Structure

Physi-Chem Properties

Molecular Weight:  286.08
Volume:  285.119
LogP:  3.816
LogD:  3.003
LogS:  -4.132
# Rotatable Bonds:  2
TPSA:  68.9
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.733
Synthetic Accessibility Score:  2.271
Fsp3:  0.188
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.883
MDCK Permeability:  1.7431679225410335e-05
Pgp-inhibitor:  0.036
Pgp-substrate:  0.248
Human Intestinal Absorption (HIA):  0.013
20% Bioavailability (F20%):  0.003
30% Bioavailability (F30%):  0.459

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.024
Plasma Protein Binding (PPB):  89.01262664794922%
Volume Distribution (VD):  0.946
Pgp-substrate:  10.379727363586426%

ADMET: Metabolism

CYP1A2-inhibitor:  0.973
CYP1A2-substrate:  0.966
CYP2C19-inhibitor:  0.78
CYP2C19-substrate:  0.339
CYP2C9-inhibitor:  0.705
CYP2C9-substrate:  0.937
CYP2D6-inhibitor:  0.759
CYP2D6-substrate:  0.929
CYP3A4-inhibitor:  0.465
CYP3A4-substrate:  0.205

ADMET: Excretion

Clearance (CL):  3.78
Half-life (T1/2):  0.362

ADMET: Toxicity

hERG Blockers:  0.016
Human Hepatotoxicity (H-HT):  0.244
Drug-inuced Liver Injury (DILI):  0.906
AMES Toxicity:  0.509
Rat Oral Acute Toxicity:  0.116
Maximum Recommended Daily Dose:  0.831
Skin Sensitization:  0.666
Carcinogencity:  0.03
Eye Corrosion:  0.235
Eye Irritation:  0.982
Respiratory Toxicity:  0.538

Download Data

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

  Natural Product: NPC310340

Natural Product ID:  NPC310340
Common Name*:   Lichexanthone
IUPAC Name:   1-hydroxy-3,6-dimethoxy-8-methylxanthen-9-one
Synonyms:   Lichexanthone
Standard InCHIKey:  QDLAGTHXVHQKRE-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C16H14O5/c1-8-4-9(19-2)6-12-14(8)16(18)15-11(17)5-10(20-3)7-13(15)21-12/h4-7,17H,1-3H3
SMILES:  Cc1cc(cc2c1c(=O)c1c(cc(cc1o2)OC)O)OC
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL470650
PubChem CID:   5358904
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

