Structure

Physi-Chem Properties

Molecular Weight:  178.03
Volume:  169.086
LogP:  1.315
LogD:  1.312
LogS:  -2.65
# Rotatable Bonds:  0
TPSA:  70.67
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.635
Synthetic Accessibility Score:  2.484
Fsp3:  0.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.776
MDCK Permeability:  9.405770470038988e-06
Pgp-inhibitor:  0.002
Pgp-substrate:  0.69
Human Intestinal Absorption (HIA):  0.012
20% Bioavailability (F20%):  0.856
30% Bioavailability (F30%):  0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.037
Plasma Protein Binding (PPB):  87.20314025878906%
Volume Distribution (VD):  0.74
Pgp-substrate:  24.106355667114258%

ADMET: Metabolism

CYP1A2-inhibitor:  0.968
CYP1A2-substrate:  0.495
CYP2C19-inhibitor:  0.166
CYP2C19-substrate:  0.06
CYP2C9-inhibitor:  0.31
CYP2C9-substrate:  0.923
CYP2D6-inhibitor:  0.614
CYP2D6-substrate:  0.577
CYP3A4-inhibitor:  0.472
CYP3A4-substrate:  0.113

ADMET: Excretion

Clearance (CL):  10.349
Half-life (T1/2):  0.905

ADMET: Toxicity

hERG Blockers:  0.055
Human Hepatotoxicity (H-HT):  0.093
Drug-inuced Liver Injury (DILI):  0.435
AMES Toxicity:  0.279
Rat Oral Acute Toxicity:  0.149
Maximum Recommended Daily Dose:  0.211
Skin Sensitization:  0.914
Carcinogencity:  0.594
Eye Corrosion:  0.523
Eye Irritation:  0.982
Respiratory Toxicity:  0.489

Download Data

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

  Natural Product: NPC185497

Natural Product ID:  NPC185497
Common Name*:   5,7-Dihydroxychromone
IUPAC Name:   5,7-dihydroxychromen-4-one
Synonyms:  
Standard InCHIKey:  NYCXYKOXLNBYID-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C9H6O4/c10-5-3-7(12)9-6(11)1-2-13-8(9)4-5/h1-4,10,12H
SMILES:  Oc1cc(O)c2c(c1)occc2=O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3604316
PubChem CID:   5281343
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000123] Benzopyrans
        • [CHEMONTID:0003410] 1-benzopyrans
          • [CHEMONTID:0000144] Chromones

