Structure

Physi-Chem Properties

Molecular Weight:  204.04
Volume:  201.042
LogP:  1.787
LogD:  1.584
LogS:  -2.881
# 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:  0.748
Synthetic Accessibility Score:  2.305
Fsp3:  0.091
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:  -4.645
MDCK Permeability:  2.3515674911323003e-05
Pgp-inhibitor:  0.009
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.008
20% Bioavailability (F20%):  0.383
30% Bioavailability (F30%):  0.586

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.377
Plasma Protein Binding (PPB):  94.35382080078125%
Volume Distribution (VD):  0.452
Pgp-substrate:  2.025162696838379%

ADMET: Metabolism

CYP1A2-inhibitor:  0.98
CYP1A2-substrate:  0.802
CYP2C19-inhibitor:  0.645
CYP2C19-substrate:  0.09
CYP2C9-inhibitor:  0.643
CYP2C9-substrate:  0.756
CYP2D6-inhibitor:  0.841
CYP2D6-substrate:  0.273
CYP3A4-inhibitor:  0.724
CYP3A4-substrate:  0.169

ADMET: Excretion

Clearance (CL):  6.474
Half-life (T1/2):  0.686

ADMET: Toxicity

hERG Blockers:  0.015
Human Hepatotoxicity (H-HT):  0.544
Drug-inuced Liver Injury (DILI):  0.512
AMES Toxicity:  0.931
Rat Oral Acute Toxicity:  0.949
Maximum Recommended Daily Dose:  0.865
Skin Sensitization:  0.866
Carcinogencity:  0.884
Eye Corrosion:  0.123
Eye Irritation:  0.979
Respiratory Toxicity:  0.431

