Structure

Physi-Chem Properties

Molecular Weight:  238.06
Volume:  247.606
LogP:  3.612
LogD:  2.997
LogS:  -3.66
# 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:  1.872
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:  -4.731
MDCK Permeability:  1.407271520292852e-05
Pgp-inhibitor:  0.005
Pgp-substrate:  0.934
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.988
30% Bioavailability (F30%):  0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.083
Plasma Protein Binding (PPB):  97.38373565673828%
Volume Distribution (VD):  0.444
Pgp-substrate:  2.8370361328125%

ADMET: Metabolism

CYP1A2-inhibitor:  0.986
CYP1A2-substrate:  0.427
CYP2C19-inhibitor:  0.874
CYP2C19-substrate:  0.069
CYP2C9-inhibitor:  0.513
CYP2C9-substrate:  0.933
CYP2D6-inhibitor:  0.668
CYP2D6-substrate:  0.89
CYP3A4-inhibitor:  0.288
CYP3A4-substrate:  0.173

ADMET: Excretion

Clearance (CL):  5.049
Half-life (T1/2):  0.491

ADMET: Toxicity

hERG Blockers:  0.091
Human Hepatotoxicity (H-HT):  0.087
Drug-inuced Liver Injury (DILI):  0.893
AMES Toxicity:  0.383
Rat Oral Acute Toxicity:  0.383
Maximum Recommended Daily Dose:  0.359
Skin Sensitization:  0.76
Carcinogencity:  0.642
Eye Corrosion:  0.01
Eye Irritation:  0.961
Respiratory Toxicity:  0.364

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

  Natural Product: NPC57601

Natural Product ID:  NPC57601
Common Name*:   7-Hydroxyflavone
IUPAC Name:   7-hydroxy-2-phenylchromen-4-one
Synonyms:   NSC-94258
Standard InCHIKey:  MQGPSCMMNJKMHQ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C15H10O3/c16-11-6-7-12-13(17)9-14(18-15(12)8-11)10-4-2-1-3-5-10/h1-9,16H
SMILES:  Oc1ccc2c(c1)oc(cc2=O)c1ccccc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL276915
PubChem CID:   5281894
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
NPO19860 Jasminum sambac Species Oleaceae Eukaryota n.a. n.a. n.a. PMID[26555361]
NPO17550 Origanum onites Species Lamiaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO17550 Origanum onites Species Lamiaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO19860 Jasminum sambac Species Oleaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17550 Origanum onites Species Lamiaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO19860 Jasminum sambac Species Oleaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19860 Jasminum sambac Species Oleaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20782 Philodendron hederaceum Species Araceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18625 Chlorocodon whitei n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO18385 Rabdosia parvifolia Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19597 Populus sieboldi Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19470 Xanthorrhoea minor Species Asphodelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20623 Dendrobium farmeri Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19860 Jasminum sambac Species Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17550 Origanum onites Species Lamiaceae 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 = 70.8 % PMID[568693]
NPT1315 Individual Protein Adenosine A1 receptor Rattus norvegicus pKi(uM) = -0.48 n.a. PMID[568696]
NPT1316 Individual Protein Adenosine A2a receptor Rattus norvegicus pKi(uM) = -0.43 n.a. PMID[568696]
NPT1315 Individual Protein Adenosine A1 receptor Rattus norvegicus Ki = 3030.0 nM PMID[568697]
NPT1316 Individual Protein Adenosine A2a receptor Rattus norvegicus Ki = 2680.0 nM PMID[568697]
NPT218 Individual Protein Adenosine A3 receptor Homo sapiens Displacement = 41.0 % PMID[568697]
NPT299 Individual Protein Androgen Receptor Rattus norvegicus IC50 > 42657.95 nM PMID[568700]
NPT1332 Individual Protein Fatty acid synthase Plasmodium falciparum IC50 = 20000.0 nM PMID[568701]
