Structure

Physi-Chem Properties

Molecular Weight:  374.08
Volume:  375.946
LogP:  3.688
LogD:  2.528
LogS:  -4.737
# Rotatable Bonds:  0
TPSA:  111.9
# H-Bond Aceptor:  6
# H-Bond Donor:  3
# Rings:  4
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.361
Synthetic Accessibility Score:  3.608
Fsp3:  0.045
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.394
MDCK Permeability:  9.268216672353446e-06
Pgp-inhibitor:  0.005
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.016
20% Bioavailability (F20%):  0.017
30% Bioavailability (F30%):  0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.001
Plasma Protein Binding (PPB):  98.12505340576172%
Volume Distribution (VD):  0.322
Pgp-substrate:  4.598417282104492%

ADMET: Metabolism

CYP1A2-inhibitor:  0.984
CYP1A2-substrate:  0.155
CYP2C19-inhibitor:  0.62
CYP2C19-substrate:  0.057
CYP2C9-inhibitor:  0.867
CYP2C9-substrate:  0.637
CYP2D6-inhibitor:  0.825
CYP2D6-substrate:  0.094
CYP3A4-inhibitor:  0.217
CYP3A4-substrate:  0.059

ADMET: Excretion

Clearance (CL):  2.037
Half-life (T1/2):  0.393

ADMET: Toxicity

hERG Blockers:  0.013
Human Hepatotoxicity (H-HT):  0.783
Drug-inuced Liver Injury (DILI):  0.96
AMES Toxicity:  0.775
Rat Oral Acute Toxicity:  0.534
Maximum Recommended Daily Dose:  0.939
Skin Sensitization:  0.95
Carcinogencity:  0.629
Eye Corrosion:  0.005
Eye Irritation:  0.941
Respiratory Toxicity:  0.583

Download Data

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

  Natural Product: NPC244699

Natural Product ID:  NPC244699
Common Name*:   Maritinone
IUPAC Name:   5-hydroxy-8-(4-hydroxy-7-methyl-5,8-dioxonaphthalen-1-yl)-2-methylnaphthalene-1,4-dione
Synonyms:   Maritinone
Standard InCHIKey:  XCRMWTKECYDCOD-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C22H14O6/c1-9-7-15(25)19-13(23)5-3-11(17(19)21(9)27)12-4-6-14(24)20-16(26)8-10(2)22(28)18(12)20/h3-8,23-24H,1-2H3
SMILES:  CC1=CC(=O)c2c(C1=O)c(ccc2O)c1ccc(c2c1C(=O)C(=CC2=O)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL512154
PubChem CID:   633024
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000325] Biphenols

*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]
NPO33133 barleria alluaudii Species Acanthaceae Eukaryota n.a. n.a. n.a. PMID[22313254]
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]
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]
NPO21383 Cnicothamnus lorentzii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
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]
NPO23517 Heterotropa aspera n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO9038 Aconitum burnatii Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18256 Aconitum excelsum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13113 Ardisia kivuensis Species Primulaceae 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]
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]
NPO13608 Plumbago zeylanica Species Plumbaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20721 Halichondria panicea Species Halichondriidae 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]

