Structure

Physi-Chem Properties

Molecular Weight:  394.18
Volume:  418.214
LogP:  6.502
LogD:  3.642
LogS:  -2.909
# Rotatable Bonds:  5
TPSA:  79.9
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.448
Synthetic Accessibility Score:  3.049
Fsp3:  0.292
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.758
MDCK Permeability:  1.440249525330728e-05
Pgp-inhibitor:  0.911
Pgp-substrate:  0.179
Human Intestinal Absorption (HIA):  0.132
20% Bioavailability (F20%):  0.378
30% Bioavailability (F30%):  0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.009
Plasma Protein Binding (PPB):  76.78469848632812%
Volume Distribution (VD):  0.95
Pgp-substrate:  18.65232276916504%

ADMET: Metabolism

CYP1A2-inhibitor:  0.456
CYP1A2-substrate:  0.427
CYP2C19-inhibitor:  0.84
CYP2C19-substrate:  0.135
CYP2C9-inhibitor:  0.874
CYP2C9-substrate:  0.893
CYP2D6-inhibitor:  0.061
CYP2D6-substrate:  0.228
CYP3A4-inhibitor:  0.187
CYP3A4-substrate:  0.096

ADMET: Excretion

Clearance (CL):  7.533
Half-life (T1/2):  0.157

ADMET: Toxicity

hERG Blockers:  0.004
Human Hepatotoxicity (H-HT):  0.976
Drug-inuced Liver Injury (DILI):  0.976
AMES Toxicity:  0.203
Rat Oral Acute Toxicity:  0.663
Maximum Recommended Daily Dose:  0.028
Skin Sensitization:  0.689
Carcinogencity:  0.153
Eye Corrosion:  0.003
Eye Irritation:  0.168
Respiratory Toxicity:  0.496

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Structure MOL file  
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Similar NPs/Drugs  

  Natural Product: NPC168247

Natural Product ID:  NPC168247
Common Name*:   Cudraxanthone G
IUPAC Name:   1,5-dihydroxy-3-methoxy-2,4-bis(3-methylbut-2-enyl)xanthen-9-one
Synonyms:   Cudraxanthone G
Standard InCHIKey:  IOCHCPAWAFKZJS-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C24H26O5/c1-13(2)9-11-16-21(27)19-20(26)15-7-6-8-18(25)23(15)29-24(19)17(22(16)28-5)12-10-14(3)4/h6-10,25,27H,11-12H2,1-5H3
SMILES:  CC(=CCc1c(c2c(=O)c3cccc(c3oc2c(CC=C(C)C)c1OC)O)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL494664
PubChem CID:   42645953
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
NPO7811 Scleronephthya pallida Species Nephtheidae Eukaryota n.a. n.a. n.a. PMID[10075773]
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]
NPO10376 Arcyria denudata Species Trichiidae Eukaryota n.a. n.a. n.a. PMID[16933891]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[18464091]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[18558747]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO19764 Tithonia diversifolia Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota stem bark Pangradin village, Jasinga, West Java, Indonesia 2005-AUG PMID[19839614]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[20817450]
NPO19764 Tithonia diversifolia Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23501116]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. pericarp n.a. PMID[24555285]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[24717154]
NPO21003 Cystoseira tamariscifolia Species Sargassaceae Eukaryota n.a. n.a. n.a. PMID[25640118]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota fruit hulls Madras, Tamil Nadu, India 1993-MAR PMID[9213587]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO20116 Ilex cornuta Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10849 Eucalyptus camaldulensis Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10391 Dolomiaea souliei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10849 Eucalyptus camaldulensis Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6249 Garcinia mangostana Species Clusiaceae 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[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]
NPO10391 Dolomiaea souliei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10376 Arcyria denudata Species Trichiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20927 Scirpophaga incertulas Species Crambidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25216 Senecio vellereus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8354 Aster bellidiastrum 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]
NPO12600 Trametes cinnabarina Species Coriolaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15534 Parablechnum procerum Species Blechnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO825 Stranvaesia davidiana Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3449 Lonicera hypoleuca Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19764 Tithonia diversifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9717 Wibelia divaricata Species Davalliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20116 Ilex cornuta Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10221 Streptomyces alboniger Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO9019 Asplenium antiquum Species Aspleniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10056 Nicotiana sylvestris Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21675 Persicaria sibirica Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7534 Leptogorgia sarmentosa Species Gorgoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8560 Aplidium tabascum Species Polyclinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21003 Cystoseira tamariscifolia Species Sargassaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24931 Myelochroa aurulenta Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9741 Actinopyga agassizi Species Holothuriidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3338 Vatica obscura Species Dipterocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10849 Eucalyptus camaldulensis Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3707 Chromatium okenii Species Chromatiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO8927 Poria selecta Species Coccinellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6249 Garcinia mangostana 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]
NPO27924 Serpocaulon triseriale Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13990 Montanoa atriplicifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10391 Dolomiaea souliei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7811 Scleronephthya pallida Species Nephtheidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4064 Halimodendron halodendron Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27328 Echinopsis candicans Species Cactaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24016 Cladanthus mixtus 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
NPT441 Individual Protein Cytochrome P450 19A1 Homo sapiens Activity = 57.8 % PMID[570488]