*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
NPO25426 Arachis hypogaea Species n.a. n.a. n.a. n.a. 2007; 2008 DOI[10.1007/s11746-010-1589-7]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.1016/j.foodchem.2009.03.042]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.3136/fstr.15.499]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.5897/AJB10.140]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.5897/AJB2010.000-3252]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota Flowers n.a. n.a. DOI[10.5897/JMPR.9000078]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[10606602]
NPO809 Leitneria floridana Species Simaroubaceae Eukaryota n.a. aerial part n.a. PMID[11141127]
NPO25426 Arachis hypogaea Species n.a. n.a. n.a. cotyledon n.a. PMID[11283027]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. flower n.a. PMID[12130858]
NPO25426 Arachis hypogaea Species n.a. n.a. n.a. seed n.a. PMID[12670184]
NPO24454 Begonia nantoensis Species Begoniaceae Eukaryota n.a. rhizome n.a. PMID[14993759]
NPO27517 Crinum latifolium Species Amaryllidaceae Eukaryota n.a. leaf n.a. PMID[15595606]
NPO30804 Cudrania tricuspidata Species Moraceae Eukaryota n.a. root n.a. PMID[15787460]
NPO30804 Cudrania tricuspidata Species Moraceae Eukaryota n.a. n.a. n.a. PMID[15787460]
NPO30804 Cudrania tricuspidata Species Moraceae Eukaryota n.a. n.a. n.a. PMID[16203143]
NPO5645 Silybum marianum Species Asteraceae Eukaryota n.a. whole plant n.a. PMID[16394559]
NPO5635 Bauhinia purpurea Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[16562827]
NPO30804 Cudrania tricuspidata Species Moraceae Eukaryota n.a. n.a. n.a. PMID[16919944]
NPO5635 Bauhinia purpurea Species Fabaceae Eukaryota roots Phitsanulok Province, Thailand 2004-MAY PMID[17480099]
NPO5635 Bauhinia purpurea Species Fabaceae Eukaryota n.a. root n.a. PMID[17480099]
NPO30804 Cudrania tricuspidata Species Moraceae Eukaryota root bark n.a. n.a. PMID[17608532]
NPO30804 Cudrania tricuspidata Species Moraceae Eukaryota n.a. n.a. n.a. PMID[17950599]
NPO30804 Cudrania tricuspidata Species Moraceae Eukaryota fruits n.a. n.a. PMID[19113968]
NPO30804 Cudrania tricuspidata Species Moraceae Eukaryota Roots n.a. n.a. PMID[19191562]
NPO30804 Cudrania tricuspidata Species Moraceae Eukaryota n.a. root n.a. PMID[19280148]
NPO30804 Cudrania tricuspidata Species Moraceae Eukaryota n.a. n.a. n.a. PMID[19285413]
NPO30804 Cudrania tricuspidata Species Moraceae Eukaryota n.a. n.a. n.a. PMID[19660948]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. PMID[20815207]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[21319773]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. leaf n.a. PMID[21319773]
NPO30804 Cudrania tricuspidata Species Moraceae Eukaryota n.a. root n.a. PMID[21319773]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. bark n.a. PMID[21319773]
NPO25426 Arachis hypogaea Species n.a. n.a. n.a. seed n.a. PMID[21348467]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. leaf n.a. PMID[22207282]
NPO25426 Arachis hypogaea Species n.a. n.a. n.a. n.a. n.a. PMID[22537213]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[23806866]
NPO5645 Silybum marianum Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[24456525]
NPO5645 Silybum marianum Species Asteraceae Eukaryota Seeds n.a. n.a. PMID[24597776]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers Tongxiang, China n.a. PMID[24621197]
NPO28265 Morus alba Species Moraceae Eukaryota root bark University of Veterinary and Pharmaceutical Sciences Brno (UVPS Brno), Brno, Czech Republic 2011-APR PMID[24901948]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. Konya, Turkey 2007-APR PMID[24901948]
NPO8797 Cudrania tricuspidata Species Moraceae Eukaryota Root barks n.a. n.a. PMID[25051453]
NPO30804 Cudrania tricuspidata Species Moraceae Eukaryota Roots n.a. n.a. PMID[25322455]
NPO28265 Morus alba Species Moraceae Eukaryota leaves Chungbuk, Korea n.a. PMID[25935644]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[25981820]
NPO5755.1 Bauhinia glauca Under-species n.a. n.a. n.a. n.a. n.a. PMID[26096681]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[26099993]
NPO30804 Cudrania tricuspidata Species Moraceae Eukaryota root barks purchased from the local herbal market, Chungbuk, Korea 2012-JUL PMID[26227773]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. latex n.a. PMID[27294120]
NPO8797 Cudrania tricuspidata Species Moraceae Eukaryota n.a. n.a. n.a. PMID[27420919]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota Flowers n.a. n.a. PMID[28156114]
NPO25426 Arachis hypogaea Species n.a. n.a. Peanut Skins n.a. n.a. PMID[28231711]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota Flowers n.a. n.a. PMID[28248102]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[29400471]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota Aerial Parts n.a. n.a. PMID[30726671]
