Structure

Physi-Chem Properties

Molecular Weight:  502.18
Volume:  484.917
LogP:  2.805
LogD:  1.984
LogS:  -3.802
# Rotatable Bonds:  5
TPSA:  133.14
# H-Bond Aceptor:  10
# H-Bond Donor:  3
# Rings:  5
# Heavy Atoms:  10

MedChem Properties

QED Drug-Likeness Score:  0.535
Synthetic Accessibility Score:  4.588
Fsp3:  0.5
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.544
MDCK Permeability:  4.733645255328156e-05
Pgp-inhibitor:  0.133
Pgp-substrate:  0.985
Human Intestinal Absorption (HIA):  0.011
20% Bioavailability (F20%):  0.0
30% Bioavailability (F30%):  0.042

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.094
Plasma Protein Binding (PPB):  91.25843048095703%
Volume Distribution (VD):  0.719
Pgp-substrate:  10.44253158569336%

ADMET: Metabolism

CYP1A2-inhibitor:  0.027
CYP1A2-substrate:  0.136
CYP2C19-inhibitor:  0.038
CYP2C19-substrate:  0.806
CYP2C9-inhibitor:  0.102
CYP2C9-substrate:  0.719
CYP2D6-inhibitor:  0.097
CYP2D6-substrate:  0.315
CYP3A4-inhibitor:  0.301
CYP3A4-substrate:  0.336

ADMET: Excretion

Clearance (CL):  6.687
Half-life (T1/2):  0.142

ADMET: Toxicity

hERG Blockers:  0.237
Human Hepatotoxicity (H-HT):  0.842
Drug-inuced Liver Injury (DILI):  0.956
AMES Toxicity:  0.163
Rat Oral Acute Toxicity:  0.505
Maximum Recommended Daily Dose:  0.942
Skin Sensitization:  0.888
Carcinogencity:  0.054
Eye Corrosion:  0.003
Eye Irritation:  0.024
Respiratory Toxicity:  0.948

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

  Natural Product: NPC107109

Natural Product ID:  NPC107109
Common Name*:   6-O-Methylalaternin
IUPAC Name:   1,2,8-trihydroxy-6-methoxy-3-methylanthracene-9,10-dione
Synonyms:   6-O-Methylalaternin
Standard InCHIKey:  IOPGGNYCFGEWPF-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C16H12O6/c1-6-3-8-12(16(21)13(6)18)15(20)11-9(14(8)19)4-7(22-2)5-10(11)17/h3-5,17-18,21H,1-2H3
SMILES:  COc1cc(O)c2c(c1)C(=O)c1c(C2=O)c(O)c(c(c1)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL556684
PubChem CID:   177458
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000018] Anthracenes
        • [CHEMONTID:0000151] Anthraquinones
          • [CHEMONTID:0001598] Hydroxyanthraquinones