NPT1119 Individual Protein Arachidonate 12-lipoxygenase Homo sapiens IC50 > 100000.0 nM PMID[568704]
NPT1139 Individual Protein Arachidonate 15-lipoxygenase, type II Homo sapiens IC50 > 100000.0 nM PMID[568704]
NPT1265 Individual Protein Serine/threonine-protein kinase PIM1 Homo sapiens -Log IC50 = -1.15 uM PMID[568706]
NPT13 Individual Protein Tyrosine-protein kinase LCK Homo sapiens IC50 = 80.0 ug.mL-1 PMID[568709]
NPT1587 Individual Protein Estradiol 17-beta-dehydrogenase 1 Homo sapiens Activity = 16.0 % PMID[568715]
NPT1588 Individual Protein Estradiol 17-beta-dehydrogenase 2 Homo sapiens Activity = 23.1 % PMID[568715]
NPT1587 Individual Protein Estradiol 17-beta-dehydrogenase 1 Homo sapiens IC50 = 5250.0 nM PMID[568715]
NPT1588 Individual Protein Estradiol 17-beta-dehydrogenase 2 Homo sapiens IC50 > 20000.0 nM PMID[568715]
NPT249 Individual Protein Glucocorticoid receptor Homo sapiens EC150 = 3.1 uM PMID[568717]
NPT153 Individual Protein Androgen Receptor Homo sapiens EC150 = 3.1 uM PMID[568717]
NPT441 Individual Protein Cytochrome P450 19A1 Homo sapiens IC50 = 30.5 nM PMID[568719]
NPT208 Individual Protein Cytochrome P450 1A2 Homo sapiens IC50 = 240.0 nM PMID[568722]
NPT1621 Individual Protein Calmodulin Homo sapiens IC50 = 37100.0 nM PMID[568723]
NPT1621 Individual Protein Calmodulin Homo sapiens Ratio IC50 = 0.54 n.a. PMID[568723]
NPT520 Cell Line 3T3-L1 Mus musculus Activity = 17.1 % PMID[568725]
NPT520 Cell Line 3T3-L1 Mus musculus Activity = 13.7 % PMID[568725]
NPT520 Cell Line 3T3-L1 Mus musculus Activity = 12.2 % PMID[568725]
NPT520 Cell Line 3T3-L1 Mus musculus Activity = 5.3 % PMID[568725]
NPT233 Individual Protein Carbonic anhydrase II Homo sapiens Ki = 2240.0 nM PMID[568730]
NPT233 Individual Protein Carbonic anhydrase II Homo sapiens Ki = 2320.0 nM PMID[568730]
NPT157 Individual Protein Breast cancer type 1 susceptibility protein Homo sapiens Potency n.a. 10000.0 nM PMID[568728]
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus Inhibition = 24.35 % PMID[568731]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 16360.1 nM PMID[568728]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 25929.0 nM PMID[568728]
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus IC50 = 85000.0 nM PMID[568736]
NPT570 Individual Protein Arachidonate 5-lipoxygenase Homo sapiens Inhibition = 53.1 % PMID[568737]
NPT65 Cell Line HepG2 Homo sapiens Activity = 98.8 % PMID[568739]
NPT83 Cell Line MCF7 Homo sapiens Activity = 26.6 % PMID[568739]
NPT111 Cell Line K562 Homo sapiens Activity = 22.3 % PMID[568739]
NPT1270 Individual Protein Aldo-keto reductase family 1 member B10 Homo sapiens Inhibition = 19.0 % PMID[568740]
NPT1270 Individual Protein Aldo-keto reductase family 1 member B10 Homo sapiens IC50 = 160000.0 nM PMID[568740]
NPT41 Individual Protein Aldose reductase Homo sapiens IC50 = 12300.0 nM PMID[568740]
NPT1270 Individual Protein Aldo-keto reductase family 1 member B10 Homo sapiens IC50 = 8300.0 nM PMID[568740]
NPT1270 Individual Protein Aldo-keto reductase family 1 member B10 Homo sapiens Ratio IC50 = 10.0 n.a. PMID[568740]
NPT1604 Individual Protein Cytochrome P450 1B1 Homo sapiens IC50 = 250.0 nM PMID[568741]
NPT1588 Individual Protein Estradiol 17-beta-dehydrogenase 2 Homo sapiens IC50 > 20000.0 nM PMID[568743]
NPT1588 Individual Protein Estradiol 17-beta-dehydrogenase 2 Homo sapiens Activity = 23.1 % PMID[568743]
NPT2266 Individual Protein Fructose-1,6-bisphosphatase Homo sapiens Inhibition < 20.0 % PMID[568744]
NPT3213 Individual Protein MAP kinase signal-integrating kinase 2 Homo sapiens Inhibition > 50.0 % PMID[568746]
NPT711 Individual Protein Aldose reductase Bos taurus IC50 = 14650.0 nM PMID[568692]
NPT711 Individual Protein Aldose reductase Bos taurus IC50 = 45210.0 nM PMID[568692]
