Structure

Physi-Chem Properties

Molecular Weight:  238.06
Volume:  247.606
LogP:  3.846
LogD:  3.02
LogS:  -3.688
# Rotatable Bonds:  1
TPSA:  50.44
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.708
Synthetic Accessibility Score:  1.931
Fsp3:  0.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.803
MDCK Permeability:  1.440442429156974e-05
Pgp-inhibitor:  0.096
Pgp-substrate:  0.405
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.989
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.09
Plasma Protein Binding (PPB):  97.67887878417969%
Volume Distribution (VD):  0.468
Pgp-substrate:  2.5304181575775146%

ADMET: Metabolism

CYP1A2-inhibitor:  0.99
CYP1A2-substrate:  0.476
CYP2C19-inhibitor:  0.837
CYP2C19-substrate:  0.068
CYP2C9-inhibitor:  0.704
CYP2C9-substrate:  0.914
CYP2D6-inhibitor:  0.495
CYP2D6-substrate:  0.762
CYP3A4-inhibitor:  0.304
CYP3A4-substrate:  0.166

ADMET: Excretion

Clearance (CL):  3.18
Half-life (T1/2):  0.444

ADMET: Toxicity

hERG Blockers:  0.037
Human Hepatotoxicity (H-HT):  0.056
Drug-inuced Liver Injury (DILI):  0.861
AMES Toxicity:  0.695
Rat Oral Acute Toxicity:  0.176
Maximum Recommended Daily Dose:  0.048
Skin Sensitization:  0.772
Carcinogencity:  0.654
Eye Corrosion:  0.023
Eye Irritation:  0.966
Respiratory Toxicity:  0.498

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

  Natural Product: NPC197425

Natural Product ID:  NPC197425
Common Name*:   5-Hydroxyflavone
IUPAC Name:   5-hydroxy-2-phenylchromen-4-one
Synonyms:   NSC-26745
Standard InCHIKey:  IYBLVRRCNVHZQJ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C15H10O3/c16-11-7-4-8-13-15(11)12(17)9-14(18-13)10-5-2-1-3-6-10/h1-9,16H
SMILES:  Oc1cccc2c1c(=O)cc(o2)c1ccccc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL16807
PubChem CID:   68112
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001615] Flavones

