Structure

Physi-Chem Properties

Molecular Weight:  408.16
Volume:  418.447
LogP:  6.042
LogD:  3.849
LogS:  -2.62
# Rotatable Bonds:  3
TPSA:  89.13
# H-Bond Aceptor:  6
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.465
Synthetic Accessibility Score:  3.292
Fsp3:  0.292
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.777
MDCK Permeability:  1.588467239344027e-05
Pgp-inhibitor:  0.927
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.263
20% Bioavailability (F20%):  0.004
30% Bioavailability (F30%):  0.017

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.004
Plasma Protein Binding (PPB):  85.38764190673828%
Volume Distribution (VD):  0.673
Pgp-substrate:  15.131011962890625%

ADMET: Metabolism

CYP1A2-inhibitor:  0.452
CYP1A2-substrate:  0.593
CYP2C19-inhibitor:  0.791
CYP2C19-substrate:  0.155
CYP2C9-inhibitor:  0.871
CYP2C9-substrate:  0.865
CYP2D6-inhibitor:  0.171
CYP2D6-substrate:  0.207
CYP3A4-inhibitor:  0.286
CYP3A4-substrate:  0.136

ADMET: Excretion

Clearance (CL):  2.219
Half-life (T1/2):  0.193

ADMET: Toxicity

hERG Blockers:  0.007
Human Hepatotoxicity (H-HT):  0.965
Drug-inuced Liver Injury (DILI):  0.98
AMES Toxicity:  0.239
Rat Oral Acute Toxicity:  0.987
Maximum Recommended Daily Dose:  0.409
Skin Sensitization:  0.788
Carcinogencity:  0.808
Eye Corrosion:  0.003
Eye Irritation:  0.076
Respiratory Toxicity:  0.693

Download Data

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

  Natural Product: NPC204879

Natural Product ID:  NPC204879
Common Name*:   5-O-Methylxanthone V1
IUPAC Name:   5,9-dihydroxy-10-methoxy-2,2-dimethyl-12-(3-methylbut-2-enyl)pyrano[3,2-b]xanthen-6-one
Synonyms:   5-O-Methylxanthone V1
Standard InCHIKey:  PZHQEWQFKUTZTQ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C24H24O6/c1-12(2)6-7-15-20-14(10-11-24(3,4)30-20)19(27)17-18(26)13-8-9-16(25)23(28-5)22(13)29-21(15)17/h6,8-11,25,27H,7H2,1-5H3
SMILES:  CC(=CCc1c2c(C=CC(C)(C)O2)c(c2c(=O)c3ccc(c(c3oc12)OC)O)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2147810
PubChem CID:   12178329
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000123] Benzopyrans
        • [CHEMONTID:0003410] 1-benzopyrans
          • [CHEMONTID:0002817] Dibenzopyrans
            • [CHEMONTID:0000200] Xanthenes
              • [CHEMONTID:0000204] Xanthones
                • [CHEMONTID:0003518] 4-prenylated xanthones