NPT2 Others Unspecified Ratio = 3.1 n.a. PMID[568692]
NPT805 Protein Complex GABA-A receptor; anion channel Rattus norvegicus Ki = 4200.0 nM PMID[568694]
NPT805 Protein Complex GABA-A receptor; anion channel Rattus norvegicus GABA ratio = 1.14 n.a. PMID[568694]
NPT2731 Protein Family Monoamine oxidase Homo sapiens IC50 = 120.0 nM PMID[568695]
NPT29 Organism Rattus norvegicus Rattus norvegicus Systolic blood pressure = 217.0 n.a. PMID[568698]
NPT29 Organism Rattus norvegicus Rattus norvegicus Protection = 75.0 % PMID[568699]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum IC50 = 65500.0 nM PMID[568701]
NPT958 Individual Protein Estradiol 17-beta-dehydrogenase 3 Homo sapiens IC50 = 66980.0 nM PMID[568702]
NPT2 Others Unspecified IC50 = 146500.0 nM PMID[568703]
NPT792 Individual Protein Arachidonate 15-lipoxygenase Homo sapiens IC50 > 100000.0 nM PMID[568704]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 >= 100000.0 nM PMID[568705]
NPT2 Others Unspecified IC50 = 80.0 ug.mL-1 PMID[568707]
NPT2 Others Unspecified Activity = 54.2 % PMID[568708]
NPT2 Others Unspecified Activity = 91.3 % PMID[568708]
NPT2 Others Unspecified Activity = 95.1 % PMID[568708]
NPT2 Others Unspecified IC50 = 1400.0 nM PMID[568708]
NPT2 Others Unspecified logKi = 0.623 n.a. PMID[568710]
NPT2 Others Unspecified ID50 > 419.7 uM PMID[568711]
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens IC50 = 38000.0 nM PMID[568713]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 100000.0 nM PMID[568713]
NPT35 Others n.a. Activity = 5.3 mg/L PMID[568718]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 20.4 % PMID[568720]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 36.0 % PMID[568720]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 35.5 % PMID[568720]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 8.8 % PMID[568720]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = -12.18 % PMID[568720]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = -10.03 % PMID[568720]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = -12.69 % PMID[568720]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = -12.79 % PMID[568720]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = -4.81 % PMID[568720]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 7.39 % PMID[568720]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = -6.19 % PMID[568720]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 5.05 % PMID[568720]
NPT29 Organism Rattus norvegicus Rattus norvegicus Activity = 38.5 % PMID[568720]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium pID50 = 5.456 n.a. PMID[568721]
NPT177 Tissue Aorta Rattus norvegicus IC50 = 37800.0 nM PMID[568723]
NPT177 Tissue Aorta Rattus norvegicus IC50 = 167040.0 nM PMID[568723]
NPT177 Tissue Aorta Rattus norvegicus Emax = 80.59 % PMID[568723]
NPT177 Tissue Aorta Rattus norvegicus Emax = 40.39 % PMID[568723]
NPT968 Protein Family Adrenergic receptor alpha-1 Rattus norvegicus Kd = 246.04 nM PMID[568724]
NPT668 Individual Protein P-glycoprotein 1 Homo sapiens Kd = 34673.69 nM PMID[568727]
NPT21702 PROTEIN-PROTEIN INTERACTION Importin subunit beta-1/Snurportin-1 Homo sapiens Potency n.a. 10000.0 nM PMID[568728]
NPT20798 PROTEIN COMPLEX GTP-binding nuclear protein Ran/Importin subunit beta-1/Snurportin-1 Homo sapiens Potency n.a. 5173.5 nM PMID[568728]
NPT2 Others Unspecified Potency n.a. 11220.2 nM PMID[568728]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Ratio = 2.04 n.a. PMID[568729]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Ratio = 2.52 n.a. PMID[568729]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Ratio = 15.13 n.a. PMID[568729]
NPT632 Tissue Brain Rattus norvegicus Activity = 0.42 nmol PMID[568729]
NPT632 Tissue Brain Rattus norvegicus Activity = 0.48 nmol PMID[568729]
