Structure

Physi-Chem Properties

Molecular Weight:  374.08
Volume:  375.946
LogP:  3.87
LogD:  2.433
LogS:  -4.404
# Rotatable Bonds:  0
TPSA:  115.06
# H-Bond Aceptor:  6
# H-Bond Donor:  4
# Rings:  4
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.353
Synthetic Accessibility Score:  3.373
Fsp3:  0.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  2
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.879
MDCK Permeability:  7.474856829503551e-06
Pgp-inhibitor:  0.005
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.016
20% Bioavailability (F20%):  0.99
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.002
Plasma Protein Binding (PPB):  98.1302719116211%
Volume Distribution (VD):  0.389
Pgp-substrate:  6.044496536254883%

ADMET: Metabolism

CYP1A2-inhibitor:  0.964
CYP1A2-substrate:  0.076
CYP2C19-inhibitor:  0.184
CYP2C19-substrate:  0.05
CYP2C9-inhibitor:  0.677
CYP2C9-substrate:  0.2
CYP2D6-inhibitor:  0.364
CYP2D6-substrate:  0.142
CYP3A4-inhibitor:  0.168
CYP3A4-substrate:  0.063

ADMET: Excretion

Clearance (CL):  3.278
Half-life (T1/2):  0.183

ADMET: Toxicity

hERG Blockers:  0.012
Human Hepatotoxicity (H-HT):  0.671
Drug-inuced Liver Injury (DILI):  0.981
AMES Toxicity:  0.855
Rat Oral Acute Toxicity:  0.403
Maximum Recommended Daily Dose:  0.895
Skin Sensitization:  0.947
Carcinogencity:  0.857
Eye Corrosion:  0.003
Eye Irritation:  0.895
Respiratory Toxicity:  0.043

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

  Natural Product: NPC34414

Natural Product ID:  NPC34414
Common Name*:   Chitranone
IUPAC Name:   5-hydroxy-3-(1-hydroxy-6-methyl-5,8-dioxonaphthalen-2-yl)-2-methylnaphthalene-1,4-dione
Synonyms:   Chitranone
Standard InCHIKey:  ITGPISXKMZIRAV-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C22H14O6/c1-9-8-15(24)18-13(19(9)25)7-6-12(21(18)27)16-10(2)20(26)11-4-3-5-14(23)17(11)22(16)28/h3-8,23,27H,1-2H3
SMILES:  CC1=CC(=O)c2c(ccc(C3=C(C)C(=O)c4cccc(c4C3=O)O)c2O)C1=O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL470658
PubChem CID:   633072
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000023] Naphthalenes
        • [CHEMONTID:0000153] Naphthoquinones

