Structure

Physi-Chem Properties

Molecular Weight:  438.2
Volume:  461.596
LogP:  6.386
LogD:  3.921
LogS:  -5.195
# Rotatable Bonds:  7
TPSA:  78.13
# H-Bond Aceptor:  6
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.368
Synthetic Accessibility Score:  3.134
Fsp3:  0.346
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:  -4.823
MDCK Permeability:  1.370292102365056e-05
Pgp-inhibitor:  0.995
Pgp-substrate:  0.006
Human Intestinal Absorption (HIA):  0.05
20% Bioavailability (F20%):  0.03
30% Bioavailability (F30%):  0.056

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.016
Plasma Protein Binding (PPB):  81.90569305419922%
Volume Distribution (VD):  0.916
Pgp-substrate:  18.453840255737305%

ADMET: Metabolism

CYP1A2-inhibitor:  0.162
CYP1A2-substrate:  0.977
CYP2C19-inhibitor:  0.839
CYP2C19-substrate:  0.85
CYP2C9-inhibitor:  0.903
CYP2C9-substrate:  0.935
CYP2D6-inhibitor:  0.244
CYP2D6-substrate:  0.864
CYP3A4-inhibitor:  0.293
CYP3A4-substrate:  0.277

ADMET: Excretion

Clearance (CL):  4.509
Half-life (T1/2):  0.136

ADMET: Toxicity

hERG Blockers:  0.023
Human Hepatotoxicity (H-HT):  0.765
Drug-inuced Liver Injury (DILI):  0.822
AMES Toxicity:  0.406
Rat Oral Acute Toxicity:  0.37
Maximum Recommended Daily Dose:  0.082
Skin Sensitization:  0.699
Carcinogencity:  0.129
Eye Corrosion:  0.003
Eye Irritation:  0.078
Respiratory Toxicity:  0.635

