Structure

Physi-Chem Properties

Molecular Weight:  238.06
Volume:  247.606
LogP:  3.555
LogD:  2.963
LogS:  -3.719
# 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:  1.828
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:  -4.655
MDCK Permeability:  1.4108096365816891e-05
Pgp-inhibitor:  0.005
Pgp-substrate:  0.847
Human Intestinal Absorption (HIA):  0.007
20% Bioavailability (F20%):  0.981
30% Bioavailability (F30%):  0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.075
Plasma Protein Binding (PPB):  97.62123107910156%
Volume Distribution (VD):  0.444
Pgp-substrate:  2.8337502479553223%

ADMET: Metabolism

CYP1A2-inhibitor:  0.984
CYP1A2-substrate:  0.32
CYP2C19-inhibitor:  0.836
CYP2C19-substrate:  0.067
CYP2C9-inhibitor:  0.42
CYP2C9-substrate:  0.933
CYP2D6-inhibitor:  0.473
CYP2D6-substrate:  0.906
CYP3A4-inhibitor:  0.224
CYP3A4-substrate:  0.228

ADMET: Excretion

Clearance (CL):  4.824
Half-life (T1/2):  0.471

ADMET: Toxicity

hERG Blockers:  0.102
Human Hepatotoxicity (H-HT):  0.062
Drug-inuced Liver Injury (DILI):  0.914
AMES Toxicity:  0.471
Rat Oral Acute Toxicity:  0.367
Maximum Recommended Daily Dose:  0.1
Skin Sensitization:  0.625
Carcinogencity:  0.776
Eye Corrosion:  0.01
Eye Irritation:  0.966
Respiratory Toxicity:  0.255

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

  Natural Product: NPC22783

Natural Product ID:  NPC22783
Common Name*:   2-(4-Hydroxyphenyl)Chromen-4-One
IUPAC Name:   2-(4-hydroxyphenyl)chromen-4-one
Synonyms:   NSC-22357
Standard InCHIKey:  SHGLJXBLXNNCTE-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C15H10O3/c16-11-7-5-10(6-8-11)15-9-13(17)12-3-1-2-4-14(12)18-15/h1-9,16H
SMILES:  Oc1ccc(cc1)c1cc(=O)c2c(o1)cccc2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL327209
PubChem CID:   229016
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0002991] Hydroxyflavonoids
          • [CHEMONTID:0003006] Monohydroxyflavonoids

