Structure

Physi-Chem Properties

Molecular Weight:  254.06
Volume:  256.396
LogP:  3.351
LogD:  2.59
LogS:  -3.701
# Rotatable Bonds:  1
TPSA:  70.67
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.655
Synthetic Accessibility Score:  2.102
Fsp3:  0.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.861
MDCK Permeability:  1.50593386933906e-05
Pgp-inhibitor:  0.037
Pgp-substrate:  0.028
Human Intestinal Absorption (HIA):  0.011
20% Bioavailability (F20%):  0.917
30% Bioavailability (F30%):  0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.025
Plasma Protein Binding (PPB):  98.77176666259766%
Volume Distribution (VD):  0.409
Pgp-substrate:  2.4146859645843506%

ADMET: Metabolism

CYP1A2-inhibitor:  0.979
CYP1A2-substrate:  0.142
CYP2C19-inhibitor:  0.413
CYP2C19-substrate:  0.066
CYP2C9-inhibitor:  0.572
CYP2C9-substrate:  0.704
CYP2D6-inhibitor:  0.521
CYP2D6-substrate:  0.364
CYP3A4-inhibitor:  0.159
CYP3A4-substrate:  0.138

ADMET: Excretion

Clearance (CL):  4.809
Half-life (T1/2):  0.768

ADMET: Toxicity

hERG Blockers:  0.008
Human Hepatotoxicity (H-HT):  0.156
Drug-inuced Liver Injury (DILI):  0.973
AMES Toxicity:  0.555
Rat Oral Acute Toxicity:  0.336
Maximum Recommended Daily Dose:  0.072
Skin Sensitization:  0.859
Carcinogencity:  0.759
Eye Corrosion:  0.004
Eye Irritation:  0.88
Respiratory Toxicity:  0.375

Download Data

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

  Natural Product: NPC168803

Natural Product ID:  NPC168803
Common Name*:   7,8-Dihydroxyflavone
IUPAC Name:   7,8-dihydroxy-2-phenylchromen-4-one
Synonyms:   7,8-Dihydroxy-Flavone; 7,8-Dihydroxyflavone
Standard InCHIKey:  COCYGNDCWFKTMF-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C15H10O4/c16-11-7-6-10-12(17)8-13(19-15(10)14(11)18)9-4-2-1-3-5-9/h1-8,16,18H
SMILES:  Oc1ccc2c(c1O)oc(cc2=O)c1ccccc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL75267
PubChem CID:   1880
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
NPO30745 Chrysanthemum morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[8158164]
NPO30745 Chrysanthemum morifolium Species Asteraceae Eukaryota n.a. inflorescence n.a. PMID[8158164]
NPO30745 Chrysanthemum morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30745 Chrysanthemum morifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]