*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
NPO17255 Chondrosia corticata Species Chondrillidae Eukaryota n.a. n.a. n.a. PMID[15568783]
NPO16860 Stemphylium globuliferum Species Pleosporaceae Eukaryota n.a. n.a. n.a. PMID[19271717]
NPO16860 Stemphylium globuliferum Species Pleosporaceae Eukaryota Mentha pulegium n.a. n.a. PMID[19271717]
NPO22865 Neopetrosia proxima Species Petrosiidae Eukaryota n.a. Caribbean sea n.a. PMID[20727745]
NPO22865 Neopetrosia proxima Species Petrosiidae Eukaryota n.a. n.a. n.a. PMID[21341726]
NPO17255 Chondrosia corticata Species Chondrillidae Eukaryota n.a. reef slopes on the south side of Cocos Lagoon, Guam n.a. PMID[21550239]
NPO18542 Salvia sahendica Species Lamiaceae Eukaryota n.a. collected from the plants natural habitat in Tabriz, Northwestern Iran, at an altitude of 1400 m n.a. PMID[21775156]
NPO16860 Stemphylium globuliferum Species Pleosporaceae Eukaryota Stems n.a. n.a. PMID[23664494]
NPO16860 Stemphylium globuliferum Species Pleosporaceae Eukaryota isolated from fresh Juncus acutus Lake Wadi el Natrun, Egypt 2012-NOV PMID[25010124]
NPO18279 Paraconiothyrium brasiliense Species Didymosphaeriaceae Eukaryota n.a. n.a. n.a. PMID[25760674]
NPO18194 Primula modesta Species Primulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18194 Primula modesta Species Primulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17255 Chondrosia corticata Species Chondrillidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13444 Centaurea ptosimopappoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16860 Stemphylium globuliferum Species Pleosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15888 Streptogonopus phipsoni n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO18542 Salvia sahendica Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19726 Limnatis nilotica Species Hirudinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19101 Deutzia gracilis Species Hydrangeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18944 Vernonia filigera Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19321 0tholaena californica Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19382 Corallina elongata Species Corallinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18194 Primula modesta Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14894 Udotea conglutinata Species Udoteaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22865 Neopetrosia proxima Species Petrosiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18279 Paraconiothyrium brasiliense Species Didymosphaeriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18687 Pterocarpus gracilis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18080 Peltophorum ferrugineum 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
NPT1598 Individual Protein Casein kinase II alpha Homo sapiens IC50 > 10.0 ug.mL-1 PMID[509012]
NPT2575 Individual Protein Platelet-derived growth factor receptor beta Homo sapiens IC50 > 10.0 ug.mL-1 PMID[509012]
NPT1436 Individual Protein Focal adhesion kinase 1 Homo sapiens IC50 > 10.0 ug.mL-1 PMID[509012]
NPT286 Individual Protein Receptor protein-tyrosine kinase erbB-2 Homo sapiens IC50 > 10.0 ug.mL-1 PMID[509012]
NPT2572 Individual Protein Ephrin type-B receptor 4 Homo sapiens IC50 > 10.0 ug.mL-1 PMID[509012]
NPT1371 Individual Protein Cyclin-dependent kinase 2 Homo sapiens IC50 > 10.0 ug.mL-1 PMID[509012]
NPT1434 Individual Protein Serine/threonine-protein kinase B-raf Homo sapiens IC50 > 10.0 ug.mL-1 PMID[509012]
NPT1660 Individual Protein NUAK family SNF1-like kinase 1 Homo sapiens IC50 > 10.0 ug.mL-1 PMID[509012]
NPT2571 Individual Protein Mitogen-activated protein kinase kinase kinase 8 Homo sapiens IC50 = 7.3 ug.mL-1 PMID[509012]
NPT1864 Cell Line L5178Y Mus musculus Activity = 4.9 % PMID[509012]
NPT2576 Individual Protein Tyrosine-protein kinase TIE-2 Homo sapiens IC50 = 4.5 ug.mL-1 PMID[509012]
NPT1702 Individual Protein Serine/threonine-protein kinase PLK4 Homo sapiens IC50 = 4.4 ug.mL-1 PMID[509012]
NPT1337 Individual Protein Hepatocyte growth factor receptor Homo sapiens IC50 = 4.3 ug.mL-1 PMID[509012]
NPT1864 Cell Line L5178Y Mus musculus EC50 = 4.2 ug.mL-1 PMID[509012]
NPT285 Individual Protein Epidermal growth factor receptor erbB1 Homo sapiens IC50 = 4.0 ug.mL-1 PMID[509012]
NPT2574 Individual Protein Insulin receptor Homo sapiens IC50 = 3.9 ug.mL-1 PMID[509012]
NPT1432 Individual Protein Serine/threonine-protein kinase Aurora-A Homo sapiens IC50 = 3.0 ug.mL-1 PMID[509012]
NPT1438 Individual Protein Insulin-like growth factor I receptor Homo sapiens IC50 = 2.8 ug.mL-1 PMID[509012]
NPT2573 Individual Protein Vascular endothelial growth factor receptor 3 Homo sapiens IC50 = 2.7 ug.mL-1 PMID[509012]
NPT1650 Individual Protein Tyrosine-protein kinase receptor FLT3 Homo sapiens IC50 = 2.5 ug.mL-1 PMID[509012]
NPT36 Individual Protein Tyrosine-protein kinase SRC Homo sapiens IC50 = 1.8 ug.mL-1 PMID[509012]
NPT1433 Individual Protein Serine/threonine-protein kinase Aurora-B Homo sapiens IC50 = 1.8 ug.mL-1 PMID[509012]
NPT1478 Individual Protein Vascular endothelial growth factor receptor 2 Homo sapiens IC50 = 1.2 ug.mL-1 PMID[509012]
NPT831 Individual Protein Serine/threonine-protein kinase PLK1 Homo sapiens IC50 > 10.0 ug.mL-1 PMID[509012]
NPT728 Individual Protein Serine/threonine-protein kinase AKT Homo sapiens IC50 > 10.0 ug.mL-1 PMID[509012]
NPT1560 Protein Complex Cyclin-dependent kinase 4/cyclin D1 Homo sapiens IC50 = 3.6 ug.mL-1 PMID[509012]