*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]
NPO24045 Lespedeza homoloba Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24284 Hypoestes serpens Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24045 Lespedeza homoloba Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15440 Chamaemelum nobile Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18557 Epicoccum nigrum Species Didymellaceae Eukaryota n.a. n.a. n.a. Database[Title]
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]
NPO15440 Chamaemelum nobile Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24173 Plutella xylostella Species Plutellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18557 Epicoccum nigrum Species Didymellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24045 Lespedeza homoloba Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24284 Hypoestes serpens Species Acanthaceae 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
NPT13 Individual Protein Tyrosine-protein kinase LCK Homo sapiens IC50 = 504000.0 nM PMID[449406]
NPT13 Individual Protein Tyrosine-protein kinase LCK Homo sapiens IC50 = 100.0 ug.mL-1 PMID[449410]
NPT48 Individual Protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 39810.7 nM PMID[449412]
NPT537 Individual Protein Ras-related protein Rab-9A Homo sapiens Potency = 5623.4 nM PMID[449412]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency = 28183.8 nM PMID[449412]
NPT56 Individual Protein Beta-lactamase AmpC Escherichia coli K-12 Potency = 10000.0 nM PMID[449412]
NPT538 Individual Protein Niemann-Pick C1 protein Homo sapiens Potency = 5623.4 nM PMID[449412]
NPT59 Individual Protein DNA polymerase beta Homo sapiens Potency = 28183.8 nM PMID[449412]
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 18348.9 nM PMID[449412]
NPT64 Individual Protein ATPase family AAA domain-containing protein 5 Homo sapiens Potency n.a. 20587.8 nM PMID[449412]
NPT484 Individual Protein Luciferin 4-monooxygenase Photinus pyralis Potency n.a. 10691.0 nM PMID[449412]
NPT101 Individual Protein Glucagon-like peptide 1 receptor Homo sapiens Potency n.a. 8912.5 nM PMID[449412]
NPT157 Individual Protein Breast cancer type 1 susceptibility protein Homo sapiens Potency n.a. 31622.8 nM PMID[449412]
NPT11 Individual Protein Guanine nucleotide-binding protein G(s), subunit alpha Homo sapiens Potency n.a. 50118.7 nM PMID[449412]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 2511.9 nM PMID[449412]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 29092.9 nM PMID[449412]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 20596.2 nM PMID[449412]
NPT588 Individual Protein Tankyrase-1 Homo sapiens IC50 = 794.33 nM PMID[449416]
NPT588 Individual Protein Tankyrase-1 Homo sapiens IC50 = 788.0 nM PMID[449416]
NPT570 Individual Protein Arachidonate 5-lipoxygenase Homo sapiens Inhibition = 38.4 % PMID[449417]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 144670.0 nM PMID[449419]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 48280.0 nM PMID[449419]
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 3770.0 nM PMID[449419]
NPT113 Cell Line RAW264.7 Mus musculus Activity = 96.09 % PMID[449419]
NPT113 Cell Line RAW264.7 Mus musculus Inhibition = 37.5 % PMID[449419]
NPT2266 Individual Protein Fructose-1,6-bisphosphatase Homo sapiens Inhibition < 20.0 % PMID[449420]
NPT29 Organism Rattus norvegicus Rattus norvegicus Protection = 63.0 % PMID[449408]
NPT2 Others Unspecified IC50 = 120.0 ug.mL-1 PMID[449409]
NPT536 Uncleic Acid microRNA 21 Homo sapiens Potency = 7362.1 nM PMID[449412]
NPT93 Individual Protein Survival motor neuron protein Homo sapiens Potency = 12589.3 nM PMID[449412]
NPT188 Organism Candida parapsilosis Candida parapsilosis MIC = 200000.0 nM PMID[449413]
NPT21702 PROTEIN-PROTEIN INTERACTION Importin subunit beta-1/Snurportin-1 Homo sapiens Potency n.a. 25118.9 nM PMID[449412]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 11689.1 nM PMID[449412]
NPT2 Others Unspecified Potency n.a. 7943.3 nM PMID[449412]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 10417.9 nM PMID[449412]
NPT2 Others Unspecified Potency n.a. 31622.8 nM PMID[449412]
NPT755 Individual Protein Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 Homo sapiens Potency n.a. 39810.7 nM PMID[449412]
NPT2 Others Unspecified Inhibition < 40.0 % PMID[449415]
NPT2 Others Unspecified IC50 = 40300.0 nM PMID[449415]
NPT27 Others Unspecified Activity > 98.0 % PMID[449415]
NPT2 Others Unspecified Potency n.a. 14125.4 nM PMID[449412]