NPO28265 Morus alba Species Moraceae Eukaryota Root barks n.a. n.a. PMID[3097265]
NPO17626 Gentiana algida Species Gentianaceae Eukaryota n.a. whole plant n.a. PMID[8588862]
NPO25426 Arachis hypogaea Species n.a. n.a. Oil n.a. n.a. Database[FooDB]
NPO25426 Arachis hypogaea Species n.a. n.a. Seed n.a. n.a. Database[FooDB]
NPO25426 Arachis hypogaea Species n.a. n.a. n.a. n.a. Database[FooDB]
NPO25426 Arachis hypogaea Species n.a. n.a. n.a. n.a. Database[FooDB]
NPO25426 Arachis hypogaea Species n.a. n.a. Leaf n.a. n.a. Database[FooDB]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25426 Arachis hypogaea Species n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO30804 Cudrania tricuspidata Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4014 Erigeron breviscapus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO27517 Crinum latifolium Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24454 Begonia nantoensis Species Begoniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17626 Gentiana algida Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5645 Silybum marianum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25426 Arachis hypogaea Species n.a. n.a. Oils n.a. Database[Phenol-Explorer]
NPO25426 Arachis hypogaea Species n.a. n.a. Seeds n.a. Database[Phenol-Explorer]
NPO4014 Erigeron breviscapus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8797 Cudrania tricuspidata Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5645 Silybum marianum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25716 Persicaria orientalis Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24454 Begonia nantoensis Species Begoniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25426 Arachis hypogaea Species n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO17626 Gentiana algida Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO27517 Crinum latifolium Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO30804 Cudrania tricuspidata Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17626 Gentiana algida Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25426 Arachis hypogaea Species n.a. n.a. n.a. n.a. n.a. Database[TCM_Taiwan]
NPO5645 Silybum marianum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25716 Persicaria orientalis Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4014 Erigeron breviscapus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5645 Silybum marianum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7317 Citrus aurantium Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2455 Thermopsis mollis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9881 Petrosia hebes Species Petrosiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6828 Purpura aperta Species Muricidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4014 Erigeron breviscapus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9608 Lepraria citrina Species Stereocaulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24454 Begonia nantoensis Species Begoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO809 Leitneria floridana Species Simaroubaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4628 Aloe deltoideodonta Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17626 Gentiana algida Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8807 Laurentia longiflora n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO4382 Elmerrillia papuana n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO25426 Arachis hypogaea Species n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO8977 0tholaena aschenborniana Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25475 Syphonota geographica Species Aplysiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20440 Chrysanthemum x morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3357 Alnus cordata Species Betulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5645 Silybum marianum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1490 Goldfussia yunnanensis n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO5635 Bauhinia purpurea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27517 Crinum latifolium Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22258 Chrysanthemum indicum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8797 Cudrania tricuspidata Species Moraceae 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
NPT1120 Individual Protein Pancreatic triacylglycerol lipase Sus scrofa Inhibition = 17.5 % PMID[511253]
NPT1120 Individual Protein Pancreatic triacylglycerol lipase Sus scrofa IC50 > 100000.0 nM PMID[511253]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 6.83 % PMID[511252]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. EC50 = 1900.0 nM PMID[511254]