*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
NPO22192 Cribraria cancellata Species Cribrariaceae Eukaryota n.a. n.a. n.a. PMID[14695806]
NPO16657 Diospyros maritima Species Ebenaceae Eukaryota bark Indonesia n.a. PMID[15270571]
NPO13608 Plumbago zeylanica Species Plumbaginaceae Eukaryota n.a. root n.a. PMID[16078700]
NPO20721 Halichondria panicea Species Halichondriidae Eukaryota n.a. n.a. n.a. PMID[20695474]
NPO18296 Diospyros kaki Species Ebenaceae Eukaryota n.a. calyx n.a. PMID[21561086]
NPO16657 Diospyros maritima Species Ebenaceae Eukaryota n.a. n.a. n.a. PMID[22313254]
NPO13608 Plumbago zeylanica Species Plumbaginaceae Eukaryota n.a. n.a. n.a. PMID[23848163]
NPO18296 Diospyros kaki Species Ebenaceae Eukaryota n.a. fruit n.a. PMID[24086493]
NPO22069 Persea major Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[2614421]
NPO20721 Halichondria panicea Species Halichondriidae Eukaryota n.a. n.a. n.a. PMID[27035556]
NPO18256 Aconitum excelsum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13608 Plumbago zeylanica Species Plumbaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23045 Lotus helleri Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16657 Diospyros maritima Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18296 Diospyros kaki Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16657 Diospyros maritima Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13608 Plumbago zeylanica Species Plumbaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18256 Aconitum excelsum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23045 Lotus helleri Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18296 Diospyros kaki Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18296 Diospyros kaki Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16657 Diospyros maritima Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18296 Diospyros kaki Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20094 Loranthus micranthus Species Loranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19736 Haplopappus glutinosus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21383 Cnicothamnus lorentzii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23517 Heterotropa aspera n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO18256 Aconitum excelsum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9038 Aconitum burnatii Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17645.1 Orobanche cernua var. cumana Varieties Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13113 Ardisia kivuensis Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18387 Sedum formosanum Species Crassulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22196 Kickxia ramosissima Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20721 Halichondria panicea Species Halichondriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13608 Plumbago zeylanica Species Plumbaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23432 Viguiera oaxacana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22192 Cribraria cancellata Species Cribrariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23865 Scorzonera veratrifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18296 Diospyros kaki Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22999 Cussonia spicata Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22069 Persea major Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18921 Athrixia phylicoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16657 Diospyros maritima Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22831 Isodon angustifolius Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23045 Lotus helleri Species Fabaceae 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
NPT91 Cell Line KB Homo sapiens ED50 = 0.3 ug ml-1 PMID[491642]
NPT1034 Cell Line Lu1 Homo sapiens ED50 = 1.1 ug ml-1 PMID[491642]
NPT858 Cell Line LNCaP Homo sapiens ED50 = 2.2 ug ml-1 PMID[491642]
NPT737 Cell Line HUVEC Homo sapiens ED50 = 2.1 ug ml-1 PMID[491642]
NPT729 Organism Micrococcus luteus Micrococcus luteus IC50 = 10.0 ug.mL-1 PMID[491642]
NPT729 Organism Micrococcus luteus Micrococcus luteus Activity > 1000.0 ug ml-1 PMID[491642]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus IC50 = 90.0 ug.mL-1 PMID[491642]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus Activity > 1000.0 ug ml-1 PMID[491642]
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis IC50 = 6.0 ug.mL-1 PMID[491642]
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis Activity = 20.0 ug ml-1 PMID[491642]
NPT1513 Organism Mycobacterium avium Mycobacterium avium IC50 = 5.0 ug.mL-1 PMID[491642]
NPT1513 Organism Mycobacterium avium Mycobacterium avium Activity = 90.0 ug ml-1 PMID[491642]
NPT20 Organism Candida albicans Candida albicans IC50 = 10.0 ug.mL-1 PMID[491642]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans IC50 = 3.0 ug.mL-1 PMID[491642]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans Activity = 10.0 ug ml-1 PMID[491642]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae IC50 = 3.0 ug.mL-1 PMID[491642]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae Activity = 10.0 ug ml-1 PMID[491642]
NPT21 Organism Aspergillus niger Aspergillus niger IC50 = 6.0 ug.mL-1 PMID[491642]
NPT21 Organism Aspergillus niger Aspergillus niger Activity > 1000.0 ug ml-1 PMID[491642]
NPT20 Organism Candida albicans Candida albicans Activity > 1000.0 ug ml-1 PMID[491642]