☑ 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 NPC22783 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
0.9449 High Similarity NPC57601
0.9444 High Similarity NPC113006
0.9426 High Similarity NPC193805
0.9375 High Similarity NPC172262
0.936 High Similarity NPC197425
0.935 High Similarity NPC2771
0.9297 High Similarity NPC50898
0.9297 High Similarity NPC78540
0.9297 High Similarity NPC213216
0.9297 High Similarity NPC274121
0.9286 High Similarity NPC39753
0.9286 High Similarity NPC115998
0.9225 High Similarity NPC248872
0.9213 High Similarity NPC137264
0.9187 High Similarity NPC93730
0.9167 High Similarity NPC32298
0.916 High Similarity NPC266597
0.916 High Similarity NPC250266
0.916 High Similarity NPC228661
0.916 High Similarity NPC299379
0.9154 High Similarity NPC9985
0.9154 High Similarity NPC239495
0.9127 High Similarity NPC125887
0.9091 High Similarity NPC54243
0.9084 High Similarity NPC473887
0.9084 High Similarity NPC187432
0.9084 High Similarity NPC127447
0.9084 High Similarity NPC231772
0.9084 High Similarity NPC194281
0.9084 High Similarity NPC216361
0.9084 High Similarity NPC47815
0.9084 High Similarity NPC29353
0.9084 High Similarity NPC256042
0.9084 High Similarity NPC281917
0.9084 High Similarity NPC116775
0.9084 High Similarity NPC124784
0.9084 High Similarity NPC234133
0.9084 High Similarity NPC13408
0.907 High Similarity NPC128216
0.9015 High Similarity NPC290291
0.9015 High Similarity NPC275055
0.9015 High Similarity NPC84585
0.9015 High Similarity NPC476480
0.8984 High Similarity NPC7569
0.8955 High Similarity NPC475680
0.8955 High Similarity NPC261227
0.8955 High Similarity NPC172986
0.8955 High Similarity NPC269652
0.8955 High Similarity NPC305355
0.8955 High Similarity NPC270883
0.8955 High Similarity NPC281207
0.8947 High Similarity NPC472460
0.8947 High Similarity NPC99333
0.8947 High Similarity NPC329225
0.8947 High Similarity NPC201395
0.8947 High Similarity NPC147686
0.8947 High Similarity NPC280284
0.8947 High Similarity NPC188947
0.8939 High Similarity NPC240593
0.8934 High Similarity NPC35744
0.8915 High Similarity NPC301717
0.8915 High Similarity NPC5515
0.8915 High Similarity NPC270369
0.8906 High Similarity NPC187907
0.8889 High Similarity NPC118840
0.8889 High Similarity NPC205006
0.8889 High Similarity NPC147688
0.8889 High Similarity NPC64908
0.8889 High Similarity NPC136840
0.8889 High Similarity NPC156590
0.8889 High Similarity NPC110969
0.8881 High Similarity NPC143799
0.8881 High Similarity NPC301217
0.8881 High Similarity NPC18260
0.8881 High Similarity NPC78913
0.8881 High Similarity NPC55018
0.8881 High Similarity NPC241838
0.8881 High Similarity NPC261234
0.8881 High Similarity NPC96565
0.8881 High Similarity NPC152042
0.8881 High Similarity NPC220062
0.8881 High Similarity NPC303633
0.8881 High Similarity NPC216978
0.8872 High Similarity NPC160972
0.8872 High Similarity NPC296490
0.8872 High Similarity NPC79943
0.8872 High Similarity NPC32441
0.8872 High Similarity NPC287246
0.8872 High Similarity NPC12296
0.8872 High Similarity NPC254841
0.8872 High Similarity NPC243083
0.8872 High Similarity NPC295261
0.8872 High Similarity NPC188879
0.8872 High Similarity NPC107586
0.8872 High Similarity NPC13768
0.8864 High Similarity NPC151113
0.8864 High Similarity NPC234560
0.8864 High Similarity NPC39426
