Structure

Physi-Chem Properties

Molecular Weight:  408.16
Volume:  418.447
LogP:  5.591
LogD:  3.694
LogS:  -3.126
# 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:  0.468
Synthetic Accessibility Score:  3.435
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:  -4.797
MDCK Permeability:  1.7518344975542277e-05
Pgp-inhibitor:  0.998
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.534
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.007
Plasma Protein Binding (PPB):  92.16651916503906%
Volume Distribution (VD):  0.909
Pgp-substrate:  11.219725608825684%

ADMET: Metabolism

CYP1A2-inhibitor:  0.637
CYP1A2-substrate:  0.737
CYP2C19-inhibitor:  0.671
CYP2C19-substrate:  0.185
CYP2C9-inhibitor:  0.859
CYP2C9-substrate:  0.9
CYP2D6-inhibitor:  0.208
CYP2D6-substrate:  0.219
CYP3A4-inhibitor:  0.365
CYP3A4-substrate:  0.223

ADMET: Excretion

Clearance (CL):  1.354
Half-life (T1/2):  0.209

ADMET: Toxicity

hERG Blockers:  0.007
Human Hepatotoxicity (H-HT):  0.574
Drug-inuced Liver Injury (DILI):  0.97
AMES Toxicity:  0.208
Rat Oral Acute Toxicity:  0.98
Maximum Recommended Daily Dose:  0.512
Skin Sensitization:  0.704
Carcinogencity:  0.841
Eye Corrosion:  0.003
Eye Irritation:  0.472
Respiratory Toxicity:  0.831

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

  Natural Product: NPC57715

Natural Product ID:  NPC57715
Common Name*:   10-O-Methylmacluraxanthone
IUPAC Name:   5,9-dihydroxy-10-methoxy-2,2-dimethyl-12-(2-methylbut-3-en-2-yl)pyrano[3,2-b]xanthen-6-one
Synonyms:   10-O-Methylmacluraxanthone
Standard InCHIKey:  XPXBUMXEOVNYQI-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C24H24O6/c1-7-23(2,3)16-19-13(10-11-24(4,5)30-19)18(27)15-17(26)12-8-9-14(25)21(28-6)20(12)29-22(15)16/h7-11,25,27H,1H2,2-6H3
SMILES:  C=CC(c1c2OC(C)(C)C=Cc2c(c2c1oc1c(OC)c(O)ccc1c2=O)O)(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2147811
PubChem CID:   71458306
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:0003521] Pyranoxanthones

*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
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]
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]
NPO22290 Garcinia linii Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20116 Ilex cornuta Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22290 Garcinia linii Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
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]
NPO13990 Montanoa atriplicifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20116 Ilex cornuta Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19000 Crepis crocea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO825 Stranvaesia davidiana Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9019 Asplenium antiquum Species Aspleniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21675 Persicaria sibirica Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21003 Cystoseira tamariscifolia Species Sargassaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3338 Vatica obscura Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27328 Echinopsis candicans Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20927 Scirpophaga incertulas Species Crambidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15534 Parablechnum procerum Species Blechnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24016 Cladanthus mixtus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22290 Garcinia linii Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16024 Piper sumatranum Species Piperaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19764 Tithonia diversifolia Species Asteraceae 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
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 4.0 ug.mL-1 PMID[504096]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 2.0 ug.mL-1 PMID[504096]
NPT19 Organism Escherichia coli Escherichia coli MIC = 128.0 ug.mL-1 PMID[504096]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium MIC = 128.0 ug.mL-1 PMID[504096]