☑ 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 NPC34414 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
1.0 High Similarity NPC146647
0.9758 High Similarity NPC55949
0.9683 High Similarity NPC53896
0.968 High Similarity NPC244699
0.9606 High Similarity NPC50924
0.9603 High Similarity NPC58685
0.944 High Similarity NPC48248
0.944 High Similarity NPC282923
0.9431 High Similarity NPC142956
0.9426 High Similarity NPC307174
0.938 High Similarity NPC283088
0.9375 High Similarity NPC225051
0.935 High Similarity NPC375356
0.928 High Similarity NPC3224
0.9268 High Similarity NPC300274
0.9237 High Similarity NPC305060
0.9231 High Similarity NPC80035
0.9225 High Similarity NPC115458
0.9219 High Similarity NPC205992
0.9213 High Similarity NPC99731
0.92 High Similarity NPC103540
0.918 High Similarity NPC206778
0.918 High Similarity NPC285829
0.916 High Similarity NPC474813
0.916 High Similarity NPC155211
0.9141 High Similarity NPC199253
0.9141 High Similarity NPC136588
0.9127 High Similarity NPC306765
0.9127 High Similarity NPC96915
0.912 High Similarity NPC173978
0.9091 High Similarity NPC245923
0.9023 High Similarity NPC13715
0.9015 High Similarity NPC193358
0.9015 High Similarity NPC272268
0.9 High Similarity NPC70622
0.8992 High Similarity NPC31799
0.8976 High Similarity NPC231774
0.8968 High Similarity NPC310540
0.8931 High Similarity NPC52407
0.8923 High Similarity NPC474517
0.8923 High Similarity NPC17083
0.8923 High Similarity NPC72669
0.8906 High Similarity NPC471530
0.8881 High Similarity NPC4214
0.8864 High Similarity NPC472262
0.8864 High Similarity NPC288089
0.8864 High Similarity NPC287604
0.8864 High Similarity NPC161964
0.8852 High Similarity NPC108288
0.8846 High Similarity NPC198305
0.8837 High Similarity NPC96024
0.8828 High Similarity NPC160499
0.8819 High Similarity NPC152525
0.8819 High Similarity NPC68756
0.8815 High Similarity NPC26924
0.8815 High Similarity NPC138099
0.8815 High Similarity NPC242994
0.8815 High Similarity NPC1268
0.8806 High Similarity NPC53414
0.8806 High Similarity NPC471905
0.8806 High Similarity NPC53206
0.8797 High Similarity NPC258502
0.8797 High Similarity NPC161632
0.877 High Similarity NPC161304
0.8769 High Similarity NPC278928
0.8759 High Similarity NPC19631
0.8759 High Similarity NPC69755
0.8759 High Similarity NPC239136
0.875 High Similarity NPC315578
0.875 High Similarity NPC181560
0.875 High Similarity NPC169452
0.875 High Similarity NPC96421
0.8741 High Similarity NPC416
0.8741 High Similarity NPC61398
0.8731 High Similarity NPC315275
0.8731 High Similarity NPC254847
0.8722 High Similarity NPC12070
0.8712 High Similarity NPC246693
0.8712 High Similarity NPC242358
0.8712 High Similarity NPC309430
0.8712 High Similarity NPC110609
0.8702 High Similarity NPC31539
0.8699 High Similarity NPC477453
0.8696 High Similarity NPC471682
0.8692 High Similarity NPC237225
0.8686 High Similarity NPC246638
0.8686 High Similarity NPC124365
0.8682 High Similarity NPC254492
0.8672 High Similarity NPC234890
0.8672 High Similarity NPC199273
0.8672 High Similarity NPC236189
0.8672 High Similarity NPC74507
0.8667 High Similarity NPC36868
0.8661 High Similarity NPC91478
0.8657 High Similarity NPC249272
0.8647 High Similarity NPC171968
0.8647 High Similarity NPC314048
0.8647 High Similarity NPC294226
0.8647 High Similarity NPC114183
0.864 High Similarity NPC232178
0.8636 High Similarity NPC85342
0.8636 High Similarity NPC93015
0.8633 High Similarity NPC79627
0.8623 High Similarity NPC257644
0.8623 High Similarity NPC193555
0.8615 High Similarity NPC72667