☑ 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
NPT83 Cell Line MCF7 Homo sapiens IC50 = 27500.0 nM PMID[548106]
NPT2732 Individual Protein Aldehyde dehydrogenase Homo sapiens Control = 92.6 % PMID[548107]
NPT2732 Individual Protein Aldehyde dehydrogenase Homo sapiens Control = 92.3 % PMID[548107]
NPT2732 Individual Protein Aldehyde dehydrogenase Homo sapiens Control = 59.9 % PMID[548107]
NPT322 Individual Protein DNA topoisomerase II beta Homo sapiens CC50 = 95.0 ug.mL-1 PMID[548109]
NPT144 Individual Protein Telomerase reverse transcriptase Homo sapiens IC50 = 36000.0 nM PMID[548110]
NPT13 Individual Protein Tyrosine-protein kinase LCK Homo sapiens IC50 = 80.0 ug.mL-1 PMID[548112]
NPT759 Cell Line H9 Homo sapiens IC50 = 14000.0 nM PMID[548113]
NPT149 Individual Protein Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Homo sapiens Potency = 10000.0 nM PMID[548116]
NPT48 Individual Protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 7943.3 nM PMID[548116]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 31622.8 nM PMID[548116]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 28183.8 nM PMID[548116]
NPT531 Individual Protein Nuclear receptor ROR-gamma Mus musculus Potency = 35481.3 nM PMID[548116]
NPT583 Individual Protein Inositol monophosphatase 1 Rattus norvegicus Potency = 15848.9 nM PMID[548116]
NPT282 Individual Protein MAP kinase ERK2 Homo sapiens Potency = 2511.9 nM PMID[548116]
NPT55 Individual Protein Putative fructose-1,6-bisphosphate aldolase Giardia intestinalis Potency = 7924.5 nM PMID[548116]
NPT151 Individual Protein 15-hydroxyprostaglandin dehydrogenase [NAD+] Homo sapiens Potency = 3162.3 nM PMID[548116]
NPT539 Individual Protein Cellular tumor antigen p53 Homo sapiens Potency = 12589.3 nM PMID[548116]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Potency = 39810.7 nM PMID[548116]
NPT531 Individual Protein Nuclear receptor ROR-gamma Mus musculus Potency = 10000.0 nM PMID[548116]
NPT443 Individual Protein Histone acetyltransferase GCN5 Homo sapiens Potency n.a. 39810.7 nM PMID[548116]
NPT1139 Individual Protein Arachidonate 15-lipoxygenase, type II Homo sapiens Potency n.a. 15848.9 nM PMID[548116]
NPT198 Individual Protein Vitamin D receptor Homo sapiens Potency n.a. 12589.3 nM PMID[548116]
NPT199 Individual Protein DNA polymerase kappa Homo sapiens Potency n.a. 8912.5 nM PMID[548116]
NPT444 Individual Protein Ubiquitin carboxyl-terminal hydrolase 1 Homo sapiens Potency n.a. 56234.1 nM PMID[548116]
NPT81 Cell Line A549 Homo sapiens IC50 = 37250.0 nM PMID[548118]
NPT380 Cell Line U-251 Homo sapiens IC50 = 50110.0 nM PMID[548118]
NPT198 Individual Protein Vitamin D receptor Homo sapiens Potency n.a. 19952.6 nM PMID[548116]
NPT198 Individual Protein Vitamin D receptor Homo sapiens Potency n.a. 23109.3 nM PMID[548116]
NPT198 Individual Protein Vitamin D receptor Homo sapiens Potency n.a. 31622.8 nM PMID[548116]
NPT198 Individual Protein Vitamin D receptor Homo sapiens Potency n.a. 25118.9 nM PMID[548116]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 20596.2 nM PMID[548116]
NPT3270 Individual Protein Neurotrophic tyrosine kinase receptor type 2 Homo sapiens Kd = 320.0 nM PMID[548120]
NPT49 Individual Protein DNA-(apurinic or apyrimidinic site) lyase Homo sapiens Potency n.a. 5623.4 nM PMID[548116]
NPT144 Individual Protein Telomerase reverse transcriptase Homo sapiens IC50 = 36000.0 nM PMID[548121]
NPT4195 Individual Protein Transcriptional activator protein lasR Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228) Inhibition > 70.0 % PMID[548123]