☑ 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[491680]
NPT1034 Cell Line Lu1 Homo sapiens ED50 = 1.4 ug ml-1 PMID[491680]
NPT858 Cell Line LNCaP Homo sapiens ED50 = 2.2 ug ml-1 PMID[491680]
NPT737 Cell Line HUVEC Homo sapiens ED50 = 2.2 ug ml-1 PMID[491680]
NPT369 Cell Line ACHN Homo sapiens EC50 = 1500.0 nM PMID[491682]
NPT369 Cell Line ACHN Homo sapiens EC50 = 5800.0 nM PMID[491682]
NPT369 Cell Line ACHN Homo sapiens Ratio EC50 = 3.8 n.a. PMID[491682]
NPT729 Organism Micrococcus luteus Micrococcus luteus IC50 = 200.0 ug.mL-1 PMID[491680]
NPT729 Organism Micrococcus luteus Micrococcus luteus Activity > 1000.0 ug ml-1 PMID[491680]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus IC50 = 9.0 ug.mL-1 PMID[491680]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus Activity = 300.0 ug ml-1 PMID[491680]
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis IC50 = 20.0 ug.mL-1 PMID[491680]
NPT602 Organism Mycobacterium smegmatis Mycobacterium smegmatis Activity = 80.0 ug ml-1 PMID[491680]
NPT1513 Organism Mycobacterium avium Mycobacterium avium IC50 = 600.0 ug.mL-1 PMID[491680]
NPT1513 Organism Mycobacterium avium Mycobacterium avium Activity > 1000.0 ug ml-1 PMID[491680]
NPT20 Organism Candida albicans Candida albicans IC50 = 40.0 ug.mL-1 PMID[491680]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans IC50 = 20.0 ug.mL-1 PMID[491680]
NPT85 Organism Filobasidiella neoformans Cryptococcus neoformans Activity = 200.0 ug ml-1 PMID[491680]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae IC50 = 9.0 ug.mL-1 PMID[491680]
NPT312 Organism Saccharomyces cerevisiae Saccharomyces cerevisiae Activity = 80.0 ug ml-1 PMID[491680]
NPT21 Organism Aspergillus niger Aspergillus niger IC50 = 40.0 ug.mL-1 PMID[491680]
NPT21 Organism Aspergillus niger Aspergillus niger Activity > 1000.0 ug ml-1 PMID[491680]
NPT20 Organism Candida albicans Candida albicans Activity = 40.0 ug ml-1 PMID[491680]
NPT1381 Organism Aedes aegypti Aedes aegypti LC50 = 40.66 ug.mL-1 PMID[491681]
NPT1381 Organism Aedes aegypti Aedes aegypti LC90 = 53.87 ug ml-1 PMID[491681]