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

  Natural Product: NPC165257

Natural Product ID:  NPC165257
Common Name*:   2-Methoxyjuglone
IUPAC Name:   5-hydroxy-2-methoxynaphthalene-1,4-dione
Synonyms:   2-Methoxyjuglone
Standard InCHIKey:  GATGZQSBJAZYRT-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C11H8O4/c1-15-9-5-8(13)10-6(11(9)14)3-2-4-7(10)12/h2-5,12H,1H3
SMILES:  COC1=CC(=O)c2c(cccc2O)C1=O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL480099
PubChem CID:   10104346
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
NPO26892 Juglans mandshurica Species Juglandaceae Eukaryota roots n.a. n.a. PMID[12444709]
NPO18674 Juglans regia Species Juglandaceae Eukaryota n.a. root n.a. PMID[14727919]
NPO18674 Juglans regia Species Juglandaceae Eukaryota n.a. xylem n.a. PMID[14727919]
NPO18674 Juglans regia Species Juglandaceae Eukaryota n.a. bark n.a. PMID[14727919]
NPO18674 Juglans regia Species Juglandaceae Eukaryota n.a. leaf n.a. PMID[14727919]
NPO18674 Juglans regia Species Juglandaceae Eukaryota n.a. pericarp n.a. PMID[18496782]
NPO18674 Juglans regia Species Juglandaceae Eukaryota n.a. n.a. n.a. PMID[25466114]
NPO18674 Juglans regia Species Juglandaceae Eukaryota Flowers n.a. n.a. PMID[28737396]
NPO40992 Penicillium thomii YPGA3 Strain Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[32902982]
NPO26892 Juglans mandshurica Species Juglandaceae Eukaryota Roots n.a. n.a. PMID[9599266]
NPO18674 Juglans regia Species Juglandaceae Eukaryota n.a. leaf n.a. Database[Article]
NPO18674 Juglans regia Species Juglandaceae Eukaryota Embryo n.a. n.a. Database[FooDB]
NPO18674 Juglans regia Species Juglandaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO18674 Juglans regia Species Juglandaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO18674 Juglans regia Species Juglandaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO18674 Juglans regia Species Juglandaceae Eukaryota Stem Bark n.a. n.a. Database[FooDB]
NPO18674 Juglans regia Species Juglandaceae Eukaryota Testa n.a. n.a. Database[FooDB]
NPO18674 Juglans regia Species Juglandaceae Eukaryota n.a. n.a. Database[FooDB]
NPO18674 Juglans regia Species Juglandaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18674 Juglans regia Species Juglandaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20411 Engelhardia roxburghiana Species Juglandaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26892 Juglans mandshurica Species Juglandaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18674 Juglans regia Species Juglandaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18674 Juglans regia Species Juglandaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20411 Engelhardia roxburghiana Species Juglandaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18674 Juglans regia Species Juglandaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26892 Juglans mandshurica Species Juglandaceae 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
NPT139 Cell Line HT-29 Homo sapiens IC50 = 2.63 ug.mL-1 PMID[480878]
NPT81 Cell Line A549 Homo sapiens IC50 = 0.08 ug.mL-1 PMID[480878]
NPT1357 Cell Line H22 Mus musculus Activity = 67.0 % PMID[480880]