*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
NPO9520 Cratoxylum sumatranum Species Hypericaceae Eukaryota n.a. stem n.a. PMID[11908969]
NPO9520 Cratoxylum sumatranum Species Hypericaceae Eukaryota n.a. leaf n.a. PMID[11908969]
NPO9520 Cratoxylum sumatranum Species Hypericaceae Eukaryota n.a. twig n.a. PMID[11908969]
NPO19764 Tithonia diversifolia Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[11975495]
NPO24016 Cladanthus mixtus Species Asteraceae Eukaryota Roots n.a. n.a. PMID[14738379]
NPO19764 Tithonia diversifolia Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO16745 Scorzonera judaica Species Asteraceae Eukaryota n.a. tuberous root n.a. PMID[21650157]
NPO16745 Scorzonera judaica Species Asteraceae Eukaryota roots Daba desert reserve (50 km South of Amman), Jordan 2009-APR PMID[21650157]
NPO32914 Garcinia propinqua Species Clusiaceae Eukaryota twigs n.a. n.a. PMID[22963193]
NPO19764 Tithonia diversifolia Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23501116]
NPO21003 Cystoseira tamariscifolia Species Sargassaceae Eukaryota n.a. n.a. n.a. PMID[25640118]
NPO32914 Garcinia propinqua Species Clusiaceae Eukaryota Stem Bark n.a. n.a. PMID[28489373]
NPO19227 Hippoglossus hippoglossus Species Pleuronectidae Eukaryota n.a. n.a. Database[FooDB]
NPO19227 Hippoglossus hippoglossus Species Pleuronectidae Eukaryota n.a. n.a. Database[FooDB]
NPO16038 Ribes rubrum Species Grossulariaceae Eukaryota n.a. n.a. Database[FooDB]
NPO16038 Ribes rubrum Species Grossulariaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO16038 Ribes rubrum Species Grossulariaceae Eukaryota Fruits n.a. Database[FooDB]
NPO20116 Ilex cornuta Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16038 Ribes rubrum Species Grossulariaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO20116 Ilex cornuta Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19764 Tithonia diversifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20116 Ilex cornuta Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20116 Ilex cornuta Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11770 Amphicome emodi n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO17438 Polygala virgata Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16024 Piper sumatranum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19560 Populus italica Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13990 Montanoa atriplicifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9520 Cratoxylum sumatranum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14950 Ardisia polycephala Species Primulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18657 Galanthus gracilis Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6106 Hymeniacidon perlevis Species Halichondriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27328 Echinopsis candicans Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18005 Artemisia leucodes Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19359 Parmotrema delicatulum Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16745 Scorzonera judaica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19000 Crepis crocea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20927 Scirpophaga incertulas Species Crambidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO825 Stranvaesia davidiana Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18995 Gaultheria itoana Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15534 Parablechnum procerum Species Blechnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9019 Asplenium antiquum Species Aspleniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19764 Tithonia diversifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21675 Persicaria sibirica Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13263 Verbena brasiliensis Species Verbenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21003 Cystoseira tamariscifolia Species Sargassaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19501 Pseudosuberites hyalinus Species Suberitidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20116 Ilex cornuta Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3338 Vatica obscura Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24016 Cladanthus mixtus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16038 Ribes rubrum Species Grossulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19227 Hippoglossus hippoglossus Species Pleuronectidae 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
NPT19 Organism Escherichia coli Escherichia coli MIC = 128.0 ug.mL-1 PMID[488241]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium MIC = 128.0 ug.mL-1 PMID[488241]