NPT2632 Organism Syrian golden hamster Mesocricetus auratus Suppression = 0.0 % PMID[548107]
NPT27 Others Unspecified AUC = 111.0 nM hr ml PMID[548107]
NPT27 Others Unspecified Tmax = 0.5 hr PMID[548107]
NPT2731 Protein Family Monoamine oxidase Homo sapiens Inhibition = 4.6 % PMID[548107]
NPT2731 Protein Family Monoamine oxidase Homo sapiens Inhibition = 7.9 % PMID[548107]
NPT2731 Protein Family Monoamine oxidase Homo sapiens Inhibition = 25.4 % PMID[548107]
NPT2731 Protein Family Monoamine oxidase Homo sapiens Inhibition = 53.2 % PMID[548107]
NPT2731 Protein Family Monoamine oxidase Homo sapiens IC50 = 17000.0 nM PMID[548107]
NPT2 Others Unspecified Control = 79.1 % PMID[548107]
NPT1567 Protein Complex DNA gyrase Escherichia coli K-12 IC50 = 89.2 ug.mL-1 PMID[548109]
NPT19 Organism Escherichia coli Escherichia coli MIC = 125.0 ug.mL-1 PMID[548109]
NPT19 Organism Escherichia coli Escherichia coli MIC = 7.8 ug.mL-1 PMID[548109]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium MIC > 125.0 ug.mL-1 PMID[548109]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium MIC = 15.6 ug.mL-1 PMID[548109]
NPT1521 Organism Stenotrophomonas maltophilia Stenotrophomonas maltophilia MIC > 125.0 ug.mL-1 PMID[548109]
NPT1521 Organism Stenotrophomonas maltophilia Stenotrophomonas maltophilia MIC = 125.0 ug.mL-1 PMID[548109]
NPT19 Organism Escherichia coli Escherichia coli MIC > 125.0 ug.mL-1 PMID[548109]
NPT19 Organism Escherichia coli Escherichia coli MIC = 62.5 ug.mL-1 PMID[548109]
NPT17 Organism Staphylococcus epidermidis Staphylococcus epidermidis MIC = 31.25 ug.mL-1 PMID[548109]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 62.5 ug.mL-1 PMID[548109]
NPT2 Others Unspecified IC50 = 80.0 ug.mL-1 PMID[548111]
NPT27 Others Unspecified TI = 1.0 n.a. PMID[548113]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 = 10000.0 nM PMID[548113]
NPT35 Others n.a. Activity = 108.0 mg/L PMID[548114]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. deltaA = 0.49 n.a. PMID[548115]
NPT2 Others Unspecified Potency = 31622.8 nM PMID[548116]
NPT93 Individual Protein Survival motor neuron protein Homo sapiens Potency = 35481.3 nM PMID[548116]
NPT94 Individual Protein Aldehyde dehydrogenase 1A1 Homo sapiens Potency = 3981.1 nM PMID[548116]
NPT792 Individual Protein Arachidonate 15-lipoxygenase Homo sapiens Potency = 5011.9 nM PMID[548116]
NPT197 Protein-Protein Interaction Menin/Histone-lysine N-methyltransferase MLL Homo sapiens Potency = 28183.8 nM PMID[548116]
NPT981 Individual Protein Inhibitor of nuclear factor kappa B kinase beta subunit Homo sapiens IC50 = 9820.0 nM PMID[548118]
NPT2 Others Unspecified Potency n.a. 8436.8 nM PMID[548116]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 107.29 % PMID[548119]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 140.55 % PMID[548119]
NPT2 Others Unspecified Potency n.a. 22387.2 nM PMID[548116]
NPT2 Others Unspecified Potency n.a. 31622.8 nM PMID[548116]
NPT2 Others Unspecified Potency n.a. 35481.3 nM PMID[548116]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 96.2 % PMID[548122]
NPT35 Others n.a. Activity = 1.4 % PMID[548122]
NPT35 Others n.a. Activity = 3.7 % PMID[548122]
NPT35 Others n.a. IC50 = 15500.0 nM PMID[548122]
NPT22152 SINGLE PROTEIN Regulatory protein RhlR Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228) Inhibition > 70.0 % PMID[548123]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM PMID[548124]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM PMID[548124]