NPT632 Tissue Brain Rattus norvegicus Activity = 0.91 nmol PMID[568729]
NPT947 Individual Protein Carbonic anhydrase I Homo sapiens Ki = 3370.0 nM PMID[568730]
NPT947 Individual Protein Carbonic anhydrase I Homo sapiens Ki = 3430.0 nM PMID[568730]
NPT948 Individual Protein Carbonic anhydrase IX Homo sapiens Ki = 4920.0 nM PMID[568730]
NPT948 Individual Protein Carbonic anhydrase IX Homo sapiens Ki = 4850.0 nM PMID[568730]
NPT949 Individual Protein Carbonic anhydrase XII Homo sapiens Ki = 8400.0 nM PMID[568730]
NPT949 Individual Protein Carbonic anhydrase XII Homo sapiens Ki = 8510.0 nM PMID[568730]
NPT67 Individual Protein Cholinesterase Equus caballus Inhibition = -0.25 % PMID[568731]
NPT1192 Organism Spodoptera frugiperda Spodoptera frugiperda log10LT50 = 2.029 n.a. PMID[568732]
NPT1192 Organism Spodoptera frugiperda Spodoptera frugiperda LT50 = 106.94 hr PMID[568732]
NPT1 Others Radical scavenging activity Inhibition = 2.8 % PMID[568733]
NPT1175 Organism Spodoptera litura Spodoptera litura ED50 > 10.0 umol/cm2 PMID[568734]
NPT2 Others Unspecified Inhibition < 40.0 % PMID[568735]
NPT2 Others Unspecified IC50 = 33000.0 nM PMID[568735]
NPT27 Others Unspecified Activity > 98.0 % PMID[568735]
NPT78 Individual Protein Beta amyloid A4 protein Homo sapiens Inhibition = 27.2 % PMID[568736]
NPT2 Others Unspecified Ratio IC50 > 1.2 n.a. PMID[568736]
NPT67 Individual Protein Cholinesterase Equus caballus IC50 > 100000.0 nM PMID[568736]
NPT2 Others Unspecified Potency n.a. 5011.9 nM PMID[568728]
NPT2 Others Unspecified Potency n.a. 6309.6 nM PMID[568738]
NPT2 Others Unspecified Kapp = 450.0 /M PMID[568739]
NPT2 Others Unspecified Kapp = 311.0 /M PMID[568739]
NPT21750 LIPID Lipid bilayer n.a. T = 31.9 degrees C PMID[568739]
NPT21750 LIPID Lipid bilayer n.a. T = 31.8 degrees C PMID[568739]
NPT21750 LIPID Lipid bilayer n.a. T = 27.4 degrees C PMID[568739]
NPT21750 LIPID Lipid bilayer n.a. Tm = 40.7 degrees C PMID[568739]
NPT21750 LIPID Lipid bilayer n.a. Tm = 40.5 degrees C PMID[568739]
NPT21750 LIPID Lipid bilayer n.a. Tm = 40.4 degrees C PMID[568739]
NPT21750 LIPID Lipid bilayer n.a. Tm = 39.8 degrees C PMID[568739]
NPT1 Others Radical scavenging activity IC50 = 24.2 ug.mL-1 PMID[568739]
NPT2 Others Unspecified Potency n.a. 3162.3 nM PMID[568728]
NPT27 Others Unspecified EC50 > 50000.0 nM PMID[568740]
NPT22036 CELL-LINE HL Homo sapiens Activity = 71.1 % PMID[568742]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 20000.0 nM PMID[568745]
NPT20555 ORGANISM SARS-CoV-2 Severe acute respiratory syndrome coronavirus 2 IC50 > 19952.62 nM PMID[568745]

☑ 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 NPC57601 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
0.9922 High Similarity NPC172262
0.9844 High Similarity NPC78540
0.9844 High Similarity NPC274121
0.9844 High Similarity NPC50898
0.9844 High Similarity NPC213216
0.9695 High Similarity NPC228661
0.9695 High Similarity NPC299379
0.9695 High Similarity NPC266597
0.9695 High Similarity NPC250266
0.9692 High Similarity NPC239495
0.9692 High Similarity NPC9985
0.9688 High Similarity NPC113006
0.9618 High Similarity NPC116775
0.9618 High Similarity NPC187432
0.9618 High Similarity NPC234133
0.9618 High Similarity NPC127447
0.9618 High Similarity NPC473887
0.9618 High Similarity NPC281917
0.9618 High Similarity NPC47815
0.9618 High Similarity NPC13408
0.9618 High Similarity NPC256042
0.9618 High Similarity NPC194281
0.9618 High Similarity NPC124784
0.9618 High Similarity NPC216361
0.9618 High Similarity NPC231772
0.9618 High Similarity NPC29353
0.9606 High Similarity NPC197425
0.9545 High Similarity NPC290291
0.9545 High Similarity NPC275055
0.9545 High Similarity NPC84585
0.9545 High Similarity NPC476480
0.9531 High Similarity NPC39753
0.9531 High Similarity NPC115998
0.9478 High Similarity NPC172986