☑ 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 NPC204879 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
0.9933 High Similarity NPC474681
0.9933 High Similarity NPC218313
0.9867 High Similarity NPC5322
0.9867 High Similarity NPC472455
0.9867 High Similarity NPC6633
0.9867 High Similarity NPC133970
0.9804 High Similarity NPC472448
0.9804 High Similarity NPC83922
0.9801 High Similarity NPC52889
0.98 High Similarity NPC117992
0.98 High Similarity NPC152951
0.98 High Similarity NPC230149
0.98 High Similarity NPC57674
0.98 High Similarity NPC234255
0.98 High Similarity NPC168247
0.98 High Similarity NPC472280
0.98 High Similarity NPC256925
0.98 High Similarity NPC200246
0.9739 High Similarity NPC29876
0.9739 High Similarity NPC57715
0.9739 High Similarity NPC234644
0.9739 High Similarity NPC167678
0.9737 High Similarity NPC74178
0.9737 High Similarity NPC184755
0.9735 High Similarity NPC470600
0.9733 High Similarity NPC273462
0.9733 High Similarity NPC33051
0.9733 High Similarity NPC227337
0.9733 High Similarity NPC49402
0.9733 High Similarity NPC70433
0.9675 High Similarity NPC474150
0.9675 High Similarity NPC474162
0.9673 High Similarity NPC204290
0.9673 High Similarity NPC119209
0.9673 High Similarity NPC188433
0.9673 High Similarity NPC476980
0.9673 High Similarity NPC192686
0.9673 High Similarity NPC118256
0.9673 High Similarity NPC471973
0.9667 High Similarity NPC237994
0.961 High Similarity NPC259456
0.961 High Similarity NPC134783
0.961 High Similarity NPC474038
0.9605 High Similarity NPC471985
0.9605 High Similarity NPC282307
0.9605 High Similarity NPC170026
0.96 High Similarity NPC154345
0.9551 High Similarity NPC275780
0.9551 High Similarity NPC472450
0.9551 High Similarity NPC239752
0.9548 High Similarity NPC474033
0.9548 High Similarity NPC474034
0.9548 High Similarity NPC261470
0.9545 High Similarity NPC475784
0.9545 High Similarity NPC474960
0.9542 High Similarity NPC187745
0.9542 High Similarity NPC78225
0.9542 High Similarity NPC262286
0.9542 High Similarity NPC180011
0.9542 High Similarity NPC284820
0.9542 High Similarity NPC136674
0.9542 High Similarity NPC219867
0.9542 High Similarity NPC304008
0.9542 High Similarity NPC27337
0.9542 High Similarity NPC473272
0.9542 High Similarity NPC161960
0.9542 High Similarity NPC291508
0.9542 High Similarity NPC36852
0.9542 High Similarity NPC476981
0.9536 High Similarity NPC39732
0.9536 High Similarity NPC257648
0.9536 High Similarity NPC477231
0.9536 High Similarity NPC60972
0.9536 High Similarity NPC471982
0.9533 High Similarity NPC29231
0.9494 High Similarity NPC288813
0.949 High Similarity NPC39091
0.9487 High Similarity NPC189473
0.9487 High Similarity NPC303460
0.9487 High Similarity NPC124038
0.9487 High Similarity NPC186686
0.9487 High Similarity NPC23298
0.9487 High Similarity NPC472625
0.9487 High Similarity NPC306321
0.9484 High Similarity NPC471210
0.9484 High Similarity NPC26326
0.9484 High Similarity NPC472632
0.9484 High Similarity NPC258331
0.9477 High Similarity NPC278778
0.9477 High Similarity NPC138243
0.9477 High Similarity NPC195796
0.9477 High Similarity NPC191146
0.9477 High Similarity NPC291878
0.9477 High Similarity NPC35038
0.9477 High Similarity NPC115853
0.9477 High Similarity NPC68093
0.9474 High Similarity NPC170492
0.947 High Similarity NPC31363