0.8613 High Similarity NPC225243
0.8594 High Similarity NPC275145
0.8594 High Similarity NPC135062
0.8593 High Similarity NPC474311
0.8593 High Similarity NPC141934
0.8583 High Similarity NPC120545
0.8582 High Similarity NPC282780
0.8582 High Similarity NPC270899
0.8582 High Similarity NPC166480
0.8582 High Similarity NPC44437
0.8571 High Similarity NPC471683
0.8561 High Similarity NPC475741
0.8561 High Similarity NPC27659
0.8561 High Similarity NPC66593
0.8561 High Similarity NPC117609
0.8551 High Similarity NPC305845
0.8551 High Similarity NPC204045
0.854 High Similarity NPC143438
0.854 High Similarity NPC470407
0.8538 High Similarity NPC227741
0.8538 High Similarity NPC49647
0.8538 High Similarity NPC51037
0.8538 High Similarity NPC1991
0.8538 High Similarity NPC136342
0.8538 High Similarity NPC295202
0.8529 High Similarity NPC53001
0.8527 High Similarity NPC164014
0.8519 High Similarity NPC22222
0.8519 High Similarity NPC281513
0.8516 High Similarity NPC282577
0.8507 High Similarity NPC254603
0.8507 High Similarity NPC267205
0.8504 High Similarity NPC472046
0.85 High Similarity NPC21599
0.85 High Similarity NPC193703
0.8489 Intermediate Similarity NPC474300
0.8489 Intermediate Similarity NPC135524
0.8485 Intermediate Similarity NPC25736
0.8485 Intermediate Similarity NPC57552
0.8485 Intermediate Similarity NPC276238
0.8485 Intermediate Similarity NPC171460
0.8473 Intermediate Similarity NPC176130
0.8473 Intermediate Similarity NPC78364
0.8473 Intermediate Similarity NPC69424
0.8473 Intermediate Similarity NPC84672
0.8472 Intermediate Similarity NPC144283
0.8467 Intermediate Similarity NPC87723
0.8467 Intermediate Similarity NPC61590
0.8462 Intermediate Similarity NPC131799
0.8456 Intermediate Similarity NPC191976
0.8456 Intermediate Similarity NPC472308
0.8444 Intermediate Similarity NPC1249
0.8438 Intermediate Similarity NPC154696
0.8429 Intermediate Similarity NPC53016
0.8429 Intermediate Similarity NPC476473
0.8425 Intermediate Similarity NPC473662
0.8425 Intermediate Similarity NPC7151
0.8425 Intermediate Similarity NPC216297
0.8421 Intermediate Similarity NPC108129
0.8417 Intermediate Similarity NPC187843
0.8413 Intermediate Similarity NPC41567
0.8409 Intermediate Similarity NPC165257
0.8406 Intermediate Similarity NPC295339
0.8406 Intermediate Similarity NPC190457
0.8397 Intermediate Similarity NPC71610
0.8397 Intermediate Similarity NPC15837
0.8394 Intermediate Similarity NPC62272
0.838 Intermediate Similarity NPC300540
0.838 Intermediate Similarity NPC147250
0.838 Intermediate Similarity NPC314437
0.8372 Intermediate Similarity NPC176208
0.8372 Intermediate Similarity NPC244351
0.8372 Intermediate Similarity NPC283514
0.8369 Intermediate Similarity NPC244691
0.8369 Intermediate Similarity NPC10764
0.8369 Intermediate Similarity NPC471906
0.8369 Intermediate Similarity NPC48762
0.8359 Intermediate Similarity NPC32322
0.8359 Intermediate Similarity NPC259703
0.8357 Intermediate Similarity NPC469520
0.8357 Intermediate Similarity NPC73061
0.8346 Intermediate Similarity NPC109123
0.8345 Intermediate Similarity NPC183345
0.8333 Intermediate Similarity NPC173980
0.8333 Intermediate Similarity NPC269414
0.8333 Intermediate Similarity NPC206207
0.8322 Intermediate Similarity NPC37709
0.8322 Intermediate Similarity NPC119767
0.8321 Intermediate Similarity NPC118919
0.8321 Intermediate Similarity NPC123506
0.8321 Intermediate Similarity NPC86524
0.832 Intermediate Similarity NPC240163
0.831 Intermediate Similarity NPC478019
0.831 Intermediate Similarity NPC34482