*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
NPO15275 Briareum asbestinum Species Briareidae Eukaryota n.a. n.a. n.a. PMID[12662092]
NPO20214 Ruprechtia tangarana Species Polygonaceae Eukaryota n.a. n.a. n.a. PMID[12932125]
NPO13075 Gustavia hexapetala Species Lecythidaceae Eukaryota n.a. Peru 1979 PMID[15217278]
NPO8520 Mucor spinosus Species Mucoraceae Eukaryota n.a. n.a. n.a. PMID[15844967]
NPO14038 Oriciopsis glaberrima n.a. n.a. n.a. n.a. stem n.a. PMID[16508179]
NPO15275 Briareum asbestinum Species Briareidae Eukaryota n.a. Caribbean n.a. PMID[1686898]
NPO31410 Cupania cinerea Species Sapindaceae Eukaryota n.a. bark n.a. PMID[21438586]
NPO29532 Vigna angularis Species Fabaceae Eukaryota Leaf Diffusate n.a. n.a. Database[FooDB]
NPO29532 Vigna angularis Species Fabaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO29532 Vigna angularis Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO29532 Vigna angularis Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO14407 Stachyurus praecox Species Stachyuraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29532 Vigna angularis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29532 Vigna angularis Species Fabaceae Eukaryota Seeds n.a. Database[Phenol-Explorer]
NPO17495 Isodon amethystoides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29532 Vigna angularis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14407 Stachyurus praecox Species Stachyuraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14038 Oriciopsis glaberrima n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO3998 Neolitsea pulchella Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29532 Vigna angularis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14567 Ursinia anethoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10765 Dracaena concinna Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8520 Mucor spinosus Species Mucoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10542 Liparis keitaoensis Species Liparidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15275 Briareum asbestinum Species Briareidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15862 Eminium lehmannii Species Araceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14335 Ophiorrhiza kuroiwae Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29532 Vigna angularis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4424 Salvia amplexicaulis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13075 Gustavia hexapetala Species Lecythidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1787 Agathis lanceolata Species Araucariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14236 Physalis coztomatl Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13009 Laurencia saitoi Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13389 Cystoseira barbatula Species Sargassaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14407 Stachyurus praecox Species Stachyuraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3426 Pseudocyphellaria hirsuta Species Lobariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3998 Neolitsea pulchella Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15020 Flindersia amboinensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13247 Stevia pilosa Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17495 Isodon amethystoides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20214 Ruprechtia tangarana Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2360 Jatropha mahafalensis Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10423 Sibthorpia europaea Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18894 Karenia mikimotoi Species Kareniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14038 Oriciopsis glaberrima n.a. n.a. n.a. 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