0.947 High Similarity NPC256406
0.9427 High Similarity NPC300053
0.9427 High Similarity NPC303174
0.9427 High Similarity NPC108433
0.9427 High Similarity NPC50960
0.9427 High Similarity NPC62261
0.9423 High Similarity NPC229632
0.9423 High Similarity NPC476247
0.9423 High Similarity NPC329760
0.9419 High Similarity NPC28241
0.9419 High Similarity NPC328102
0.9419 High Similarity NPC472624
0.9419 High Similarity NPC174953
0.9416 High Similarity NPC474055
0.9416 High Similarity NPC67876
0.9416 High Similarity NPC129684
0.9416 High Similarity NPC472963
0.9416 High Similarity NPC471209
0.9416 High Similarity NPC299520
0.9416 High Similarity NPC472598
0.9416 High Similarity NPC78071
0.9412 High Similarity NPC256612
0.9412 High Similarity NPC113906
0.9412 High Similarity NPC45849
0.9412 High Similarity NPC200761
0.9412 High Similarity NPC470327
0.9412 High Similarity NPC20830
0.9412 High Similarity NPC477503
0.9408 High Similarity NPC472912
0.9404 High Similarity NPC88804
0.9404 High Similarity NPC3825
0.9404 High Similarity NPC472279
0.94 High Similarity NPC196277
0.94 High Similarity NPC43669
0.94 High Similarity NPC272721
0.9367 High Similarity NPC37870
0.9367 High Similarity NPC235610
0.9367 High Similarity NPC472449
0.9367 High Similarity NPC43319
0.9363 High Similarity NPC236521
0.9363 High Similarity NPC152659
0.9363 High Similarity NPC248638
0.9359 High Similarity NPC266314
0.9359 High Similarity NPC471212
0.9359 High Similarity NPC472634
0.9359 High Similarity NPC61010
0.9359 High Similarity NPC471211
0.9355 High Similarity NPC53545
0.9355 High Similarity NPC55738
0.9355 High Similarity NPC117418
0.9355 High Similarity NPC187792
0.9355 High Similarity NPC250214
0.9355 High Similarity NPC95936
0.9355 High Similarity NPC473990
0.9355 High Similarity NPC235448
0.9351 High Similarity NPC209614
0.9351 High Similarity NPC472916
0.9351 High Similarity NPC276444
0.9351 High Similarity NPC474638
0.9351 High Similarity NPC472907
0.9351 High Similarity NPC470328
0.9351 High Similarity NPC472626
0.9351 High Similarity NPC265511
0.9346 High Similarity NPC206238
0.9346 High Similarity NPC472905
0.9346 High Similarity NPC292214
0.9346 High Similarity NPC74924
0.9346 High Similarity NPC47781
0.9346 High Similarity NPC213896
0.9346 High Similarity NPC22519
0.9346 High Similarity NPC160951
0.9346 High Similarity NPC69394
0.9346 High Similarity NPC18727
0.9346 High Similarity NPC255350
0.9346 High Similarity NPC145379
0.9346 High Similarity NPC271779
0.9346 High Similarity NPC274327
0.9346 High Similarity NPC176775
0.9346 High Similarity NPC469550
0.9346 High Similarity NPC88645
0.9346 High Similarity NPC192083
0.9346 High Similarity NPC183878
0.9346 High Similarity NPC167091
0.9346 High Similarity NPC231018
0.9338 High Similarity NPC48479
0.9338 High Similarity NPC137062
0.9338 High Similarity NPC139293
0.9338 High Similarity NPC183950
0.9338 High Similarity NPC195763
0.9338 High Similarity NPC69430
0.9338 High Similarity NPC177298
0.9338 High Similarity NPC264550
0.9338 High Similarity NPC264289
0.9338 High Similarity NPC52005
0.9338 High Similarity NPC333691
0.9338 High Similarity NPC171916
0.9338 High Similarity NPC223579
0.9338 High Similarity NPC38545
0.9338 High Similarity NPC40290
0.9338 High Similarity NPC287101
0.9338 High Similarity NPC142876
0.9338 High Similarity NPC200060