☑ 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 NPC168803 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
0.979 High Similarity NPC45873
0.9789 High Similarity NPC196277
0.9789 High Similarity NPC272721
0.9789 High Similarity NPC43669
0.972 High Similarity NPC17286
0.972 High Similarity NPC259713
0.972 High Similarity NPC216318
0.972 High Similarity NPC296197
0.9718 High Similarity NPC77378
0.9716 High Similarity NPC70136
0.9655 High Similarity NPC60972
0.9655 High Similarity NPC39732
0.9653 High Similarity NPC29231
0.965 High Similarity NPC12367
0.965 High Similarity NPC118726
0.9645 High Similarity NPC279121
0.9586 High Similarity NPC31363
0.9586 High Similarity NPC225731
0.9586 High Similarity NPC251110
0.9583 High Similarity NPC287101
0.9583 High Similarity NPC52005
0.9583 High Similarity NPC223579
0.9583 High Similarity NPC183950
0.9583 High Similarity NPC137062
0.958 High Similarity NPC74881
0.958 High Similarity NPC275772
0.958 High Similarity NPC130230
0.958 High Similarity NPC51443
0.958 High Similarity NPC188074
0.958 High Similarity NPC125449
0.958 High Similarity NPC239312
0.9574 High Similarity NPC175013
0.9524 High Similarity NPC20830
0.9524 High Similarity NPC472280
0.9524 High Similarity NPC256612
0.9521 High Similarity NPC27208
0.9521 High Similarity NPC257648
0.9521 High Similarity NPC256283
0.9521 High Similarity NPC275722
0.9521 High Similarity NPC71334
0.9521 High Similarity NPC293183
0.9521 High Similarity NPC120163
0.9521 High Similarity NPC275836
0.9521 High Similarity NPC241498
0.9521 High Similarity NPC100887
0.9521 High Similarity NPC222830
0.9521 High Similarity NPC188203
0.9521 High Similarity NPC131624
0.9521 High Similarity NPC55205
0.9521 High Similarity NPC477231
0.9521 High Similarity NPC239128
0.9521 High Similarity NPC198826
0.9521 High Similarity NPC187498
0.9521 High Similarity NPC83508
0.9521 High Similarity NPC212678
0.9521 High Similarity NPC57030
0.9521 High Similarity NPC301323
0.9521 High Similarity NPC162313
0.9521 High Similarity NPC25270
0.9521 High Similarity NPC156222
0.9517 High Similarity NPC61620
0.9517 High Similarity NPC248102
0.9517 High Similarity NPC260582
0.9514 High Similarity NPC120464
0.951 High Similarity NPC20791
0.951 High Similarity NPC179271
0.9507 High Similarity NPC59551
0.9459 High Similarity NPC133970
0.9459 High Similarity NPC6633
0.9459 High Similarity NPC265511
0.9459 High Similarity NPC5322
0.9459 High Similarity NPC472455
0.9456 High Similarity NPC167091
0.9456 High Similarity NPC145379
0.9456 High Similarity NPC292214
0.9456 High Similarity NPC227337
0.9456 High Similarity NPC22519
0.9456 High Similarity NPC255350
0.9456 High Similarity NPC271779
0.9456 High Similarity NPC183878
0.9456 High Similarity NPC273462
0.9456 High Similarity NPC206238
0.9456 High Similarity NPC231018
0.9456 High Similarity NPC88645
0.9456 High Similarity NPC47781
0.9456 High Similarity NPC70433
0.9456 High Similarity NPC49402
0.9456 High Similarity NPC69394
0.9456 High Similarity NPC176775
0.9456 High Similarity NPC274327
0.9456 High Similarity NPC33051
0.9456 High Similarity NPC160951
0.9452 High Similarity NPC54394
0.9452 High Similarity NPC200740
0.9452 High Similarity NPC125062
0.9452 High Similarity NPC252933
0.9448 High Similarity NPC48479
0.9448 High Similarity NPC142876