0.8846 High Similarity NPC64359
0.8846 High Similarity NPC475589
0.8846 High Similarity NPC313618
0.8846 High Similarity NPC31872
0.8846 High Similarity NPC473584
0.8846 High Similarity NPC308037
0.8846 High Similarity NPC284424
0.8837 High Similarity NPC278787
0.8824 High Similarity NPC226636
0.8824 High Similarity NPC11561
0.8815 High Similarity NPC241100
0.8815 High Similarity NPC103342
0.8815 High Similarity NPC159275
0.8815 High Similarity NPC230285
0.8815 High Similarity NPC103904
0.8815 High Similarity NPC69769
0.8815 High Similarity NPC59951
0.8815 High Similarity NPC235239
0.8815 High Similarity NPC146679
0.8815 High Similarity NPC184536
0.8806 High Similarity NPC118813
0.8806 High Similarity NPC124269
0.8797 High Similarity NPC87545
0.8797 High Similarity NPC235428
0.8779 High Similarity NPC10971
0.8779 High Similarity NPC25937
0.8779 High Similarity NPC212631
0.8779 High Similarity NPC205468
0.8779 High Similarity NPC257756
0.8779 High Similarity NPC87231
0.8779 High Similarity NPC129132
0.8769 High Similarity NPC141549
0.876 High Similarity NPC60558
0.8759 High Similarity NPC38219
0.875 High Similarity NPC3188
0.875 High Similarity NPC262094
0.875 High Similarity NPC90582
0.875 High Similarity NPC41721
0.875 High Similarity NPC14871
0.875 High Similarity NPC282300
0.875 High Similarity NPC103362
0.8741 High Similarity NPC310135
0.8741 High Similarity NPC274784
0.8741 High Similarity NPC53181
0.8741 High Similarity NPC329203
0.8741 High Similarity NPC20709
0.8741 High Similarity NPC265871
0.8741 High Similarity NPC217186
0.8741 High Similarity NPC222342
0.8741 High Similarity NPC150648
0.8741 High Similarity NPC316480
0.8741 High Similarity NPC225153
0.8731 High Similarity NPC303644
0.8731 High Similarity NPC332594
0.8731 High Similarity NPC162680
0.8731 High Similarity NPC209560
0.8731 High Similarity NPC294409
0.8731 High Similarity NPC181124
0.8731 High Similarity NPC7013
0.8731 High Similarity NPC116632
0.8731 High Similarity NPC212767
0.872 High Similarity NPC314329
0.8712 High Similarity NPC192304
0.8712 High Similarity NPC175098
0.8712 High Similarity NPC263670
0.8712 High Similarity NPC292998
0.8712 High Similarity NPC223457
0.8712 High Similarity NPC56031
0.8712 High Similarity NPC108113
0.8712 High Similarity NPC188646
0.8712 High Similarity NPC93756
0.8712 High Similarity NPC337373
0.8712 High Similarity NPC472365
0.8712 High Similarity NPC242294
0.8712 High Similarity NPC139813
0.8712 High Similarity NPC312318
0.8702 High Similarity NPC475008
0.8702 High Similarity NPC278556
0.8702 High Similarity NPC262359
0.8702 High Similarity NPC186097
0.8702 High Similarity NPC475009
0.8696 High Similarity NPC311741
0.8696 High Similarity NPC234629
0.8696 High Similarity NPC70136
0.8692 High Similarity NPC185497
0.8686 High Similarity NPC169479
0.8686 High Similarity NPC217083
0.8686 High Similarity NPC62840
0.8686 High Similarity NPC200694
0.8686 High Similarity NPC144499
0.8686 High Similarity NPC159855
0.8686 High Similarity NPC299080
0.8686 High Similarity NPC473042
0.8686 High Similarity NPC214236
0.8686 High Similarity NPC59739
0.8686 High Similarity NPC202981
0.8686 High Similarity NPC78803
0.8686 High Similarity NPC293852
0.8682 High Similarity NPC80694
0.8682 High Similarity NPC186098
0.8676 High Similarity NPC150522
0.8676 High Similarity NPC284550

