Structure

Physi-Chem Properties

Molecular Weight:  218.06
Volume:  218.338
LogP:  2.361
LogD:  2.399
LogS:  -3.092
# Rotatable Bonds:  1
TPSA:  63.6
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.779
Synthetic Accessibility Score:  2.31
Fsp3:  0.167
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.647
MDCK Permeability:  2.4032518922467716e-05
Pgp-inhibitor:  0.046
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.891

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.172
Plasma Protein Binding (PPB):  94.36717224121094%
Volume Distribution (VD):  0.503
Pgp-substrate:  2.3391194343566895%

ADMET: Metabolism

CYP1A2-inhibitor:  0.984
CYP1A2-substrate:  0.842
CYP2C19-inhibitor:  0.856
CYP2C19-substrate:  0.092
CYP2C9-inhibitor:  0.813
CYP2C9-substrate:  0.657
CYP2D6-inhibitor:  0.945
CYP2D6-substrate:  0.11
CYP3A4-inhibitor:  0.811
CYP3A4-substrate:  0.162

ADMET: Excretion

Clearance (CL):  6.742
Half-life (T1/2):  0.273

ADMET: Toxicity

hERG Blockers:  0.015
Human Hepatotoxicity (H-HT):  0.062
Drug-inuced Liver Injury (DILI):  0.534
AMES Toxicity:  0.892
Rat Oral Acute Toxicity:  0.718
Maximum Recommended Daily Dose:  0.218
Skin Sensitization:  0.564
Carcinogencity:  0.552
Eye Corrosion:  0.043
Eye Irritation:  0.983
Respiratory Toxicity:  0.122

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

  Natural Product: NPC237225

Natural Product ID:  NPC237225
Common Name*:   3-O-Methyl Droserone
IUPAC Name:   5-hydroxy-3-methoxy-2-methylnaphthalene-1,4-dione
Synonyms:   3-O-Methyl Droserone
Standard InCHIKey:  WIQMWNKYSYJIQG-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C12H10O4/c1-6-10(14)7-4-3-5-8(13)9(7)11(15)12(6)16-2/h3-5,13H,1-2H3
SMILES:  CC1=C(C(=O)c2c(cccc2O)C1=O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1094241
PubChem CID:   12322315
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]
NPO20721 Halichondria panicea Species Halichondriidae Eukaryota n.a. n.a. n.a. PMID[20695474]
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]
NPO23045 Lotus helleri Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23045 Lotus helleri Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18256 Aconitum excelsum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
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]
NPO22192 Cribraria cancellata Species Cribrariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21383 Cnicothamnus lorentzii Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18921 Athrixia phylicoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9038 Aconitum burnatii Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22831 Isodon angustifolius Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13113 Ardisia kivuensis Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20094 Loranthus micranthus Species Loranthaceae 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]
NPO23432 Viguiera oaxacana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23045 Lotus helleri Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19736 Haplopappus glutinosus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23865 Scorzonera veratrifolia 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]
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]

☑ 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
NPT1381 Organism Aedes aegypti Aedes aegypti LC50 = 31.47 ug.mL-1 PMID[502715]
NPT1381 Organism Aedes aegypti Aedes aegypti LC90 = 55.72 ug ml-1 PMID[502715]