Download Data

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

  Natural Product: NPC165977

Natural Product ID:  NPC165977
Common Name*:   Fuscaxanthone C
IUPAC Name:   1-hydroxy-3,6,7-trimethoxy-2,8-bis(3-methylbut-2-enyl)xanthen-9-one
Synonyms:   Di-O-Methylmangostin
Standard InCHIKey:  FCIKYGUVHWZSJV-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C26H30O6/c1-14(2)8-10-16-18(29-5)12-20-23(24(16)27)25(28)22-17(11-9-15(3)4)26(31-7)21(30-6)13-19(22)32-20/h8-9,12-13,27H,10-11H2,1-7H3
SMILES:  COc1c(OC)cc2c(c1CC=C(C)C)c(=O)c1c(o2)cc(c(c1O)CC=C(C)C)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL464524
PubChem CID:   231412
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:0003519] 8-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
NPO25472 Garcinia cowa Species Clusiaceae Eukaryota n.a. n.a. n.a. DOI[10.1071/CH03175]
NPO7811 Scleronephthya pallida Species Nephtheidae Eukaryota n.a. n.a. n.a. PMID[10075773]
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]
NPO25472 Garcinia cowa Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO6249 Garcinia mangostana Species Clusiaceae 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]
NPO25472 Garcinia cowa Species Clusiaceae Eukaryota twigs n.a. n.a. PMID[20058933]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. PMID[20817450]
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]
NPO25472 Garcinia cowa Species Clusiaceae Eukaryota young fruits Khokkhon, Tha Bo District, Nong Khai Province, Thailand 2011-Aug PMID[25651042]
NPO25472 Garcinia cowa Species Clusiaceae Eukaryota flowers Pakook, Muang District, Chiang Rai Province, Thailand 2013-Feb PMID[25651042]
NPO25472 Garcinia cowa Species Clusiaceae Eukaryota Leaves n.a. n.a. PMID[31860303]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota fruit hulls Madras, Tamil Nadu, India 1993-MAR PMID[9213587]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. Database[FooDB]
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. n.a. Database[HerDing]
NPO25472 Garcinia cowa 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]
NPO11161 Cratoxylum arborescens Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11161 Cratoxylum arborescens Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10391 Dolomiaea souliei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6249 Garcinia mangostana Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10849 Eucalyptus camaldulensis Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25472 Garcinia cowa Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10391 Dolomiaea souliei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7811 Scleronephthya pallida Species Nephtheidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27924 Serpocaulon triseriale Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10391 Dolomiaea souliei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4064 Halimodendron halodendron Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25216 Senecio vellereus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10376 Arcyria denudata Species Trichiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9717 Wibelia divaricata Species Davalliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8354 Aster bellidiastrum 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]
NPO3449 Lonicera hypoleuca Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10221 Streptomyces alboniger Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO11161 Cratoxylum arborescens Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10056 Nicotiana sylvestris Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7534 Leptogorgia sarmentosa Species Gorgoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24931 Myelochroa aurulenta Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8560 Aplidium tabascum Species Polyclinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25472 Garcinia cowa Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9741 Actinopyga agassizi Species Holothuriidae 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]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT139 Cell Line HT-29 Homo sapiens ED50 > 10.0 uM PMID[461176]
NPT139 Cell Line HT-29 Homo sapiens IC50 = 1400.0 nM PMID[461176]
NPT2646 Organism Alternaria tenuis Alternaria tenuis Inhibition = 14.0 % PMID[461175]
NPT2646 Organism Alternaria tenuis Alternaria tenuis Inhibition = 22.0 % PMID[461175]
NPT2646 Organism Alternaria tenuis Alternaria tenuis Inhibition = 16.0 % PMID[461175]
NPT2647 Organism Drechslera Drechslera Inhibition = 7.0 % PMID[461175]
NPT2647 Organism Drechslera Drechslera Inhibition = 9.0 % PMID[461175]
NPT2647 Organism Drechslera Drechslera Inhibition = 27.0 % PMID[461175]
NPT2647 Organism Drechslera Drechslera Inhibition = 41.0 % PMID[461175]
NPT2648 Organism Fusarium oxysporum f. sp. vasinfectum Fusarium oxysporum f. sp. vasinfectum Inhibition = 5.0 % PMID[461175]
NPT2648 Organism Fusarium oxysporum f. sp. vasinfectum Fusarium oxysporum f. sp. vasinfectum Inhibition = 12.0 % PMID[461175]
NPT2648 Organism Fusarium oxysporum f. sp. vasinfectum Fusarium oxysporum f. sp. vasinfectum Inhibition = 16.0 % PMID[461175]
NPT2648 Organism Fusarium oxysporum f. sp. vasinfectum Fusarium oxysporum f. sp. vasinfectum Inhibition = 17.0 % PMID[461175]
NPT721 Individual Protein Nuclear factor NF-kappa-B p65 subunit Homo sapiens IC50 > 10000.0 nM PMID[461176]
NPT2 Others Unspecified Inhibition = 53.8 % PMID[461177]
NPT314 Organism Bacillus cereus Bacillus cereus MIC > 128.0 ug.mL-1 PMID[461177]
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 128.0 ug.mL-1 PMID[461177]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 128.0 ug.mL-1 PMID[461177]
NPT19 Organism Escherichia coli Escherichia coli MIC = 64.0 ug.mL-1 PMID[461177]
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium MIC = 128.0 ug.mL-1 PMID[461177]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC = 128.0 ug.mL-1 PMID[461177]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC > 300.0 ug.mL-1 PMID[461178]
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 75.0 ug.mL-1 PMID[461178]
NPT175 Organism Enterococcus faecalis Enterococcus faecalis MIC = 150.0 ug.mL-1 PMID[461178]
NPT175 Organism Enterococcus faecalis Enterococcus faecalis MIC = 300.0 ug.mL-1 PMID[461178]
NPT1242 Organism Salmonella typhi Salmonella enterica subsp. enterica serovar Typhi MIC = 300.0 ug.mL-1 PMID[461178]
NPT1243 Organism Shigella sonnei Shigella sonnei MIC > 300.0 ug.mL-1 PMID[461178]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC = 300.0 ug.mL-1 PMID[461178]