☑ 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 NPC57715 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
0.9934 High Similarity NPC188433
0.9869 High Similarity NPC234644
0.9803 High Similarity NPC180011
0.9803 High Similarity NPC219867
0.9742 High Similarity NPC306321
0.9742 High Similarity NPC303460
0.9739 High Similarity NPC204879
0.9737 High Similarity NPC115853
0.9673 High Similarity NPC161960
0.9673 High Similarity NPC187745
0.9673 High Similarity NPC474681
0.9673 High Similarity NPC304008
0.9673 High Similarity NPC218313
0.9671 High Similarity NPC256925
0.9671 High Similarity NPC200246
0.962 High Similarity NPC288813
0.9608 High Similarity NPC5322
0.9608 High Similarity NPC133970
0.9608 High Similarity NPC472455
0.9608 High Similarity NPC6633
0.9608 High Similarity NPC470600
0.956 High Similarity NPC472276
0.9551 High Similarity NPC472448
0.9551 High Similarity NPC474162
0.9551 High Similarity NPC474150
0.9551 High Similarity NPC83922
0.9548 High Similarity NPC471973
0.9545 High Similarity NPC52889
0.9542 High Similarity NPC57674
0.9542 High Similarity NPC152951
0.9542 High Similarity NPC230149
0.9542 High Similarity NPC117992
0.9542 High Similarity NPC168247
0.9542 High Similarity NPC472280
0.9542 High Similarity NPC234255
0.949 High Similarity NPC205265
0.949 High Similarity NPC472281
0.9487 High Similarity NPC29876
0.9487 High Similarity NPC167678
0.9484 High Similarity NPC235448
0.9484 High Similarity NPC184755
0.9484 High Similarity NPC74178
0.9477 High Similarity NPC227337
0.9477 High Similarity NPC273462
0.9477 High Similarity NPC70433
0.9477 High Similarity NPC49402
0.9477 High Similarity NPC33051
0.943 High Similarity NPC472450
0.943 High Similarity NPC472277
0.943 High Similarity NPC275780
0.943 High Similarity NPC239752
0.9427 High Similarity NPC78332
0.9427 High Similarity NPC261470
0.9423 High Similarity NPC119209
0.9423 High Similarity NPC474960
0.9423 High Similarity NPC476980
0.9423 High Similarity NPC204290
0.9423 High Similarity NPC28241
0.9423 High Similarity NPC118256
0.9423 High Similarity NPC192686
0.9419 High Similarity NPC136674
0.9419 High Similarity NPC79053
0.9412 High Similarity NPC237994
0.9371 High Similarity NPC39091
0.9367 High Similarity NPC18100
0.9367 High Similarity NPC189473
0.9367 High Similarity NPC187491
0.9367 High Similarity NPC220313
0.9367 High Similarity NPC23298
0.9367 High Similarity NPC186686
0.9367 High Similarity NPC319200
0.9367 High Similarity NPC12461
0.9363 High Similarity NPC472906
0.9363 High Similarity NPC134783
0.9363 High Similarity NPC472275
0.9363 High Similarity NPC474038
0.9363 High Similarity NPC259456
0.9359 High Similarity NPC172770
0.9359 High Similarity NPC185258
0.9355 High Similarity NPC471985
0.9355 High Similarity NPC282307
0.9355 High Similarity NPC170026
0.9346 High Similarity NPC154345
0.9308 High Similarity NPC303174
0.9308 High Similarity NPC50960
0.9308 High Similarity NPC62261
0.9304 High Similarity NPC474034
0.9304 High Similarity NPC474033
0.9304 High Similarity NPC229632
0.9304 High Similarity NPC329760
0.9304 High Similarity NPC206605
0.9299 High Similarity NPC476280
0.9299 High Similarity NPC475784
0.9299 High Similarity NPC80375
0.9299 High Similarity NPC297212
0.9295 High Similarity NPC36852
0.9295 High Similarity NPC476981
0.9295 High Similarity NPC299520