☑ 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 NPC185497 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
0.9919 High Similarity NPC60558
0.9683 High Similarity NPC65060
0.9535 High Similarity NPC39426
0.9535 High Similarity NPC234560
0.952 High Similarity NPC186098
0.952 High Similarity NPC80694
0.9462 High Similarity NPC235428
0.9462 High Similarity NPC87545
0.9453 High Similarity NPC129132
0.9453 High Similarity NPC257756
0.9453 High Similarity NPC87231
0.9453 High Similarity NPC212631
0.9453 High Similarity NPC205468
0.944 High Similarity NPC128428
0.944 High Similarity NPC305518
0.9389 High Similarity NPC212767
0.9389 High Similarity NPC209560
0.9389 High Similarity NPC294409
0.9389 High Similarity NPC162680
0.9389 High Similarity NPC7013
0.9389 High Similarity NPC116632
0.9389 High Similarity NPC303644
0.9389 High Similarity NPC181124
0.938 High Similarity NPC188646
0.938 High Similarity NPC56031
0.938 High Similarity NPC472365
0.938 High Similarity NPC312318
0.938 High Similarity NPC263670
0.938 High Similarity NPC242294
0.938 High Similarity NPC175098
0.938 High Similarity NPC139813
0.938 High Similarity NPC223457
0.938 High Similarity NPC192304
0.938 High Similarity NPC337373
0.9375 High Similarity NPC308037
0.9375 High Similarity NPC475589
0.9375 High Similarity NPC64359
0.9375 High Similarity NPC31872
0.9375 High Similarity NPC473584
0.9375 High Similarity NPC262359
0.9375 High Similarity NPC313618
0.9318 High Similarity NPC279668
0.9318 High Similarity NPC309154
0.9318 High Similarity NPC90665
0.9318 High Similarity NPC12175
0.9318 High Similarity NPC278323
0.9318 High Similarity NPC55162
0.9313 High Similarity NPC193792
0.9308 High Similarity NPC286336
0.9308 High Similarity NPC164136
0.9308 High Similarity NPC172262
0.9302 High Similarity NPC25937
0.9297 High Similarity NPC270369
0.9297 High Similarity NPC5515
0.9297 High Similarity NPC250057
0.9291 High Similarity NPC212379
0.9291 High Similarity NPC8005
0.9291 High Similarity NPC69235
0.9291 High Similarity NPC78662
0.9248 High Similarity NPC295384
0.9248 High Similarity NPC49242
0.9242 High Similarity NPC250266
0.9242 High Similarity NPC266597
0.9242 High Similarity NPC290291
0.9242 High Similarity NPC188879
0.9242 High Similarity NPC275055
0.9237 High Similarity NPC60667
0.9231 High Similarity NPC50898
0.9231 High Similarity NPC82225
0.9231 High Similarity NPC144051
0.9231 High Similarity NPC18877
0.9231 High Similarity NPC57601
0.9231 High Similarity NPC28753
0.9231 High Similarity NPC20560
0.9231 High Similarity NPC294593
0.9231 High Similarity NPC78540
0.9231 High Similarity NPC213216
0.9231 High Similarity NPC159623
0.9231 High Similarity NPC204960
0.9231 High Similarity NPC274121
0.9219 High Similarity NPC42292
0.9219 High Similarity NPC247779
0.9219 High Similarity NPC307732
0.9179 High Similarity NPC144118
0.9179 High Similarity NPC80962
0.9179 High Similarity NPC326109
0.9179 High Similarity NPC101366
0.9179 High Similarity NPC213659
0.9179 High Similarity NPC204985
0.9179 High Similarity NPC259166
0.9179 High Similarity NPC219917
0.9179 High Similarity NPC172250
0.9179 High Similarity NPC215311
0.9179 High Similarity NPC48624
0.9173 High Similarity NPC147686
0.9173 High Similarity NPC472460
0.9173 High Similarity NPC99333
0.9173 High Similarity NPC124269