  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 NPC22783 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
0.8947 High Similarity NPD1549 Phase 2
0.8872 High Similarity NPD1550 Clinical (unspecified phase)
0.8872 High Similarity NPD1552 Clinical (unspecified phase)
0.8864 High Similarity NPD1510 Phase 2
0.8846 High Similarity NPD1240 Approved
0.874 High Similarity NPD1203 Approved
0.872 High Similarity NPD1547 Clinical (unspecified phase)
0.8712 High Similarity NPD1607 Approved
0.8623 High Similarity NPD1511 Approved
0.8561 High Similarity NPD7410 Clinical (unspecified phase)
0.8561 High Similarity NPD4378 Clinical (unspecified phase)
0.855 High Similarity NPD2313 Discontinued
0.854 High Similarity NPD3750 Approved
0.8519 High Similarity NPD2796 Approved
0.85 High Similarity NPD1512 Approved
0.8456 Intermediate Similarity NPD2344 Approved
0.8385 Intermediate Similarity NPD2798 Approved
0.8382 Intermediate Similarity NPD1551 Phase 2
0.8359 Intermediate Similarity NPD9717 Approved
0.8333 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8309 Intermediate Similarity NPD2799 Discontinued
0.8214 Intermediate Similarity NPD2309 Approved
0.8175 Intermediate Similarity NPD3748 Approved
0.8145 Intermediate Similarity NPD1241 Discontinued
0.8138 Intermediate Similarity NPD4380 Phase 2
0.811 Intermediate Similarity NPD1548 Phase 1
0.8099 Intermediate Similarity NPD6799 Approved
0.8095 Intermediate Similarity NPD2801 Approved
0.8082 Intermediate Similarity NPD7411 Suspended
0.8056 Intermediate Similarity NPD5403 Approved
0.8054 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8042 Intermediate Similarity NPD5401 Approved
0.803 Intermediate Similarity NPD2797 Approved
0.8027 Intermediate Similarity NPD1934 Approved
0.8 Intermediate Similarity NPD1201 Approved
0.8 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD422 Phase 1
0.7986 Intermediate Similarity NPD2935 Discontinued
0.7985 Intermediate Similarity NPD6832 Phase 2
0.7973 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7969 Intermediate Similarity NPD9545 Approved
0.7955 Intermediate Similarity NPD3225 Approved
0.7953 Intermediate Similarity NPD9493 Approved
0.7945 Intermediate Similarity NPD3226 Approved
0.7943 Intermediate Similarity NPD1243 Approved
0.7939 Intermediate Similarity NPD1481 Phase 2
0.7933 Intermediate Similarity NPD3749 Approved
0.7933 Intermediate Similarity NPD7075 Discontinued
0.7929 Intermediate Similarity NPD2346 Discontinued
0.7919 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7914 Intermediate Similarity NPD4308 Phase 3
0.7905 Intermediate Similarity NPD6801 Discontinued
0.7895 Intermediate Similarity NPD1470 Approved
0.7887 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7868 Intermediate Similarity NPD3764 Approved
0.7868 Intermediate Similarity NPD3268 Approved
0.7867 Intermediate Similarity NPD7768 Phase 2
0.7867 Intermediate Similarity NPD3882 Suspended
0.7863 Intermediate Similarity NPD1535 Discovery
0.7852 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7852 Intermediate Similarity NPD7819 Suspended
0.7803 Intermediate Similarity NPD1608 Approved
0.7778 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.777 Intermediate Similarity NPD6599 Discontinued
0.7762 Intermediate Similarity NPD4628 Phase 3
0.7737 Intermediate Similarity NPD411 Approved
0.7737 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD1610 Phase 2
0.7698 Intermediate Similarity NPD1933 Approved
0.7698 Intermediate Similarity NPD447 Suspended
0.7692 Intermediate Similarity NPD2800 Approved
0.7692 Intermediate Similarity NPD1894 Discontinued
0.7682 Intermediate Similarity NPD3817 Phase 2
0.7682 Intermediate Similarity NPD5402 Approved
0.7674 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7671 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7669 Intermediate Similarity NPD3972 Approved
0.766 Intermediate Similarity NPD7033 Discontinued
0.7643 Intermediate Similarity NPD3818 Discontinued
0.763 Intermediate Similarity NPD3267 Approved
0.763 Intermediate Similarity NPD3266 Approved
0.763 Intermediate Similarity NPD1164 Approved
0.7628 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7626 Intermediate Similarity NPD943 Approved
0.7626 Intermediate Similarity NPD4307 Phase 2
0.76 Intermediate Similarity NPD9266 Approved
0.76 Intermediate Similarity NPD74 Approved
0.7576 Intermediate Similarity NPD17 Approved
0.7574 Intermediate Similarity NPD1019 Discontinued
0.7571 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7568 Intermediate Similarity NPD920 Approved
0.7566 Intermediate Similarity NPD2296 Approved
0.7556 Intermediate Similarity NPD1876 Approved
0.752 Intermediate Similarity NPD9267 Approved
0.752 Intermediate Similarity NPD9263 Approved
0.752 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.752 Intermediate Similarity NPD9264 Approved