☑ 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 NPC165977 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 NPC217677
0.9868 High Similarity NPC14353
0.9868 High Similarity NPC475886
0.9868 High Similarity NPC228785
0.9868 High Similarity NPC474287
0.9868 High Similarity NPC56085
0.9803 High Similarity NPC474187
0.9803 High Similarity NPC61010
0.9803 High Similarity NPC278052
0.9803 High Similarity NPC474186
0.9803 High Similarity NPC474351
0.9803 High Similarity NPC475883
0.9803 High Similarity NPC40491
0.9801 High Similarity NPC100123
0.9739 High Similarity NPC229632
0.9737 High Similarity NPC320359
0.9735 High Similarity NPC241904
0.9735 High Similarity NPC300727
0.9675 High Similarity NPC248638
0.9675 High Similarity NPC220313
0.9675 High Similarity NPC7483
0.9675 High Similarity NPC197168
0.9675 High Similarity NPC474350
0.9675 High Similarity NPC236132
0.9675 High Similarity NPC236521
0.9675 High Similarity NPC152659
0.9673 High Similarity NPC66288
0.9671 High Similarity NPC476242
0.9669 High Similarity NPC274730
0.9669 High Similarity NPC142339
0.9613 High Similarity NPC239752
0.9613 High Similarity NPC25361
0.9613 High Similarity NPC472450
0.9613 High Similarity NPC326520
0.9613 High Similarity NPC275780
0.961 High Similarity NPC52204
0.961 High Similarity NPC25152
0.9605 High Similarity NPC36852
0.9605 High Similarity NPC262286
0.9605 High Similarity NPC78225
0.9605 High Similarity NPC236796
0.9551 High Similarity NPC39091
0.9551 High Similarity NPC170245
0.9548 High Similarity NPC189473
0.9548 High Similarity NPC23298
0.9548 High Similarity NPC270837
0.9545 High Similarity NPC32694
0.9539 High Similarity NPC138243
0.9539 High Similarity NPC191146
0.9539 High Similarity NPC68093
0.9536 High Similarity NPC89474
0.9533 High Similarity NPC117579
0.949 High Similarity NPC117854
0.949 High Similarity NPC6588
0.949 High Similarity NPC477154
0.9484 High Similarity NPC294965
0.9481 High Similarity NPC36217
0.9481 High Similarity NPC119224
0.9481 High Similarity NPC299436
0.9481 High Similarity NPC45146
0.9481 High Similarity NPC235018
0.9481 High Similarity NPC200746
0.9477 High Similarity NPC136674
0.9477 High Similarity NPC181960
0.9477 High Similarity NPC469584
0.9477 High Similarity NPC476981
0.9477 High Similarity NPC223787
0.9474 High Similarity NPC472909
0.9474 High Similarity NPC113906
0.9474 High Similarity NPC37392
0.9467 High Similarity NPC179183
0.9467 High Similarity NPC227122
0.9427 High Similarity NPC472449
0.9427 High Similarity NPC37870
0.9423 High Similarity NPC41301
0.9423 High Similarity NPC146134
0.9423 High Similarity NPC475985
0.9423 High Similarity NPC273959
0.9419 High Similarity NPC266314
0.9416 High Similarity NPC95936
0.9416 High Similarity NPC250214
0.9416 High Similarity NPC329091
0.9416 High Similarity NPC235448
0.9408 High Similarity NPC280937
0.9408 High Similarity NPC472915
0.9404 High Similarity NPC202157
0.9404 High Similarity NPC149614
0.9404 High Similarity NPC226973
0.9404 High Similarity NPC208043
0.94 High Similarity NPC328119
0.9363 High Similarity NPC473286
0.9359 High Similarity NPC329760
0.9359 High Similarity NPC472448
0.9359 High Similarity NPC470694
0.9359 High Similarity NPC201800
0.9359 High Similarity NPC83922
0.9355 High Similarity NPC204290
0.9355 High Similarity NPC476980
0.9355 High Similarity NPC80375