☑ 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 NPC107109 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
0.9865 High Similarity NPC14561
0.9865 High Similarity NPC5379
0.9865 High Similarity NPC77807
0.9799 High Similarity NPC37543
0.9799 High Similarity NPC199463
0.9799 High Similarity NPC178976
0.9669 High Similarity NPC84571
0.9605 High Similarity NPC311740
0.9597 High Similarity NPC93552
0.9589 High Similarity NPC289042
0.9589 High Similarity NPC312929
0.9589 High Similarity NPC118027
0.9589 High Similarity NPC245584
0.9589 High Similarity NPC56433
0.9589 High Similarity NPC190648
0.9589 High Similarity NPC126767
0.953 High Similarity NPC149889
0.953 High Similarity NPC312338
0.9463 High Similarity NPC473201
0.9463 High Similarity NPC302783
0.9396 High Similarity NPC294646
0.9396 High Similarity NPC280295
0.9396 High Similarity NPC290954
0.9396 High Similarity NPC147735
0.9396 High Similarity NPC470568
0.9396 High Similarity NPC255641
0.9384 High Similarity NPC19896
0.9355 High Similarity NPC101769
0.9333 High Similarity NPC470569
0.9333 High Similarity NPC118427
0.9333 High Similarity NPC78505
0.9272 High Similarity NPC154683
0.9272 High Similarity NPC164912
0.9272 High Similarity NPC40356
0.9267 High Similarity NPC85131
0.9262 High Similarity NPC203077
0.9262 High Similarity NPC238279
0.9262 High Similarity NPC166036
0.9241 High Similarity NPC165979
0.9241 High Similarity NPC163130
0.9221 High Similarity NPC245891
0.9221 High Similarity NPC104876
0.9221 High Similarity NPC85121
0.9211 High Similarity NPC208806
0.92 High Similarity NPC171916
0.92 High Similarity NPC38545
0.92 High Similarity NPC134293
0.9195 High Similarity NPC34802
0.9184 High Similarity NPC167663
0.9184 High Similarity NPC287722
0.9172 High Similarity NPC26386
0.9167 High Similarity NPC470694
0.9167 High Similarity NPC294965
0.9161 High Similarity NPC119224
0.915 High Similarity NPC226656
0.915 High Similarity NPC66508
0.9139 High Similarity NPC472279
0.9125 High Similarity NPC158226
0.9122 High Similarity NPC193703
0.9122 High Similarity NPC21599
0.9122 High Similarity NPC48762
0.9122 High Similarity NPC105213
0.9116 High Similarity NPC284556
0.9116 High Similarity NPC301178
0.9116 High Similarity NPC94076
0.9116 High Similarity NPC182255
0.9114 High Similarity NPC29160
0.9108 High Similarity NPC236132
0.9108 High Similarity NPC270837
0.9091 High Similarity NPC142339
0.9085 High Similarity NPC214632
0.9079 High Similarity NPC256406
0.9073 High Similarity NPC264550
0.9073 High Similarity NPC329933
0.9073 High Similarity NPC40290
0.9073 High Similarity NPC264289
0.9073 High Similarity NPC69430
0.9073 High Similarity NPC195763
0.9073 High Similarity NPC142876
0.9073 High Similarity NPC200060
0.9073 High Similarity NPC333691
0.9073 High Similarity NPC139293
0.906 High Similarity NPC73416
0.906 High Similarity NPC34482
0.906 High Similarity NPC49282
0.906 High Similarity NPC160777
0.9057 High Similarity NPC234331
0.9054 High Similarity NPC84266
0.9054 High Similarity NPC471417
0.9051 High Similarity NPC303174
0.9038 High Similarity NPC14353
0.9038 High Similarity NPC228785
0.9038 High Similarity NPC56085
0.9032 High Similarity NPC236796
0.9032 High Similarity NPC136674
0.9026 High Similarity NPC39184
0.9026 High Similarity NPC113906
0.9026 High Similarity NPC134287