0.9295 High Similarity NPC262286
0.9295 High Similarity NPC129684
0.9295 High Similarity NPC284820
0.9295 High Similarity NPC27337
0.9295 High Similarity NPC473272
0.9295 High Similarity NPC78225
0.9295 High Similarity NPC472963
0.9295 High Similarity NPC291508
0.9286 High Similarity NPC39732
0.9286 High Similarity NPC60972
0.9286 High Similarity NPC257648
0.9286 High Similarity NPC471982
0.9286 High Similarity NPC477231
0.9281 High Similarity NPC29231
0.9255 High Similarity NPC165456
0.925 High Similarity NPC37870
0.925 High Similarity NPC235610
0.925 High Similarity NPC43319
0.925 High Similarity NPC472449
0.9245 High Similarity NPC248638
0.9245 High Similarity NPC152659
0.9245 High Similarity NPC124038
0.9245 High Similarity NPC236521
0.9245 High Similarity NPC472625
0.9241 High Similarity NPC26326
0.9241 High Similarity NPC472632
0.9241 High Similarity NPC32694
0.9241 High Similarity NPC471210
0.9241 High Similarity NPC61010
0.9241 High Similarity NPC258331
0.9236 High Similarity NPC46736
0.9236 High Similarity NPC55738
0.9236 High Similarity NPC197856
0.9231 High Similarity NPC3980
0.9231 High Similarity NPC472907
0.9231 High Similarity NPC278778
0.9231 High Similarity NPC35038
0.9231 High Similarity NPC191146
0.9231 High Similarity NPC68093
0.9231 High Similarity NPC291878
0.9231 High Similarity NPC195796
0.9231 High Similarity NPC138243
0.9226 High Similarity NPC472905
0.9226 High Similarity NPC170492
0.9226 High Similarity NPC469550
0.9221 High Similarity NPC31363
0.9221 High Similarity NPC256406
0.9211 High Similarity NPC77378
0.9202 High Similarity NPC310794
0.9193 High Similarity NPC476306
0.9193 High Similarity NPC8965
0.9193 High Similarity NPC218226
0.9187 High Similarity NPC108433
0.9187 High Similarity NPC293319
0.9187 High Similarity NPC300053
0.9182 High Similarity NPC476247
0.9182 High Similarity NPC25152
0.9177 High Similarity NPC174953
0.9177 High Similarity NPC14353
0.9177 High Similarity NPC139036
0.9177 High Similarity NPC228785
0.9177 High Similarity NPC45146
0.9177 High Similarity NPC235018
0.9177 High Similarity NPC472624
0.9177 High Similarity NPC328102
0.9177 High Similarity NPC36217
0.9177 High Similarity NPC56085
0.9177 High Similarity NPC476283
0.9172 High Similarity NPC474055
0.9172 High Similarity NPC67876
0.9172 High Similarity NPC78071
0.9172 High Similarity NPC471209
0.9172 High Similarity NPC472598
0.9167 High Similarity NPC477503
0.9167 High Similarity NPC20830
0.9167 High Similarity NPC255807
0.9167 High Similarity NPC256612
0.9167 High Similarity NPC470327
0.9167 High Similarity NPC113906
0.9167 High Similarity NPC45849
0.9167 High Similarity NPC200761
0.9167 High Similarity NPC31018
0.9161 High Similarity NPC161277
0.9161 High Similarity NPC472912
0.9161 High Similarity NPC39007
0.9161 High Similarity NPC260979
0.9161 High Similarity NPC166201
0.9156 High Similarity NPC472279
0.9156 High Similarity NPC88804
0.9156 High Similarity NPC3825
0.915 High Similarity NPC43669
0.915 High Similarity NPC196277
0.915 High Similarity NPC272721
0.9136 High Similarity NPC177480
0.913 High Similarity NPC120593
0.9125 High Similarity NPC207690
0.9125 High Similarity NPC473313
0.9125 High Similarity NPC146134
0.9125 High Similarity NPC329669
0.9125 High Similarity NPC472278
0.9125 High Similarity NPC41301
0.9125 High Similarity NPC476295