NPT1357 Cell Line H22 Mus musculus Activity = 56.0 % PMID[480880]
NPT65 Cell Line HepG2 Homo sapiens Activity = 0.0 % PMID[480880]
NPT65 Cell Line HepG2 Homo sapiens Activity = 46.0 % PMID[480880]
NPT65 Cell Line HepG2 Homo sapiens Activity = 54.0 % PMID[480880]
NPT65 Cell Line HepG2 Homo sapiens Activity = 33.0 % PMID[480880]
NPT65 Cell Line HepG2 Homo sapiens Activity = 2.0 % PMID[480880]
NPT65 Cell Line HepG2 Homo sapiens Activity = 52.0 % PMID[480880]
NPT65 Cell Line HepG2 Homo sapiens Activity = 18.0 % PMID[480880]
NPT65 Cell Line HepG2 Homo sapiens Activity = 66.0 % PMID[480880]
NPT65 Cell Line HepG2 Homo sapiens Activity = 32.0 % PMID[480880]
NPT65 Cell Line HepG2 Homo sapiens Activity = 6.0 % PMID[480880]
NPT65 Cell Line HepG2 Homo sapiens Activity = 1.0 % PMID[480880]
NPT65 Cell Line HepG2 Homo sapiens Activity = 64.0 % PMID[480880]
NPT65 Cell Line HepG2 Homo sapiens Activity = 35.0 % PMID[480880]
NPT65 Cell Line HepG2 Homo sapiens Activity = 4.0 % PMID[480880]
NPT65 Cell Line HepG2 Homo sapiens Activity = 49.0 % PMID[480880]
NPT65 Cell Line HepG2 Homo sapiens Activity = 50.0 % PMID[480880]
NPT65 Cell Line HepG2 Homo sapiens Activity = 59.0 % PMID[480880]
NPT65 Cell Line HepG2 Homo sapiens Activity = 41.0 % PMID[480880]
NPT65 Cell Line HepG2 Homo sapiens Activity = 7.0 % PMID[480880]
NPT65 Cell Line HepG2 Homo sapiens Activity = 61.0 % PMID[480880]
NPT65 Cell Line HepG2 Homo sapiens Activity = 37.0 % PMID[480880]
NPT65 Cell Line HepG2 Homo sapiens Activity = 62.0 % PMID[480880]
NPT65 Cell Line HepG2 Homo sapiens Activity = 38.0 % PMID[480880]
NPT65 Cell Line HepG2 Homo sapiens Activity = 34.0 % PMID[480880]
NPT65 Cell Line HepG2 Homo sapiens Activity = 5.0 % PMID[480880]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 2.7 ug.mL-1 PMID[480880]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 3.7 ug.mL-1 PMID[480880]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 3.8 ug.mL-1 PMID[480880]
NPT165 Cell Line HeLa Homo sapiens IC50 = 1180.0 nM PMID[480881]
NPT165 Cell Line HeLa Homo sapiens IC50 = 1290.0 nM PMID[480881]
NPT165 Cell Line HeLa Homo sapiens INCC50 = 0.59 uM PMID[480881]
NPT165 Cell Line HeLa Homo sapiens Ratio = 2.19 n.a. PMID[480881]
NPT407 Cell Line COLO 205 Homo sapiens IC50 = 2300.0 nM PMID[480882]
NPT396 Cell Line T47D Homo sapiens IC50 = 2000.0 nM PMID[480882]
NPT111 Cell Line K562 Homo sapiens IC50 = 1400.0 nM PMID[480882]
NPT113 Cell Line RAW264.7 Mus musculus Inhibition < 30.0 % PMID[480883]
NPT784 Cell Line MDA-MB-468 Homo sapiens IC50 = 4900.0 nM PMID[480883]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 11000.0 nM PMID[480883]
NPT83 Cell Line MCF7 Homo sapiens Activity > 50.0 % PMID[480883]
NPT784 Cell Line MDA-MB-468 Homo sapiens Activity > 50.0 % PMID[480883]
NPT790 Organism Mycobacterium tuberculosis H37Rv Mycobacterium tuberculosis H37Rv MIC = 30.0 ug.mL-1 PMID[480879]
NPT27 Others Unspecified IC50 = 1930.0 nM PMID[480881]
NPT23295 CELL-LINE LNCaP C4-2B Homo sapiens IC50 = 13000.0 nM PMID[480883]
NPT23295 CELL-LINE LNCaP C4-2B Homo sapiens IC50 = 6400.0 nM PMID[480883]
NPT23295 CELL-LINE LNCaP C4-2B Homo sapiens Activity > 50.0 % PMID[480883]