☑ 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 NPC237225 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
0.9835 High Similarity NPC51037
0.9677 High Similarity NPC198305
0.9669 High Similarity NPC310540
0.9516 High Similarity NPC165257
0.9449 High Similarity NPC171968
0.937 High Similarity NPC309430
0.9355 High Similarity NPC231774
0.9291 High Similarity NPC205360
0.9256 High Similarity NPC206778
0.9256 High Similarity NPC285829
0.9237 High Similarity NPC173980
0.92 High Similarity NPC1991
0.9147 High Similarity NPC254603
0.9113 High Similarity NPC135062
0.9048 High Similarity NPC306765
0.9032 High Similarity NPC307174
0.9023 High Similarity NPC477408
0.8984 High Similarity NPC278928
0.8926 High Similarity NPC108288
0.8923 High Similarity NPC88864
0.8898 High Similarity NPC3224
0.8881 High Similarity NPC114620
0.8881 High Similarity NPC103337
0.8864 High Similarity NPC281513
0.8864 High Similarity NPC22222
0.8862 High Similarity NPC232178
0.8855 High Similarity NPC193169
0.881 High Similarity NPC375356
0.8779 High Similarity NPC110609
0.8779 High Similarity NPC246693
0.8779 High Similarity NPC477406
0.8779 High Similarity NPC242358
0.8769 High Similarity NPC475741
0.8769 High Similarity NPC117609
0.8769 High Similarity NPC27659
0.8769 High Similarity NPC136588
0.8769 High Similarity NPC199253
0.875 High Similarity NPC96915
0.874 High Similarity NPC74507
0.874 High Similarity NPC234890
0.873 High Similarity NPC300274
0.873 High Similarity NPC164947
0.8696 High Similarity NPC477409
0.8692 High Similarity NPC34414
0.8692 High Similarity NPC146647
0.8682 High Similarity NPC45537
0.8672 High Similarity NPC287473
0.8672 High Similarity NPC103540
0.8661 High Similarity NPC182646
0.8657 High Similarity NPC232996
0.864 High Similarity NPC473662
0.864 High Similarity NPC216297
0.864 High Similarity NPC7151
0.8636 High Similarity NPC70622
0.8626 High Similarity NPC55949
0.8615 High Similarity NPC282923
0.8594 High Similarity NPC152525
0.8594 High Similarity NPC68756
0.8594 High Similarity NPC142956
0.8593 High Similarity NPC284184
0.8593 High Similarity NPC301341
0.8571 High Similarity NPC52407
0.8561 High Similarity NPC29932
0.8561 High Similarity NPC244699
0.8561 High Similarity NPC205992
0.855 High Similarity NPC99731
0.8538 High Similarity NPC471530
0.8537 High Similarity NPC240163
0.8537 High Similarity NPC161304
0.8519 High Similarity NPC38158
0.8519 High Similarity NPC141934
0.8519 High Similarity NPC86524
0.8511 High Similarity NPC476821
0.8507 High Similarity NPC50924
0.85 High Similarity NPC474630
0.8485 Intermediate Similarity NPC31799
0.848 Intermediate Similarity NPC41567
0.8478 Intermediate Similarity NPC110810
0.8478 Intermediate Similarity NPC283292
0.8478 Intermediate Similarity NPC84273
0.8473 Intermediate Similarity NPC48248
0.8473 Intermediate Similarity NPC179898
0.8468 Intermediate Similarity NPC477453
0.8467 Intermediate Similarity NPC111422
0.8467 Intermediate Similarity NPC299405
0.8467 Intermediate Similarity NPC306835
0.8467 Intermediate Similarity NPC29771
0.8467 Intermediate Similarity NPC216312
0.8467 Intermediate Similarity NPC471602
0.8467 Intermediate Similarity NPC256463
0.8467 Intermediate Similarity NPC476477
0.8462 Intermediate Similarity NPC15837
0.845 Intermediate Similarity NPC474766
0.844 Intermediate Similarity NPC136878
0.8433 Intermediate Similarity NPC53896
0.8433 Intermediate Similarity NPC225051
0.8406 Intermediate Similarity NPC241349
0.8406 Intermediate Similarity NPC327916
0.8406 Intermediate Similarity NPC32749
0.8406 Intermediate Similarity NPC42262
0.8406 Intermediate Similarity NPC147542
0.8406 Intermediate Similarity NPC220496
0.8406 Intermediate Similarity NPC37992
0.8406 Intermediate Similarity NPC156872
0.84 Intermediate Similarity NPC269414
0.8397 Intermediate Similarity NPC470841