NPT168 Cell Line P388 Mus musculus GI50 > 10.0 ug.mL-1 PMID[522333]
NPT1081 Cell Line BXPC-3 Homo sapiens GI50 = 2.5 ug.mL-1 PMID[522333]
NPT83 Cell Line MCF7 Homo sapiens GI50 = 4.1 ug.mL-1 PMID[522333]
NPT395 Cell Line SF-268 Homo sapiens GI50 = 3.0 ug.mL-1 PMID[522333]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 = 7.1 ug.mL-1 PMID[522333]
NPT575 Cell Line KM-20L2 Homo sapiens GI50 = 2.0 ug.mL-1 PMID[522333]
NPT90 Cell Line DU-145 Homo sapiens GI50 = 3.7 ug.mL-1 PMID[522333]
NPT839 Cell Line L6 Rattus norvegicus IC50 = 52100.0 nM PMID[522335]
NPT113 Cell Line RAW264.7 Mus musculus Inhibition = 32.02 % PMID[522337]
NPT965 Organism Amaranthus hypochondriacus Amaranthus hypochondriacus IC50 > 2000000.0 nM PMID[522332]
NPT117 Organism Echinochloa crus-galli Echinochloa crus-galli IC50 > 2000000.0 nM PMID[522332]
NPT485 Organism Plasmodium falciparum (isolate K1 / Thailand) Plasmodium falciparum K1 IC50 > 20000.0 nM PMID[522335]
NPT844 Organism Trypanosoma brucei rhodesiense Trypanosoma brucei rhodesiense IC50 > 90000.0 nM PMID[522335]
NPT2701 Organism Pythium debaryanum Pythium debaryanum ED50 = 148.95 ug ml-1 PMID[522336]
NPT961 Organism Pythium aphanidermatum Pythium aphanidermatum ED50 = 174.14 ug ml-1 PMID[522336]
NPT2702 Organism Fusarium udum Fusarium udum ED50 = 151.03 ug ml-1 PMID[522336]
NPT2703 Organism Rhizoctonia bataticola Rhizoctonia bataticola ED50 = 133.76 ug ml-1 PMID[522336]
NPT529 Organism Rhizoctonia solani Rhizoctonia solani ED50 = 202.5 ug ml-1 PMID[522336]
NPT722 Organism Athelia rolfsii Athelia rolfsii ED50 = 273.33 ug ml-1 PMID[522336]
NPT2701 Organism Pythium debaryanum Pythium debaryanum Inhibition = 9.03 % PMID[522336]
NPT2701 Organism Pythium debaryanum Pythium debaryanum Inhibition = 28.4 % PMID[522336]
NPT2701 Organism Pythium debaryanum Pythium debaryanum Inhibition = 42.03 % PMID[522336]
NPT961 Organism Pythium aphanidermatum Pythium aphanidermatum Inhibition = 13.03 % PMID[522336]
NPT961 Organism Pythium aphanidermatum Pythium aphanidermatum Inhibition = 23.4 % PMID[522336]
NPT961 Organism Pythium aphanidermatum Pythium aphanidermatum Inhibition = 42.66 % PMID[522336]
NPT2702 Organism Fusarium udum Fusarium udum Inhibition = 20.33 % PMID[522336]
NPT2702 Organism Fusarium udum Fusarium udum Inhibition = 24.53 % PMID[522336]
NPT2702 Organism Fusarium udum Fusarium udum Inhibition = 53.33 % PMID[522336]
NPT2703 Organism Rhizoctonia bataticola Rhizoctonia bataticola Inhibition = 11.43 % PMID[522336]
NPT2703 Organism Rhizoctonia bataticola Rhizoctonia bataticola Inhibition = 30.26 % PMID[522336]
NPT2703 Organism Rhizoctonia bataticola Rhizoctonia bataticola Inhibition = 50.0 % PMID[522336]
NPT529 Organism Rhizoctonia solani Rhizoctonia solani Inhibition = 19.63 % PMID[522336]
NPT529 Organism Rhizoctonia solani Rhizoctonia solani Inhibition = 29.36 % PMID[522336]
NPT529 Organism Rhizoctonia solani Rhizoctonia solani Inhibition = 41.0 % PMID[522336]
NPT722 Organism Athelia rolfsii Athelia rolfsii Inhibition = 16.67 % PMID[522336]
NPT722 Organism Athelia rolfsii Athelia rolfsii Inhibition = 23.2 % PMID[522336]
NPT722 Organism Athelia rolfsii Athelia rolfsii Inhibition = 37.33 % PMID[522336]