  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 NPC57715 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
0.9103 High Similarity NPD2393 Clinical (unspecified phase)
0.9103 High Similarity NPD2801 Approved
0.9038 High Similarity NPD1934 Approved
0.8868 High Similarity NPD3882 Suspended
0.8766 High Similarity NPD1511 Approved
0.872 High Similarity NPD6167 Clinical (unspecified phase)
0.872 High Similarity NPD6168 Clinical (unspecified phase)
0.872 High Similarity NPD6166 Phase 2
0.8704 High Similarity NPD5494 Approved
0.8671 High Similarity NPD4380 Phase 2
0.8654 High Similarity NPD1512 Approved
0.8614 High Similarity NPD3818 Discontinued
0.859 High Similarity NPD7410 Clinical (unspecified phase)
0.859 High Similarity NPD4378 Clinical (unspecified phase)
0.8563 High Similarity NPD7054 Approved
0.8519 High Similarity NPD4868 Clinical (unspecified phase)
0.8512 High Similarity NPD7472 Approved
0.8512 High Similarity NPD7074 Phase 3
0.8466 Intermediate Similarity NPD7075 Discontinued
0.8457 Intermediate Similarity NPD3817 Phase 2
0.8395 Intermediate Similarity NPD7819 Suspended
0.8395 Intermediate Similarity NPD1465 Phase 2
0.8395 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8373 Intermediate Similarity NPD6232 Discontinued
0.8363 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8354 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8353 Intermediate Similarity NPD6797 Phase 2
0.8344 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD7473 Discontinued
0.8333 Intermediate Similarity NPD6801 Discontinued
0.8323 Intermediate Similarity NPD1549 Phase 2
0.8304 Intermediate Similarity NPD7251 Discontinued
0.8272 Intermediate Similarity NPD7411 Suspended
0.8258 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8258 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8256 Intermediate Similarity NPD7808 Phase 3
0.8247 Intermediate Similarity NPD1510 Phase 2
0.8235 Intermediate Similarity NPD5844 Phase 1
0.821 Intermediate Similarity NPD6599 Discontinued
0.8204 Intermediate Similarity NPD6959 Discontinued
0.8194 Intermediate Similarity NPD2796 Approved
0.8153 Intermediate Similarity NPD2800 Approved
0.8129 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8105 Intermediate Similarity NPD1240 Approved
0.8105 Intermediate Similarity NPD943 Approved
0.8063 Intermediate Similarity NPD6799 Approved
0.8059 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8035 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8024 Intermediate Similarity NPD3749 Approved
0.8 Intermediate Similarity NPD3926 Phase 2
0.8 Intermediate Similarity NPD1607 Approved
0.7988 Intermediate Similarity NPD1247 Approved
0.7987 Intermediate Similarity NPD3750 Approved
0.7976 Intermediate Similarity NPD919 Approved
0.7964 Intermediate Similarity NPD7768 Phase 2
0.7904 Intermediate Similarity NPD5402 Approved
0.7886 Intermediate Similarity NPD6559 Discontinued
0.7862 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7848 Intermediate Similarity NPD6100 Approved
0.7848 Intermediate Similarity NPD6099 Approved
0.7805 Intermediate Similarity NPD5403 Approved
0.7784 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD6651 Approved
0.7764 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7764 Intermediate Similarity NPD4628 Phase 3
0.7736 Intermediate Similarity NPD2935 Discontinued
0.7727 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7702 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD920 Approved
0.7697 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7683 Intermediate Similarity NPD5401 Approved
0.7683 Intermediate Similarity NPD2534 Approved
0.7683 Intermediate Similarity NPD2532 Approved
0.7683 Intermediate Similarity NPD2533 Approved
0.768 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7673 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7673 Intermediate Similarity NPD2799 Discontinued
0.7673 Intermediate Similarity NPD3748 Approved
0.7662 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7643 Intermediate Similarity NPD1613 Approved
0.7643 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7611 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7605 Intermediate Similarity NPD3226 Approved
0.7596 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7595 Intermediate Similarity NPD230 Phase 1
0.7595 Intermediate Similarity NPD447 Suspended
0.7593 Intermediate Similarity NPD1243 Approved
0.7578 Intermediate Similarity NPD2346 Discontinued
0.7578 Intermediate Similarity NPD2344 Approved
0.7562 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7557 Intermediate Similarity NPD3751 Discontinued
0.7542 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7528 Intermediate Similarity NPD5953 Discontinued
0.7516 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD1551 Phase 2
0.7516 Intermediate Similarity NPD2313 Discontinued
0.7514 Intermediate Similarity NPD7286 Phase 2
0.7486 Intermediate Similarity NPD7685 Pre-registration