0.9173 High Similarity NPC280284
0.9173 High Similarity NPC25427
0.9173 High Similarity NPC188947
0.9173 High Similarity NPC329225
0.9167 High Similarity NPC12165
0.9167 High Similarity NPC150399
0.9167 High Similarity NPC473887
0.9167 High Similarity NPC168105
0.9167 High Similarity NPC222633
0.9167 High Similarity NPC234133
0.9167 High Similarity NPC472367
0.9167 High Similarity NPC127447
0.9167 High Similarity NPC194281
0.9167 High Similarity NPC476333
0.9167 High Similarity NPC472364
0.9167 High Similarity NPC231772
0.9167 High Similarity NPC66349
0.9167 High Similarity NPC186838
0.9167 High Similarity NPC41461
0.9167 High Similarity NPC25287
0.9167 High Similarity NPC477243
0.9167 High Similarity NPC240593
0.9167 High Similarity NPC47815
0.9167 High Similarity NPC98115
0.9167 High Similarity NPC1486
0.9167 High Similarity NPC29353
0.9167 High Similarity NPC473391
0.9167 High Similarity NPC477242
0.9167 High Similarity NPC124784
0.9167 High Similarity NPC477244
0.9167 High Similarity NPC249606
0.9167 High Similarity NPC274109
0.916 High Similarity NPC125920
0.9154 High Similarity NPC10971
0.9154 High Similarity NPC203817
0.9141 High Similarity NPC230818
0.9127 High Similarity NPC65041
0.9111 High Similarity NPC268204
0.9111 High Similarity NPC52789
0.9111 High Similarity NPC26051
0.9111 High Similarity NPC469404
0.9111 High Similarity NPC55832
0.9104 High Similarity NPC473076
0.9104 High Similarity NPC261234
0.9104 High Similarity NPC283429
0.9104 High Similarity NPC201541
0.9104 High Similarity NPC23257
0.9104 High Similarity NPC469523
0.9104 High Similarity NPC470211
0.9098 High Similarity NPC287246
0.9098 High Similarity NPC476480
0.9098 High Similarity NPC13768
0.9098 High Similarity NPC299379
0.9098 High Similarity NPC295261
0.9098 High Similarity NPC296490
0.9098 High Similarity NPC79943
0.9098 High Similarity NPC32441
0.9098 High Similarity NPC160972
0.9098 High Similarity NPC472419
0.9098 High Similarity NPC107586
0.9098 High Similarity NPC84585
0.9098 High Similarity NPC153979
0.9098 High Similarity NPC12296
0.9098 High Similarity NPC243083
0.9098 High Similarity NPC317119
0.9091 High Similarity NPC151113
0.9091 High Similarity NPC131039
0.9091 High Similarity NPC9985
0.9091 High Similarity NPC156092
0.9091 High Similarity NPC13575
0.9091 High Similarity NPC239495
0.9084 High Similarity NPC108113
0.9084 High Similarity NPC93756
0.9077 High Similarity NPC186097
0.9077 High Similarity NPC475009
0.9077 High Similarity NPC475008
0.9077 High Similarity NPC164236
0.9077 High Similarity NPC66384
0.9077 High Similarity NPC113006
0.9077 High Similarity NPC309717
0.9077 High Similarity NPC112192
0.9077 High Similarity NPC189106
0.9077 High Similarity NPC128348
0.907 High Similarity NPC84772
0.9062 High Similarity NPC293453
0.9037 High Similarity NPC253822
0.9037 High Similarity NPC471587
0.9037 High Similarity NPC281207
0.9037 High Similarity NPC269652
0.903 High Similarity NPC118813
0.903 High Similarity NPC21350
0.903 High Similarity NPC471620
0.903 High Similarity NPC472368
0.9023 High Similarity NPC187432
0.9023 High Similarity NPC187826
0.9023 High Similarity NPC13408
0.9023 High Similarity NPC116775
0.9023 High Similarity NPC216361
0.9023 High Similarity NPC213603
0.9023 High Similarity NPC174999
0.9023 High Similarity NPC256042
0.9023 High Similarity NPC281917