☑ 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 NPC310340 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
0.9853 High Similarity NPC275734
0.9568 High Similarity NPC73028
0.9507 High Similarity NPC27221
0.9507 High Similarity NPC256672
0.9507 High Similarity NPC7025
0.9504 High Similarity NPC267509
0.9444 High Similarity NPC232645
0.9444 High Similarity NPC72958
0.9441 High Similarity NPC473978
0.9441 High Similarity NPC100985
0.9441 High Similarity NPC97029
0.9441 High Similarity NPC158338
0.9441 High Similarity NPC288036
0.9441 High Similarity NPC65589
0.9441 High Similarity NPC97028
0.9437 High Similarity NPC22005
0.9437 High Similarity NPC7943
0.9437 High Similarity NPC123202
0.9437 High Similarity NPC259632
0.9433 High Similarity NPC134621
0.9433 High Similarity NPC32470
0.9429 High Similarity NPC202981
0.9424 High Similarity NPC182421
0.9379 High Similarity NPC474843
0.9379 High Similarity NPC87708
0.9375 High Similarity NPC202595
0.9375 High Similarity NPC470107
0.9375 High Similarity NPC227122
0.9375 High Similarity NPC325983
0.9371 High Similarity NPC106328
0.9371 High Similarity NPC35150
0.9366 High Similarity NPC187282
0.9366 High Similarity NPC290133
0.9366 High Similarity NPC237208
0.9366 High Similarity NPC196114
0.9366 High Similarity NPC24136
0.9362 High Similarity NPC113770
0.9362 High Similarity NPC95123
0.9362 High Similarity NPC66404
0.9357 High Similarity NPC49108
0.9357 High Similarity NPC105648
0.9353 High Similarity NPC274784
0.9353 High Similarity NPC329203
0.9353 High Similarity NPC20709
0.9353 High Similarity NPC265871
0.9353 High Similarity NPC310135
0.9353 High Similarity NPC222342
0.9353 High Similarity NPC150648
0.9353 High Similarity NPC316480
0.9353 High Similarity NPC225153
0.9353 High Similarity NPC140890
0.9343 High Similarity NPC242712
0.931 High Similarity NPC474417
0.931 High Similarity NPC478148
0.931 High Similarity NPC149526
0.9306 High Similarity NPC65775
0.9306 High Similarity NPC10027
0.9296 High Similarity NPC29577
0.9296 High Similarity NPC271288
0.9296 High Similarity NPC311144
0.9296 High Similarity NPC184649
0.9296 High Similarity NPC303185
0.9286 High Similarity NPC6407
0.9286 High Similarity NPC284550
0.9286 High Similarity NPC188243
0.9286 High Similarity NPC129853
0.9286 High Similarity NPC110228
0.9286 High Similarity NPC220106
0.9286 High Similarity NPC76445
0.9281 High Similarity NPC280284
0.9281 High Similarity NPC99333
0.9281 High Similarity NPC57380
0.9281 High Similarity NPC118813
0.9281 High Similarity NPC188947
0.9275 High Similarity NPC194281
0.9275 High Similarity NPC47815
0.9275 High Similarity NPC231772
0.9275 High Similarity NPC473887
0.9275 High Similarity NPC127447
0.9275 High Similarity NPC29353
0.9275 High Similarity NPC234133
0.9275 High Similarity NPC124784
0.9252 High Similarity NPC67396
0.9247 High Similarity NPC40356
0.9247 High Similarity NPC154683
0.9241 High Similarity NPC295036
0.9241 High Similarity NPC151473
0.9241 High Similarity NPC60413
0.9231 High Similarity NPC299011
0.9231 High Similarity NPC477955
0.9225 High Similarity NPC18585
0.9225 High Similarity NPC166138
0.9225 High Similarity NPC19896
0.9225 High Similarity NPC106985
0.922 High Similarity NPC324386
0.922 High Similarity NPC213322
0.922 High Similarity NPC4743
0.922 High Similarity NPC96692