0.8394 Intermediate Similarity NPC61590
0.8385 Intermediate Similarity NPC123506
0.8382 Intermediate Similarity NPC315275
0.8382 Intermediate Similarity NPC155211
0.8382 Intermediate Similarity NPC474311
0.838 Intermediate Similarity NPC252208
0.837 Intermediate Similarity NPC288089
0.8369 Intermediate Similarity NPC28632
0.8358 Intermediate Similarity NPC17843
0.8358 Intermediate Similarity NPC58685
0.8345 Intermediate Similarity NPC124365
0.8345 Intermediate Similarity NPC471444
0.8345 Intermediate Similarity NPC257003
0.8333 Intermediate Similarity NPC295339
0.8333 Intermediate Similarity NPC1268
0.8333 Intermediate Similarity NPC247250
0.8333 Intermediate Similarity NPC767
0.8333 Intermediate Similarity NPC26924
0.8321 Intermediate Similarity NPC305060
0.8321 Intermediate Similarity NPC227741
0.8321 Intermediate Similarity NPC49647
0.8321 Intermediate Similarity NPC264022
0.8321 Intermediate Similarity NPC160499
0.8321 Intermediate Similarity NPC471452
0.8321 Intermediate Similarity NPC295202
0.8321 Intermediate Similarity NPC136342
0.8309 Intermediate Similarity NPC80035
0.8309 Intermediate Similarity NPC283088
0.8309 Intermediate Similarity NPC161632
0.8308 Intermediate Similarity NPC173978
0.8298 Intermediate Similarity NPC274085
0.8298 Intermediate Similarity NPC89664
0.8298 Intermediate Similarity NPC475201
0.8296 Intermediate Similarity NPC115458
0.8296 Intermediate Similarity NPC59459
0.8296 Intermediate Similarity NPC294226
0.8295 Intermediate Similarity NPC282577
0.8295 Intermediate Similarity NPC46634
0.8295 Intermediate Similarity NPC217756
0.8295 Intermediate Similarity NPC91478
0.8286 Intermediate Similarity NPC69755
0.8286 Intermediate Similarity NPC474300
0.8284 Intermediate Similarity NPC17083
0.8281 Intermediate Similarity NPC472046
0.8273 Intermediate Similarity NPC315578
0.8264 Intermediate Similarity NPC120171
0.8264 Intermediate Similarity NPC224584
0.8258 Intermediate Similarity NPC324209
0.8254 Intermediate Similarity NPC125252
0.8248 Intermediate Similarity NPC193358
0.8248 Intermediate Similarity NPC474813
0.8248 Intermediate Similarity NPC272268
0.8248 Intermediate Similarity NPC475549
0.8244 Intermediate Similarity NPC131799
0.8235 Intermediate Similarity NPC44437
0.8231 Intermediate Similarity NPC477153
0.8231 Intermediate Similarity NPC273683
0.8227 Intermediate Similarity NPC143898
0.8227 Intermediate Similarity NPC476473
0.8227 Intermediate Similarity NPC469885
0.8222 Intermediate Similarity NPC478190
0.8217 Intermediate Similarity NPC120545
0.8209 Intermediate Similarity NPC31539
0.8209 Intermediate Similarity NPC253488
0.8194 Intermediate Similarity NPC94781
0.8188 Intermediate Similarity NPC238108
0.8188 Intermediate Similarity NPC53414
0.8188 Intermediate Similarity NPC53206
0.8188 Intermediate Similarity NPC245923
0.8182 Intermediate Similarity NPC34715
0.8182 Intermediate Similarity NPC300540
0.8175 Intermediate Similarity NPC325646
0.8175 Intermediate Similarity NPC258502
0.8175 Intermediate Similarity NPC22644
0.8175 Intermediate Similarity NPC28951
0.8169 Intermediate Similarity NPC79627
0.8169 Intermediate Similarity NPC103910
0.8169 Intermediate Similarity NPC471906
0.8168 Intermediate Similarity NPC91475
0.8168 Intermediate Similarity NPC265910
0.8162 Intermediate Similarity NPC263817
0.8162 Intermediate Similarity NPC314048
0.8148 Intermediate Similarity NPC93015
0.8148 Intermediate Similarity NPC85342
0.8148 Intermediate Similarity NPC477412
0.8145 Intermediate Similarity NPC231717
0.8143 Intermediate Similarity NPC183345
0.814 Intermediate Similarity NPC190971
0.8138 Intermediate Similarity NPC226578
0.8138 Intermediate Similarity NPC280753
0.8138 Intermediate Similarity NPC44378
0.8134 Intermediate Similarity NPC25736
0.8134 Intermediate Similarity NPC171460
0.8129 Intermediate Similarity NPC4214