☑ 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 NPC165257 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
0.9672 High Similarity NPC51037
0.9524 High Similarity NPC309430
0.9516 High Similarity NPC237225
0.9355 High Similarity NPC231774
0.9297 High Similarity NPC254603
0.9213 High Similarity NPC198305
0.9194 High Similarity NPC310540
0.9048 High Similarity NPC1991
0.9 High Similarity NPC171968
0.8943 High Similarity NPC206778
0.8943 High Similarity NPC285829
0.8926 High Similarity NPC108288
0.8923 High Similarity NPC88864
0.8915 High Similarity NPC475741
0.8898 High Similarity NPC3224
0.8881 High Similarity NPC114620
0.8881 High Similarity NPC103337
0.8855 High Similarity NPC193169
0.8846 High Similarity NPC205360
0.8837 High Similarity NPC278928
0.881 High Similarity NPC135062
0.8806 High Similarity NPC173980
0.876 High Similarity NPC179898
0.873 High Similarity NPC307174
0.871 High Similarity NPC232178
0.8696 High Similarity NPC477409
0.8672 High Similarity NPC103540
0.8657 High Similarity NPC141934
0.8657 High Similarity NPC38158
0.8636 High Similarity NPC246693
0.8636 High Similarity NPC110609
0.8636 High Similarity NPC242358
0.8615 High Similarity NPC282923
0.8605 High Similarity NPC306765
0.8603 High Similarity NPC477408
0.8561 High Similarity NPC29932
0.855 High Similarity NPC99731
0.854 High Similarity NPC156872
0.8529 High Similarity NPC61590
0.8519 High Similarity NPC86524
0.8516 High Similarity NPC375356
0.8511 High Similarity NPC476821
0.85 High Similarity NPC28632
0.85 High Similarity NPC474630
0.8496 Intermediate Similarity NPC477406
0.8496 Intermediate Similarity NPC17843
0.8496 Intermediate Similarity NPC70622
0.8492 Intermediate Similarity NPC473662
0.8492 Intermediate Similarity NPC216297
0.8492 Intermediate Similarity NPC7151
0.8485 Intermediate Similarity NPC117609
0.8485 Intermediate Similarity NPC27659
0.8478 Intermediate Similarity NPC283292
0.8473 Intermediate Similarity NPC247250
0.8473 Intermediate Similarity NPC767
0.8468 Intermediate Similarity NPC477453
0.8467 Intermediate Similarity NPC52358
0.8467 Intermediate Similarity NPC299405
0.8467 Intermediate Similarity NPC306835
0.8467 Intermediate Similarity NPC26924
0.8467 Intermediate Similarity NPC295339
0.8467 Intermediate Similarity NPC111422
0.8467 Intermediate Similarity NPC471602
0.8467 Intermediate Similarity NPC29771
0.8467 Intermediate Similarity NPC476477
0.8467 Intermediate Similarity NPC256463
0.8467 Intermediate Similarity NPC1268
0.8467 Intermediate Similarity NPC216312
0.8444 Intermediate Similarity NPC281513
0.8444 Intermediate Similarity NPC22222
0.8438 Intermediate Similarity NPC300274
0.8438 Intermediate Similarity NPC164947
0.8429 Intermediate Similarity NPC475201
0.8421 Intermediate Similarity NPC205992
0.8409 Intermediate Similarity NPC34414
0.8409 Intermediate Similarity NPC146647
0.8406 Intermediate Similarity NPC241349
0.8406 Intermediate Similarity NPC327916
0.8406 Intermediate Similarity NPC32749
0.8406 Intermediate Similarity NPC42262
0.8406 Intermediate Similarity NPC220496
0.8406 Intermediate Similarity NPC147542
0.8406 Intermediate Similarity NPC37992
0.8406 Intermediate Similarity NPC315578
0.8387 Intermediate Similarity NPC161304
0.8387 Intermediate Similarity NPC240163
0.8385 Intermediate Similarity NPC287473
0.8382 Intermediate Similarity NPC315275
0.8372 Intermediate Similarity NPC182646
0.8358 Intermediate Similarity NPC58685
0.8358 Intermediate Similarity NPC478190
0.8358 Intermediate Similarity NPC477407
0.8346 Intermediate Similarity NPC136588
0.8346 Intermediate Similarity NPC199253
0.8345 Intermediate Similarity NPC257003
0.8345 Intermediate Similarity NPC110810
0.8345 Intermediate Similarity NPC471444
0.8321 Intermediate Similarity NPC96915
0.8321 Intermediate Similarity NPC471452
0.831 Intermediate Similarity NPC136878
0.8309 Intermediate Similarity NPC283088
0.8309 Intermediate Similarity NPC27407
0.8308 Intermediate Similarity NPC173978