0.9355 High Similarity NPC471973
0.9355 High Similarity NPC246478
0.9355 High Similarity NPC139036
0.9351 High Similarity NPC475267
0.9351 High Similarity NPC472910
0.9351 High Similarity NPC474208
0.9351 High Similarity NPC474836
0.9351 High Similarity NPC96167
0.9351 High Similarity NPC472914
0.9351 High Similarity NPC245758
0.9351 High Similarity NPC472911
0.9351 High Similarity NPC162869
0.9351 High Similarity NPC156057
0.9351 High Similarity NPC472913
0.9351 High Similarity NPC48208
0.9351 High Similarity NPC222814
0.9346 High Similarity NPC57674
0.9346 High Similarity NPC470327
0.9346 High Similarity NPC230149
0.9346 High Similarity NPC117992
0.9346 High Similarity NPC31018
0.9346 High Similarity NPC477503
0.9346 High Similarity NPC226025
0.9346 High Similarity NPC168247
0.9346 High Similarity NPC255807
0.9346 High Similarity NPC45849
0.9346 High Similarity NPC200761
0.9346 High Similarity NPC152951
0.9342 High Similarity NPC471982
0.9342 High Similarity NPC101996
0.9342 High Similarity NPC199100
0.9342 High Similarity NPC180234
0.9342 High Similarity NPC120537
0.9338 High Similarity NPC338131
0.9338 High Similarity NPC306821
0.9338 High Similarity NPC151473
0.9308 High Similarity NPC99613
0.9308 High Similarity NPC49487
0.9304 High Similarity NPC29160
0.9304 High Similarity NPC120593
0.9299 High Similarity NPC207690
0.9299 High Similarity NPC474240
0.9299 High Similarity NPC186686
0.9295 High Similarity NPC167678
0.9295 High Similarity NPC258331
0.9295 High Similarity NPC472275
0.9295 High Similarity NPC29876
0.929 High Similarity NPC172770
0.929 High Similarity NPC152904
0.929 High Similarity NPC185258
0.929 High Similarity NPC474290
0.929 High Similarity NPC210459
0.929 High Similarity NPC85121
0.9286 High Similarity NPC35038
0.9286 High Similarity NPC278778
0.9286 High Similarity NPC209614
0.9286 High Similarity NPC472626
0.9286 High Similarity NPC195796
0.9286 High Similarity NPC472916
0.9286 High Similarity NPC470328
0.9286 High Similarity NPC291878
0.9286 High Similarity NPC255106
0.9286 High Similarity NPC235165
0.9281 High Similarity NPC255350
0.9281 High Similarity NPC33051
0.9281 High Similarity NPC280530
0.9281 High Similarity NPC86485
0.9281 High Similarity NPC167091
0.9281 High Similarity NPC176775
0.9281 High Similarity NPC250822
0.9281 High Similarity NPC75279
0.9281 High Similarity NPC160951
0.9281 High Similarity NPC271779
0.9281 High Similarity NPC206238
0.9281 High Similarity NPC231018
0.9281 High Similarity NPC47781
0.9281 High Similarity NPC69394
0.9281 High Similarity NPC95842
0.9281 High Similarity NPC227337
0.9281 High Similarity NPC178964
0.9281 High Similarity NPC145379
0.9281 High Similarity NPC22519
0.9281 High Similarity NPC276409
0.9281 High Similarity NPC49402
0.9281 High Similarity NPC273462
0.9281 High Similarity NPC70433
0.9281 High Similarity NPC292214
0.9281 High Similarity NPC274327
0.9281 High Similarity NPC183878
0.9281 High Similarity NPC88645
0.9276 High Similarity NPC308451
0.9276 High Similarity NPC171010
0.9272 High Similarity NPC266499
0.9267 High Similarity NPC62536
0.9267 High Similarity NPC33265
0.9245 High Similarity NPC234331
0.9241 High Similarity NPC475888
0.9241 High Similarity NPC293319
0.9236 High Similarity NPC474150
0.9236 High Similarity NPC474162
0.9236 High Similarity NPC81679