  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 NPC237225 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
0.8926 High Similarity NPD405 Clinical (unspecified phase)
0.8672 High Similarity NPD1470 Approved
0.8359 Intermediate Similarity NPD1201 Approved
0.8116 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7986 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7872 Intermediate Similarity NPD2346 Discontinued
0.7847 Intermediate Similarity NPD3300 Phase 2
0.777 Intermediate Similarity NPD3226 Approved
0.7752 Intermediate Similarity NPD9493 Approved
0.7746 Intermediate Similarity NPD1471 Phase 3
0.7676 Intermediate Similarity NPD2935 Discontinued
0.7571 Intermediate Similarity NPD943 Approved
0.7569 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.754 Intermediate Similarity NPD9266 Approved
0.754 Intermediate Similarity NPD74 Approved
0.75 Intermediate Similarity NPD2344 Approved
0.7465 Intermediate Similarity NPD1607 Approved
0.746 Intermediate Similarity NPD9263 Approved
0.746 Intermediate Similarity NPD9267 Approved
0.746 Intermediate Similarity NPD9264 Approved
0.7447 Intermediate Similarity NPD1240 Approved
0.7445 Intermediate Similarity NPD1164 Approved
0.7432 Intermediate Similarity NPD7390 Discontinued
0.7431 Intermediate Similarity NPD5406 Approved
0.7431 Intermediate Similarity NPD5405 Approved
0.7431 Intermediate Similarity NPD5408 Approved
0.7431 Intermediate Similarity NPD5404 Approved
0.7429 Intermediate Similarity NPD2313 Discontinued
0.7394 Intermediate Similarity NPD447 Suspended
0.7391 Intermediate Similarity NPD2798 Approved
0.7388 Intermediate Similarity NPD2932 Approved
0.7383 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7361 Intermediate Similarity NPD1510 Phase 2
0.7361 Intermediate Similarity NPD2799 Discontinued
0.7361 Intermediate Similarity NPD3299 Clinical (unspecified phase)
0.7353 Intermediate Similarity NPD9717 Approved
0.7347 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7319 Intermediate Similarity NPD1203 Approved
0.7313 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD411 Approved
0.7297 Intermediate Similarity NPD2309 Approved
0.7267 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD2534 Approved
0.7267 Intermediate Similarity NPD2532 Approved
0.7267 Intermediate Similarity NPD2533 Approved
0.7259 Intermediate Similarity NPD3019 Approved
0.7244 Intermediate Similarity NPD3882 Suspended
0.7233 Intermediate Similarity NPD6232 Discontinued
0.7231 Intermediate Similarity NPD1609 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD1512 Approved
0.7205 Intermediate Similarity NPD7473 Discontinued
0.7197 Intermediate Similarity NPD9281 Approved
0.7153 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD9261 Approved
0.7122 Intermediate Similarity NPD1876 Approved
0.7122 Intermediate Similarity NPD1283 Approved
0.7115 Intermediate Similarity NPD7819 Suspended
0.7111 Intermediate Similarity NPD9545 Approved
0.7095 Intermediate Similarity NPD1549 Phase 2
0.7092 Intermediate Similarity NPD9494 Approved
0.7087 Intermediate Similarity NPD164 Approved
0.7087 Intermediate Similarity NPD1237 Approved
0.7086 Intermediate Similarity NPD1511 Approved
0.7075 Intermediate Similarity NPD1551 Phase 2
0.7063 Intermediate Similarity NPD3764 Approved
0.7059 Intermediate Similarity NPD1651 Approved
0.7054 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7047 Intermediate Similarity NPD2800 Approved
0.7034 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7016 Intermediate Similarity NPD288 Approved
0.7014 Intermediate Similarity NPD520 Approved
0.7007 Intermediate Similarity NPD4626 Approved
0.7006 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD2801 Approved
0.7 Intermediate Similarity NPD7003 Approved
0.7 Intermediate Similarity NPD3750 Approved
0.6992 Remote Similarity NPD1241 Discontinued
0.6984 Remote Similarity NPD289 Clinical (unspecified phase)
0.6982 Remote Similarity NPD8150 Discontinued
0.6981 Remote Similarity NPD7075 Discontinued
0.6978 Remote Similarity NPD3972 Approved
0.6974 Remote Similarity NPD6799 Approved
0.6962 Remote Similarity NPD5402 Approved
0.6957 Remote Similarity NPD6959 Discontinued
0.6946 Remote Similarity NPD4955 Approved
0.6946 Remote Similarity NPD5034 Approved
0.6946 Remote Similarity NPD4954 Approved
0.6946 Remote Similarity NPD5028 Approved
0.6946 Remote Similarity NPD5026 Approved
0.6946 Remote Similarity NPD36 Approved
0.6943 Remote Similarity NPD1934 Approved
0.6935 Remote Similarity NPD844 Approved
0.6923 Remote Similarity NPD6599 Discontinued
0.6923 Remote Similarity NPD6832 Phase 2
0.6923 Remote Similarity NPD4380 Phase 2