  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 NPC34414 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
0.92 High Similarity NPD1470 Approved
0.888 High Similarity NPD1201 Approved
0.8852 High Similarity NPD405 Clinical (unspecified phase)
0.8731 High Similarity NPD1509 Clinical (unspecified phase)
0.8394 Intermediate Similarity NPD5404 Approved
0.8394 Intermediate Similarity NPD5406 Approved
0.8394 Intermediate Similarity NPD5405 Approved
0.8394 Intermediate Similarity NPD5408 Approved
0.8333 Intermediate Similarity NPD2346 Discontinued
0.8112 Intermediate Similarity NPD7390 Discontinued
0.8082 Intermediate Similarity NPD3226 Approved
0.8042 Intermediate Similarity NPD3300 Phase 2
0.7931 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.791 Intermediate Similarity NPD1164 Approved
0.7863 Intermediate Similarity NPD2932 Approved
0.777 Intermediate Similarity NPD943 Approved
0.7754 Intermediate Similarity NPD2313 Discontinued
0.7746 Intermediate Similarity NPD2935 Discontinued
0.7727 Intermediate Similarity NPD3019 Approved
0.7721 Intermediate Similarity NPD2798 Approved
0.768 Intermediate Similarity NPD2342 Discontinued
0.7676 Intermediate Similarity NPD3299 Clinical (unspecified phase)
0.7676 Intermediate Similarity NPD2799 Discontinued
0.7674 Intermediate Similarity NPD5951 Approved
0.7594 Intermediate Similarity NPD7163 Clinical (unspecified phase)
0.7569 Intermediate Similarity NPD2344 Approved
0.7534 Intermediate Similarity NPD7003 Approved
0.7519 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7519 Intermediate Similarity NPD7635 Approved
0.75 Intermediate Similarity NPD3764 Approved
0.748 Intermediate Similarity NPD9266 Approved
0.748 Intermediate Similarity NPD74 Approved
0.7431 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7424 Intermediate Similarity NPD9493 Approved
0.7415 Intermediate Similarity NPD3750 Approved
0.7413 Intermediate Similarity NPD1607 Approved
0.7405 Intermediate Similarity NPD6232 Discontinued
0.7402 Intermediate Similarity NPD9264 Approved
0.7402 Intermediate Similarity NPD9263 Approved
0.7402 Intermediate Similarity NPD9267 Approved
0.7375 Intermediate Similarity NPD7473 Discontinued
0.7368 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD2309 Approved
0.7329 Intermediate Similarity NPD1471 Phase 3
0.7319 Intermediate Similarity NPD1283 Approved
0.731 Intermediate Similarity NPD1510 Phase 2
0.7299 Intermediate Similarity NPD4878 Approved
0.729 Intermediate Similarity NPD7819 Suspended
0.7279 Intermediate Similarity NPD3026 Approved
0.7279 Intermediate Similarity NPD3023 Approved
0.7273 Intermediate Similarity NPD1240 Approved
0.7266 Intermediate Similarity NPD1203 Approved
0.7259 Intermediate Similarity NPD3024 Approved
0.7259 Intermediate Similarity NPD3025 Approved
0.7259 Intermediate Similarity NPD1651 Approved
0.7246 Intermediate Similarity NPD8150 Discontinued
0.7236 Intermediate Similarity NPD288 Approved
0.7233 Intermediate Similarity NPD6959 Discontinued
0.7226 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD1929 Approved
0.7222 Intermediate Similarity NPD1931 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD1930 Approved
0.7219 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7209 Intermediate Similarity NPD6831 Clinical (unspecified phase)
0.7194 Intermediate Similarity NPD1876 Approved
0.7192 Intermediate Similarity NPD4308 Phase 3
0.7181 Intermediate Similarity NPD8166 Discontinued
0.716 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7154 Intermediate Similarity NPD844 Approved
0.7143 Intermediate Similarity NPD9281 Approved
0.7143 Intermediate Similarity NPD7458 Discontinued
0.7143 Intermediate Similarity NPD1932 Approved
0.7133 Intermediate Similarity NPD411 Approved
0.7105 Intermediate Similarity NPD2533 Approved
0.7105 Intermediate Similarity NPD2532 Approved
0.7105 Intermediate Similarity NPD2534 Approved
0.7101 Intermediate Similarity NPD1281 Approved
0.7099 Intermediate Similarity NPD4141 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD4380 Phase 2
0.7095 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7087 Intermediate Similarity NPD9261 Approved
0.708 Intermediate Similarity NPD3412 Clinical (unspecified phase)
0.708 Intermediate Similarity NPD4626 Approved
0.7075 Intermediate Similarity NPD3748 Approved
0.707 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7067 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7066 Intermediate Similarity NPD8312 Approved
0.7066 Intermediate Similarity NPD8313 Approved
0.7063 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD7008 Discontinued
0.705 Intermediate Similarity NPD3972 Approved
0.705 Intermediate Similarity NPD9717 Approved
0.7048 Intermediate Similarity NPD5031 Approved
0.7048 Intermediate Similarity NPD5029 Approved