0.9448 High Similarity NPC177298
0.9448 High Similarity NPC69430
0.9448 High Similarity NPC40290
0.9448 High Similarity NPC195763
0.9448 High Similarity NPC264289
0.9448 High Similarity NPC195351
0.9448 High Similarity NPC200060
0.9448 High Similarity NPC264550
0.9448 High Similarity NPC333691
0.9448 High Similarity NPC139293
0.9444 High Similarity NPC95864
0.9444 High Similarity NPC12200
0.9444 High Similarity NPC108406
0.9396 High Similarity NPC218313
0.9396 High Similarity NPC474681
0.9392 High Similarity NPC213622
0.9392 High Similarity NPC234255
0.9392 High Similarity NPC167815
0.9392 High Similarity NPC44079
0.9392 High Similarity NPC183597
0.9392 High Similarity NPC200246
0.9392 High Similarity NPC50715
0.9392 High Similarity NPC208197
0.9392 High Similarity NPC168247
0.9392 High Similarity NPC2476
0.9392 High Similarity NPC227325
0.9392 High Similarity NPC163780
0.9392 High Similarity NPC152951
0.9392 High Similarity NPC196439
0.9392 High Similarity NPC117992
0.9392 High Similarity NPC128863
0.9392 High Similarity NPC4455
0.9392 High Similarity NPC138360
0.9392 High Similarity NPC280339
0.9392 High Similarity NPC201136
0.9392 High Similarity NPC146165
0.9392 High Similarity NPC92659
0.9392 High Similarity NPC57674
0.9392 High Similarity NPC2928
0.9392 High Similarity NPC230149
0.9392 High Similarity NPC201451
0.9392 High Similarity NPC26227
0.9388 High Similarity NPC39007
0.9388 High Similarity NPC82325
0.9388 High Similarity NPC279989
0.9388 High Similarity NPC142540
0.9388 High Similarity NPC161277
0.9388 High Similarity NPC237994
0.9388 High Similarity NPC199100
0.9388 High Similarity NPC120537
0.9388 High Similarity NPC101996
0.9388 High Similarity NPC180234
0.9384 High Similarity NPC77858
0.9384 High Similarity NPC151473
0.9384 High Similarity NPC184136
0.9384 High Similarity NPC306821
0.9379 High Similarity NPC195202
0.9379 High Similarity NPC203747
0.9379 High Similarity NPC276930
0.9379 High Similarity NPC194653
0.9379 High Similarity NPC139364
0.9379 High Similarity NPC80710
0.9379 High Similarity NPC254702
0.9379 High Similarity NPC194856
0.9379 High Similarity NPC119059
0.9375 High Similarity NPC169749
0.9375 High Similarity NPC209278
0.9371 High Similarity NPC142165
0.9371 High Similarity NPC38065
0.9371 High Similarity NPC242893
0.9333 High Similarity NPC204879
0.9329 High Similarity NPC43243
0.9329 High Similarity NPC266960
0.9329 High Similarity NPC245546
0.9329 High Similarity NPC98661
0.9329 High Similarity NPC472916
0.9329 High Similarity NPC247017
0.9329 High Similarity NPC474638
0.9329 High Similarity NPC49824
0.9324 High Similarity NPC75279
0.9324 High Similarity NPC270620
0.9324 High Similarity NPC469550
0.9324 High Similarity NPC250822
0.9324 High Similarity NPC276409
0.9324 High Similarity NPC236223
0.9324 High Similarity NPC179126
0.9324 High Similarity NPC78326
0.932 High Similarity NPC149614
0.932 High Similarity NPC133953
0.932 High Similarity NPC308451
0.932 High Similarity NPC208043
0.932 High Similarity NPC260895
0.932 High Similarity NPC171010
0.932 High Similarity NPC50403
0.932 High Similarity NPC226973
0.932 High Similarity NPC154345
0.932 High Similarity NPC28274
0.9315 High Similarity NPC270465
0.9315 High Similarity NPC159103
0.9315 High Similarity NPC87125
0.9315 High Similarity NPC183959
0.9315 High Similarity NPC1612