☑ 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 NPC168247 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
1.0 High Similarity NPC117992
1.0 High Similarity NPC57674
1.0 High Similarity NPC152951
1.0 High Similarity NPC230149
0.9932 High Similarity NPC49402
0.9932 High Similarity NPC33051
0.9932 High Similarity NPC227337
0.9932 High Similarity NPC70433
0.9932 High Similarity NPC273462
0.9865 High Similarity NPC256925
0.98 High Similarity NPC204879
0.9799 High Similarity NPC472455
0.9733 High Similarity NPC262286
0.9733 High Similarity NPC78225
0.9733 High Similarity NPC180011
0.9733 High Similarity NPC161960
0.9733 High Similarity NPC219867
0.9733 High Similarity NPC304008
0.9733 High Similarity NPC474681
0.9733 High Similarity NPC291508
0.9733 High Similarity NPC187745
0.9733 High Similarity NPC36852
0.9733 High Similarity NPC218313
0.9732 High Similarity NPC234255
0.9732 High Similarity NPC472280
0.973 High Similarity NPC257648
0.973 High Similarity NPC477231
0.9728 High Similarity NPC29231
0.9667 High Similarity NPC195796
0.9667 High Similarity NPC6633
0.9667 High Similarity NPC133970
0.9667 High Similarity NPC291878
0.9667 High Similarity NPC115853
0.9667 High Similarity NPC191146
0.9667 High Similarity NPC68093
0.9667 High Similarity NPC278778
0.9667 High Similarity NPC138243
0.9667 High Similarity NPC5322
0.9667 High Similarity NPC470600
0.9667 High Similarity NPC35038
0.9662 High Similarity NPC31363
0.9608 High Similarity NPC83922
0.9608 High Similarity NPC472448
0.9605 High Similarity NPC476980
0.9603 High Similarity NPC472598
0.9603 High Similarity NPC136674
0.9603 High Similarity NPC474055
0.9603 High Similarity NPC27337
0.9603 High Similarity NPC299520
0.9603 High Similarity NPC129684
0.9603 High Similarity NPC52889
0.96 High Similarity NPC45849
0.96 High Similarity NPC113906
0.96 High Similarity NPC470327
0.96 High Similarity NPC200761
0.96 High Similarity NPC477503
0.96 High Similarity NPC200246
0.9597 High Similarity NPC39732
0.9597 High Similarity NPC472912
0.9597 High Similarity NPC60972
0.9597 High Similarity NPC237994
0.9597 High Similarity NPC471982
0.9595 High Similarity NPC472279
0.9592 High Similarity NPC196277
0.9592 High Similarity NPC272721
0.9592 High Similarity NPC43669
0.9545 High Similarity NPC124038
0.9542 High Similarity NPC266314
0.9542 High Similarity NPC134783
0.9542 High Similarity NPC57715
0.9542 High Similarity NPC258331
0.9542 High Similarity NPC234644
0.9542 High Similarity NPC29876
0.9542 High Similarity NPC167678
0.9539 High Similarity NPC235448
0.9539 High Similarity NPC95936
0.9539 High Similarity NPC74178
0.9539 High Similarity NPC184755
0.9539 High Similarity NPC250214
0.9536 High Similarity NPC472916
0.9536 High Similarity NPC209614
0.9536 High Similarity NPC472626
0.9536 High Similarity NPC470328
0.9533 High Similarity NPC167091
0.9533 High Similarity NPC88645
0.9533 High Similarity NPC206238
0.9533 High Similarity NPC292214
0.9533 High Similarity NPC469550
0.9533 High Similarity NPC192083
0.9533 High Similarity NPC213896
0.9533 High Similarity NPC271779
0.9533 High Similarity NPC18727
0.953 High Similarity NPC154345
0.953 High Similarity NPC256406
0.9524 High Similarity NPC77378
0.9484 High Similarity NPC300053
0.9484 High Similarity NPC108433
0.9484 High Similarity NPC472277
0.9481 High Similarity NPC474034