0.9478 High Similarity NPC281207
0.9478 High Similarity NPC269652
0.9478 High Similarity NPC261227
0.9478 High Similarity NPC305355
0.9478 High Similarity NPC475680
0.9478 High Similarity NPC270883
0.9474 High Similarity NPC472460
0.9474 High Similarity NPC99333
0.9474 High Similarity NPC147686
0.9474 High Similarity NPC201395
0.9474 High Similarity NPC280284
0.9474 High Similarity NPC188947
0.9474 High Similarity NPC329225
0.947 High Similarity NPC240593
0.9466 High Similarity NPC248872
0.9457 High Similarity NPC137264
0.9457 High Similarity NPC5515
0.9457 High Similarity NPC270369
0.9449 High Similarity NPC22783
0.9407 High Similarity NPC136840
0.9407 High Similarity NPC147688
0.9407 High Similarity NPC110969
0.9407 High Similarity NPC156590
0.9407 High Similarity NPC64908
0.9407 High Similarity NPC118840
0.9407 High Similarity NPC205006
0.9403 High Similarity NPC78913
0.9403 High Similarity NPC55018
0.9403 High Similarity NPC216978
0.9403 High Similarity NPC220062
0.9403 High Similarity NPC301217
0.9403 High Similarity NPC303633
0.9403 High Similarity NPC143799
0.9403 High Similarity NPC241838
0.9403 High Similarity NPC261234
0.9403 High Similarity NPC18260
0.9403 High Similarity NPC152042
0.9403 High Similarity NPC96565
0.9398 High Similarity NPC254841
0.9398 High Similarity NPC13768
0.9398 High Similarity NPC160972
0.9398 High Similarity NPC295261
0.9398 High Similarity NPC243083
0.9398 High Similarity NPC107586
0.9398 High Similarity NPC287246
0.9398 High Similarity NPC32441
0.9398 High Similarity NPC12296
0.9398 High Similarity NPC296490
0.9398 High Similarity NPC79943
0.9398 High Similarity NPC188879
0.9394 High Similarity NPC151113
0.9394 High Similarity NPC39426
0.9394 High Similarity NPC234560
0.9385 High Similarity NPC284424
0.9385 High Similarity NPC31872
0.9385 High Similarity NPC473584
0.9385 High Similarity NPC313618
0.9385 High Similarity NPC64359
0.9385 High Similarity NPC475589
0.9385 High Similarity NPC308037
0.9338 High Similarity NPC11561
0.9338 High Similarity NPC226636
0.9333 High Similarity NPC103342
0.9333 High Similarity NPC103904
0.9333 High Similarity NPC146679
0.9333 High Similarity NPC184536
0.9333 High Similarity NPC59951
0.9333 High Similarity NPC159275
0.9333 High Similarity NPC69769
0.9333 High Similarity NPC235239
0.9333 High Similarity NPC241100
0.9333 High Similarity NPC230285
0.9328 High Similarity NPC124269
0.9328 High Similarity NPC118813
0.9323 High Similarity NPC87545
0.9323 High Similarity NPC235428
0.9313 High Similarity NPC129132
0.9313 High Similarity NPC87231
0.9313 High Similarity NPC128216
0.9313 High Similarity NPC257756
0.9313 High Similarity NPC10971
0.9313 High Similarity NPC212631
0.9313 High Similarity NPC25937
0.9313 High Similarity NPC205468
0.9302 High Similarity NPC60558
0.927 High Similarity NPC38219
0.9265 High Similarity NPC90582
0.9265 High Similarity NPC3188
0.9265 High Similarity NPC262094
0.9265 High Similarity NPC282300
0.9265 High Similarity NPC14871
0.9265 High Similarity NPC103362
0.9259 High Similarity NPC53181
0.9259 High Similarity NPC217186
0.9259 High Similarity NPC316480
0.9259 High Similarity NPC20709
0.9259 High Similarity NPC310135
0.9259 High Similarity NPC329203
0.9259 High Similarity NPC150648
0.9259 High Similarity NPC265871
0.9259 High Similarity NPC225153
0.9259 High Similarity NPC274784
0.9259 High Similarity NPC222342
0.9254 High Similarity NPC7013
0.9254 High Similarity NPC303644
0.9254 High Similarity NPC116632
0.9254 High Similarity NPC162680
0.9254 High Similarity NPC181124
0.9254 High Similarity NPC209560
0.9254 High Similarity NPC212767
0.9254 High Similarity NPC294409
0.9242 High Similarity NPC312318
0.9242 High Similarity NPC108113
0.9242 High Similarity NPC93756
0.9242 High Similarity NPC223457
0.9242 High Similarity NPC472365