*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
NPO22583 Daedaleopsis confragosa Species Coriolaceae Eukaryota n.a. n.a. n.a. PMID[11014261]
NPO18557 Epicoccum nigrum Species Didymellaceae Eukaryota n.a. n.a. n.a. PMID[17711348]
NPO18557 Epicoccum nigrum Species Didymellaceae Eukaryota n.a. n.a. n.a. PMID[19919067]
NPO18557 Epicoccum nigrum Species Didymellaceae Eukaryota n.a. The fungus is isolated from the leaves of L. rhodostegia, collected in June 2007 at Nanning, Guangxi Province, China 2007-JUN PMID[20550196]
NPO15440 Chamaemelum nobile Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23501116]
NPO18557 Epicoccum nigrum Species Didymellaceae Eukaryota n.a. n.a. n.a. PMID[24328302]
NPO15440 Chamaemelum nobile Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[24471493]
NPO15440 Chamaemelum nobile Species Asteraceae Eukaryota Flowers n.a. n.a. PMID[28116906]
NPO15440 Chamaemelum nobile Species Asteraceae Eukaryota Flower n.a. n.a. Database[FooDB]
NPO15440 Chamaemelum nobile Species Asteraceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO2688 Pericarpium pyri n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO24045 Lespedeza homoloba Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15440 Chamaemelum nobile Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24284 Hypoestes serpens Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2688 Pericarpium pyri n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO24045 Lespedeza homoloba Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18557 Epicoccum nigrum Species Didymellaceae Eukaryota n.a. n.a. n.a. Database[Title]
NPO24045 Lespedeza homoloba Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24173 Plutella xylostella Species Plutellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24284 Hypoestes serpens Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22583 Daedaleopsis confragosa Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24329 Primula farinosa Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20617 Tilletia laevis Species Tilletiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24216 Lolium perenne Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23916 Anthocleista grandiflora Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23957 Helleborus caucasicus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17647 Schkuhria multiflora Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16234 Orgyia australis postica Species Lymantriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18557 Epicoccum nigrum Species Didymellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15440 Chamaemelum nobile 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
NPT581 Individual Protein Cyclooxygenase-2 Mus musculus Inhibition = 45.0 % PMID[514092]
NPT1315 Individual Protein Adenosine A1 receptor Rattus norvegicus pKi(uM) = -0.34 n.a. PMID[514094]
NPT1316 Individual Protein Adenosine A2a receptor Rattus norvegicus pKi(uM) = -0.79 n.a. PMID[514095]
NPT1315 Individual Protein Adenosine A1 receptor Rattus norvegicus Ki = 2170.0 nM PMID[514096]
NPT1316 Individual Protein Adenosine A2a receptor Rattus norvegicus Ki = 6200.0 nM PMID[514096]
NPT218 Individual Protein Adenosine A3 receptor Homo sapiens Displacement = 47.0 % PMID[514096]
NPT91 Cell Line KB Homo sapiens ED50 = 20.0 ug ml-1 PMID[514101]
NPT1044 Individual Protein DNA topoisomerase II alpha Homo sapiens Activity < 50.0 % PMID[514102]
NPT153 Individual Protein Androgen Receptor Homo sapiens IC50 = 300.0 nM PMID[514103]
NPT249 Individual Protein Glucocorticoid receptor Homo sapiens EC150 = 6.0 uM PMID[514103]
NPT153 Individual Protein Androgen Receptor Homo sapiens EC150 = 6.0 uM PMID[514103]
NPT1338 Individual Protein Sialidase 2 Homo sapiens IC50 > 1000000.0 nM PMID[514105]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 15848.9 nM PMID[514107]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Potency = 6309.6 nM PMID[514108]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Potency = 19952.6 nM PMID[514107]
NPT61 Individual Protein Beta-glucocerebrosidase Homo sapiens Potency n.a. 11220.2 nM PMID[514107]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 2310.9 nM PMID[514111]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 35481.3 nM PMID[514111]