  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 NPC165977 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
0.9281 High Similarity NPD2801 Approved
0.9156 High Similarity NPD2393 Clinical (unspecified phase)
0.9091 High Similarity NPD1934 Approved
0.8987 High Similarity NPD5494 Approved
0.8875 High Similarity NPD6232 Discontinued
0.8827 High Similarity NPD7473 Discontinued
0.8758 High Similarity NPD4378 Clinical (unspecified phase)
0.872 High Similarity NPD5844 Phase 1
0.8693 High Similarity NPD1511 Approved
0.8679 High Similarity NPD3882 Suspended
0.8671 High Similarity NPD7819 Suspended
0.865 High Similarity NPD6166 Phase 2
0.865 High Similarity NPD6167 Clinical (unspecified phase)
0.865 High Similarity NPD6168 Clinical (unspecified phase)
0.8581 High Similarity NPD1512 Approved
0.858 High Similarity NPD6959 Discontinued
0.85 High Similarity NPD3817 Phase 2
0.8481 Intermediate Similarity NPD4380 Phase 2
0.8447 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8443 Intermediate Similarity NPD7074 Phase 3
0.8438 Intermediate Similarity NPD1465 Phase 2
0.8434 Intermediate Similarity NPD3818 Discontinued
0.8421 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8421 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8402 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8395 Intermediate Similarity NPD7075 Discontinued
0.8385 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8383 Intermediate Similarity NPD7054 Approved
0.8366 Intermediate Similarity NPD1549 Phase 2
0.8333 Intermediate Similarity NPD7472 Approved
0.8323 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.828 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.828 Intermediate Similarity NPD2532 Approved
0.828 Intermediate Similarity NPD2534 Approved
0.828 Intermediate Similarity NPD2533 Approved
0.8247 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8242 Intermediate Similarity NPD1247 Approved
0.8199 Intermediate Similarity NPD7411 Suspended
0.8194 Intermediate Similarity NPD2800 Approved
0.8187 Intermediate Similarity NPD7808 Phase 3
0.8176 Intermediate Similarity NPD6797 Phase 2
0.8171 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.817 Intermediate Similarity NPD1510 Phase 2
0.8146 Intermediate Similarity NPD1240 Approved
0.8129 Intermediate Similarity NPD7251 Discontinued
0.8117 Intermediate Similarity NPD2796 Approved
0.8117 Intermediate Similarity NPD2935 Discontinued
0.8061 Intermediate Similarity NPD3749 Approved
0.8059 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8052 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.8039 Intermediate Similarity NPD1607 Approved
0.8037 Intermediate Similarity NPD6801 Discontinued
0.8036 Intermediate Similarity NPD3926 Phase 2
0.8025 Intermediate Similarity NPD3750 Approved
0.8011 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7988 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7987 Intermediate Similarity NPD6799 Approved
0.7965 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7963 Intermediate Similarity NPD3226 Approved
0.7949 Intermediate Similarity NPD2346 Discontinued
0.7939 Intermediate Similarity NPD5402 Approved
0.7919 Intermediate Similarity NPD6559 Discontinued
0.7914 Intermediate Similarity NPD6599 Discontinued
0.791 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7908 Intermediate Similarity NPD943 Approved
0.7904 Intermediate Similarity NPD919 Approved
0.7892 Intermediate Similarity NPD7768 Phase 2
0.7885 Intermediate Similarity NPD6099 Approved
0.7885 Intermediate Similarity NPD6100 Approved
0.7875 Intermediate Similarity NPD7390 Discontinued
0.7821 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7818 Intermediate Similarity NPD37 Approved
0.7815 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7798 Intermediate Similarity NPD6234 Discontinued
0.7784 Intermediate Similarity NPD4965 Approved
0.7784 Intermediate Similarity NPD4967 Phase 2
0.7784 Intermediate Similarity NPD4966 Approved
0.7765 Intermediate Similarity NPD5711 Approved
0.7765 Intermediate Similarity NPD5710 Approved
0.7763 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7742 Intermediate Similarity NPD447 Suspended
0.7736 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.773 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7707 Intermediate Similarity NPD3748 Approved
0.7707 Intermediate Similarity NPD2799 Discontinued
0.7707 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7706 Intermediate Similarity NPD7199 Phase 2
0.7692 Intermediate Similarity NPD6651 Approved
0.7688 Intermediate Similarity NPD3751 Discontinued
0.7677 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7677 Intermediate Similarity NPD1613 Approved
0.7661 Intermediate Similarity NPD3787 Discontinued
0.7628 Intermediate Similarity NPD230 Phase 1
0.7625 Intermediate Similarity NPD1243 Approved
0.7622 Intermediate Similarity NPD920 Approved