0.9026 High Similarity NPC234485
0.9026 High Similarity NPC168247
0.9026 High Similarity NPC152951
0.9026 High Similarity NPC117992
0.9026 High Similarity NPC230149
0.9026 High Similarity NPC38898
0.9026 High Similarity NPC130589
0.9026 High Similarity NPC57674
0.902 High Similarity NPC324233
0.902 High Similarity NPC470337
0.902 High Similarity NPC51824
0.902 High Similarity NPC180944
0.902 High Similarity NPC323626
0.902 High Similarity NPC113608
0.902 High Similarity NPC470338
0.902 High Similarity NPC268992
0.9013 High Similarity NPC10467
0.9013 High Similarity NPC151473
0.9007 High Similarity NPC203747
0.9007 High Similarity NPC194653
0.9007 High Similarity NPC2569
0.9007 High Similarity NPC472056
0.9007 High Similarity NPC139364
0.9007 High Similarity NPC80710
0.9007 High Similarity NPC27221
0.9007 High Similarity NPC7025
0.9007 High Similarity NPC254702
0.9007 High Similarity NPC256672
0.9007 High Similarity NPC172329
0.9 High Similarity NPC138978
0.9 High Similarity NPC470570
0.9 High Similarity NPC49487
0.9 High Similarity NPC99613
0.8993 High Similarity NPC242893
0.8993 High Similarity NPC142165
0.8993 High Similarity NPC38065
0.8987 High Similarity NPC207690
0.8986 High Similarity NPC49108
0.8981 High Similarity NPC61010
0.8981 High Similarity NPC278052
0.8981 High Similarity NPC66288
0.8981 High Similarity NPC40491
0.8981 High Similarity NPC32694
0.898 High Similarity NPC203063
0.8974 High Similarity NPC100123
0.8974 High Similarity NPC210459
0.8974 High Similarity NPC324736
0.8974 High Similarity NPC45846
0.8974 High Similarity NPC235448
0.8974 High Similarity NPC477410
0.8968 High Similarity NPC472455
0.8968 High Similarity NPC475799
0.8968 High Similarity NPC279605
0.8968 High Similarity NPC13779
0.8961 High Similarity NPC49402
0.8961 High Similarity NPC33051
0.8961 High Similarity NPC70433
0.8961 High Similarity NPC227337
0.8961 High Similarity NPC89474
0.8961 High Similarity NPC127172
0.8961 High Similarity NPC273462
0.8954 High Similarity NPC46882
0.8954 High Similarity NPC132990
0.8954 High Similarity NPC478148
0.8954 High Similarity NPC154345
0.8954 High Similarity NPC474417
0.8954 High Similarity NPC144283
0.8954 High Similarity NPC19980
0.8954 High Similarity NPC202157
0.8954 High Similarity NPC45291
0.8954 High Similarity NPC149526
0.8947 High Similarity NPC288036
0.8947 High Similarity NPC65589
0.8947 High Similarity NPC97029
0.8947 High Similarity NPC158338
0.8947 High Similarity NPC80370
0.8947 High Similarity NPC100985
0.8947 High Similarity NPC97028
0.894 High Similarity NPC77598
0.894 High Similarity NPC125449
0.894 High Similarity NPC22005
0.894 High Similarity NPC7943
0.894 High Similarity NPC123202
0.894 High Similarity NPC188074
0.8933 High Similarity NPC157133
0.8933 High Similarity NPC28632
0.8926 High Similarity NPC254659
0.8924 High Similarity NPC329760
0.8917 High Similarity NPC470810
0.8917 High Similarity NPC297212
0.8917 High Similarity NPC161947
0.8917 High Similarity NPC36217
0.8917 High Similarity NPC155302
0.8917 High Similarity NPC471973
0.8917 High Similarity NPC470342
0.8917 High Similarity NPC472052
0.8917 High Similarity NPC235018
0.8917 High Similarity NPC321399
0.8917 High Similarity NPC45146
0.8917 High Similarity NPC472060
0.8917 High Similarity NPC320359
0.8912 High Similarity NPC1268