  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 NPC185497 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
0.9535 High Similarity NPD1510 Phase 2
0.9375 High Similarity NPD1240 Approved
0.9231 High Similarity NPD1607 Approved
0.9173 High Similarity NPD1549 Phase 2
0.9098 High Similarity NPD1552 Clinical (unspecified phase)
0.9098 High Similarity NPD1550 Clinical (unspecified phase)
0.875 High Similarity NPD970 Clinical (unspecified phase)
0.8643 High Similarity NPD4378 Clinical (unspecified phase)
0.8623 High Similarity NPD1878 Clinical (unspecified phase)
0.8603 High Similarity NPD2796 Approved
0.8601 High Similarity NPD4380 Phase 2
0.8571 High Similarity NPD1511 Approved
0.8511 High Similarity NPD7410 Clinical (unspecified phase)
0.8467 Intermediate Similarity NPD1551 Phase 2
0.8451 Intermediate Similarity NPD1512 Approved
0.844 Intermediate Similarity NPD6799 Approved
0.8288 Intermediate Similarity NPD7411 Suspended
0.8255 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8248 Intermediate Similarity NPD6651 Approved
0.8239 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.8231 Intermediate Similarity NPD1934 Approved
0.8227 Intermediate Similarity NPD3750 Approved
0.8188 Intermediate Similarity NPD3882 Suspended
0.8176 Intermediate Similarity NPD2801 Approved
0.8176 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8133 Intermediate Similarity NPD7075 Discontinued
0.8125 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.8121 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.812 Intermediate Similarity NPD1203 Approved
0.8108 Intermediate Similarity NPD6801 Discontinued
0.8102 Intermediate Similarity NPD943 Approved
0.8095 Intermediate Similarity NPD6599 Discontinued
0.8088 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.8062 Intermediate Similarity NPD9545 Approved
0.8054 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8054 Intermediate Similarity NPD7819 Suspended
0.8047 Intermediate Similarity NPD9493 Approved
0.803 Intermediate Similarity NPD9717 Approved
0.8028 Intermediate Similarity NPD2800 Approved
0.8028 Intermediate Similarity NPD1243 Approved
0.8014 Intermediate Similarity NPD5403 Approved
0.8014 Intermediate Similarity NPD920 Approved
0.8 Intermediate Similarity NPD5401 Approved
0.7955 Intermediate Similarity NPD422 Phase 1
0.7943 Intermediate Similarity NPD2935 Discontinued
0.7923 Intermediate Similarity NPD1548 Phase 1
0.7902 Intermediate Similarity NPD2654 Approved
0.7902 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7895 Intermediate Similarity NPD3749 Approved
0.7881 Intermediate Similarity NPD3817 Phase 2
0.7877 Intermediate Similarity NPD2532 Approved
0.7877 Intermediate Similarity NPD2534 Approved
0.7877 Intermediate Similarity NPD2533 Approved
0.7872 Intermediate Similarity NPD3748 Approved
0.7834 Intermediate Similarity NPD3818 Discontinued
0.7829 Intermediate Similarity NPD7768 Phase 2
0.7821 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.782 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7786 Intermediate Similarity NPD230 Phase 1
0.7762 Intermediate Similarity NPD2344 Approved
0.7746 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7746 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7707 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7707 Intermediate Similarity NPD6166 Phase 2
0.7707 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7698 Intermediate Similarity NPD74 Approved
0.7698 Intermediate Similarity NPD9266 Approved
0.7681 Intermediate Similarity NPD6832 Phase 2
0.7674 Intermediate Similarity NPD1241 Discontinued
0.7673 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7673 Intermediate Similarity NPD7054 Approved
0.7664 Intermediate Similarity NPD2798 Approved
0.7647 Intermediate Similarity NPD5402 Approved
0.7628 Intermediate Similarity NPD6959 Discontinued
0.7625 Intermediate Similarity NPD7472 Approved
0.7619 Intermediate Similarity NPD9264 Approved
0.7619 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD9263 Approved
0.7619 Intermediate Similarity NPD9267 Approved
0.7613 Intermediate Similarity NPD919 Approved
0.7597 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.758 Intermediate Similarity NPD6232 Discontinued
0.7578 Intermediate Similarity NPD6797 Phase 2
0.7578 Intermediate Similarity NPD5953 Discontinued
0.7571 Intermediate Similarity NPD1296 Phase 2
0.7571 Intermediate Similarity NPD411 Approved
0.7571 Intermediate Similarity NPD2313 Discontinued
0.7562 Intermediate Similarity NPD7286 Phase 2
0.7556 Intermediate Similarity NPD1610 Phase 2
0.7551 Intermediate Similarity NPD2309 Approved
0.7547 Intermediate Similarity NPD7473 Discontinued
0.7536 Intermediate Similarity NPD1019 Discontinued
0.7531 Intermediate Similarity NPD7251 Discontinued
0.7516 Intermediate Similarity NPD1247 Approved
0.7516 Intermediate Similarity NPD7074 Phase 3