  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 NPC204879 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
0.9346 High Similarity NPD2393 Clinical (unspecified phase)
0.9346 High Similarity NPD2801 Approved
0.9281 High Similarity NPD1934 Approved
0.9103 High Similarity NPD3882 Suspended
0.9007 High Similarity NPD1511 Approved
0.8944 High Similarity NPD6166 Phase 2
0.8944 High Similarity NPD6168 Clinical (unspecified phase)
0.8944 High Similarity NPD6167 Clinical (unspecified phase)
0.8903 High Similarity NPD4380 Phase 2
0.8889 High Similarity NPD1512 Approved
0.8834 High Similarity NPD3818 Discontinued
0.8824 High Similarity NPD4378 Clinical (unspecified phase)
0.8824 High Similarity NPD7410 Clinical (unspecified phase)
0.8812 High Similarity NPD5494 Approved
0.878 High Similarity NPD7054 Approved
0.8742 High Similarity NPD4868 Clinical (unspecified phase)
0.8727 High Similarity NPD7074 Phase 3
0.8727 High Similarity NPD7472 Approved
0.8688 High Similarity NPD7075 Discontinued
0.8679 High Similarity NPD3817 Phase 2
0.8616 High Similarity NPD7096 Clinical (unspecified phase)
0.8571 High Similarity NPD4338 Clinical (unspecified phase)
0.8571 High Similarity NPD4381 Clinical (unspecified phase)
0.8563 High Similarity NPD6797 Phase 2
0.8553 High Similarity NPD1549 Phase 2
0.8512 High Similarity NPD7251 Discontinued
0.85 High Similarity NPD7819 Suspended
0.8491 Intermediate Similarity NPD7411 Suspended
0.8487 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8487 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8477 Intermediate Similarity NPD1510 Phase 2
0.8476 Intermediate Similarity NPD6232 Discontinued
0.8462 Intermediate Similarity NPD7808 Phase 3
0.8447 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8438 Intermediate Similarity NPD6801 Discontinued
0.8434 Intermediate Similarity NPD7473 Discontinued
0.8421 Intermediate Similarity NPD2796 Approved
0.8385 Intermediate Similarity NPD1465 Phase 2
0.8333 Intermediate Similarity NPD943 Approved
0.8333 Intermediate Similarity NPD1240 Approved
0.8333 Intermediate Similarity NPD5844 Phase 1
0.8333 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.828 Intermediate Similarity NPD6799 Approved
0.8235 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8224 Intermediate Similarity NPD1607 Approved
0.8193 Intermediate Similarity NPD6959 Discontinued
0.8193 Intermediate Similarity NPD1247 Approved
0.8182 Intermediate Similarity NPD919 Approved
0.8155 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8121 Intermediate Similarity NPD3749 Approved
0.811 Intermediate Similarity NPD5402 Approved
0.8095 Intermediate Similarity NPD3926 Phase 2
0.8089 Intermediate Similarity NPD3750 Approved
0.8086 Intermediate Similarity NPD6599 Discontinued
0.8081 Intermediate Similarity NPD6559 Discontinued
0.8061 Intermediate Similarity NPD7768 Phase 2
0.8012 Intermediate Similarity NPD5403 Approved
0.7962 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7949 Intermediate Similarity NPD2935 Discontinued
0.7947 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7911 Intermediate Similarity NPD2800 Approved
0.7911 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7901 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7888 Intermediate Similarity NPD5401 Approved
0.7881 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7869 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7857 Intermediate Similarity NPD1613 Approved
0.7857 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7806 Intermediate Similarity NPD447 Suspended
0.7806 Intermediate Similarity NPD230 Phase 1
0.7799 Intermediate Similarity NPD1243 Approved
0.7791 Intermediate Similarity NPD920 Approved
0.7778 Intermediate Similarity NPD2533 Approved
0.7778 Intermediate Similarity NPD2534 Approved
0.7778 Intermediate Similarity NPD2532 Approved
0.7771 Intermediate Similarity NPD3748 Approved
0.7771 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD2799 Discontinued
0.7765 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD2313 Discontinued
0.7722 Intermediate Similarity NPD6100 Approved
0.7722 Intermediate Similarity NPD6099 Approved
0.7722 Intermediate Similarity NPD1551 Phase 2
0.7714 Intermediate Similarity NPD5953 Discontinued
0.7697 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD3226 Approved
0.7692 Intermediate Similarity NPD1933 Approved
0.768 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7673 Intermediate Similarity NPD2344 Approved
0.7673 Intermediate Similarity NPD2346 Discontinued
0.7669 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7662 Intermediate Similarity NPD3027 Phase 3
0.7658 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7654 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD9494 Approved
0.7644 Intermediate Similarity NPD3751 Discontinued
0.7643 Intermediate Similarity NPD6651 Approved
0.764 Intermediate Similarity NPD4628 Phase 3