0.922 High Similarity NPC96408
0.922 High Similarity NPC94076
0.922 High Similarity NPC156190
0.922 High Similarity NPC279650
0.922 High Similarity NPC312391
0.922 High Similarity NPC258630
0.922 High Similarity NPC250755
0.922 High Similarity NPC182255
0.922 High Similarity NPC17170
0.922 High Similarity NPC166689
0.922 High Similarity NPC3188
0.9214 High Similarity NPC261234
0.9214 High Similarity NPC78913
0.9214 High Similarity NPC18260
0.9209 High Similarity NPC13768
0.9209 High Similarity NPC107586
0.9209 High Similarity NPC287246
0.9209 High Similarity NPC32441
0.9209 High Similarity NPC296490
0.9209 High Similarity NPC250266
0.9209 High Similarity NPC266597
0.9209 High Similarity NPC275055
0.9209 High Similarity NPC290291
0.9209 High Similarity NPC228661
0.9209 High Similarity NPC12296
0.9209 High Similarity NPC243083
0.9209 High Similarity NPC79943
0.9209 High Similarity NPC295261
0.9203 High Similarity NPC9985
0.9203 High Similarity NPC239495
0.9189 High Similarity NPC24640
0.9184 High Similarity NPC178964
0.9184 High Similarity NPC210942
0.9184 High Similarity NPC89474
0.9184 High Similarity NPC329844
0.9184 High Similarity NPC95842
0.9184 High Similarity NPC280530
0.9184 High Similarity NPC169990
0.9178 High Similarity NPC106372
0.9178 High Similarity NPC227166
0.9178 High Similarity NPC258249
0.9178 High Similarity NPC58668
0.9178 High Similarity NPC202157
0.9178 High Similarity NPC115324
0.9172 High Similarity NPC291049
0.9172 High Similarity NPC266499
0.9172 High Similarity NPC233267
0.9172 High Similarity NPC6923
0.9167 High Similarity NPC34802
0.9167 High Similarity NPC312929
0.9167 High Similarity NPC308200
0.9167 High Similarity NPC10990
0.9167 High Similarity NPC289042
0.9167 High Similarity NPC300988
0.9167 High Similarity NPC56433
0.9167 High Similarity NPC245584
0.9167 High Similarity NPC118027
0.9167 High Similarity NPC12305
0.9167 High Similarity NPC190648
0.9167 High Similarity NPC126767
0.9161 High Similarity NPC470674
0.9161 High Similarity NPC470890
0.9161 High Similarity NPC469764
0.9161 High Similarity NPC312789
0.9161 High Similarity NPC117716
0.9161 High Similarity NPC470673
0.9155 High Similarity NPC64915
0.9155 High Similarity NPC161506
0.9155 High Similarity NPC107572
0.9155 High Similarity NPC37496
0.9155 High Similarity NPC78
0.9155 High Similarity NPC306829
0.9155 High Similarity NPC40833
0.9155 High Similarity NPC76338
0.9155 High Similarity NPC166934
0.9155 High Similarity NPC148757
0.9155 High Similarity NPC76372
0.9155 High Similarity NPC125855
0.9155 High Similarity NPC167624
0.9155 High Similarity NPC84266
0.9155 High Similarity NPC194432
0.9155 High Similarity NPC144499
0.9155 High Similarity NPC220998
0.9155 High Similarity NPC177354
0.9155 High Similarity NPC166482
0.9155 High Similarity NPC159855
0.9155 High Similarity NPC328164
0.9155 High Similarity NPC32739
0.9155 High Similarity NPC169479
0.9155 High Similarity NPC10937
0.9155 High Similarity NPC265040
0.9155 High Similarity NPC324436
0.9155 High Similarity NPC1089
0.9155 High Similarity NPC223500
0.9155 High Similarity NPC324134
0.9155 High Similarity NPC296917
0.9155 High Similarity NPC227579
0.9155 High Similarity NPC182852
0.9155 High Similarity NPC66515
0.9155 High Similarity NPC228504
0.9149 High Similarity NPC159275
0.9149 High Similarity NPC69769