☑ 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 NPC244699 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
0.9764 High Similarity NPC50924
0.9685 High Similarity NPC53896
0.968 High Similarity NPC146647
0.968 High Similarity NPC34414
0.9603 High Similarity NPC55949
0.9535 High Similarity NPC283088
0.937 High Similarity NPC99731
0.9302 High Similarity NPC58685
0.9291 High Similarity NPC48248
0.9231 High Similarity NPC225051
0.92 High Similarity NPC375356
0.9141 High Similarity NPC282923
0.9134 High Similarity NPC3224
0.9127 High Similarity NPC142956
0.912 High Similarity NPC300274
0.912 High Similarity NPC307174
0.9091 High Similarity NPC80035
0.9077 High Similarity NPC72669
0.9077 High Similarity NPC474517
0.9055 High Similarity NPC103540
0.9032 High Similarity NPC206778
0.9032 High Similarity NPC285829
0.903 High Similarity NPC13715
0.9023 High Similarity NPC474813
0.9023 High Similarity NPC155211
0.8992 High Similarity NPC96024
0.8984 High Similarity NPC96915
0.8984 High Similarity NPC306765
0.8955 High Similarity NPC305060
0.8955 High Similarity NPC245923
0.8939 High Similarity NPC52407
0.8939 High Similarity NPC115458
0.8931 High Similarity NPC205992
0.8905 High Similarity NPC239136
0.8905 High Similarity NPC19631
0.8889 High Similarity NPC4214
0.8881 High Similarity NPC193358
0.8855 High Similarity NPC136588
0.8855 High Similarity NPC199253
0.8837 High Similarity NPC231774
0.8832 High Similarity NPC246638
0.8828 High Similarity NPC173978
0.8828 High Similarity NPC310540
0.8824 High Similarity NPC138099
0.8824 High Similarity NPC242994
0.8819 High Similarity NPC91478
0.8815 High Similarity NPC471905
0.8815 High Similarity NPC53206
0.8815 High Similarity NPC53414
0.8806 High Similarity NPC258502
0.8797 High Similarity NPC294226
0.8797 High Similarity NPC314048
0.8769 High Similarity NPC471530
0.8759 High Similarity NPC169452
0.8759 High Similarity NPC181560
0.875 High Similarity NPC416
0.875 High Similarity NPC61398
0.8741 High Similarity NPC254847
0.8741 High Similarity NPC272268
0.874 High Similarity NPC120545
0.8731 High Similarity NPC44437
0.8731 High Similarity NPC282780
0.8731 High Similarity NPC166480
0.8722 High Similarity NPC70622
0.8712 High Similarity NPC117609
0.8712 High Similarity NPC27659
0.8712 High Similarity NPC31799
0.871 High Similarity NPC108288
0.8692 High Similarity NPC254492
0.8692 High Similarity NPC160499
0.8682 High Similarity NPC164014
0.8682 High Similarity NPC199273
0.8676 High Similarity NPC36868
0.8676 High Similarity NPC53001
0.8647 High Similarity NPC85342
0.8647 High Similarity NPC17083
0.8647 High Similarity NPC93015
0.8636 High Similarity NPC276238
0.8633 High Similarity NPC69755
0.8633 High Similarity NPC193555
0.8633 High Similarity NPC469520
0.8626 High Similarity NPC72667
0.8623 High Similarity NPC96421
0.8613 High Similarity NPC87723
0.8603 High Similarity NPC315275
0.8593 High Similarity NPC12070
0.8593 High Similarity NPC288089
0.8593 High Similarity NPC287604
0.8593 High Similarity NPC472262
0.8593 High Similarity NPC161964
0.8582 High Similarity NPC246693
0.8582 High Similarity NPC110609
0.8582 High Similarity NPC242358
0.8571 High Similarity NPC66593
0.8571 High Similarity NPC198305
0.8571 High Similarity NPC31539
0.8561 High Similarity NPC237225
0.8561 High Similarity NPC305845
0.8561 High Similarity NPC204045
0.856 High Similarity NPC477453
0.8551 High Similarity NPC26924
0.8551 High Similarity NPC470407
0.8551 High Similarity NPC1268
0.8551 High Similarity NPC143438
0.855 High Similarity NPC15837
0.855 High Similarity NPC71610
0.854 High Similarity NPC62272