0.9481 High Similarity NPC474033
0.9481 High Similarity NPC476247
0.9481 High Similarity NPC474150
0.9481 High Similarity NPC474162
0.9477 High Similarity NPC472624
0.9477 High Similarity NPC188433
0.9477 High Similarity NPC228785
0.9477 High Similarity NPC471973
0.9477 High Similarity NPC282009
0.9477 High Similarity NPC36217
0.9477 High Similarity NPC192686
0.9477 High Similarity NPC14353
0.9477 High Similarity NPC118256
0.9477 High Similarity NPC56085
0.9477 High Similarity NPC287328
0.9477 High Similarity NPC119209
0.9477 High Similarity NPC204290
0.9474 High Similarity NPC472910
0.9474 High Similarity NPC474836
0.9474 High Similarity NPC67876
0.9474 High Similarity NPC472913
0.9474 High Similarity NPC222814
0.9474 High Similarity NPC48208
0.9474 High Similarity NPC472963
0.9474 High Similarity NPC96167
0.9474 High Similarity NPC472914
0.9474 High Similarity NPC476981
0.9474 High Similarity NPC223787
0.9474 High Similarity NPC99597
0.9474 High Similarity NPC210084
0.9474 High Similarity NPC162869
0.9474 High Similarity NPC156057
0.9474 High Similarity NPC245758
0.9474 High Similarity NPC474208
0.9474 High Similarity NPC472911
0.9474 High Similarity NPC475267
0.947 High Similarity NPC20830
0.947 High Similarity NPC226025
0.947 High Similarity NPC31018
0.947 High Similarity NPC321779
0.947 High Similarity NPC256612
0.947 High Similarity NPC2928
0.947 High Similarity NPC255807
0.9467 High Similarity NPC161277
0.9467 High Similarity NPC199100
0.9467 High Similarity NPC219582
0.9467 High Similarity NPC302950
0.9467 High Similarity NPC236637
0.9467 High Similarity NPC180234
0.9467 High Similarity NPC101996
0.9467 High Similarity NPC260979
0.9467 High Similarity NPC39007
0.9467 High Similarity NPC120537
0.9467 High Similarity NPC106976
0.9463 High Similarity NPC88804
0.9463 High Similarity NPC3825
0.9456 High Similarity NPC209278
0.9423 High Similarity NPC235610
0.9419 High Similarity NPC18100
0.9419 High Similarity NPC319200
0.9419 High Similarity NPC220313
0.9419 High Similarity NPC205265
0.9419 High Similarity NPC472281
0.9419 High Similarity NPC187491
0.9416 High Similarity NPC474038
0.9416 High Similarity NPC259456
0.9416 High Similarity NPC472632
0.9416 High Similarity NPC278052
0.9416 High Similarity NPC40491
0.9416 High Similarity NPC472634
0.9416 High Similarity NPC471499
0.9416 High Similarity NPC471210
0.9416 High Similarity NPC26326
0.9416 High Similarity NPC61010
0.9416 High Similarity NPC472275
0.9412 High Similarity NPC22192
0.9412 High Similarity NPC100123
0.9412 High Similarity NPC172770
0.9412 High Similarity NPC185258
0.9412 High Similarity NPC55738
0.9408 High Similarity NPC170026
0.9408 High Similarity NPC474638
0.9408 High Similarity NPC255106
0.9408 High Similarity NPC472907
0.9408 High Similarity NPC282307
0.9408 High Similarity NPC471985
0.9408 High Similarity NPC265511
0.9408 High Similarity NPC235165
0.9404 High Similarity NPC231018
0.9404 High Similarity NPC47781
0.9404 High Similarity NPC22519
0.9404 High Similarity NPC176775
0.9404 High Similarity NPC274327
0.9404 High Similarity NPC69394
0.9404 High Similarity NPC472905
0.9404 High Similarity NPC74924
0.9404 High Similarity NPC472915
0.9404 High Similarity NPC145379
0.9404 High Similarity NPC183878
0.9404 High Similarity NPC255350
0.9404 High Similarity NPC160951