  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 NPC310340 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
0.9209 High Similarity NPD1552 Clinical (unspecified phase)
0.9209 High Similarity NPD1550 Clinical (unspecified phase)
0.9143 High Similarity NPD1549 Phase 2
0.9054 High Similarity NPD7819 Suspended
0.9028 High Similarity NPD4378 Clinical (unspecified phase)
0.9007 High Similarity NPD970 Clinical (unspecified phase)
0.8986 High Similarity NPD1934 Approved
0.8929 High Similarity NPD1510 Phase 2
0.8926 High Similarity NPD2393 Clinical (unspecified phase)
0.8913 High Similarity NPD1240 Approved
0.8828 High Similarity NPD1511 Approved
0.8824 High Similarity NPD6959 Discontinued
0.8786 High Similarity NPD1607 Approved
0.875 High Similarity NPD3750 Approved
0.8742 High Similarity NPD8443 Clinical (unspecified phase)
0.8732 High Similarity NPD2796 Approved
0.8707 High Similarity NPD1512 Approved
0.8675 High Similarity NPD2801 Approved
0.8639 High Similarity NPD7410 Clinical (unspecified phase)
0.8627 High Similarity NPD3749 Approved
0.8543 High Similarity NPD7411 Suspended
0.8506 High Similarity NPD7075 Discontinued
0.8477 Intermediate Similarity NPD4380 Phase 2
0.8472 Intermediate Similarity NPD6099 Approved
0.8472 Intermediate Similarity NPD6100 Approved
0.8442 Intermediate Similarity NPD3882 Suspended
0.8431 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8425 Intermediate Similarity NPD2800 Approved
0.8418 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8418 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8418 Intermediate Similarity NPD6166 Phase 2
0.8403 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.8403 Intermediate Similarity NPD3748 Approved
0.8389 Intermediate Similarity NPD2532 Approved
0.8389 Intermediate Similarity NPD2534 Approved
0.8389 Intermediate Similarity NPD2533 Approved
0.8387 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8322 Intermediate Similarity NPD6799 Approved
0.8302 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8291 Intermediate Similarity NPD6232 Discontinued
0.8258 Intermediate Similarity NPD3817 Phase 2
0.825 Intermediate Similarity NPD7473 Discontinued
0.8235 Intermediate Similarity NPD6599 Discontinued
0.8219 Intermediate Similarity NPD1551 Phase 2
0.821 Intermediate Similarity NPD7074 Phase 3
0.8205 Intermediate Similarity NPD7768 Phase 2
0.8205 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8194 Intermediate Similarity NPD1465 Phase 2
0.817 Intermediate Similarity NPD3226 Approved
0.8165 Intermediate Similarity NPD5494 Approved
0.8163 Intermediate Similarity NPD2346 Discontinued
0.8163 Intermediate Similarity NPD2344 Approved
0.8148 Intermediate Similarity NPD7054 Approved
0.8129 Intermediate Similarity NPD6801 Discontinued
0.8112 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.8098 Intermediate Similarity NPD7472 Approved
0.8095 Intermediate Similarity NPD2935 Discontinued
0.8086 Intermediate Similarity NPD3818 Discontinued
0.8079 Intermediate Similarity NPD7390 Discontinued
0.8054 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8054 Intermediate Similarity NPD1243 Approved
0.8049 Intermediate Similarity NPD6797 Phase 2
0.8037 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8037 Intermediate Similarity NPD5844 Phase 1
0.8014 Intermediate Similarity NPD6651 Approved
0.8 Intermediate Similarity NPD943 Approved
0.8 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD7251 Discontinued
0.7986 Intermediate Similarity NPD1610 Phase 2
0.7972 Intermediate Similarity NPD4908 Phase 1
0.7952 Intermediate Similarity NPD7808 Phase 3
0.7947 Intermediate Similarity NPD2309 Approved
0.7917 Intermediate Similarity NPD4625 Phase 3
0.7905 Intermediate Similarity NPD2799 Discontinued
0.7892 Intermediate Similarity NPD6559 Discontinued
0.7887 Intermediate Similarity NPD1203 Approved
0.7881 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7862 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7857 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7857 Intermediate Similarity NPD1201 Approved
0.7844 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7844 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.784 Intermediate Similarity NPD5711 Approved
0.784 Intermediate Similarity NPD5710 Approved
0.7806 Intermediate Similarity NPD5403 Approved
0.7806 Intermediate Similarity NPD920 Approved
0.7801 Intermediate Similarity NPD1608 Approved
0.7799 Intermediate Similarity NPD5402 Approved
0.7792 Intermediate Similarity NPD5401 Approved
0.7791 Intermediate Similarity NPD3926 Phase 2
0.7778 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7778 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7763 Intermediate Similarity NPD4628 Phase 3
0.7762 Intermediate Similarity NPD1470 Approved
0.7746 Intermediate Similarity NPD4749 Approved
0.774 Intermediate Similarity NPD3268 Approved
0.774 Intermediate Similarity NPD2313 Discontinued
0.7725 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7725 Intermediate Similarity NPD5953 Discontinued