0.8538 High Similarity NPC152525
0.8538 High Similarity NPC236189
0.8538 High Similarity NPC74507
0.8538 High Similarity NPC234890
0.8538 High Similarity NPC68756
0.8529 High Similarity NPC249272
0.8529 High Similarity NPC161632
0.8527 High Similarity NPC282577
0.8527 High Similarity NPC176208
0.8527 High Similarity NPC283514
0.8519 High Similarity NPC171968
0.8519 High Similarity NPC114183
0.8519 High Similarity NPC267205
0.8511 High Similarity NPC79627
0.8511 High Similarity NPC21599
0.8511 High Similarity NPC10764
0.8511 High Similarity NPC193703
0.8504 High Similarity NPC232178
0.85 High Similarity NPC135524
0.8496 Intermediate Similarity NPC171460
0.8496 Intermediate Similarity NPC278928
0.8489 Intermediate Similarity NPC315578
0.8485 Intermediate Similarity NPC176130
0.8485 Intermediate Similarity NPC78364
0.8485 Intermediate Similarity NPC69424
0.8485 Intermediate Similarity NPC84672
0.8483 Intermediate Similarity NPC144283
0.848 Intermediate Similarity NPC161304
0.8467 Intermediate Similarity NPC141934
0.8467 Intermediate Similarity NPC474311
0.8467 Intermediate Similarity NPC191976
0.8462 Intermediate Similarity NPC37709
0.8462 Intermediate Similarity NPC135062
0.8456 Intermediate Similarity NPC270899
0.8451 Intermediate Similarity NPC478019
0.845 Intermediate Similarity NPC154696
0.845 Intermediate Similarity NPC198336
0.8444 Intermediate Similarity NPC309430
0.8444 Intermediate Similarity NPC175738
0.844 Intermediate Similarity NPC471682
0.844 Intermediate Similarity NPC296752
0.844 Intermediate Similarity NPC199936
0.8433 Intermediate Similarity NPC108129
0.8433 Intermediate Similarity NPC475741
0.8429 Intermediate Similarity NPC187843
0.8429 Intermediate Similarity NPC477275
0.8429 Intermediate Similarity NPC124365
0.8421 Intermediate Similarity NPC234175
0.8421 Intermediate Similarity NPC95537
0.8417 Intermediate Similarity NPC190457
0.8414 Intermediate Similarity NPC205766
0.8409 Intermediate Similarity NPC51037
0.8409 Intermediate Similarity NPC1991
0.8406 Intermediate Similarity NPC147418
0.8394 Intermediate Similarity NPC281513
0.8394 Intermediate Similarity NPC22222
0.8392 Intermediate Similarity NPC314437
0.8392 Intermediate Similarity NPC147250
0.8385 Intermediate Similarity NPC164947
0.838 Intermediate Similarity NPC477913
0.838 Intermediate Similarity NPC48762
0.838 Intermediate Similarity NPC471906
0.838 Intermediate Similarity NPC244691
0.8372 Intermediate Similarity NPC32322
0.8372 Intermediate Similarity NPC190971
0.8372 Intermediate Similarity NPC259703
0.837 Intermediate Similarity NPC41847
0.8369 Intermediate Similarity NPC73061
0.8369 Intermediate Similarity NPC257644
0.8369 Intermediate Similarity NPC474300
0.8369 Intermediate Similarity NPC85310
0.8358 Intermediate Similarity NPC25736
0.8358 Intermediate Similarity NPC92624
0.8357 Intermediate Similarity NPC225243
0.8357 Intermediate Similarity NPC203063
0.8345 Intermediate Similarity NPC61590
0.8345 Intermediate Similarity NPC206207
0.8333 Intermediate Similarity NPC119767
0.8333 Intermediate Similarity NPC472135
0.8333 Intermediate Similarity NPC86524
0.8333 Intermediate Similarity NPC123506
0.8333 Intermediate Similarity NPC475549
0.8333 Intermediate Similarity NPC118919
0.8322 Intermediate Similarity NPC34482
0.8322 Intermediate Similarity NPC471683
0.8321 Intermediate Similarity NPC202225
0.8321 Intermediate Similarity NPC275145
0.831 Intermediate Similarity NPC476473
0.831 Intermediate Similarity NPC313047
0.831 Intermediate Similarity NPC451542
0.831 Intermediate Similarity NPC53016
0.831 Intermediate Similarity NPC295712
0.831 Intermediate Similarity NPC474203