0.8308 Intermediate Similarity NPC142956
0.8308 Intermediate Similarity NPC234890
0.8308 Intermediate Similarity NPC74507
0.8298 Intermediate Similarity NPC274085
0.8298 Intermediate Similarity NPC89664
0.8296 Intermediate Similarity NPC115458
0.8295 Intermediate Similarity NPC217756
0.8286 Intermediate Similarity NPC474300
0.8286 Intermediate Similarity NPC49108
0.8284 Intermediate Similarity NPC470831
0.8284 Intermediate Similarity NPC214702
0.8284 Intermediate Similarity NPC17083
0.8284 Intermediate Similarity NPC244699
0.8264 Intermediate Similarity NPC84142
0.8264 Intermediate Similarity NPC226578
0.8264 Intermediate Similarity NPC224584
0.8264 Intermediate Similarity NPC120171
0.8258 Intermediate Similarity NPC470841
0.8258 Intermediate Similarity NPC324209
0.8258 Intermediate Similarity NPC45537
0.8254 Intermediate Similarity NPC269414
0.8254 Intermediate Similarity NPC125252
0.8248 Intermediate Similarity NPC232996
0.8239 Intermediate Similarity NPC474309
0.8239 Intermediate Similarity NPC475923
0.8235 Intermediate Similarity NPC288089
0.8235 Intermediate Similarity NPC50924
0.8235 Intermediate Similarity NPC282780
0.8235 Intermediate Similarity NPC166480
0.8235 Intermediate Similarity NPC44437
0.8227 Intermediate Similarity NPC143898
0.8227 Intermediate Similarity NPC476473
0.8227 Intermediate Similarity NPC21873
0.8227 Intermediate Similarity NPC469885
0.8214 Intermediate Similarity NPC84273
0.8214 Intermediate Similarity NPC124365
0.8209 Intermediate Similarity NPC147757
0.8209 Intermediate Similarity NPC31799
0.8209 Intermediate Similarity NPC55949
0.8207 Intermediate Similarity NPC164762
0.8201 Intermediate Similarity NPC92655
0.8195 Intermediate Similarity NPC48248
0.8194 Intermediate Similarity NPC94781
0.8189 Intermediate Similarity NPC41567
0.8188 Intermediate Similarity NPC284184
0.8188 Intermediate Similarity NPC53414
0.8188 Intermediate Similarity NPC301341
0.8188 Intermediate Similarity NPC53206
0.8188 Intermediate Similarity NPC305060
0.8182 Intermediate Similarity NPC34715
0.8182 Intermediate Similarity NPC15837
0.8182 Intermediate Similarity NPC8745
0.8175 Intermediate Similarity NPC161632
0.8175 Intermediate Similarity NPC142027
0.8175 Intermediate Similarity NPC325646
0.8175 Intermediate Similarity NPC28951
0.8169 Intermediate Similarity NPC103910
0.8169 Intermediate Similarity NPC19896
0.8168 Intermediate Similarity NPC474803
0.8168 Intermediate Similarity NPC265910
0.8168 Intermediate Similarity NPC91475
0.8168 Intermediate Similarity NPC474766
0.8168 Intermediate Similarity NPC68756
0.8168 Intermediate Similarity NPC13238
0.8168 Intermediate Similarity NPC152525
0.8162 Intermediate Similarity NPC53896
0.8162 Intermediate Similarity NPC52407
0.8162 Intermediate Similarity NPC225051
0.8154 Intermediate Similarity NPC46634
0.8151 Intermediate Similarity NPC91809
0.8148 Intermediate Similarity NPC189823
0.8148 Intermediate Similarity NPC198249
0.8148 Intermediate Similarity NPC219892
0.8145 Intermediate Similarity NPC231717
0.8143 Intermediate Similarity NPC49242
0.8138 Intermediate Similarity NPC80370
0.8138 Intermediate Similarity NPC280753
0.8138 Intermediate Similarity NPC44378
0.8134 Intermediate Similarity NPC92624
0.8129 Intermediate Similarity NPC9121
0.8129 Intermediate Similarity NPC177307
0.8129 Intermediate Similarity NPC197666
0.8129 Intermediate Similarity NPC416
0.8129 Intermediate Similarity NPC61398
0.8129 Intermediate Similarity NPC13715
0.8129 Intermediate Similarity NPC126739
0.8125 Intermediate Similarity NPC472135
0.812 Intermediate Similarity NPC471530
0.812 Intermediate Similarity NPC473787
0.8116 Intermediate Similarity NPC254847
0.8116 Intermediate Similarity NPC272268
0.8116 Intermediate Similarity NPC474813
0.8106 Intermediate Similarity NPC201728
0.8106 Intermediate Similarity NPC123506
0.8106 Intermediate Similarity NPC262671
0.8106 Intermediate Similarity NPC10926
0.8106 Intermediate Similarity NPC477454