NPT208 Individual Protein Cytochrome P450 1A2 Homo sapiens IC50 = 310.0 nM PMID[514113]
NPT1603 Individual Protein Cytochrome P450 1A1 Homo sapiens IC50 = 4030.0 nM PMID[514113]
NPT160 Individual Protein TAR DNA-binding protein 43 Homo sapiens Potency n.a. 89125.1 nM PMID[514111]
NPT153 Individual Protein Androgen Receptor Homo sapiens IC50 = 831.76 nM PMID[514114]
NPT153 Individual Protein Androgen Receptor Homo sapiens IC50 = 840.0 nM PMID[514114]
NPT11 Individual Protein Guanine nucleotide-binding protein G(s), subunit alpha Homo sapiens Potency n.a. 31622.8 nM PMID[514111]
NPT65 Cell Line HepG2 Homo sapiens Activity = 88.8 % PMID[514117]
NPT83 Cell Line MCF7 Homo sapiens Activity = 28.6 % PMID[514117]
NPT111 Cell Line K562 Homo sapiens Activity = 26.7 % PMID[514117]
NPT1604 Individual Protein Cytochrome P450 1B1 Homo sapiens IC50 = 210.0 nM PMID[514119]
NPT2266 Individual Protein Fructose-1,6-bisphosphatase Homo sapiens Inhibition < 20.0 % PMID[514121]
NPT711 Individual Protein Aldose reductase Bos taurus Inhibition = 0.0 % PMID[514091]
NPT805 Protein Complex GABA-A receptor; anion channel Rattus norvegicus Ki = 1900.0 nM PMID[514093]
NPT805 Protein Complex GABA-A receptor; anion channel Rattus norvegicus GABA ratio = 1.03 n.a. PMID[514093]
NPT29 Organism Rattus norvegicus Rattus norvegicus Protection = 58.0 % PMID[514097]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 65900.0 nM PMID[514098]
NPT2 Others Unspecified Inhibition = 17.0 % PMID[514099]
NPT2 Others Unspecified Activity = 14.6 % PMID[514100]
NPT2 Others Unspecified Activity = 95.7 % PMID[514100]
NPT2 Others Unspecified Activity = 98.9 % PMID[514100]
NPT2 Others Unspecified IC50 = 425.0 nM PMID[514100]
NPT35 Others n.a. Activity = 11.6 mg/L PMID[514104]
NPT2 Others Unspecified IC50 > 1000000.0 nM PMID[514105]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium pID50 = 5.357 n.a. PMID[514106]
NPT2 Others Unspecified Potency = 316.2 nM PMID[514107]
NPT93 Individual Protein Survival motor neuron protein Homo sapiens Potency = 31622.8 nM PMID[514107]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 39810.7 nM PMID[514107]
NPT792 Individual Protein Arachidonate 15-lipoxygenase Homo sapiens Potency = 19952.6 nM PMID[514107]
NPT197 Protein-Protein Interaction Menin/Histone-lysine N-methyltransferase MLL Homo sapiens Potency = 39810.7 nM PMID[514107]
NPT2 Others Unspecified Potency = 15848.9 nM PMID[514108]
NPT2 Others Unspecified Inhibition = 115.9 % PMID[514110]
NPT698 Individual Protein Regulator of G-protein signaling 4 Homo sapiens Potency n.a. 8436.8 nM PMID[514108]
NPT8 Individual Protein DNA polymerase iota Homo sapiens Potency n.a. 89125.1 nM PMID[514111]
NPT1 Others Radical scavenging activity Inhibition = 0.6 % PMID[514112]
NPT27 Others Unspecified Selectivity ratio = 10.0 n.a. PMID[514113]
NPT2 Others Unspecified Inhibition < 40.0 % PMID[514115]
NPT2 Others Unspecified IC50 = 96000.0 nM PMID[514115]
NPT2 Others Unspecified Inhibition = 30.1 % PMID[514115]
NPT27 Others Unspecified Activity > 98.0 % PMID[514115]
NPT2 Others Unspecified Potency n.a. 15848.9 nM PMID[514108]
NPT2 Others Unspecified Potency n.a. 11220.2 nM PMID[514107]
NPT2 Others Unspecified Potency n.a. 1122.0 nM PMID[514107]
NPT2 Others Unspecified Potency n.a. 14125.4 nM PMID[514108]
NPT2 Others Unspecified Kapp = 313.0 /M PMID[514117]
NPT2 Others Unspecified Kapp = 229.0 /M PMID[514117]
NPT21750 LIPID Lipid bilayer n.a. T = 32.3 degrees C PMID[514117]
NPT21750 LIPID Lipid bilayer n.a. T = 32.0 degrees C PMID[514117]
NPT21750 LIPID Lipid bilayer n.a. T = 30.3 degrees C PMID[514117]
NPT21750 LIPID Lipid bilayer n.a. Tm = 41.1 degrees C PMID[514117]
NPT21750 LIPID Lipid bilayer n.a. Tm = 40.7 degrees C PMID[514117]
NPT21750 LIPID Lipid bilayer n.a. Tm = 40.6 degrees C PMID[514117]
NPT21750 LIPID Lipid bilayer n.a. Tm = 39.6 degrees C PMID[514117]
NPT1 Others Radical scavenging activity IC50 = 23.8 ug.mL-1 PMID[514117]
NPT2 Others Unspecified Potency n.a. 5623.4 nM PMID[514107]
NPT2 Others Unspecified Potency n.a. 5623.4 nM PMID[514111]
NPT471 Organism Trypanosoma brucei brucei Trypanosoma brucei brucei IC50 < 30000.0 nM PMID[514120]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM PMID[514122]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM PMID[514122]