  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 NPC107109 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
0.9045 High Similarity NPD6232 Discontinued
0.8994 High Similarity NPD7473 Discontinued
0.8839 High Similarity NPD2393 Clinical (unspecified phase)
0.8836 High Similarity NPD1509 Clinical (unspecified phase)
0.8654 High Similarity NPD1934 Approved
0.8618 High Similarity NPD1511 Approved
0.8599 High Similarity NPD2801 Approved
0.8571 High Similarity NPD1607 Approved
0.8506 High Similarity NPD1512 Approved
0.8491 Intermediate Similarity NPD3882 Suspended
0.8456 Intermediate Similarity NPD1510 Phase 2
0.8435 Intermediate Similarity NPD943 Approved
0.8435 Intermediate Similarity NPD1240 Approved
0.8395 Intermediate Similarity NPD6959 Discontinued
0.8365 Intermediate Similarity NPD7819 Suspended
0.8323 Intermediate Similarity NPD2533 Approved
0.8323 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8323 Intermediate Similarity NPD2534 Approved
0.8323 Intermediate Similarity NPD2532 Approved
0.8291 Intermediate Similarity NPD4380 Phase 2
0.8289 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8261 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8242 Intermediate Similarity NPD6166 Phase 2
0.8242 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8242 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8228 Intermediate Similarity NPD3226 Approved
0.8205 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8204 Intermediate Similarity NPD5844 Phase 1
0.817 Intermediate Similarity NPD1549 Phase 2
0.8144 Intermediate Similarity NPD3818 Discontinued
0.8141 Intermediate Similarity NPD7390 Discontinued
0.8137 Intermediate Similarity NPD1465 Phase 2
0.811 Intermediate Similarity NPD5494 Approved
0.8105 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8105 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8098 Intermediate Similarity NPD7075 Discontinued
0.8092 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.8086 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8025 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8012 Intermediate Similarity NPD7411 Suspended
0.7988 Intermediate Similarity NPD3749 Approved
0.7975 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7975 Intermediate Similarity NPD3817 Phase 2
0.7959 Intermediate Similarity NPD1470 Approved
0.795 Intermediate Similarity NPD6599 Discontinued
0.7949 Intermediate Similarity NPD3750 Approved
0.7943 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7941 Intermediate Similarity NPD7074 Phase 3
0.7922 Intermediate Similarity NPD2796 Approved
0.7922 Intermediate Similarity NPD2935 Discontinued
0.7895 Intermediate Similarity NPD230 Phase 1
0.7885 Intermediate Similarity NPD2800 Approved
0.7882 Intermediate Similarity NPD7054 Approved
0.7871 Intermediate Similarity NPD2346 Discontinued
0.7853 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7853 Intermediate Similarity NPD6801 Discontinued
0.7836 Intermediate Similarity NPD7472 Approved
0.7831 Intermediate Similarity NPD6234 Discontinued
0.7818 Intermediate Similarity NPD7768 Phase 2
0.7811 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7799 Intermediate Similarity NPD6799 Approved
0.7791 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7791 Intermediate Similarity NPD6797 Phase 2
0.7771 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7764 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7751 Intermediate Similarity NPD3926 Phase 2
0.7746 Intermediate Similarity NPD6559 Discontinued
0.7746 Intermediate Similarity NPD7251 Discontinued
0.7744 Intermediate Similarity NPD37 Approved
0.7727 Intermediate Similarity NPD6651 Approved
0.7722 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7701 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD5408 Approved
0.7692 Intermediate Similarity NPD6099 Approved
0.7692 Intermediate Similarity NPD5405 Approved
0.7692 Intermediate Similarity NPD5406 Approved
0.7692 Intermediate Similarity NPD5404 Approved
0.7692 Intermediate Similarity NPD5710 Approved
0.7692 Intermediate Similarity NPD6100 Approved
0.7692 Intermediate Similarity NPD1551 Phase 2
0.7692 Intermediate Similarity NPD5711 Approved
0.7687 Intermediate Similarity NPD1201 Approved
0.7658 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7643 Intermediate Similarity NPD2344 Approved
0.7633 Intermediate Similarity NPD1247 Approved
0.7628 Intermediate Similarity NPD3748 Approved
0.7619 Intermediate Similarity NPD919 Approved
0.7606 Intermediate Similarity NPD8151 Discontinued
0.7605 Intermediate Similarity NPD4967 Phase 2
0.7605 Intermediate Similarity NPD4965 Approved
0.7605 Intermediate Similarity NPD4966 Approved
0.76 Intermediate Similarity NPD7808 Phase 3
0.7572 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7554 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7554 Intermediate Similarity NPD6777 Approved
0.7554 Intermediate Similarity NPD6780 Approved
0.7554 Intermediate Similarity NPD6776 Approved