0.9242 High Similarity NPC337373
0.9242 High Similarity NPC242294
0.9242 High Similarity NPC292998
0.9242 High Similarity NPC175098
0.9242 High Similarity NPC188646
0.9242 High Similarity NPC56031
0.9242 High Similarity NPC263670
0.9242 High Similarity NPC192304
0.9242 High Similarity NPC139813
0.9237 High Similarity NPC278556
0.9237 High Similarity NPC262359
0.9231 High Similarity NPC185497
0.9225 High Similarity NPC80694
0.9225 High Similarity NPC186098
0.9213 High Similarity NPC193805
0.9203 High Similarity NPC234629
0.9203 High Similarity NPC311741
0.9203 High Similarity NPC70136
0.9197 High Similarity NPC202981
0.9197 High Similarity NPC217083
0.9197 High Similarity NPC293852
0.9197 High Similarity NPC59739
0.9197 High Similarity NPC169479
0.9197 High Similarity NPC299080
0.9197 High Similarity NPC144499
0.9197 High Similarity NPC200694
0.9197 High Similarity NPC159855
0.9197 High Similarity NPC473042
0.9197 High Similarity NPC78803
0.9197 High Similarity NPC62840
0.9197 High Similarity NPC214236
0.9191 High Similarity NPC188243
0.9191 High Similarity NPC284550
0.9191 High Similarity NPC76445
0.9191 High Similarity NPC6407
0.9191 High Similarity NPC129853
0.9191 High Similarity NPC110228
0.9191 High Similarity NPC150522
0.9185 High Similarity NPC278323
0.9185 High Similarity NPC279668
0.9185 High Similarity NPC309154
0.9185 High Similarity NPC12175
0.9185 High Similarity NPC276905
0.9185 High Similarity NPC55162
0.9185 High Similarity NPC90665
0.9179 High Similarity NPC193792
0.9173 High Similarity NPC125920
0.9173 High Similarity NPC286336
0.9167 High Similarity NPC101294
0.9167 High Similarity NPC473655

  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 NPC57601 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
0.9474 High Similarity NPD1549 Phase 2
0.9398 High Similarity NPD1550 Clinical (unspecified phase)
0.9398 High Similarity NPD1552 Clinical (unspecified phase)
0.9394 High Similarity NPD1510 Phase 2
0.9385 High Similarity NPD1240 Approved
0.9242 High Similarity NPD1607 Approved
0.913 High Similarity NPD1511 Approved
0.9065 High Similarity NPD4378 Clinical (unspecified phase)
0.9065 High Similarity NPD7410 Clinical (unspecified phase)
0.9037 High Similarity NPD2796 Approved
0.9 High Similarity NPD1512 Approved
0.8777 High Similarity NPD3750 Approved
0.8623 High Similarity NPD1551 Phase 2
0.8621 High Similarity NPD4380 Phase 2
0.8592 High Similarity NPD6799 Approved
0.8571 High Similarity NPD2801 Approved
0.8562 High Similarity NPD7411 Suspended
0.8561 High Similarity NPD1203 Approved
0.8523 High Similarity NPD4381 Clinical (unspecified phase)
0.8503 High Similarity NPD1934 Approved
0.85 High Similarity NPD970 Clinical (unspecified phase)
0.8446 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.844 Intermediate Similarity NPD1243 Approved
0.8417 Intermediate Similarity NPD3748 Approved
0.84 Intermediate Similarity NPD3749 Approved
0.84 Intermediate Similarity NPD7075 Discontinued
0.8389 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8378 Intermediate Similarity NPD6801 Discontinued
0.8372 Intermediate Similarity NPD1548 Phase 1
0.8333 Intermediate Similarity NPD3882 Suspended
0.8322 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8322 Intermediate Similarity NPD7819 Suspended
0.8298 Intermediate Similarity NPD2344 Approved
0.8288 Intermediate Similarity NPD5403 Approved
0.8276 Intermediate Similarity NPD5401 Approved
0.8264 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.8258 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.8258 Intermediate Similarity NPD422 Phase 1
0.8248 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.8243 Intermediate Similarity NPD6599 Discontinued
0.8195 Intermediate Similarity NPD9717 Approved