☑ 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 NPC197425 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 NPC39753
0.9919 High Similarity NPC115998
0.9839 High Similarity NPC137264
0.976 High Similarity NPC113006
0.9683 High Similarity NPC128216
0.9606 High Similarity NPC50898
0.9606 High Similarity NPC78540
0.9606 High Similarity NPC274121
0.9606 High Similarity NPC57601
0.9606 High Similarity NPC213216
0.9531 High Similarity NPC172262
0.9531 High Similarity NPC248872
0.952 High Similarity NPC187907
0.9431 High Similarity NPC193805
0.9385 High Similarity NPC187432
0.9385 High Similarity NPC256042
0.9385 High Similarity NPC29353
0.9385 High Similarity NPC234133
0.9385 High Similarity NPC124784
0.9385 High Similarity NPC47815
0.9385 High Similarity NPC473887
0.9385 High Similarity NPC194281
0.9385 High Similarity NPC116775
0.9385 High Similarity NPC216361
0.9385 High Similarity NPC281917
0.9385 High Similarity NPC13408
0.9385 High Similarity NPC231772
0.9385 High Similarity NPC127447
0.936 High Similarity NPC22783
0.936 High Similarity NPC41721
0.9313 High Similarity NPC250266
0.9313 High Similarity NPC266597
0.9313 High Similarity NPC299379
0.9313 High Similarity NPC228661
0.9308 High Similarity NPC239495
0.9308 High Similarity NPC9985
0.9242 High Similarity NPC201395
0.9219 High Similarity NPC5515
0.9219 High Similarity NPC270369
0.9173 High Similarity NPC78913
0.9173 High Similarity NPC18260
0.9173 High Similarity NPC241838
0.9173 High Similarity NPC143799
0.9173 High Similarity NPC55018
0.9173 High Similarity NPC301217
0.9173 High Similarity NPC152042
0.9173 High Similarity NPC303633
0.9173 High Similarity NPC96565
0.9173 High Similarity NPC220062
0.9173 High Similarity NPC216978
0.9167 High Similarity NPC13768
0.9167 High Similarity NPC84585
0.9167 High Similarity NPC243083
0.9167 High Similarity NPC476480
0.9167 High Similarity NPC79943
0.9167 High Similarity NPC287246
0.9167 High Similarity NPC12296
0.9167 High Similarity NPC290291
0.9167 High Similarity NPC275055
0.9167 High Similarity NPC32441
0.9167 High Similarity NPC295261
0.9167 High Similarity NPC296490
0.9167 High Similarity NPC107586
0.9147 High Similarity NPC31872
0.9147 High Similarity NPC473584
0.9147 High Similarity NPC475589
0.9104 High Similarity NPC103904
0.9104 High Similarity NPC305355
0.9104 High Similarity NPC146679
0.9104 High Similarity NPC281207
0.9104 High Similarity NPC230285
0.9104 High Similarity NPC59951
0.9104 High Similarity NPC269652
0.9104 High Similarity NPC475680
0.9104 High Similarity NPC241100
0.9104 High Similarity NPC270883
0.9104 High Similarity NPC103342
0.9104 High Similarity NPC172986
0.9104 High Similarity NPC159275
0.9104 High Similarity NPC184536
0.9104 High Similarity NPC261227
0.9098 High Similarity NPC99333
0.9098 High Similarity NPC188947
0.9098 High Similarity NPC329225
0.9098 High Similarity NPC280284
0.9098 High Similarity NPC18457
0.9098 High Similarity NPC472460
0.9098 High Similarity NPC118813
0.9098 High Similarity NPC147686
0.9091 High Similarity NPC240593
0.9077 High Similarity NPC25937
0.9077 High Similarity NPC10971
0.9037 High Similarity NPC156590
0.9037 High Similarity NPC90582
0.9037 High Similarity NPC147688
0.9037 High Similarity NPC282300
0.9037 High Similarity NPC205006
0.9037 High Similarity NPC14871