0.7554 Intermediate Similarity NPD6779 Approved
0.7554 Intermediate Similarity NPD6778 Approved
0.7554 Intermediate Similarity NPD6781 Approved
0.7554 Intermediate Similarity NPD6782 Approved
0.7547 Intermediate Similarity NPD1243 Approved
0.7516 Intermediate Similarity NPD2799 Discontinued
0.7514 Intermediate Similarity NPD7228 Approved
0.7514 Intermediate Similarity NPD3751 Discontinued
0.75 Intermediate Similarity NPD9494 Approved
0.75 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD4628 Phase 3
0.75 Intermediate Similarity NPD7003 Approved
0.7486 Intermediate Similarity NPD5953 Discontinued
0.7472 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7458 Intermediate Similarity NPD8313 Approved
0.7458 Intermediate Similarity NPD8312 Approved
0.7455 Intermediate Similarity NPD7458 Discontinued
0.7453 Intermediate Similarity NPD2309 Approved
0.7451 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD5402 Approved
0.7439 Intermediate Similarity NPD920 Approved
0.7433 Intermediate Similarity NPD7435 Discontinued
0.743 Intermediate Similarity NPD8150 Discontinued
0.7427 Intermediate Similarity NPD7199 Phase 2
0.7403 Intermediate Similarity NPD3027 Phase 3
0.7403 Intermediate Similarity NPD4625 Phase 3
0.74 Intermediate Similarity NPD9269 Phase 2
0.7372 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD1613 Approved
0.7362 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD2313 Discontinued
0.7355 Intermediate Similarity NPD3764 Approved
0.7351 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7349 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7341 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.734 Intermediate Similarity NPD7697 Approved
0.734 Intermediate Similarity NPD7696 Phase 3
0.734 Intermediate Similarity NPD7698 Approved
0.7333 Intermediate Similarity NPD5403 Approved
0.7325 Intermediate Similarity NPD447 Suspended
0.732 Intermediate Similarity NPD2798 Approved
0.7317 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD5401 Approved
0.7312 Intermediate Similarity NPD1471 Phase 3
0.7303 Intermediate Similarity NPD1283 Approved
0.7303 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7302 Intermediate Similarity NPD7871 Phase 2
0.7302 Intermediate Similarity NPD7870 Phase 2
0.7301 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7285 Intermediate Similarity NPD3972 Approved
0.7283 Intermediate Similarity NPD6535 Approved
0.7283 Intermediate Similarity NPD6534 Approved
0.7277 Intermediate Similarity NPD7701 Phase 2
0.7273 Intermediate Similarity NPD7286 Phase 2
0.7248 Intermediate Similarity NPD1651 Approved
0.7244 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7244 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7239 Intermediate Similarity NPD6190 Approved
0.7202 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7202 Intermediate Similarity NPD7874 Approved
0.7196 Intermediate Similarity NPD6823 Phase 2
0.719 Intermediate Similarity NPD1876 Approved
0.7184 Intermediate Similarity NPD7229 Phase 3
0.7184 Intermediate Similarity NPD3787 Discontinued
0.7178 Intermediate Similarity NPD8166 Discontinued
0.7166 Intermediate Similarity NPD7699 Phase 2
0.7166 Intermediate Similarity NPD7700 Phase 2
0.7165 Intermediate Similarity NPD7801 Approved
0.7162 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD8434 Phase 2
0.7143 Intermediate Similarity NPD1203 Approved
0.7133 Intermediate Similarity NPD9268 Approved
0.7127 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.7119 Intermediate Similarity NPD7177 Discontinued
0.7117 Intermediate Similarity NPD2654 Approved
0.7115 Intermediate Similarity NPD4908 Phase 1
0.7108 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD1933 Approved
0.7105 Intermediate Similarity NPD1281 Approved
0.7086 Intermediate Similarity NPD4626 Approved
0.7081 Intermediate Similarity NPD4308 Phase 3
0.7065 Intermediate Similarity NPD4287 Approved
0.7056 Intermediate Similarity NPD7240 Approved
0.7045 Intermediate Similarity NPD5242 Approved
0.7043 Intermediate Similarity NPD6213 Phase 3
0.7043 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7043 Intermediate Similarity NPD6212 Phase 3
0.7035 Intermediate Similarity NPD4288 Approved
0.7032 Intermediate Similarity NPD1164 Approved
0.7031 Intermediate Similarity NPD8320 Phase 1
0.7031 Intermediate Similarity NPD8319 Approved
0.7025 Intermediate Similarity NPD411 Approved
0.7021 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7013 Intermediate Similarity NPD4749 Approved
0.6993 Remote Similarity NPD1610 Phase 2
0.6993 Remote Similarity NPD1547 Clinical (unspecified phase)
0.699 Remote Similarity NPD7783 Phase 2
0.699 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6988 Remote Similarity NPD3300 Phase 2
0.6987 Remote Similarity NPD6917 Clinical (unspecified phase)
0.6964 Remote Similarity NPD6273 Approved
0.6961 Remote Similarity NPD7685 Pre-registration

  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