0.7724 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7708 Intermediate Similarity NPD2798 Approved
0.7698 Intermediate Similarity NPD1548 Phase 1
0.7688 Intermediate Similarity NPD4288 Approved
0.7677 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7677 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7676 Intermediate Similarity NPD9717 Approved
0.7667 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7654 Intermediate Similarity NPD919 Approved
0.7651 Intermediate Similarity NPD3751 Discontinued
0.7639 Intermediate Similarity NPD2797 Approved
0.7635 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7635 Intermediate Similarity NPD1613 Approved
0.7619 Intermediate Similarity NPD3764 Approved
0.7606 Intermediate Similarity NPD422 Phase 1
0.7605 Intermediate Similarity NPD7286 Phase 2
0.7603 Intermediate Similarity NPD6832 Phase 2
0.7595 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7589 Intermediate Similarity NPD17 Approved
0.7584 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7584 Intermediate Similarity NPD230 Phase 1
0.7584 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7582 Intermediate Similarity NPD2654 Approved
0.758 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7572 Intermediate Similarity NPD4287 Approved
0.7566 Intermediate Similarity NPD1471 Phase 3
0.7561 Intermediate Similarity NPD7199 Phase 2
0.7561 Intermediate Similarity NPD1247 Approved
0.755 Intermediate Similarity NPD4308 Phase 3
0.755 Intermediate Similarity NPD7033 Discontinued
0.7517 Intermediate Similarity NPD3266 Approved
0.7517 Intermediate Similarity NPD3267 Approved
0.7515 Intermediate Similarity NPD3787 Discontinued
0.7515 Intermediate Similarity NPD7229 Phase 3
0.75 Intermediate Similarity NPD411 Approved
0.75 Intermediate Similarity NPD5404 Approved
0.75 Intermediate Similarity NPD5408 Approved
0.75 Intermediate Similarity NPD4360 Phase 2
0.75 Intermediate Similarity NPD4363 Phase 3
0.75 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5406 Approved
0.75 Intermediate Similarity NPD5405 Approved
0.7486 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.747 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7467 Intermediate Similarity NPD1933 Approved
0.7467 Intermediate Similarity NPD447 Suspended
0.7448 Intermediate Similarity NPD3225 Approved
0.7448 Intermediate Similarity NPD1876 Approved
0.7431 Intermediate Similarity NPD3972 Approved
0.7415 Intermediate Similarity NPD2861 Phase 2
0.7389 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7384 Intermediate Similarity NPD8313 Approved
0.7384 Intermediate Similarity NPD8312 Approved
0.7368 Intermediate Similarity NPD3658 Clinical (unspecified phase)
0.7362 Intermediate Similarity NPD2296 Approved
0.736 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.736 Intermediate Similarity NPD4361 Phase 2
0.7346 Intermediate Similarity NPD37 Approved
0.7333 Intermediate Similarity NPD6234 Discontinued
0.7329 Intermediate Similarity NPD1283 Approved
0.7324 Intermediate Similarity NPD9545 Approved
0.7317 Intermediate Similarity NPD4965 Approved
0.7317 Intermediate Similarity NPD4966 Approved
0.7317 Intermediate Similarity NPD4967 Phase 2
0.7308 Intermediate Similarity NPD7003 Approved
0.7305 Intermediate Similarity NPD9493 Approved
0.7305 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7296 Intermediate Similarity NPD6273 Approved
0.7285 Intermediate Similarity NPD4307 Phase 2
0.7285 Intermediate Similarity NPD4060 Phase 1
0.7284 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD1651 Approved
0.7267 Intermediate Similarity NPD1296 Phase 2
0.7239 Intermediate Similarity NPD6844 Discontinued
0.7237 Intermediate Similarity NPD5124 Phase 1
0.7237 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7235 Intermediate Similarity NPD7177 Discontinued
0.7219 Intermediate Similarity NPD2403 Approved
0.7214 Intermediate Similarity NPD1241 Discontinued
0.72 Intermediate Similarity NPD3027 Phase 3
0.7198 Intermediate Similarity NPD6778 Approved
0.7198 Intermediate Similarity NPD6779 Approved
0.7198 Intermediate Similarity NPD6777 Approved
0.7198 Intermediate Similarity NPD6776 Approved
0.7198 Intermediate Similarity NPD6782 Approved
0.7198 Intermediate Similarity NPD6780 Approved
0.7198 Intermediate Similarity NPD6781 Approved
0.7175 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7169 Intermediate Similarity NPD6971 Discontinued
0.7168 Intermediate Similarity NPD6104 Discontinued
0.7166 Intermediate Similarity NPD8151 Discontinued
0.7162 Intermediate Similarity NPD1164 Approved
0.7161 Intermediate Similarity NPD4477 Approved
0.7161 Intermediate Similarity NPD4476 Approved
0.716 Intermediate Similarity NPD7458 Discontinued
0.7152 Intermediate Similarity NPD6798 Discontinued
0.7151 Intermediate Similarity NPD1729 Discontinued
0.7143 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD7228 Approved
0.7134 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7127 Intermediate Similarity NPD8090 Clinical (unspecified phase)

  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