0.6918 Remote Similarity NPD230 Phase 1
0.6917 Remote Similarity NPD7635 Approved
0.6906 Remote Similarity NPD1281 Approved
0.6901 Remote Similarity NPD1019 Discontinued
0.6899 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6887 Remote Similarity NPD8166 Discontinued
0.6886 Remote Similarity NPD5031 Approved
0.6886 Remote Similarity NPD5030 Phase 2
0.6886 Remote Similarity NPD5029 Approved
0.6886 Remote Similarity NPD5027 Approved
0.6884 Remote Similarity NPD3412 Clinical (unspecified phase)
0.687 Remote Similarity NPD6831 Clinical (unspecified phase)
0.687 Remote Similarity NPD2182 Approved
0.6859 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6857 Remote Similarity NPD9269 Phase 2
0.6855 Remote Similarity NPD3817 Phase 2
0.6849 Remote Similarity NPD4060 Phase 1
0.6848 Remote Similarity NPD3751 Discontinued
0.6835 Remote Similarity NPD3023 Approved
0.6835 Remote Similarity NPD6844 Discontinued
0.6835 Remote Similarity NPD3026 Approved
0.6821 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6818 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6815 Remote Similarity NPD5951 Approved
0.6815 Remote Similarity NPD690 Clinical (unspecified phase)
0.6812 Remote Similarity NPD9268 Approved
0.6812 Remote Similarity NPD3024 Approved
0.6812 Remote Similarity NPD3025 Approved
0.6809 Remote Similarity NPD1755 Approved
0.6802 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6794 Remote Similarity NPD2342 Discontinued
0.6784 Remote Similarity NPD5037 Approved
0.6784 Remote Similarity NPD5038 Approved
0.6781 Remote Similarity NPD6663 Approved
0.6779 Remote Similarity NPD4308 Phase 3
0.6776 Remote Similarity NPD6398 Clinical (unspecified phase)
0.677 Remote Similarity NPD3749 Approved
0.6767 Remote Similarity NPD4141 Clinical (unspecified phase)
0.6757 Remote Similarity NPD6651 Approved
0.6752 Remote Similarity NPD7458 Discontinued
0.675 Remote Similarity NPD2296 Approved
0.675 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6748 Remote Similarity NPD1247 Approved
0.6738 Remote Similarity NPD4878 Approved
0.6738 Remote Similarity NPD1608 Approved
0.6736 Remote Similarity NPD5736 Approved
0.6733 Remote Similarity NPD2796 Approved
0.6731 Remote Similarity NPD5403 Approved
0.673 Remote Similarity NPD6801 Discontinued
0.6727 Remote Similarity NPD6166 Phase 2
0.6727 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6727 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6725 Remote Similarity NPD5036 Approved
0.6712 Remote Similarity NPD3268 Approved
0.671 Remote Similarity NPD5401 Approved
0.6707 Remote Similarity NPD5710 Approved
0.6707 Remote Similarity NPD5711 Approved
0.6706 Remote Similarity NPD8313 Approved
0.6706 Remote Similarity NPD8312 Approved
0.6694 Remote Similarity NPD650 Approved
0.6692 Remote Similarity NPD4750 Phase 3
0.6691 Remote Similarity NPD5691 Approved
0.669 Remote Similarity NPD4379 Clinical (unspecified phase)
0.669 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6688 Remote Similarity NPD7236 Approved
0.6667 Remote Similarity NPD3748 Approved
0.6667 Remote Similarity NPD6273 Approved
0.6667 Remote Similarity NPD4628 Phase 3
0.6667 Remote Similarity NPD7411 Suspended
0.6648 Remote Similarity NPD6534 Approved
0.6648 Remote Similarity NPD6782 Approved
0.6648 Remote Similarity NPD6778 Approved
0.6648 Remote Similarity NPD6777 Approved
0.6648 Remote Similarity NPD6781 Approved
0.6648 Remote Similarity NPD6780 Approved
0.6648 Remote Similarity NPD6776 Approved
0.6648 Remote Similarity NPD6779 Approved
0.6648 Remote Similarity NPD6535 Approved
0.6646 Remote Similarity NPD2649 Approved
0.6646 Remote Similarity NPD2651 Approved
0.6643 Remote Similarity NPD1778 Approved
0.6643 Remote Similarity NPD7163 Clinical (unspecified phase)
0.664 Remote Similarity NPD845 Approved
0.663 Remote Similarity NPD7435 Discontinued
0.6627 Remote Similarity NPD6797 Phase 2
0.6626 Remote Similarity NPD919 Approved
0.6624 Remote Similarity NPD920 Approved
0.6623 Remote Similarity NPD6099 Approved
0.6623 Remote Similarity NPD6100 Approved
0.6623 Remote Similarity NPD6190 Approved
0.6622 Remote Similarity NPD2979 Phase 3
0.6615 Remote Similarity NPD1929 Approved
0.6615 Remote Similarity NPD1931 Clinical (unspecified phase)
0.6615 Remote Similarity NPD1930 Approved
0.6609 Remote Similarity NPD6836 Approved
0.6607 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6605 Remote Similarity NPD7768 Phase 2
0.6597 Remote Similarity NPD2797 Approved
0.6596 Remote Similarity NPD3496 Discontinued
0.6596 Remote Similarity NPD4879 Approved
0.659 Remote Similarity NPD8434 Phase 2

  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