similarity NPC90904
0.5965 Remote Similarity NPC323574
0.5965 Remote Similarity NPC329128
0.5965 Remote Similarity NPC322158
0.5957 Remote Similarity NPC99700
0.5926 Remote Similarity NPC273545
0.5918 Remote Similarity NPC313405
0.5909 Remote Similarity NPC12040
0.5909 Remote Similarity NPC76881
0.5893 Remote Similarity NPC112363
0.589 Remote Similarity NPC275530
0.5882 Remote Similarity NPC316217
0.5882 Remote Similarity NPC222792
0.587 Remote Similarity NPC198126
0.5862 Remote Similarity NPC100096
0.5862 Remote Similarity NPC329095
0.5857 Remote Similarity NPC184550
0.5857 Remote Similarity NPC185419
0.5833 Remote Similarity NPC473948
0.5833 Remote Similarity NPC289979
0.5833 Remote Similarity NPC7814
0.5818 Remote Similarity NPC63182
0.5818 Remote Similarity NPC176017
0.5818 Remote Similarity NPC73906
0.5818 Remote Similarity NPC52700
0.5818 Remote Similarity NPC145045
0.5818 Remote Similarity NPC105329
0.5818 Remote Similarity NPC165846
0.5818 Remote Similarity NPC255377
0.5818 Remote Similarity NPC21209
0.5818 Remote Similarity NPC69445
0.5818 Remote Similarity NPC92246
0.5818 Remote Similarity NPC289758
0.5818 Remote Similarity NPC199857
0.5818 Remote Similarity NPC285364
0.5811 Remote Similarity NPC470014
0.5789 Remote Similarity NPC26253
0.5778 Remote Similarity NPC234005
0.5775 Remote Similarity NPC291228
0.5775 Remote Similarity NPC308096
0.5769 Remote Similarity NPC240109
0.5763 Remote Similarity NPC320043
0.5763 Remote Similarity NPC103672
0.5745 Remote Similarity NPC281883
0.5735 Remote Similarity NPC206601
0.5733 Remote Similarity NPC99651
0.5714 Remote Similarity NPC42526
0.5714 Remote Similarity NPC192065
0.5714 Remote Similarity NPC293908
0.5714 Remote Similarity NPC321087
0.5714 Remote Similarity NPC277475
0.5714 Remote Similarity NPC325034
0.5714 Remote Similarity NPC66052
0.5714 Remote Similarity NPC86412
0.569 Remote Similarity NPC55678
0.5686 Remote Similarity NPC325454
0.5676 Remote Similarity NPC474003
0.5672 Remote Similarity NPC476655
0.5672 Remote Similarity NPC469926
0.5672 Remote Similarity NPC476657
0.5672 Remote Similarity NPC476654
0.5667 Remote Similarity NPC323361
0.5667 Remote Similarity NPC130683
0.566 Remote Similarity NPC325307
0.566 Remote Similarity NPC322956
0.5652 Remote Similarity NPC50228
0.5652 Remote Similarity NPC97736
0.5652 Remote Similarity NPC250619
0.5652 Remote Similarity NPC174368
0.5625 Remote Similarity NPC328710
0.5625 Remote Similarity NPC217218
0.5625 Remote Similarity NPC286695
0.5625 Remote Similarity NPC18224
0.5616 Remote Similarity NPC81052
0.5616 Remote Similarity NPC179922
0.5616 Remote Similarity NPC217725
0.5614 Remote Similarity NPC14144
0.5614 Remote Similarity NPC106872
0.5606 Remote Similarity NPC106216
0.5606 Remote Similarity NPC88898
0.56 Remote Similarity NPC475616
0.56 Remote Similarity NPC11796
0.56 Remote Similarity NPC218817
0.56 Remote Similarity NPC233231

  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 NPC46254 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
0.7818 Intermediate Similarity NPD8959 Approved
0.7547 Intermediate Similarity NPD64 Approved
0.7547 Intermediate Similarity NPD66 Approved
0.7547 Intermediate Similarity NPD9008 Approved
0.7547 Intermediate Similarity NPD9010 Approved