0.75 Intermediate Similarity NPD3972 Approved
0.75 Intermediate Similarity NPD2799 Discontinued
0.75 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD7808 Phase 3
0.7485 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD4628 Phase 3
0.7482 Intermediate Similarity NPD9494 Approved
0.7452 Intermediate Similarity NPD5494 Approved
0.7413 Intermediate Similarity NPD447 Suspended
0.7391 Intermediate Similarity NPD3225 Approved
0.7379 Intermediate Similarity NPD7033 Discontinued
0.7372 Intermediate Similarity NPD9269 Phase 2
0.7355 Intermediate Similarity NPD1465 Phase 2
0.7348 Intermediate Similarity NPD9281 Approved
0.7338 Intermediate Similarity NPD1164 Approved
0.7338 Intermediate Similarity NPD1470 Approved
0.7333 Intermediate Similarity NPD9268 Approved
0.7329 Intermediate Similarity NPD6099 Approved
0.7329 Intermediate Similarity NPD6100 Approved
0.7324 Intermediate Similarity NPD3268 Approved
0.7317 Intermediate Similarity NPD6559 Discontinued
0.7305 Intermediate Similarity NPD4908 Phase 1
0.7303 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7302 Intermediate Similarity NPD9261 Approved
0.7301 Intermediate Similarity NPD1729 Discontinued
0.7299 Intermediate Similarity NPD1201 Approved
0.7292 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.726 Intermediate Similarity NPD4308 Phase 3
0.725 Intermediate Similarity NPD5711 Approved
0.725 Intermediate Similarity NPD5710 Approved
0.7248 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD7390 Discontinued
0.7214 Intermediate Similarity NPD2797 Approved
0.7212 Intermediate Similarity NPD6104 Discontinued
0.7208 Intermediate Similarity NPD3226 Approved
0.7205 Intermediate Similarity NPD3926 Phase 2
0.7203 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7203 Intermediate Similarity NPD3764 Approved
0.7197 Intermediate Similarity NPD4288 Approved
0.7183 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD5124 Phase 1
0.7172 Intermediate Similarity NPD1933 Approved
0.7153 Intermediate Similarity NPD520 Approved
0.7152 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD1876 Approved
0.7134 Intermediate Similarity NPD5844 Phase 1
0.7122 Intermediate Similarity NPD1481 Phase 2
0.7122 Intermediate Similarity NPD1608 Approved
0.7103 Intermediate Similarity NPD1613 Approved
0.7103 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7103 Intermediate Similarity NPD3140 Approved
0.7103 Intermediate Similarity NPD3142 Approved
0.7097 Intermediate Similarity NPD7458 Discontinued
0.7092 Intermediate Similarity NPD3266 Approved
0.7092 Intermediate Similarity NPD3267 Approved
0.7087 Intermediate Similarity NPD940 Approved
0.7087 Intermediate Similarity NPD846 Approved
0.708 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7067 Intermediate Similarity NPD1652 Phase 2
0.7063 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7052 Intermediate Similarity NPD4360 Phase 2
0.7052 Intermediate Similarity NPD4363 Phase 3
0.705 Intermediate Similarity NPD1535 Discovery
0.7047 Intermediate Similarity NPD2346 Discontinued
0.7014 Intermediate Similarity NPD3027 Phase 3
0.7011 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD4361 Phase 2
0.7007 Intermediate Similarity NPD1894 Discontinued
0.6993 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6986 Remote Similarity NPD4307 Phase 2
0.6981 Remote Similarity NPD2296 Approved
0.698 Remote Similarity NPD5404 Approved
0.698 Remote Similarity NPD5406 Approved
0.698 Remote Similarity NPD5408 Approved
0.698 Remote Similarity NPD5405 Approved
0.697 Remote Similarity NPD3751 Discontinued
0.6951 Remote Similarity NPD7784 Clinical (unspecified phase)
0.695 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6948 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6933 Remote Similarity NPD1471 Phase 3
0.6923 Remote Similarity NPD1653 Approved
0.6923 Remote Similarity NPD9697 Approved
0.6919 Remote Similarity NPD4287 Approved
0.6908 Remote Similarity NPD7003 Approved
0.6906 Remote Similarity NPD1778 Approved
0.6906 Remote Similarity NPD17 Approved
0.6899 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6883 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6863 Remote Similarity NPD2354 Approved
0.6855 Remote Similarity NPD6844 Discontinued
0.6849 Remote Similarity NPD6798 Discontinued
0.6848 Remote Similarity NPD2403 Approved
0.6839 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6839 Remote Similarity NPD4662 Approved
0.6839 Remote Similarity NPD4661 Approved
0.6831 Remote Similarity NPD4749 Approved
0.6821 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6818 Remote Similarity NPD1358 Approved
0.6818 Remote Similarity NPD7440 Discontinued
0.6809 Remote Similarity NPD1091 Approved
0.6806 Remote Similarity NPD6917 Clinical (unspecified phase)
0.6792 Remote Similarity NPD5889 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