  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 NPC165257 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 NPD651 Clinical (unspecified phase)
0.8116 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7943 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7826 Intermediate Similarity NPD943 Approved
0.7826 Intermediate Similarity NPD1240 Approved
0.777 Intermediate Similarity NPD3226 Approved
0.7752 Intermediate Similarity NPD9493 Approved
0.773 Intermediate Similarity NPD1510 Phase 2
0.7714 Intermediate Similarity NPD1607 Approved
0.7708 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7603 Intermediate Similarity NPD3300 Phase 2
0.7582 Intermediate Similarity NPD3882 Suspended
0.754 Intermediate Similarity NPD9266 Approved
0.754 Intermediate Similarity NPD74 Approved
0.75 Intermediate Similarity NPD2344 Approved
0.75 Intermediate Similarity NPD1471 Phase 3
0.75 Intermediate Similarity NPD2346 Discontinued
0.75 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD9545 Approved
0.746 Intermediate Similarity NPD9263 Approved
0.746 Intermediate Similarity NPD9267 Approved
0.746 Intermediate Similarity NPD9264 Approved
0.745 Intermediate Similarity NPD1512 Approved
0.7448 Intermediate Similarity NPD1549 Phase 2
0.7431 Intermediate Similarity NPD5406 Approved
0.7431 Intermediate Similarity NPD5405 Approved
0.7431 Intermediate Similarity NPD5408 Approved
0.7431 Intermediate Similarity NPD5404 Approved
0.7431 Intermediate Similarity NPD2935 Discontinued
0.7429 Intermediate Similarity NPD3764 Approved
0.7391 Intermediate Similarity NPD2798 Approved
0.7379 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7379 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7353 Intermediate Similarity NPD9717 Approved
0.7347 Intermediate Similarity NPD3750 Approved
0.7338 Intermediate Similarity NPD7819 Suspended
0.7323 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7319 Intermediate Similarity NPD1164 Approved
0.7319 Intermediate Similarity NPD1203 Approved
0.7315 Intermediate Similarity NPD6799 Approved
0.7315 Intermediate Similarity NPD7390 Discontinued
0.7315 Intermediate Similarity NPD1511 Approved
0.731 Intermediate Similarity NPD1551 Phase 2
0.7297 Intermediate Similarity NPD2309 Approved
0.7273 Intermediate Similarity NPD447 Suspended
0.7267 Intermediate Similarity NPD2534 Approved
0.7267 Intermediate Similarity NPD2532 Approved
0.7267 Intermediate Similarity NPD2533 Approved
0.7241 Intermediate Similarity NPD2799 Discontinued
0.7233 Intermediate Similarity NPD6232 Discontinued
0.7226 Intermediate Similarity NPD2801 Approved
0.7205 Intermediate Similarity NPD7473 Discontinued
0.7197 Intermediate Similarity NPD7075 Discontinued
0.7197 Intermediate Similarity NPD9281 Approved
0.7185 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7183 Intermediate Similarity NPD411 Approved
0.7183 Intermediate Similarity NPD2313 Discontinued
0.7179 Intermediate Similarity NPD5402 Approved
0.7162 Intermediate Similarity NPD2800 Approved
0.7161 Intermediate Similarity NPD1934 Approved
0.7153 Intermediate Similarity NPD230 Phase 1
0.7153 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7152 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD9261 Approved
0.7143 Intermediate Similarity NPD6599 Discontinued
0.7132 Intermediate Similarity NPD2932 Approved
0.7123 Intermediate Similarity NPD3299 Clinical (unspecified phase)
0.7122 Intermediate Similarity NPD1876 Approved
0.7115 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD1608 Approved
0.7099 Intermediate Similarity NPD1609 Clinical (unspecified phase)
0.7092 Intermediate Similarity NPD9494 Approved
0.7089 Intermediate Similarity NPD3749 Approved
0.7087 Intermediate Similarity NPD1237 Approved
0.7075 Intermediate Similarity NPD2796 Approved
0.707 Intermediate Similarity NPD3817 Phase 2
0.7059 Intermediate Similarity NPD5403 Approved
0.7055 Intermediate Similarity NPD3751 Discontinued
0.7047 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD5401 Approved
0.7032 Intermediate Similarity NPD4380 Phase 2
0.7018 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7014 Intermediate Similarity NPD520 Approved
0.7007 Intermediate Similarity NPD3748 Approved
0.7007 Intermediate Similarity NPD3019 Approved
0.6992 Remote Similarity NPD1241 Discontinued
0.6986 Remote Similarity NPD6651 Approved
0.6982 Remote Similarity NPD8150 Discontinued
0.6978 Remote Similarity NPD9269 Phase 2