0.7616 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.761 Intermediate Similarity NPD2344 Approved
0.7597 Intermediate Similarity NPD4625 Phase 3
0.7586 Intermediate Similarity NPD7228 Approved
0.7578 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7571 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7557 Intermediate Similarity NPD5953 Discontinued
0.7548 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7548 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7548 Intermediate Similarity NPD2313 Discontinued
0.7547 Intermediate Similarity NPD1551 Phase 2
0.7546 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7543 Intermediate Similarity NPD7286 Phase 2
0.7542 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7528 Intermediate Similarity NPD8313 Approved
0.7528 Intermediate Similarity NPD8312 Approved
0.7527 Intermediate Similarity NPD6778 Approved
0.7527 Intermediate Similarity NPD6782 Approved
0.7527 Intermediate Similarity NPD6776 Approved
0.7527 Intermediate Similarity NPD6777 Approved
0.7527 Intermediate Similarity NPD6779 Approved
0.7527 Intermediate Similarity NPD6781 Approved
0.7527 Intermediate Similarity NPD6780 Approved
0.7516 Intermediate Similarity NPD1933 Approved
0.7515 Intermediate Similarity NPD5403 Approved
0.75 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD3027 Phase 3
0.7469 Intermediate Similarity NPD4628 Phase 3
0.7457 Intermediate Similarity NPD7229 Phase 3
0.7423 Intermediate Similarity NPD2309 Approved
0.7419 Intermediate Similarity NPD4908 Phase 1
0.7407 Intermediate Similarity NPD7696 Phase 3
0.7407 Intermediate Similarity NPD7697 Approved
0.7407 Intermediate Similarity NPD7435 Discontinued
0.7407 Intermediate Similarity NPD7698 Approved
0.7403 Intermediate Similarity NPD8150 Discontinued
0.7396 Intermediate Similarity NPD8151 Discontinued
0.7394 Intermediate Similarity NPD5401 Approved
0.7378 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD7871 Phase 2
0.7368 Intermediate Similarity NPD7870 Phase 2
0.7365 Intermediate Similarity NPD1653 Approved
0.7362 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7351 Intermediate Similarity NPD4360 Phase 2
0.7351 Intermediate Similarity NPD4363 Phase 3
0.7338 Intermediate Similarity NPD1470 Approved
0.7321 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.732 Intermediate Similarity NPD7783 Phase 2
0.732 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7314 Intermediate Similarity NPD5242 Approved
0.7308 Intermediate Similarity NPD8434 Phase 2
0.7303 Intermediate Similarity NPD1201 Approved
0.7303 Intermediate Similarity NPD1610 Phase 2
0.7273 Intermediate Similarity NPD2403 Approved
0.7263 Intermediate Similarity NPD6823 Phase 2
0.7258 Intermediate Similarity NPD6535 Approved
0.7258 Intermediate Similarity NPD6534 Approved
0.7254 Intermediate Similarity NPD7701 Phase 2
0.7244 Intermediate Similarity NPD9494 Approved
0.7244 Intermediate Similarity NPD2861 Phase 2
0.7235 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7233 Intermediate Similarity NPD4060 Phase 1
0.7226 Intermediate Similarity NPD1203 Approved
0.7222 Intermediate Similarity NPD5405 Approved
0.7222 Intermediate Similarity NPD5406 Approved
0.7222 Intermediate Similarity NPD7240 Approved
0.7222 Intermediate Similarity NPD5404 Approved
0.7222 Intermediate Similarity NPD5408 Approved
0.7215 Intermediate Similarity NPD3268 Approved
0.7212 Intermediate Similarity NPD6190 Approved
0.7209 Intermediate Similarity NPD5353 Approved
0.7208 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7208 Intermediate Similarity NPD4749 Approved
0.7193 Intermediate Similarity NPD6844 Discontinued
0.719 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7186 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD7874 Approved
0.7179 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD2798 Approved
0.7178 Intermediate Similarity NPD1471 Phase 3
0.7143 Intermediate Similarity NPD1608 Approved
0.7143 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7700 Phase 2
0.7143 Intermediate Similarity NPD7699 Phase 2
0.7143 Intermediate Similarity NPD7801 Approved
0.7135 Intermediate Similarity NPD4287 Approved
0.7128 Intermediate Similarity NPD4361 Phase 2
0.7128 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7127 Intermediate Similarity NPD7685 Pre-registration
0.7118 Intermediate Similarity NPD7458 Discontinued
0.7115 Intermediate Similarity NPD2797 Approved
0.711 Intermediate Similarity NPD4288 Approved
0.7107 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD3764 Approved
0.7091 Intermediate Similarity NPD2654 Approved
0.7091 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD6674 Discontinued
0.709 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD6832 Phase 2
0.7088 Intermediate Similarity NPD7549 Discontinued
0.7081 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD7033 Discontinued
0.7048 Intermediate Similarity NPD7003 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