0.7048 Intermediate Similarity NPD5027 Approved
0.7047 Intermediate Similarity NPD1549 Phase 2
0.7047 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD1609 Clinical (unspecified phase)
0.7044 Intermediate Similarity NPD3749 Approved
0.7031 Intermediate Similarity NPD1237 Approved
0.7027 Intermediate Similarity NPD1551 Phase 2
0.7025 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7023 Intermediate Similarity NPD4750 Phase 3
0.7015 Intermediate Similarity NPD497 Approved
0.7006 Intermediate Similarity NPD36 Approved
0.7006 Intermediate Similarity NPD4954 Approved
0.7006 Intermediate Similarity NPD5026 Approved
0.7006 Intermediate Similarity NPD5034 Approved
0.7006 Intermediate Similarity NPD5028 Approved
0.7006 Intermediate Similarity NPD4955 Approved
0.7 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.6986 Remote Similarity NPD447 Suspended
0.6984 Remote Similarity NPD3020 Approved
0.6981 Remote Similarity NPD7768 Phase 2
0.698 Remote Similarity NPD1552 Clinical (unspecified phase)
0.698 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6977 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6966 Remote Similarity NPD6663 Approved
0.6957 Remote Similarity NPD2286 Discontinued
0.6954 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6948 Remote Similarity NPD6273 Approved
0.6947 Remote Similarity NPD2329 Discontinued
0.6946 Remote Similarity NPD5030 Phase 2
0.6943 Remote Similarity NPD7411 Suspended
0.694 Remote Similarity NPD495 Approved
0.694 Remote Similarity NPD496 Approved
0.694 Remote Similarity NPD498 Approved
0.6929 Remote Similarity NPD289 Clinical (unspecified phase)
0.6928 Remote Similarity NPD1511 Approved
0.6923 Remote Similarity NPD5736 Approved
0.6918 Remote Similarity NPD8438 Clinical (unspecified phase)
0.6918 Remote Similarity NPD4307 Phase 2
0.6912 Remote Similarity NPD7325 Clinical (unspecified phase)
0.6906 Remote Similarity NPD4879 Approved
0.6901 Remote Similarity NPD2797 Approved
0.6899 Remote Similarity NPD1934 Approved
0.6899 Remote Similarity NPD6844 Discontinued
0.6897 Remote Similarity NPD3268 Approved
0.6894 Remote Similarity NPD3021 Approved
0.6894 Remote Similarity NPD3022 Approved
0.6887 Remote Similarity NPD2800 Approved
0.688 Remote Similarity NPD2859 Approved
0.688 Remote Similarity NPD2860 Approved
0.6879 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6875 Remote Similarity NPD6832 Phase 2
0.6871 Remote Similarity NPD1899 Clinical (unspecified phase)
0.687 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6863 Remote Similarity NPD6884 Clinical (unspecified phase)
0.6855 Remote Similarity NPD845 Approved
0.6855 Remote Similarity NPD2801 Approved
0.685 Remote Similarity NPD2066 Phase 3
0.6842 Remote Similarity NPD5038 Approved
0.6842 Remote Similarity NPD5037 Approved
0.6839 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6839 Remote Similarity NPD1512 Approved
0.6839 Remote Similarity NPD6213 Phase 3
0.6839 Remote Similarity NPD6212 Phase 3
0.6832 Remote Similarity NPD7075 Discontinued
0.6828 Remote Similarity NPD4625 Phase 3
0.6825 Remote Similarity NPD3495 Discontinued
0.6813 Remote Similarity NPD2296 Approved
0.6812 Remote Similarity NPD7009 Phase 2
0.6812 Remote Similarity NPD3091 Approved
0.6807 Remote Similarity NPD7177 Discontinued
0.6803 Remote Similarity NPD2979 Phase 3
0.68 Remote Similarity NPD6100 Approved
0.68 Remote Similarity NPD6534 Approved
0.68 Remote Similarity NPD6099 Approved
0.68 Remote Similarity NPD2933 Approved
0.68 Remote Similarity NPD6535 Approved
0.68 Remote Similarity NPD2796 Approved
0.68 Remote Similarity NPD2934 Approved
0.6788 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6784 Remote Similarity NPD5036 Approved
0.677 Remote Similarity NPD3882 Suspended
0.6766 Remote Similarity NPD5844 Phase 1
0.6766 Remote Similarity NPD6020 Phase 2
0.6763 Remote Similarity NPD5691 Approved
0.6763 Remote Similarity NPD6836 Approved
0.6761 Remote Similarity NPD1755 Approved
0.675 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6748 Remote Similarity NPD5494 Approved
0.6746 Remote Similarity NPD6559 Discontinued
0.6739 Remote Similarity NPD7610 Discontinued
0.6738 Remote Similarity NPD1611 Approved
0.6735 Remote Similarity NPD520 Approved
0.6732 Remote Similarity NPD4628 Phase 3
0.6714 Remote Similarity NPD4059 Approved
0.6708 Remote Similarity NPD5402 Approved
0.6704 Remote Similarity NPD6777 Approved
0.6704 Remote Similarity NPD6781 Approved
0.6704 Remote Similarity NPD6780 Approved
0.6704 Remote Similarity NPD6782 Approved
0.6704 Remote Similarity NPD6778 Approved
0.6704 Remote Similarity NPD6779 Approved
0.6704 Remote Similarity NPD6776 Approved
0.6694 Remote Similarity NPD7609 Phase 3
0.6691 Remote Similarity NPD4869 Clinical (unspecified phase)
0.6691 Remote Similarity NPD9545 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