0.8182 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8182 Intermediate Similarity NPD2800 Approved
0.8151 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.8146 Intermediate Similarity NPD3817 Phase 2
0.8129 Intermediate Similarity NPD943 Approved
0.8125 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.8116 Intermediate Similarity NPD2313 Discontinued
0.8092 Intermediate Similarity NPD7768 Phase 2
0.8089 Intermediate Similarity NPD3818 Discontinued
0.8077 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8069 Intermediate Similarity NPD2309 Approved
0.8041 Intermediate Similarity NPD920 Approved
0.7985 Intermediate Similarity NPD1610 Phase 2
0.7962 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7962 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7962 Intermediate Similarity NPD6166 Phase 2
0.7956 Intermediate Similarity NPD2798 Approved
0.7941 Intermediate Similarity NPD3225 Approved
0.7925 Intermediate Similarity NPD7054 Approved
0.7925 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7908 Intermediate Similarity NPD5402 Approved
0.7902 Intermediate Similarity NPD2799 Discontinued
0.7902 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7887 Intermediate Similarity NPD6651 Approved
0.7885 Intermediate Similarity NPD6959 Discontinued
0.7883 Intermediate Similarity NPD2797 Approved
0.7875 Intermediate Similarity NPD7472 Approved
0.7857 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7857 Intermediate Similarity NPD3268 Approved
0.7847 Intermediate Similarity NPD2935 Discontinued
0.7847 Intermediate Similarity NPD6100 Approved
0.7847 Intermediate Similarity NPD6099 Approved
0.7842 Intermediate Similarity NPD6832 Phase 2
0.7826 Intermediate Similarity NPD6797 Phase 2
0.782 Intermediate Similarity NPD9545 Approved
0.7803 Intermediate Similarity NPD9493 Approved
0.7778 Intermediate Similarity NPD7251 Discontinued
0.7778 Intermediate Similarity NPD4308 Phase 3
0.7764 Intermediate Similarity NPD7074 Phase 3
0.773 Intermediate Similarity NPD1296 Phase 2
0.773 Intermediate Similarity NPD7808 Phase 3
0.773 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.773 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD1465 Phase 2
0.7716 Intermediate Similarity NPD5953 Discontinued
0.771 Intermediate Similarity NPD1241 Discontinued
0.7707 Intermediate Similarity NPD5494 Approved
0.7702 Intermediate Similarity NPD7286 Phase 2
0.7697 Intermediate Similarity NPD3226 Approved
0.7677 Intermediate Similarity NPD4288 Approved
0.7664 Intermediate Similarity NPD1608 Approved
0.7655 Intermediate Similarity NPD7033 Discontinued
0.7643 Intermediate Similarity NPD919 Approved
0.7635 Intermediate Similarity NPD4628 Phase 3
0.7626 Intermediate Similarity NPD3267 Approved
0.7626 Intermediate Similarity NPD3266 Approved
0.761 Intermediate Similarity NPD6232 Discontinued
0.7606 Intermediate Similarity NPD411 Approved
0.7591 Intermediate Similarity NPD1201 Approved
0.7589 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7589 Intermediate Similarity NPD4908 Phase 1
0.7578 Intermediate Similarity NPD7473 Discontinued
0.7569 Intermediate Similarity NPD447 Suspended
0.7569 Intermediate Similarity NPD1933 Approved
0.7568 Intermediate Similarity NPD2654 Approved
0.7561 Intermediate Similarity NPD6559 Discontinued
0.7551 Intermediate Similarity NPD2346 Discontinued
0.755 Intermediate Similarity NPD2532 Approved
0.755 Intermediate Similarity NPD2533 Approved
0.755 Intermediate Similarity NPD2534 Approved
0.7547 Intermediate Similarity NPD1247 Approved
0.7536 Intermediate Similarity NPD1481 Phase 2
0.7536 Intermediate Similarity NPD3972 Approved
0.7534 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7518 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7517 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1470 Approved
0.75 Intermediate Similarity NPD1164 Approved