  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 NPC244699 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
0.9055 High Similarity NPD1470 Approved
0.8741 High Similarity NPD1509 Clinical (unspecified phase)
0.874 High Similarity NPD1201 Approved
0.871 High Similarity NPD405 Clinical (unspecified phase)
0.854 High Similarity NPD5406 Approved
0.854 High Similarity NPD5404 Approved
0.854 High Similarity NPD5408 Approved
0.854 High Similarity NPD5405 Approved
0.8252 Intermediate Similarity NPD7390 Discontinued
0.8195 Intermediate Similarity NPD1164 Approved
0.8085 Intermediate Similarity NPD2346 Discontinued
0.8069 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.8015 Intermediate Similarity NPD2932 Approved
0.7931 Intermediate Similarity NPD3300 Phase 2
0.7914 Intermediate Similarity NPD943 Approved
0.7887 Intermediate Similarity NPD2935 Discontinued
0.7879 Intermediate Similarity NPD3019 Approved
0.7852 Intermediate Similarity NPD3226 Approved
0.7832 Intermediate Similarity NPD2344 Approved
0.7817 Intermediate Similarity NPD2799 Discontinued
0.7692 Intermediate Similarity NPD3299 Clinical (unspecified phase)
0.7671 Intermediate Similarity NPD7003 Approved
0.7669 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7643 Intermediate Similarity NPD2313 Discontinued
0.7643 Intermediate Similarity NPD3764 Approved
0.7619 Intermediate Similarity NPD2309 Approved
0.7609 Intermediate Similarity NPD2798 Approved
0.7569 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7559 Intermediate Similarity NPD2342 Discontinued
0.7551 Intermediate Similarity NPD3750 Approved
0.7532 Intermediate Similarity NPD6232 Discontinued
0.75 Intermediate Similarity NPD7473 Discontinued
0.7464 Intermediate Similarity NPD1283 Approved
0.7448 Intermediate Similarity NPD1510 Phase 2
0.7431 Intermediate Similarity NPD1607 Approved
0.7426 Intermediate Similarity NPD3023 Approved
0.7426 Intermediate Similarity NPD3026 Approved
0.7424 Intermediate Similarity NPD5951 Approved
0.7419 Intermediate Similarity NPD7819 Suspended
0.7413 Intermediate Similarity NPD1240 Approved
0.7407 Intermediate Similarity NPD1651 Approved
0.7407 Intermediate Similarity NPD3024 Approved
0.7407 Intermediate Similarity NPD3025 Approved
0.7405 Intermediate Similarity NPD7635 Approved
0.7364 Intermediate Similarity NPD9266 Approved
0.7364 Intermediate Similarity NPD74 Approved
0.7358 Intermediate Similarity NPD6959 Discontinued
0.7353 Intermediate Similarity NPD7163 Clinical (unspecified phase)
0.7351 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7351 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7347 Intermediate Similarity NPD1471 Phase 3
0.7338 Intermediate Similarity NPD1876 Approved
0.7315 Intermediate Similarity NPD8166 Discontinued
0.7313 Intermediate Similarity NPD9493 Approved
0.7287 Intermediate Similarity NPD9263 Approved
0.7287 Intermediate Similarity NPD9264 Approved
0.7287 Intermediate Similarity NPD9267 Approved
0.7278 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD3749 Approved
0.7273 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD1281 Approved
0.7226 Intermediate Similarity NPD4380 Phase 2
0.7215 Intermediate Similarity NPD7768 Phase 2
0.7211 Intermediate Similarity NPD3748 Approved
0.7197 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7194 Intermediate Similarity NPD4878 Approved
0.7181 Intermediate Similarity NPD1549 Phase 2
0.7181 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7163 Intermediate Similarity NPD1203 Approved
0.7161 Intermediate Similarity NPD7458 Discontinued
0.7152 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD3020 Approved
0.7133 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7124 Intermediate Similarity NPD2532 Approved
0.7124 Intermediate Similarity NPD2534 Approved
0.7124 Intermediate Similarity NPD2533 Approved
0.7122 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7114 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7114 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7114 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7109 Intermediate Similarity NPD1931 Clinical (unspecified phase)
0.7109 Intermediate Similarity NPD1929 Approved
0.7109 Intermediate Similarity NPD1930 Approved
0.7103 Intermediate Similarity NPD6663 Approved
0.7101 Intermediate Similarity NPD2286 Discontinued
0.7101 Intermediate Similarity NPD4626 Approved
0.7099 Intermediate Similarity NPD6831 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD6273 Approved
0.7071 Intermediate Similarity NPD3972 Approved
0.707 Intermediate Similarity NPD7411 Suspended
0.7063 Intermediate Similarity NPD5736 Approved
0.7059 Intermediate Similarity NPD1511 Approved
0.7059 Intermediate Similarity NPD8150 Discontinued
0.7045 Intermediate Similarity NPD3021 Approved
0.7045 Intermediate Similarity NPD3022 Approved