0.7547 Intermediate Similarity NPD9011 Approved
0.7547 Intermediate Similarity NPD9009 Approved
0.7547 Intermediate Similarity NPD72 Approved
0.7547 Intermediate Similarity NPD65 Approved
0.7547 Intermediate Similarity NPD8960 Approved
0.7547 Intermediate Similarity NPD9007 Approved
0.7167 Intermediate Similarity NPD8961 Approved
0.7115 Intermediate Similarity NPD9003 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD9005 Phase 3
0.7115 Intermediate Similarity NPD9004 Approved
0.7018 Intermediate Similarity NPD73 Approved
0.6939 Remote Similarity NPD8605 Approved
0.6939 Remote Similarity NPD8604 Approved
0.6939 Remote Similarity NPD8600 Approved
0.6939 Remote Similarity NPD8598 Approved
0.6939 Remote Similarity NPD8599 Approved
0.6939 Remote Similarity NPD8602 Approved
0.6939 Remote Similarity NPD8603 Approved
0.6939 Remote Similarity NPD8601 Approved
0.6727 Remote Similarity NPD9002 Approved
0.6727 Remote Similarity NPD9001 Clinical (unspecified phase)
0.6719 Remote Similarity NPD897 Approved
0.6719 Remote Similarity NPD898 Approved
0.6719 Remote Similarity NPD896 Approved
0.6667 Remote Similarity NPD9006 Approved
0.6667 Remote Similarity NPD8964 Approved
0.6667 Remote Similarity NPD3730 Approved
0.6667 Remote Similarity NPD9126 Approved
0.6667 Remote Similarity NPD3728 Approved
0.6667 Remote Similarity NPD71 Approved
0.6667 Remote Similarity NPD9129 Approved
0.6481 Remote Similarity NPD70 Approved
0.6481 Remote Similarity NPD9121 Approved
0.6481 Remote Similarity NPD9122 Approved
0.6481 Remote Similarity NPD9128 Approved
0.6481 Remote Similarity NPD108 Approved
0.6481 Remote Similarity NPD9127 Approved
0.6481 Remote Similarity NPD9130 Phase 3
0.6481 Remote Similarity NPD9125 Approved
0.6481 Remote Similarity NPD9123 Approved
0.6481 Remote Similarity NPD109 Approved
0.6481 Remote Similarity NPD9124 Approved
0.6471 Remote Similarity NPD8957 Approved
0.629 Remote Similarity NPD9120 Clinical (unspecified phase)
0.6154 Remote Similarity NPD8788 Approved
0.6087 Remote Similarity NPD8814 Phase 3
0.6056 Remote Similarity NPD376 Approved
0.6056 Remote Similarity NPD11 Approved
0.5893 Remote Similarity NPD9139 Approved
0.5893 Remote Similarity NPD6125 Clinical (unspecified phase)
0.587 Remote Similarity NPD8618 Approved
0.5833 Remote Similarity NPD8857 Approved
0.5818 Remote Similarity NPD9000 Phase 3
0.5818 Remote Similarity NPD8997 Approved
0.5818 Remote Similarity NPD8993 Phase 1
0.5818 Remote Similarity NPD8998 Phase 2
0.5818 Remote Similarity NPD8999 Phase 3
0.5775 Remote Similarity NPD3181 Approved
0.5763 Remote Similarity NPD9049 Discontinued
0.5763 Remote Similarity NPD9050 Approved
0.5745 Remote Similarity NPD9636 Phase 2
0.5733 Remote Similarity NPD7329 Approved
0.5714 Remote Similarity NPD9052 Approved
0.5714 Remote Similarity NPD9053 Approved
0.5714 Remote Similarity NPD9051 Approved
0.5667 Remote Similarity NPD895 Approved
0.5667 Remote Similarity NPD894 Approved
0.5667 Remote Similarity NPD889 Approved
0.5667 Remote Similarity NPD887 Approved
0.566 Remote Similarity NPD9116 Phase 1
0.5652 Remote Similarity NPD8617 Approved
0.5652 Remote Similarity NPD8619 Approved
0.5614 Remote Similarity NPD8966 Approved
0.5614 Remote Similarity NPD8965 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