0.75 Intermediate Similarity NPD4307 Phase 2
0.7483 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD3764 Approved
0.7464 Intermediate Similarity NPD1535 Discovery
0.7462 Intermediate Similarity NPD74 Approved
0.7462 Intermediate Similarity NPD9266 Approved
0.7453 Intermediate Similarity NPD3926 Phase 2
0.7452 Intermediate Similarity NPD2296 Approved
0.7448 Intermediate Similarity NPD230 Phase 1
0.7448 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7447 Intermediate Similarity NPD1019 Discontinued
0.7445 Intermediate Similarity NPD17 Approved
0.7439 Intermediate Similarity NPD1729 Discontinued
0.7394 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7385 Intermediate Similarity NPD9264 Approved
0.7385 Intermediate Similarity NPD9267 Approved
0.7385 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7385 Intermediate Similarity NPD9263 Approved
0.7379 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7379 Intermediate Similarity NPD1613 Approved
0.7378 Intermediate Similarity NPD5844 Phase 1
0.7368 Intermediate Similarity NPD7390 Discontinued
0.7353 Intermediate Similarity NPD4287 Approved
0.7343 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7315 Intermediate Similarity NPD1471 Phase 3
0.7299 Intermediate Similarity NPD1894 Discontinued
0.7299 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7292 Intermediate Similarity NPD4625 Phase 3
0.7283 Intermediate Similarity NPD4363 Phase 3
0.7283 Intermediate Similarity NPD4360 Phase 2
0.7279 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD4361 Phase 2
0.7241 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7237 Intermediate Similarity NPD2354 Approved
0.7234 Intermediate Similarity NPD4749 Approved
0.7212 Intermediate Similarity NPD5940 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD3751 Discontinued
0.7211 Intermediate Similarity NPD5124 Phase 1
0.7211 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7208 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7183 Intermediate Similarity NPD1876 Approved
0.7153 Intermediate Similarity NPD9494 Approved
0.7152 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD3142 Approved
0.7143 Intermediate Similarity NPD6104 Discontinued
0.7143 Intermediate Similarity NPD3140 Approved
0.7133 Intermediate Similarity NPD5408 Approved
0.7133 Intermediate Similarity NPD5406 Approved
0.7133 Intermediate Similarity NPD5404 Approved
0.7133 Intermediate Similarity NPD5405 Approved
0.7123 Intermediate Similarity NPD6798 Discontinued
0.7107 Intermediate Similarity NPD6844 Discontinued
0.7105 Intermediate Similarity NPD1652 Phase 2
0.7099 Intermediate Similarity NPD9697 Approved
0.7097 Intermediate Similarity NPD4661 Approved
0.7097 Intermediate Similarity NPD4662 Approved
0.7089 Intermediate Similarity NPD6585 Discontinued
0.7086 Intermediate Similarity NPD2355 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD2353 Approved
0.7086 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD7440 Discontinued
0.7077 Intermediate Similarity NPD9261 Approved
0.7059 Intermediate Similarity NPD7003 Approved
0.7045 Intermediate Similarity NPD968 Approved
0.7044 Intermediate Similarity NPD5889 Approved
0.7044 Intermediate Similarity NPD5890 Approved
0.7042 Intermediate Similarity NPD9269 Phase 2
0.7037 Intermediate Similarity NPD6971 Discontinued
0.7034 Intermediate Similarity NPD2861 Phase 2
0.7032 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD7458 Discontinued
0.7007 Intermediate Similarity NPD9281 Approved
0.7 Intermediate Similarity NPD6280 Approved
0.7 Intermediate Similarity NPD940 Approved
0.7 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD7577 Discontinued
0.7 Intermediate Similarity NPD846 Approved
0.7 Intermediate Similarity NPD6279 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