0.9037 High Similarity NPC118840
0.9037 High Similarity NPC110969
0.9037 High Similarity NPC262094
0.9037 High Similarity NPC136840
0.9037 High Similarity NPC64908
0.903 High Similarity NPC265871
0.903 High Similarity NPC261234
0.903 High Similarity NPC217186
0.903 High Similarity NPC225153
0.903 High Similarity NPC274784
0.903 High Similarity NPC20709
0.903 High Similarity NPC150648
0.903 High Similarity NPC222342
0.903 High Similarity NPC316480
0.903 High Similarity NPC329203
0.903 High Similarity NPC310135
0.903 High Similarity NPC53181
0.9023 High Similarity NPC254841
0.9023 High Similarity NPC160972
0.9023 High Similarity NPC188879
0.9015 High Similarity NPC151113
0.9015 High Similarity NPC39426
0.9015 High Similarity NPC234560
0.9008 High Similarity NPC223457
0.9008 High Similarity NPC108113
0.9008 High Similarity NPC93756
0.9 High Similarity NPC308037
0.9 High Similarity NPC64359
0.9 High Similarity NPC284424
0.9 High Similarity NPC313618
0.9 High Similarity NPC475009
0.9 High Similarity NPC278556
0.9 High Similarity NPC186097
0.9 High Similarity NPC475008
0.8992 High Similarity NPC228184
0.8992 High Similarity NPC12694
0.8971 High Similarity NPC11561
0.8971 High Similarity NPC78803
0.8971 High Similarity NPC214236
0.8971 High Similarity NPC217083
0.8971 High Similarity NPC293852
0.8971 High Similarity NPC200694
0.8971 High Similarity NPC226636
0.8971 High Similarity NPC62840
0.8971 High Similarity NPC473042
0.8971 High Similarity NPC1534
0.8971 High Similarity NPC59739
0.8971 High Similarity NPC299080
0.8963 High Similarity NPC235239
0.8963 High Similarity NPC110228
0.8963 High Similarity NPC284550
0.8963 High Similarity NPC76445
0.8963 High Similarity NPC145673
0.8963 High Similarity NPC188243
0.8963 High Similarity NPC69769
0.8963 High Similarity NPC150522
0.8963 High Similarity NPC6407
0.8963 High Similarity NPC129853
0.8955 High Similarity NPC124269
0.8955 High Similarity NPC276905
0.8947 High Similarity NPC235428
0.8947 High Similarity NPC87545
0.8939 High Similarity NPC125920
0.8931 High Similarity NPC257756
0.8931 High Similarity NPC212631
0.8931 High Similarity NPC129132
0.8931 High Similarity NPC101294
0.8931 High Similarity NPC473655
0.8931 High Similarity NPC87231
0.8931 High Similarity NPC205468
0.8915 High Similarity NPC60558
0.8905 High Similarity NPC24821
0.8905 High Similarity NPC11700
0.8905 High Similarity NPC293053
0.8905 High Similarity NPC470216
0.8905 High Similarity NPC279121
0.8905 High Similarity NPC9117
0.8905 High Similarity NPC219915
0.8905 High Similarity NPC212932
0.8905 High Similarity NPC38219
0.8905 High Similarity NPC190637
0.8897 High Similarity NPC324386
0.8897 High Similarity NPC3188
0.8897 High Similarity NPC312391
0.8897 High Similarity NPC213322
0.8897 High Similarity NPC103362
0.8897 High Similarity NPC4743
0.8889 High Similarity NPC140890
0.8889 High Similarity NPC93730
0.8881 High Similarity NPC294409
0.8881 High Similarity NPC116632
0.8881 High Similarity NPC303644
0.8881 High Similarity NPC162680
0.8881 High Similarity NPC181124
0.8881 High Similarity NPC7013
0.8881 High Similarity NPC212767
0.8881 High Similarity NPC209560
0.8881 High Similarity NPC332594
0.8872 High Similarity NPC60667
0.8872 High Similarity NPC242712
0.8864 High Similarity NPC28753
0.8864 High Similarity NPC337373