0.764 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.764 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7627 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7616 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7613 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7613 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7607 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD7286 Phase 2
0.7571 Intermediate Similarity NPD7685 Pre-registration
0.7558 Intermediate Similarity NPD7199 Phase 2
0.7544 Intermediate Similarity NPD6234 Discontinued
0.753 Intermediate Similarity NPD1653 Approved
0.7514 Intermediate Similarity NPD3787 Discontinued
0.7514 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7390 Discontinued
0.7486 Intermediate Similarity NPD8312 Approved
0.7486 Intermediate Similarity NPD8313 Approved
0.7485 Intermediate Similarity NPD6190 Approved
0.7485 Intermediate Similarity NPD2309 Approved
0.7484 Intermediate Similarity NPD4908 Phase 1
0.7471 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7443 Intermediate Similarity NPD7228 Approved
0.7436 Intermediate Similarity NPD4625 Phase 3
0.7435 Intermediate Similarity NPD7584 Approved
0.7405 Intermediate Similarity NPD4360 Phase 2
0.7405 Intermediate Similarity NPD4363 Phase 3
0.7403 Intermediate Similarity NPD1203 Approved
0.7394 Intermediate Similarity NPD6776 Approved
0.7394 Intermediate Similarity NPD6778 Approved
0.7394 Intermediate Similarity NPD6780 Approved
0.7394 Intermediate Similarity NPD6782 Approved
0.7394 Intermediate Similarity NPD6779 Approved
0.7394 Intermediate Similarity NPD6777 Approved
0.7394 Intermediate Similarity NPD6781 Approved
0.7368 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7363 Intermediate Similarity NPD8150 Discontinued
0.7358 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD5124 Phase 1
0.7355 Intermediate Similarity NPD2798 Approved
0.7353 Intermediate Similarity NPD37 Approved
0.7349 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD4308 Phase 3
0.7329 Intermediate Similarity NPD7033 Discontinued
0.7326 Intermediate Similarity NPD4966 Approved
0.7326 Intermediate Similarity NPD4965 Approved
0.7326 Intermediate Similarity NPD4967 Phase 2
0.7314 Intermediate Similarity NPD5711 Approved
0.7314 Intermediate Similarity NPD5710 Approved
0.7278 Intermediate Similarity NPD3268 Approved
0.7278 Intermediate Similarity NPD7458 Discontinued
0.7278 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7277 Intermediate Similarity NPD7435 Discontinued
0.7273 Intermediate Similarity NPD5242 Approved
0.7268 Intermediate Similarity NPD8434 Phase 2
0.7268 Intermediate Similarity NPD8151 Discontinued
0.7261 Intermediate Similarity NPD6832 Phase 2
0.7255 Intermediate Similarity NPD1610 Phase 2
0.7251 Intermediate Similarity NPD6844 Discontinued
0.7246 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD1548 Phase 1
0.7208 Intermediate Similarity NPD9269 Phase 2
0.7208 Intermediate Similarity NPD9717 Approved
0.7195 Intermediate Similarity NPD2424 Discontinued
0.7193 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7189 Intermediate Similarity NPD4287 Approved
0.7188 Intermediate Similarity NPD7697 Approved
0.7188 Intermediate Similarity NPD7698 Approved
0.7188 Intermediate Similarity NPD7696 Phase 3
0.7186 Intermediate Similarity NPD4357 Discontinued
0.7181 Intermediate Similarity NPD4361 Phase 2
0.7181 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD2797 Approved
0.7179 Intermediate Similarity NPD1470 Approved
0.7178 Intermediate Similarity NPD5408 Approved
0.7178 Intermediate Similarity NPD5406 Approved
0.7178 Intermediate Similarity NPD5404 Approved
0.7178 Intermediate Similarity NPD5405 Approved
0.7168 Intermediate Similarity NPD5353 Approved
0.7168 Intermediate Similarity NPD4288 Approved
0.7161 Intermediate Similarity NPD4749 Approved
0.7152 Intermediate Similarity NPD5536 Phase 2
0.715 Intermediate Similarity NPD7871 Phase 2
0.715 Intermediate Similarity NPD7870 Phase 2
0.7143 Intermediate Similarity NPD7549 Discontinued
0.7143 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD422 Phase 1
0.7135 Intermediate Similarity NPD6823 Phase 2
0.7135 Intermediate Similarity NPD6585 Discontinued
0.7135 Intermediate Similarity NPD2403 Approved
0.7128 Intermediate Similarity NPD6535 Approved
0.7128 Intermediate Similarity NPD7701 Phase 2
0.7128 Intermediate Similarity NPD6534 Approved
0.7119 Intermediate Similarity NPD7229 Phase 3
0.7115 Intermediate Similarity NPD3225 Approved
0.7107 Intermediate Similarity NPD7783 Phase 2
0.7107 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD5049 Phase 3
0.7097 Intermediate Similarity NPD1608 Approved
0.7093 Intermediate Similarity NPD5890 Approved
0.7093 Intermediate Similarity NPD5889 Approved
0.7093 Intermediate Similarity NPD6385 Approved
0.7093 Intermediate Similarity NPD6386 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