  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 NPC168803 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
0.9645 High Similarity NPD1511 Approved
0.951 High Similarity NPD1512 Approved
0.9456 High Similarity NPD2801 Approved
0.9257 High Similarity NPD1934 Approved
0.92 High Similarity NPD3882 Suspended
0.894 High Similarity NPD2393 Clinical (unspecified phase)
0.8917 High Similarity NPD3818 Discontinued
0.8811 High Similarity NPD1510 Phase 2
0.8794 High Similarity NPD943 Approved
0.8759 High Similarity NPD1549 Phase 2
0.8758 High Similarity NPD3817 Phase 2
0.869 High Similarity NPD1552 Clinical (unspecified phase)
0.869 High Similarity NPD1550 Clinical (unspecified phase)
0.8671 High Similarity NPD6167 Clinical (unspecified phase)
0.8671 High Similarity NPD6168 Clinical (unspecified phase)
0.8671 High Similarity NPD6166 Phase 2
0.8625 High Similarity NPD7054 Approved
0.8581 High Similarity NPD4868 Clinical (unspecified phase)
0.8571 High Similarity NPD1465 Phase 2
0.8571 High Similarity NPD7472 Approved
0.8533 High Similarity NPD4378 Clinical (unspecified phase)
0.8531 High Similarity NPD1240 Approved
0.8528 High Similarity NPD4338 Clinical (unspecified phase)
0.8497 Intermediate Similarity NPD4380 Phase 2
0.8457 Intermediate Similarity NPD7074 Phase 3
0.8414 Intermediate Similarity NPD1607 Approved
0.8411 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8408 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8405 Intermediate Similarity NPD6797 Phase 2
0.8367 Intermediate Similarity NPD2796 Approved
0.8354 Intermediate Similarity NPD7251 Discontinued
0.8344 Intermediate Similarity NPD6799 Approved
0.8303 Intermediate Similarity NPD7808 Phase 3
0.8302 Intermediate Similarity NPD5494 Approved
0.8291 Intermediate Similarity NPD7075 Discontinued
0.8267 Intermediate Similarity NPD3750 Approved
0.8255 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8252 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.8219 Intermediate Similarity NPD447 Suspended
0.8217 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8199 Intermediate Similarity NPD6232 Discontinued
0.8182 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.8176 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.8165 Intermediate Similarity NPD5402 Approved
0.816 Intermediate Similarity NPD7473 Discontinued
0.8153 Intermediate Similarity NPD6801 Discontinued
0.8137 Intermediate Similarity NPD1247 Approved
0.8125 Intermediate Similarity NPD919 Approved
0.8121 Intermediate Similarity NPD1551 Phase 2
0.8101 Intermediate Similarity NPD7819 Suspended
0.8095 Intermediate Similarity NPD230 Phase 1
0.8072 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8065 Intermediate Similarity NPD5403 Approved
0.8063 Intermediate Similarity NPD3749 Approved
0.8052 Intermediate Similarity NPD5401 Approved
0.8037 Intermediate Similarity NPD3926 Phase 2
0.8027 Intermediate Similarity NPD1613 Approved
0.8027 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8025 Intermediate Similarity NPD6599 Discontinued
0.7975 Intermediate Similarity NPD7411 Suspended
0.7937 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7933 Intermediate Similarity NPD3748 Approved
0.7931 Intermediate Similarity NPD9494 Approved
0.7917 Intermediate Similarity NPD1203 Approved
0.7844 Intermediate Similarity NPD5844 Phase 1
0.7844 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7843 Intermediate Similarity NPD2800 Approved
0.7843 Intermediate Similarity NPD1243 Approved
0.7834 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7829 Intermediate Similarity NPD2344 Approved
0.7815 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7792 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.777 Intermediate Similarity NPD2313 Discontinued
0.7733 Intermediate Similarity NPD1933 Approved
0.7722 Intermediate Similarity NPD920 Approved
0.7708 Intermediate Similarity NPD9269 Phase 2
0.7707 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7706 Intermediate Similarity NPD6559 Discontinued
0.7697 Intermediate Similarity NPD6959 Discontinued
0.7692 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7673 Intermediate Similarity NPD1653 Approved
0.7669 Intermediate Similarity NPD7768 Phase 2
0.7665 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7655 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7651 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD2935 Discontinued
0.7628 Intermediate Similarity NPD2309 Approved
0.7625 Intermediate Similarity NPD3226 Approved
0.7613 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7606 Intermediate Similarity NPD1548 Phase 1
0.7586 Intermediate Similarity NPD9717 Approved
0.7584 Intermediate Similarity NPD3027 Phase 3
0.7582 Intermediate Similarity NPD2799 Discontinued
0.7574 Intermediate Similarity NPD3751 Discontinued
0.7564 Intermediate Similarity NPD4628 Phase 3