  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 NPC197425 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
0.9167 High Similarity NPD1550 Clinical (unspecified phase)
0.9167 High Similarity NPD1552 Clinical (unspecified phase)
0.9098 High Similarity NPD1549 Phase 2
0.9015 High Similarity NPD1510 Phase 2
0.9 High Similarity NPD1240 Approved
0.8905 High Similarity NPD1511 Approved
0.8864 High Similarity NPD1607 Approved
0.8841 High Similarity NPD4378 Clinical (unspecified phase)
0.8806 High Similarity NPD1551 Phase 2
0.8777 High Similarity NPD1512 Approved
0.875 High Similarity NPD1203 Approved
0.8705 High Similarity NPD7410 Clinical (unspecified phase)
0.8686 High Similarity NPD3750 Approved
0.8667 High Similarity NPD2796 Approved
0.8451 Intermediate Similarity NPD5403 Approved
0.844 Intermediate Similarity NPD5401 Approved
0.8438 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.8413 Intermediate Similarity NPD1548 Phase 1
0.8372 Intermediate Similarity NPD9717 Approved
0.8356 Intermediate Similarity NPD2801 Approved
0.8321 Intermediate Similarity NPD3748 Approved
0.8295 Intermediate Similarity NPD422 Phase 1
0.8288 Intermediate Similarity NPD1934 Approved
0.8286 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.8284 Intermediate Similarity NPD2313 Discontinued
0.8276 Intermediate Similarity NPD4380 Phase 2
0.8273 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8239 Intermediate Similarity NPD6799 Approved
0.8231 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8219 Intermediate Similarity NPD7411 Suspended
0.8188 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8182 Intermediate Similarity NPD2797 Approved
0.8176 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.812 Intermediate Similarity NPD2798 Approved
0.8106 Intermediate Similarity NPD3225 Approved
0.8085 Intermediate Similarity NPD1243 Approved
0.8067 Intermediate Similarity NPD3749 Approved
0.8067 Intermediate Similarity NPD7075 Discontinued
0.8054 Intermediate Similarity NPD5402 Approved
0.8041 Intermediate Similarity NPD6801 Discontinued
0.8015 Intermediate Similarity NPD1610 Phase 2
0.8015 Intermediate Similarity NPD3268 Approved
0.8015 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD7768 Phase 2
0.8 Intermediate Similarity NPD6832 Phase 2
0.8 Intermediate Similarity NPD3882 Suspended
0.7987 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7987 Intermediate Similarity NPD7819 Suspended
0.7969 Intermediate Similarity NPD9493 Approved
0.7958 Intermediate Similarity NPD2800 Approved
0.7943 Intermediate Similarity NPD2344 Approved
0.7933 Intermediate Similarity NPD3817 Phase 2
0.7929 Intermediate Similarity NPD4308 Phase 3
0.7917 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7905 Intermediate Similarity NPD6599 Discontinued
0.7879 Intermediate Similarity NPD1201 Approved
0.7872 Intermediate Similarity NPD6100 Approved
0.7872 Intermediate Similarity NPD6099 Approved
0.7832 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7808 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7801 Intermediate Similarity NPD2799 Discontinued
0.7778 Intermediate Similarity NPD3267 Approved
0.7778 Intermediate Similarity NPD3266 Approved
0.7771 Intermediate Similarity NPD3818 Discontinued
0.777 Intermediate Similarity NPD943 Approved
0.7756 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7756 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7756 Intermediate Similarity NPD6166 Phase 2
0.7756 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7754 Intermediate Similarity NPD1296 Phase 2
0.7754 Intermediate Similarity NPD411 Approved
0.7746 Intermediate Similarity NPD2935 Discontinued
0.7724 Intermediate Similarity NPD2309 Approved
0.7722 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7722 Intermediate Similarity NPD7054 Approved
0.7718 Intermediate Similarity NPD3226 Approved
0.7714 Intermediate Similarity NPD1933 Approved
0.7714 Intermediate Similarity NPD447 Suspended
0.7703 Intermediate Similarity NPD920 Approved
0.7692 Intermediate Similarity NPD2346 Discontinued
0.7687 Intermediate Similarity NPD1608 Approved
0.7677 Intermediate Similarity NPD6959 Discontinued
0.7676 Intermediate Similarity NPD7033 Discontinued
0.7673 Intermediate Similarity NPD7472 Approved
0.766 Intermediate Similarity NPD6651 Approved
0.7655 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD1470 Approved
0.7643 Intermediate Similarity NPD4307 Phase 2
0.7625 Intermediate Similarity NPD6797 Phase 2
0.7619 Intermediate Similarity NPD74 Approved
0.7619 Intermediate Similarity NPD9266 Approved
0.7609 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7609 Intermediate Similarity NPD4908 Phase 1
0.7597 Intermediate Similarity NPD1241 Discontinued
0.7591 Intermediate Similarity NPD1019 Discontinued
0.7589 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7582 Intermediate Similarity NPD4288 Approved