  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 NPC168247 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
0.9533 High Similarity NPD2393 Clinical (unspecified phase)
0.9467 High Similarity NPD1934 Approved
0.9404 High Similarity NPD2801 Approved
0.9281 High Similarity NPD3882 Suspended
0.906 High Similarity NPD1511 Approved
0.8994 High Similarity NPD6166 Phase 2
0.8994 High Similarity NPD6168 Clinical (unspecified phase)
0.8994 High Similarity NPD6167 Clinical (unspecified phase)
0.894 High Similarity NPD1512 Approved
0.8882 High Similarity NPD3818 Discontinued
0.8874 High Similarity NPD4378 Clinical (unspecified phase)
0.8861 High Similarity NPD5494 Approved
0.8854 High Similarity NPD7075 Discontinued
0.8831 High Similarity NPD4380 Phase 2
0.879 High Similarity NPD4868 Clinical (unspecified phase)
0.8782 High Similarity NPD7096 Clinical (unspecified phase)
0.8773 High Similarity NPD7074 Phase 3
0.8726 High Similarity NPD3817 Phase 2
0.8725 High Similarity NPD1549 Phase 2
0.8712 High Similarity NPD7054 Approved
0.8662 High Similarity NPD7819 Suspended
0.8659 High Similarity NPD7472 Approved
0.8658 High Similarity NPD1550 Clinical (unspecified phase)
0.8658 High Similarity NPD1552 Clinical (unspecified phase)
0.8634 High Similarity NPD6232 Discontinued
0.8627 High Similarity NPD7410 Clinical (unspecified phase)
0.8589 High Similarity NPD7473 Discontinued
0.8535 High Similarity NPD7411 Suspended
0.8523 High Similarity NPD1510 Phase 2
0.8503 High Similarity NPD4338 Clinical (unspecified phase)
0.8503 High Similarity NPD943 Approved
0.8503 High Similarity NPD1240 Approved
0.85 High Similarity NPD4381 Clinical (unspecified phase)
0.8494 Intermediate Similarity NPD6797 Phase 2
0.8491 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8481 Intermediate Similarity NPD6801 Discontinued
0.8467 Intermediate Similarity NPD2796 Approved
0.8443 Intermediate Similarity NPD7251 Discontinued
0.8442 Intermediate Similarity NPD6799 Approved
0.8428 Intermediate Similarity NPD1465 Phase 2
0.8393 Intermediate Similarity NPD7808 Phase 3
0.8389 Intermediate Similarity NPD1607 Approved
0.8373 Intermediate Similarity NPD5844 Phase 1
0.8274 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8263 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8242 Intermediate Similarity NPD3926 Phase 2
0.8239 Intermediate Similarity NPD6599 Discontinued
0.8232 Intermediate Similarity NPD6959 Discontinued
0.8232 Intermediate Similarity NPD1247 Approved
0.8225 Intermediate Similarity NPD6559 Discontinued
0.8221 Intermediate Similarity NPD919 Approved
0.8193 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8108 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.8105 Intermediate Similarity NPD2935 Discontinued
0.8098 Intermediate Similarity NPD7768 Phase 2
0.8065 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8065 Intermediate Similarity NPD2800 Approved
0.805 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.8049 Intermediate Similarity NPD3749 Approved
0.8041 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.8037 Intermediate Similarity NPD5402 Approved
0.8013 Intermediate Similarity NPD1613 Approved
0.8013 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8013 Intermediate Similarity NPD3750 Approved