0.6962 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6957 Remote Similarity NPD6959 Discontinued
0.6953 Remote Similarity NPD164 Approved
0.6943 Remote Similarity NPD6801 Discontinued
0.6934 Remote Similarity NPD9268 Approved
0.6933 Remote Similarity NPD6166 Phase 2
0.6933 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6933 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6923 Remote Similarity NPD6832 Phase 2
0.6918 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6887 Remote Similarity NPD4628 Phase 3
0.6887 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6884 Remote Similarity NPD17 Approved
0.688 Remote Similarity NPD288 Approved
0.6879 Remote Similarity NPD7411 Suspended
0.6879 Remote Similarity NPD1283 Approved
0.6871 Remote Similarity NPD3926 Phase 2
0.6857 Remote Similarity NPD3972 Approved
0.6852 Remote Similarity NPD1247 Approved
0.685 Remote Similarity NPD289 Clinical (unspecified phase)
0.6846 Remote Similarity NPD6099 Approved
0.6846 Remote Similarity NPD6100 Approved
0.6842 Remote Similarity NPD6190 Approved
0.6832 Remote Similarity NPD919 Approved
0.6826 Remote Similarity NPD6797 Phase 2
0.6818 Remote Similarity NPD4750 Phase 3
0.6815 Remote Similarity NPD690 Clinical (unspecified phase)
0.6813 Remote Similarity NPD7768 Phase 2
0.6812 Remote Similarity NPD1651 Approved
0.6809 Remote Similarity NPD1755 Approved
0.6802 Remote Similarity NPD8397 Clinical (unspecified phase)
0.68 Remote Similarity NPD844 Approved
0.68 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6786 Remote Similarity NPD7251 Discontinued
0.6786 Remote Similarity NPD5027 Approved
0.6786 Remote Similarity NPD5029 Approved
0.6786 Remote Similarity NPD5031 Approved
0.6783 Remote Similarity NPD1019 Discontinued
0.6776 Remote Similarity NPD7003 Approved
0.677 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6763 Remote Similarity NPD1778 Approved
0.6763 Remote Similarity NPD4626 Approved
0.675 Remote Similarity NPD2296 Approved
0.6747 Remote Similarity NPD3818 Discontinued
0.6746 Remote Similarity NPD7808 Phase 3
0.6746 Remote Similarity NPD5026 Approved
0.6746 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6746 Remote Similarity NPD5034 Approved
0.6746 Remote Similarity NPD36 Approved
0.6746 Remote Similarity NPD4955 Approved
0.6746 Remote Similarity NPD5028 Approved
0.6746 Remote Similarity NPD4954 Approved
0.6742 Remote Similarity NPD2182 Approved
0.6742 Remote Similarity NPD6831 Clinical (unspecified phase)
0.6735 Remote Similarity NPD4060 Phase 1
0.6731 Remote Similarity NPD920 Approved
0.673 Remote Similarity NPD6844 Discontinued
0.6727 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6712 Remote Similarity NPD3268 Approved
0.6711 Remote Similarity NPD1243 Approved
0.6707 Remote Similarity NPD5710 Approved
0.6707 Remote Similarity NPD5711 Approved
0.6707 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6706 Remote Similarity NPD8313 Approved
0.6706 Remote Similarity NPD8312 Approved
0.669 Remote Similarity NPD4379 Clinical (unspecified phase)
0.6687 Remote Similarity NPD5494 Approved
0.6687 Remote Similarity NPD1465 Phase 2
0.6686 Remote Similarity NPD5030 Phase 2
0.6686 Remote Similarity NPD5038 Approved
0.6686 Remote Similarity NPD5037 Approved
0.6667 Remote Similarity NPD8166 Discontinued
0.6667 Remote Similarity NPD1281 Approved
0.6667 Remote Similarity NPD4308 Phase 3
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 NPD5808 Clinical (unspecified phase)
0.6646 Remote Similarity NPD2651 Approved
0.6643 Remote Similarity NPD3412 Clinical (unspecified phase)
0.663 Remote Similarity NPD7435 Discontinued
0.6628 Remote Similarity NPD5036 Approved
0.6627 Remote Similarity NPD5953 Discontinued
0.662 Remote Similarity NPD4878 Approved
0.6607 Remote Similarity NPD7054 Approved
0.6606 Remote Similarity NPD3787 Discontinued
0.6605 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6603 Remote Similarity NPD642 Clinical (unspecified phase)
0.6601 Remote Similarity NPD2654 Approved
0.6599 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6597 Remote Similarity NPD2797 Approved
0.6596 Remote Similarity NPD3026 Approved
0.6596 Remote Similarity NPD3023 Approved
0.659 Remote Similarity NPD8434 Phase 2
0.6581 Remote Similarity NPD643 Clinical (unspecified phase)
0.6577 Remote Similarity NPD1933 Approved
0.6577 Remote Similarity NPD6355 Discontinued
0.6573 Remote Similarity NPD3600 Clinical (unspecified phase)
0.6571 Remote Similarity NPD3025 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