0.7532 Intermediate Similarity NPD6100 Approved
0.7532 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD6099 Approved
0.7517 Intermediate Similarity NPD422 Phase 1
0.7517 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD6190 Approved
0.7514 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD7199 Phase 2
0.7484 Intermediate Similarity NPD2532 Approved
0.7484 Intermediate Similarity NPD2533 Approved
0.7484 Intermediate Similarity NPD2534 Approved
0.7484 Intermediate Similarity NPD2346 Discontinued
0.7442 Intermediate Similarity NPD5953 Discontinued
0.7432 Intermediate Similarity NPD1470 Approved
0.7431 Intermediate Similarity NPD9268 Approved
0.7417 Intermediate Similarity NPD411 Approved
0.7401 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7397 Intermediate Similarity NPD1610 Phase 2
0.7396 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD2798 Approved
0.7365 Intermediate Similarity NPD6234 Discontinued
0.7365 Intermediate Similarity NPD3225 Approved
0.7356 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD4308 Phase 3
0.7347 Intermediate Similarity NPD1608 Approved
0.7342 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD6651 Approved
0.7337 Intermediate Similarity NPD3787 Discontinued
0.7326 Intermediate Similarity NPD7286 Phase 2
0.7303 Intermediate Similarity NPD3268 Approved
0.7299 Intermediate Similarity NPD7685 Pre-registration
0.7289 Intermediate Similarity NPD4288 Approved
0.7285 Intermediate Similarity NPD6832 Phase 2
0.7279 Intermediate Similarity NPD1201 Approved
0.7273 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7232 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD4357 Discontinued
0.7205 Intermediate Similarity NPD7390 Discontinued
0.72 Intermediate Similarity NPD2797 Approved
0.7193 Intermediate Similarity NPD5242 Approved
0.719 Intermediate Similarity NPD3764 Approved
0.719 Intermediate Similarity NPD1296 Phase 2
0.7172 Intermediate Similarity NPD5536 Phase 2
0.7171 Intermediate Similarity NPD4908 Phase 1
0.7169 Intermediate Similarity NPD37 Approved
0.7158 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD1471 Phase 3
0.7143 Intermediate Similarity NPD17 Approved
0.7143 Intermediate Similarity NPD4966 Approved
0.7143 Intermediate Similarity NPD4965 Approved
0.7143 Intermediate Similarity NPD4967 Phase 2
0.7134 Intermediate Similarity NPD7033 Discontinued
0.7127 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD9545 Approved
0.7119 Intermediate Similarity NPD8313 Approved
0.7119 Intermediate Similarity NPD8312 Approved
0.7113 Intermediate Similarity NPD228 Approved
0.7111 Intermediate Similarity NPD4287 Approved
0.7108 Intermediate Similarity NPD6386 Approved
0.7108 Intermediate Similarity NPD6385 Approved
0.7105 Intermediate Similarity NPD3018 Phase 2
0.7103 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7103 Intermediate Similarity NPD9493 Approved
0.7097 Intermediate Similarity NPD1558 Phase 1
0.7097 Intermediate Similarity NPD4307 Phase 2
0.7086 Intermediate Similarity NPD3266 Approved
0.7086 Intermediate Similarity NPD3267 Approved
0.7083 Intermediate Similarity NPD2296 Approved
0.7083 Intermediate Similarity NPD5353 Approved
0.7081 Intermediate Similarity NPD2354 Approved
0.7078 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7069 Intermediate Similarity NPD7228 Approved
0.7066 Intermediate Similarity NPD6844 Discontinued
0.7063 Intermediate Similarity NPD2654 Approved
0.7055 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7014 Intermediate Similarity NPD1241 Discontinued
0.7013 Intermediate Similarity NPD4625 Phase 3
0.7 Intermediate Similarity NPD8434 Phase 2
0.7 Intermediate Similarity NPD1481 Phase 2
0.6981 Remote Similarity NPD5406 Approved
0.6981 Remote Similarity NPD5404 Approved
0.6981 Remote Similarity NPD5405 Approved
0.6981 Remote Similarity NPD5408 Approved
0.6974 Remote Similarity NPD1164 Approved
0.6968 Remote Similarity NPD6798 Discontinued
0.6957 Remote Similarity NPD1652 Phase 2
0.6957 Remote Similarity NPD4363 Phase 3
0.6957 Remote Similarity NPD4360 Phase 2
0.6954 Remote Similarity NPD2982 Phase 2
0.6954 Remote Similarity NPD2403 Approved
0.6954 Remote Similarity NPD4749 Approved
0.6954 Remote Similarity NPD7784 Clinical (unspecified phase)
0.6954 Remote Similarity NPD2983 Phase 2
0.6951 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6941 Remote Similarity NPD5019 Clinical (unspecified phase)
0.6936 Remote Similarity NPD5710 Approved
0.6936 Remote Similarity NPD5711 Approved
0.6933 Remote Similarity NPD1535 Discovery
0.6928 Remote Similarity NPD1019 Discontinued
0.6919 Remote Similarity NPD4361 Phase 2
0.6919 Remote Similarity NPD4362 Clinical (unspecified phase)
0.6911 Remote Similarity NPD7584 Approved
0.6901 Remote Similarity NPD6971 Discontinued
0.6893 Remote Similarity NPD1729 Discontinued
0.6887 Remote Similarity NPD3972 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