0.8 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7961 Intermediate Similarity NPD230 Phase 1
0.7961 Intermediate Similarity NPD447 Suspended
0.7937 Intermediate Similarity NPD5403 Approved
0.7925 Intermediate Similarity NPD2533 Approved
0.7925 Intermediate Similarity NPD2532 Approved
0.7925 Intermediate Similarity NPD2534 Approved
0.7922 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7922 Intermediate Similarity NPD2799 Discontinued
0.7871 Intermediate Similarity NPD1551 Phase 2
0.7849 Intermediate Similarity NPD5953 Discontinued
0.7843 Intermediate Similarity NPD1933 Approved
0.784 Intermediate Similarity NPD3226 Approved
0.7834 Intermediate Similarity NPD1243 Approved
0.7826 Intermediate Similarity NPD920 Approved
0.7821 Intermediate Similarity NPD2346 Discontinued
0.7821 Intermediate Similarity NPD2344 Approved
0.7815 Intermediate Similarity NPD3027 Phase 3
0.7812 Intermediate Similarity NPD5401 Approved
0.7806 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.78 Intermediate Similarity NPD9494 Approved
0.7797 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7792 Intermediate Similarity NPD6651 Approved
0.7785 Intermediate Similarity NPD4628 Phase 3
0.777 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7763 Intermediate Similarity NPD2313 Discontinued
0.7763 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7756 Intermediate Similarity NPD6099 Approved
0.7756 Intermediate Similarity NPD6100 Approved
0.775 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7733 Intermediate Similarity NPD7286 Phase 2
0.7702 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD3748 Approved
0.7692 Intermediate Similarity NPD7199 Phase 2
0.7688 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7679 Intermediate Similarity NPD6234 Discontinued
0.7673 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7673 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7657 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7627 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7625 Intermediate Similarity NPD2309 Approved
0.7611 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7602 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7572 Intermediate Similarity NPD3751 Discontinued
0.7561 Intermediate Similarity NPD1653 Approved
0.755 Intermediate Similarity NPD1203 Approved
0.7531 Intermediate Similarity NPD7390 Discontinued
0.7517 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD6190 Approved
0.7516 Intermediate Similarity NPD4908 Phase 1
0.7514 Intermediate Similarity NPD8313 Approved
0.7514 Intermediate Similarity NPD8312 Approved
0.7485 Intermediate Similarity NPD37 Approved
0.7471 Intermediate Similarity NPD7228 Approved
0.7468 Intermediate Similarity NPD4625 Phase 3
0.7456 Intermediate Similarity NPD4967 Phase 2
0.7456 Intermediate Similarity NPD4966 Approved
0.7456 Intermediate Similarity NPD4965 Approved
0.7446 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7442 Intermediate Similarity NPD5710 Approved
0.7442 Intermediate Similarity NPD5711 Approved
0.7442 Intermediate Similarity NPD3787 Discontinued
0.7403 Intermediate Similarity NPD6832 Phase 2
0.7401 Intermediate Similarity NPD7685 Pre-registration
0.74 Intermediate Similarity NPD1610 Phase 2
0.7399 Intermediate Similarity NPD5242 Approved