0.7516 Intermediate Similarity NPD6166 Phase 2
0.7516 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD9697 Approved
0.7484 Intermediate Similarity NPD7054 Approved
0.7484 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7482 Intermediate Similarity NPD1296 Phase 2
0.7482 Intermediate Similarity NPD6798 Discontinued
0.7451 Intermediate Similarity NPD4288 Approved
0.744 Intermediate Similarity NPD968 Approved
0.7438 Intermediate Similarity NPD7472 Approved
0.7436 Intermediate Similarity NPD6959 Discontinued
0.7434 Intermediate Similarity NPD6844 Discontinued
0.7432 Intermediate Similarity NPD4661 Approved
0.7432 Intermediate Similarity NPD4662 Approved
0.7431 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7431 Intermediate Similarity NPD1471 Phase 3
0.7415 Intermediate Similarity NPD7440 Discontinued
0.7413 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7397 Intermediate Similarity NPD7003 Approved
0.7394 Intermediate Similarity NPD6651 Approved
0.7391 Intermediate Similarity NPD2861 Phase 2
0.7391 Intermediate Similarity NPD6797 Phase 2
0.7361 Intermediate Similarity NPD6099 Approved
0.7361 Intermediate Similarity NPD6100 Approved
0.7347 Intermediate Similarity NPD2354 Approved
0.7346 Intermediate Similarity NPD7251 Discontinued
0.7346 Intermediate Similarity NPD6559 Discontinued
0.7338 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD4908 Phase 1
0.7329 Intermediate Similarity NPD7074 Phase 3
0.7301 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD7808 Phase 3
0.7301 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7284 Intermediate Similarity NPD5953 Discontinued
0.7279 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD1465 Phase 2
0.7267 Intermediate Similarity NPD7286 Phase 2
0.7267 Intermediate Similarity NPD5049 Phase 3
0.7266 Intermediate Similarity NPD9494 Approved
0.7266 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7261 Intermediate Similarity NPD5494 Approved
0.7254 Intermediate Similarity NPD3142 Approved
0.7254 Intermediate Similarity NPD3140 Approved
0.7241 Intermediate Similarity NPD5404 Approved
0.7241 Intermediate Similarity NPD5406 Approved
0.7241 Intermediate Similarity NPD5408 Approved
0.7241 Intermediate Similarity NPD5405 Approved
0.7234 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7231 Intermediate Similarity NPD5535 Approved
0.723 Intermediate Similarity NPD3295 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7203 Intermediate Similarity NPD4340 Discontinued
0.7203 Intermediate Similarity NPD6355 Discontinued
0.72 Intermediate Similarity NPD9261 Approved
0.7197 Intermediate Similarity NPD919 Approved
0.7192 Intermediate Similarity NPD2355 Clinical (unspecified phase)
0.7192 Intermediate Similarity NPD2353 Approved
0.7185 Intermediate Similarity NPD1778 Approved
0.7183 Intermediate Similarity NPD6233 Phase 2
0.7174 Intermediate Similarity NPD1283 Approved
0.717 Intermediate Similarity NPD6232 Discontinued
0.7152 Intermediate Similarity NPD6273 Approved
0.7143 Intermediate Similarity NPD7473 Discontinued
0.7133 Intermediate Similarity NPD1613 Approved
0.7133 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7124 Intermediate Similarity NPD7458 Discontinued
0.7124 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7123 Intermediate Similarity NPD4477 Approved
0.7123 Intermediate Similarity NPD4476 Approved
0.7121 Intermediate Similarity NPD9281 Approved
0.7111 Intermediate Similarity NPD1651 Approved
0.7111 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD1247 Approved
0.7097 Intermediate Similarity NPD7577 Discontinued
0.7097 Intermediate Similarity NPD6279 Approved
0.7097 Intermediate Similarity NPD6280 Approved
0.7095 Intermediate Similarity NPD2654 Approved
0.7092 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.7092 Intermediate Similarity NPD2614 Approved
0.7086 Intermediate Similarity NPD2532 Approved
0.7086 Intermediate Similarity NPD2533 Approved
0.7086 Intermediate Similarity NPD2534 Approved
0.7086 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD1184 Approved
0.7078 Intermediate Similarity NPD6585 Discontinued
0.7068 Intermediate Similarity NPD6671 Approved
0.7063 Intermediate Similarity NPD4062 Phase 3
0.7055 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD8312 Approved
0.7048 Intermediate Similarity NPD8313 Approved
0.7042 Intermediate Similarity NPD4625 Phase 3
0.7032 Intermediate Similarity NPD5889 Approved
0.7032 Intermediate Similarity NPD5890 Approved
0.7025 Intermediate Similarity NPD955 Approved
0.7023 Intermediate Similarity NPD1609 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD454 Approved
0.7019 Intermediate Similarity NPD3926 Phase 2
0.7012 Intermediate Similarity NPD1729 Discontinued
0.7008 Intermediate Similarity NPD1237 Approved
0.7007 Intermediate Similarity NPD1538 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