0.7578 Intermediate Similarity NPD7251 Discontinued
0.7562 Intermediate Similarity NPD7074 Phase 3
0.7556 Intermediate Similarity NPD1481 Phase 2
0.7554 Intermediate Similarity NPD4625 Phase 3
0.7552 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.754 Intermediate Similarity NPD9267 Approved
0.754 Intermediate Similarity NPD9264 Approved
0.754 Intermediate Similarity NPD9263 Approved
0.7536 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7531 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7531 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7531 Intermediate Similarity NPD7808 Phase 3
0.75 Intermediate Similarity NPD4749 Approved
0.75 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7481 Intermediate Similarity NPD1535 Discovery
0.7469 Intermediate Similarity NPD6559 Discontinued
0.7463 Intermediate Similarity NPD17 Approved
0.7444 Intermediate Similarity NPD9545 Approved
0.7424 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD5953 Discontinued
0.7405 Intermediate Similarity NPD6232 Discontinued
0.7403 Intermediate Similarity NPD1465 Phase 2
0.7394 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD1613 Approved
0.7391 Intermediate Similarity NPD7286 Phase 2
0.7391 Intermediate Similarity NPD1164 Approved
0.7389 Intermediate Similarity NPD5494 Approved
0.7376 Intermediate Similarity NPD3764 Approved
0.7375 Intermediate Similarity NPD7473 Discontinued
0.7357 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.7347 Intermediate Similarity NPD2654 Approved
0.7333 Intermediate Similarity NPD2532 Approved
0.7333 Intermediate Similarity NPD2534 Approved
0.7333 Intermediate Similarity NPD2533 Approved
0.7329 Intermediate Similarity NPD5940 Clinical (unspecified phase)
0.7325 Intermediate Similarity NPD919 Approved
0.7323 Intermediate Similarity NPD968 Approved
0.7313 Intermediate Similarity NPD1894 Discontinued
0.7312 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD4628 Phase 3
0.7244 Intermediate Similarity NPD9697 Approved
0.7233 Intermediate Similarity NPD1247 Approved
0.7226 Intermediate Similarity NPD6844 Discontinued
0.7222 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD9261 Approved
0.7222 Intermediate Similarity NPD5124 Phase 1
0.7219 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD4662 Approved
0.7219 Intermediate Similarity NPD4661 Approved
0.7211 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7192 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7174 Intermediate Similarity NPD3972 Approved
0.7161 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD7390 Discontinued
0.7143 Intermediate Similarity NPD3926 Phase 2
0.7143 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD9281 Approved
0.7134 Intermediate Similarity NPD2296 Approved
0.7134 Intermediate Similarity NPD1729 Discontinued
0.7133 Intermediate Similarity NPD6798 Discontinued
0.7133 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7114 Intermediate Similarity NPD1652 Phase 2
0.7103 Intermediate Similarity NPD230 Phase 1
0.7097 Intermediate Similarity NPD6585 Discontinued
0.7095 Intermediate Similarity NPD1471 Phase 3
0.7093 Intermediate Similarity NPD4360 Phase 2
0.7093 Intermediate Similarity NPD4363 Phase 3
0.7091 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.708 Intermediate Similarity NPD1778 Approved
0.7073 Intermediate Similarity NPD5844 Phase 1
0.7071 Intermediate Similarity NPD1876 Approved
0.7059 Intermediate Similarity NPD4287 Approved
0.7052 Intermediate Similarity NPD4361 Phase 2
0.7052 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7051 Intermediate Similarity NPD5890 Approved
0.7051 Intermediate Similarity NPD5889 Approved
0.7044 Intermediate Similarity NPD955 Approved
0.7042 Intermediate Similarity NPD2861 Phase 2
0.7027 Intermediate Similarity NPD5406 Approved
0.7027 Intermediate Similarity NPD5405 Approved
0.7027 Intermediate Similarity NPD5408 Approved
0.7027 Intermediate Similarity NPD5404 Approved
0.702 Intermediate Similarity NPD3295 Clinical (unspecified phase)
0.7013 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD3751 Discontinued
0.7011 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7008 Intermediate Similarity NPD846 Approved
0.7008 Intermediate Similarity NPD940 Approved
0.7 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD290 Approved
0.6986 Remote Similarity NPD1184 Approved
0.6978 Remote Similarity NPD1091 Approved
0.6974 Remote Similarity NPD7440 Discontinued
0.6966 Remote Similarity NPD520 Approved
0.6966 Remote Similarity NPD6233 Phase 2
0.6964 Remote Similarity NPD8312 Approved
0.6964 Remote Similarity NPD8313 Approved
0.6963 Remote Similarity NPD6671 Approved
0.6954 Remote Similarity NPD7003 Approved
0.6943 Remote Similarity NPD2366 Approved
0.6937 Remote Similarity NPD6971 Discontinued
0.6929 Remote Similarity NPD1242 Phase 1

  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