0.7044 Intermediate Similarity NPD2296 Approved
0.7044 Intermediate Similarity NPD8438 Clinical (unspecified phase)
0.704 Intermediate Similarity NPD2859 Approved
0.704 Intermediate Similarity NPD2860 Approved
0.7037 Intermediate Similarity NPD9281 Approved
0.7031 Intermediate Similarity NPD1932 Approved
0.7025 Intermediate Similarity NPD1934 Approved
0.7023 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.702 Intermediate Similarity NPD2800 Approved
0.7012 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.6984 Remote Similarity NPD288 Approved
0.6981 Remote Similarity NPD2801 Approved
0.698 Remote Similarity NPD4308 Phase 3
0.6977 Remote Similarity NPD9261 Approved
0.6974 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6968 Remote Similarity NPD1512 Approved
0.6966 Remote Similarity NPD7008 Discontinued
0.6964 Remote Similarity NPD5031 Approved
0.6964 Remote Similarity NPD5029 Approved
0.6964 Remote Similarity NPD5027 Approved
0.696 Remote Similarity NPD2933 Approved
0.696 Remote Similarity NPD2934 Approved
0.6957 Remote Similarity NPD3091 Approved
0.6957 Remote Similarity NPD7075 Discontinued
0.695 Remote Similarity NPD9717 Approved
0.694 Remote Similarity NPD1609 Clinical (unspecified phase)
0.6939 Remote Similarity NPD2979 Phase 3
0.6933 Remote Similarity NPD2796 Approved
0.6923 Remote Similarity NPD4954 Approved
0.6923 Remote Similarity NPD4955 Approved
0.6923 Remote Similarity NPD5026 Approved
0.6923 Remote Similarity NPD36 Approved
0.6923 Remote Similarity NPD5028 Approved
0.6923 Remote Similarity NPD1237 Approved
0.6923 Remote Similarity NPD5034 Approved
0.6918 Remote Similarity NPD411 Approved
0.6912 Remote Similarity NPD497 Approved
0.6905 Remote Similarity NPD844 Approved
0.6897 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6894 Remote Similarity NPD3882 Suspended
0.6892 Remote Similarity NPD447 Suspended
0.6886 Remote Similarity NPD5844 Phase 1
0.6882 Remote Similarity NPD8312 Approved
0.6882 Remote Similarity NPD8313 Approved
0.6875 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6871 Remote Similarity NPD5494 Approved
0.6866 Remote Similarity NPD4141 Clinical (unspecified phase)
0.6864 Remote Similarity NPD6559 Discontinued
0.6864 Remote Similarity NPD5030 Phase 2
0.6857 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6857 Remote Similarity NPD4059 Approved
0.6849 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6842 Remote Similarity NPD2329 Discontinued
0.6838 Remote Similarity NPD498 Approved
0.6838 Remote Similarity NPD496 Approved
0.6838 Remote Similarity NPD495 Approved
0.6835 Remote Similarity NPD9545 Approved
0.6824 Remote Similarity NPD4060 Phase 1
0.6822 Remote Similarity NPD289 Clinical (unspecified phase)
0.6821 Remote Similarity NPD1551 Phase 2
0.6813 Remote Similarity NPD6844 Discontinued
0.6809 Remote Similarity NPD4879 Approved
0.6806 Remote Similarity NPD2797 Approved
0.6803 Remote Similarity NPD3268 Approved
0.68 Remote Similarity NPD5968 Phase 3
0.6791 Remote Similarity NPD4750 Phase 3
0.6786 Remote Similarity NPD6020 Phase 2
0.6786 Remote Similarity NPD4093 Discontinued
0.6786 Remote Similarity NPD5691 Approved
0.6783 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6781 Remote Similarity NPD6832 Phase 2
0.6779 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6772 Remote Similarity NPD1809 Phase 2
0.677 Remote Similarity NPD1465 Phase 2
0.6763 Remote Similarity NPD5038 Approved
0.6763 Remote Similarity NPD5037 Approved
0.6761 Remote Similarity NPD3092 Approved
0.6753 Remote Similarity NPD4628 Phase 3
0.6753 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6753 Remote Similarity NPD3400 Discontinued
0.6748 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6746 Remote Similarity NPD845 Approved
0.6738 Remote Similarity NPD3095 Discontinued
0.6735 Remote Similarity NPD4625 Phase 3
0.6733 Remote Similarity NPD6651 Approved
0.6726 Remote Similarity NPD7177 Discontinued
0.6723 Remote Similarity NPD6535 Approved
0.6723 Remote Similarity NPD6534 Approved
0.6715 Remote Similarity NPD1241 Discontinued
0.6715 Remote Similarity NPD4869 Clinical (unspecified phase)
0.6713 Remote Similarity NPD9269 Phase 2
0.6712 Remote Similarity NPD9494 Approved
0.6711 Remote Similarity NPD4477 Approved
0.6711 Remote Similarity NPD2438 Suspended
0.6711 Remote Similarity NPD4476 Approved
0.6711 Remote Similarity NPD4307 Phase 2
0.6711 Remote Similarity NPD2531 Phase 2
0.671 Remote Similarity NPD3295 Clinical (unspecified phase)
0.6708 Remote Similarity NPD6801 Discontinued
0.6707 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6707 Remote Similarity NPD6166 Phase 2
0.6707 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6705 Remote Similarity NPD5036 Approved
0.6693 Remote Similarity NPD688 Clinical (unspecified phase)

  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