0.7484 Intermediate Similarity NPD1933 Approved
0.7471 Intermediate Similarity NPD7199 Phase 2
0.747 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7457 Intermediate Similarity NPD6234 Discontinued
0.7455 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7452 Intermediate Similarity NPD3027 Phase 3
0.7439 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD9494 Approved
0.7429 Intermediate Similarity NPD3787 Discontinued
0.741 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.741 Intermediate Similarity NPD7390 Discontinued
0.7405 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD8312 Approved
0.7403 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD8313 Approved
0.7396 Intermediate Similarity NPD7458 Discontinued
0.7394 Intermediate Similarity NPD2309 Approved
0.7389 Intermediate Similarity NPD4908 Phase 1
0.7386 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7377 Intermediate Similarity NPD8434 Phase 2
0.7365 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.736 Intermediate Similarity NPD7228 Approved
0.7342 Intermediate Similarity NPD4625 Phase 3
0.734 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7337 Intermediate Similarity NPD1653 Approved
0.7326 Intermediate Similarity NPD4363 Phase 3
0.7326 Intermediate Similarity NPD4360 Phase 2
0.7316 Intermediate Similarity NPD6777 Approved
0.7316 Intermediate Similarity NPD6780 Approved
0.7316 Intermediate Similarity NPD6779 Approved
0.7316 Intermediate Similarity NPD6778 Approved
0.7316 Intermediate Similarity NPD6781 Approved
0.7316 Intermediate Similarity NPD6776 Approved
0.7316 Intermediate Similarity NPD6782 Approved
0.7289 Intermediate Similarity NPD6190 Approved
0.7283 Intermediate Similarity NPD8150 Discontinued
0.7268 Intermediate Similarity NPD7584 Approved
0.7267 Intermediate Similarity NPD37 Approved
0.7262 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7261 Intermediate Similarity NPD2798 Approved
0.7241 Intermediate Similarity NPD4967 Phase 2
0.7241 Intermediate Similarity NPD4965 Approved
0.7241 Intermediate Similarity NPD4966 Approved
0.7232 Intermediate Similarity NPD5710 Approved
0.7232 Intermediate Similarity NPD5711 Approved
0.7202 Intermediate Similarity NPD7435 Discontinued
0.7197 Intermediate Similarity NPD1203 Approved
0.7194 Intermediate Similarity NPD8151 Discontinued
0.7193 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7191 Intermediate Similarity NPD5242 Approved
0.7188 Intermediate Similarity NPD3268 Approved
0.7188 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7161 Intermediate Similarity NPD1610 Phase 2
0.7161 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD5124 Phase 1
0.7151 Intermediate Similarity NPD2403 Approved
0.7134 Intermediate Similarity NPD4308 Phase 3
0.7134 Intermediate Similarity NPD7033 Discontinued
0.7126 Intermediate Similarity NPD8166 Discontinued
0.7126 Intermediate Similarity NPD7003 Approved
0.7115 Intermediate Similarity NPD3972 Approved
0.7113 Intermediate Similarity NPD7697 Approved
0.7113 Intermediate Similarity NPD7696 Phase 3
0.7113 Intermediate Similarity NPD7698 Approved
0.7112 Intermediate Similarity NPD4287 Approved
0.7105 Intermediate Similarity NPD4361 Phase 2
0.7105 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7098 Intermediate Similarity NPD2494 Approved
0.7098 Intermediate Similarity NPD2493 Approved
0.7091 Intermediate Similarity NPD5405 Approved
0.7091 Intermediate Similarity NPD5408 Approved
0.7091 Intermediate Similarity NPD5406 Approved
0.7091 Intermediate Similarity NPD5404 Approved
0.7089 Intermediate Similarity NPD2797 Approved
0.7089 Intermediate Similarity NPD1470 Approved
0.7086 Intermediate Similarity NPD4288 Approved
0.7079 Intermediate Similarity NPD8127 Discontinued
0.7077 Intermediate Similarity NPD7870 Phase 2
0.7077 Intermediate Similarity NPD7871 Phase 2
0.707 Intermediate Similarity NPD4749 Approved
0.7069 Intermediate Similarity NPD6844 Discontinued
0.7065 Intermediate Similarity NPD7549 Discontinued
0.7063 Intermediate Similarity NPD6832 Phase 2
0.7062 Intermediate Similarity NPD6823 Phase 2
0.7059 Intermediate Similarity NPD7907 Approved
0.7056 Intermediate Similarity NPD7701 Phase 2
0.7053 Intermediate Similarity NPD6535 Approved
0.7053 Intermediate Similarity NPD6534 Approved
0.7044 Intermediate Similarity NPD4665 Approved
0.7044 Intermediate Similarity NPD4111 Phase 1
0.7039 Intermediate Similarity NPD7229 Phase 3
0.7035 Intermediate Similarity NPD7783 Phase 2
0.7035 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7029 Intermediate Similarity NPD5760 Phase 2
0.7029 Intermediate Similarity NPD5761 Phase 2
0.7027 Intermediate Similarity NPD3534 Clinical (unspecified phase)
0.7019 Intermediate Similarity NPD7095 Approved
0.7018 Intermediate Similarity NPD6273 Approved
0.7013 Intermediate Similarity NPD1548 Phase 1
0.7011 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD6104 Discontinued

  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