0.7386 Intermediate Similarity NPD2798 Approved
0.7378 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7351 Intermediate Similarity NPD9717 Approved
0.7351 Intermediate Similarity NPD9269 Phase 2
0.7337 Intermediate Similarity NPD4363 Phase 3
0.7337 Intermediate Similarity NPD4360 Phase 2
0.7326 Intermediate Similarity NPD6777 Approved
0.7326 Intermediate Similarity NPD6776 Approved
0.7326 Intermediate Similarity NPD6780 Approved
0.7326 Intermediate Similarity NPD6781 Approved
0.7326 Intermediate Similarity NPD6778 Approved
0.7326 Intermediate Similarity NPD6782 Approved
0.7326 Intermediate Similarity NPD6779 Approved
0.7321 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD1470 Approved
0.7317 Intermediate Similarity NPD4357 Discontinued
0.7308 Intermediate Similarity NPD3268 Approved
0.7305 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD7458 Discontinued
0.7297 Intermediate Similarity NPD5536 Phase 2
0.7294 Intermediate Similarity NPD5353 Approved
0.7293 Intermediate Similarity NPD8150 Discontinued
0.7293 Intermediate Similarity NPD8434 Phase 2
0.7292 Intermediate Similarity NPD8151 Discontinued
0.7278 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7277 Intermediate Similarity NPD7584 Approved
0.7273 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD4308 Phase 3
0.725 Intermediate Similarity NPD7033 Discontinued
0.7248 Intermediate Similarity NPD1548 Phase 1
0.7241 Intermediate Similarity NPD7229 Phase 3
0.7237 Intermediate Similarity NPD1608 Approved
0.7226 Intermediate Similarity NPD3018 Phase 2
0.7222 Intermediate Similarity NPD2424 Discontinued
0.7219 Intermediate Similarity NPD6386 Approved
0.7219 Intermediate Similarity NPD6385 Approved
0.7215 Intermediate Similarity NPD4060 Phase 1
0.7211 Intermediate Similarity NPD7435 Discontinued
0.7208 Intermediate Similarity NPD2797 Approved
0.7205 Intermediate Similarity NPD5408 Approved
0.7205 Intermediate Similarity NPD5406 Approved
0.7205 Intermediate Similarity NPD5405 Approved
0.7205 Intermediate Similarity NPD5404 Approved
0.7204 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7204 Intermediate Similarity NPD4361 Phase 2
0.7197 Intermediate Similarity NPD6798 Discontinued
0.7197 Intermediate Similarity NPD411 Approved
0.7191 Intermediate Similarity NPD1729 Discontinued
0.719 Intermediate Similarity NPD4749 Approved
0.7178 Intermediate Similarity NPD2654 Approved
0.7176 Intermediate Similarity NPD6844 Discontinued
0.7171 Intermediate Similarity NPD422 Phase 1
0.7171 Intermediate Similarity NPD1201 Approved
0.717 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD5124 Phase 1
0.716 Intermediate Similarity NPD1471 Phase 3
0.7159 Intermediate Similarity NPD2403 Approved
0.7151 Intermediate Similarity NPD5019 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD5049 Phase 3
0.7124 Intermediate Similarity NPD3972 Approved
0.712 Intermediate Similarity NPD7697 Approved
0.712 Intermediate Similarity NPD4287 Approved
0.712 Intermediate Similarity NPD7696 Phase 3
0.712 Intermediate Similarity NPD7698 Approved
0.7093 Intermediate Similarity NPD4288 Approved
0.7093 Intermediate Similarity NPD2296 Approved
0.7091 Intermediate Similarity NPD2354 Approved
0.7089 Intermediate Similarity NPD3764 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