Structure

Physi-Chem Properties

Molecular Weight:  238.06
Volume:  247.606
LogP:  3.225
LogD:  2.272
LogS:  -3.944
# Rotatable Bonds:  1
TPSA:  57.53
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.389
Synthetic Accessibility Score:  2.193
Fsp3:  0.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.952
MDCK Permeability:  1.2077098290319555e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.922
20% Bioavailability (F20%):  0.962
30% Bioavailability (F30%):  0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.142
Plasma Protein Binding (PPB):  97.80614471435547%
Volume Distribution (VD):  0.423
Pgp-substrate:  2.001690149307251%

ADMET: Metabolism

CYP1A2-inhibitor:  0.958
CYP1A2-substrate:  0.107
CYP2C19-inhibitor:  0.148
CYP2C19-substrate:  0.077
CYP2C9-inhibitor:  0.277
CYP2C9-substrate:  0.294
CYP2D6-inhibitor:  0.597
CYP2D6-substrate:  0.239
CYP3A4-inhibitor:  0.158
CYP3A4-substrate:  0.088

ADMET: Excretion

Clearance (CL):  4.111
Half-life (T1/2):  0.579

ADMET: Toxicity

hERG Blockers:  0.011
Human Hepatotoxicity (H-HT):  0.021
Drug-inuced Liver Injury (DILI):  0.875
AMES Toxicity:  0.518
Rat Oral Acute Toxicity:  0.029
Maximum Recommended Daily Dose:  0.858
Skin Sensitization:  0.94
Carcinogencity:  0.795
Eye Corrosion:  0.007
Eye Irritation:  0.947
Respiratory Toxicity:  0.977

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

  Natural Product: NPC196673

Natural Product ID:  NPC196673
Common Name*:   2-Hydroxymethyl-Anthraquinone
IUPAC Name:   2-(hydroxymethyl)anthracene-9,10-dione
Synonyms:   2-Hydroxymethyl-Anthraquinone
Standard InCHIKey:  JYKHAJGLEVKEAA-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C15H10O3/c16-8-9-5-6-12-13(7-9)15(18)11-4-2-1-3-10(11)14(12)17/h1-7,16H,8H2
SMILES:  OCc1ccc2c(c1)C(=O)c1c(C2=O)cccc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL21049
PubChem CID:   87014
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000018] Anthracenes
        • [CHEMONTID:0000151] Anthraquinones

*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
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. DOI[10.1016/j.tet.2012.03.006]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[10.1016/j.tet.2012.03.006]
NPO16607 Rubia yunnanensis Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[12350148]
NPO16607 Rubia yunnanensis Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[12762798]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[16317898]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[17449162]
NPO487 Tabebuia avellanedae Species Bignoniaceae Eukaryota n.a. n.a. n.a. PMID[17950604]
NPO487 Tabebuia avellanedae Species Bignoniaceae Eukaryota n.a. bark n.a. PMID[17950604]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[19235686]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. PMID[19666019]
NPO487 Tabebuia avellanedae Species Bignoniaceae Eukaryota n.a. Brazilian n.a. PMID[19674905]
NPO16607 Rubia yunnanensis Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[21044847]
NPO16607 Rubia yunnanensis Species Rubiaceae Eukaryota roots n.a. n.a. PMID[21973054]
NPO16607 Rubia yunnanensis Species Rubiaceae Eukaryota n.a. root n.a. PMID[21973054]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[22707864]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. PMID[23088673]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[2393954]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[25594733]
NPO487 Tabebuia avellanedae Species Bignoniaceae Eukaryota n.a. n.a. n.a. PMID[32044231]
NPO30900 Morinda parvifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[7097296]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. seed n.a. PMID[7912074]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30900 Morinda parvifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16607 Rubia yunnanensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11242 Gynochthodes parvifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16607 Rubia yunnanensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO30900 Morinda parvifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12083 Hydnellum zonatum Species Thelephoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO487 Tabebuia avellanedae Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11242 Gynochthodes parvifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28245 Strychnos nux-vomica Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3751 Orthantha lutea n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO16607 Rubia yunnanensis Species Rubiaceae 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
NPT2842 Cell Line EMT6 Mus musculus ED50 = 348.0 uM PMID[537326]
NPT2842 Cell Line EMT6 Mus musculus ED50 = 2.5 uM PMID[537326]
NPT2 Others Unspecified Ratio = 139.0 n.a. PMID[537326]

☑ 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 NPC196673 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
0.9189 High Similarity NPC158157
0.8807 High Similarity NPC318327
0.8793 High Similarity NPC472981
0.8716 High Similarity NPC211439
0.8649 High Similarity NPC265513
0.8649 High Similarity NPC474057
0.8611 High Similarity NPC249067
0.8571 High Similarity NPC471188
0.8571 High Similarity NPC66208
0.8537 High Similarity NPC199253
0.8537 High Similarity NPC31799
0.8537 High Similarity NPC136588
0.8534 High Similarity NPC318173
0.8519 High Similarity NPC255676
0.8468 Intermediate Similarity NPC93015
0.8443 Intermediate Similarity NPC51448
0.8443 Intermediate Similarity NPC115797
0.8417 Intermediate Similarity NPC85511
0.8407 Intermediate Similarity NPC186128
0.8403 Intermediate Similarity NPC167323
0.8403 Intermediate Similarity NPC269923
0.8403 Intermediate Similarity NPC120545
0.84 Intermediate Similarity NPC70622
0.8364 Intermediate Similarity NPC105899
0.8364 Intermediate Similarity NPC134120
0.8364 Intermediate Similarity NPC172483
0.8348 Intermediate Similarity NPC186933
0.8348 Intermediate Similarity NPC215419
0.8347 Intermediate Similarity NPC142956
0.8333 Intermediate Similarity NPC52407
0.8333 Intermediate Similarity NPC470253
0.8333 Intermediate Similarity NPC91478
0.8291 Intermediate Similarity NPC80605
0.8291 Intermediate Similarity NPC222968
0.8291 Intermediate Similarity NPC323440
0.8257 Intermediate Similarity NPC25458
0.8198 Intermediate Similarity NPC471186
0.8197 Intermediate Similarity NPC164014
0.819 Intermediate Similarity NPC306740
0.819 Intermediate Similarity NPC274839
0.819 Intermediate Similarity NPC476357
0.8182 Intermediate Similarity NPC300274
0.8182 Intermediate Similarity NPC274443
0.8174 Intermediate Similarity NPC13784
0.8174 Intermediate Similarity NPC143768
0.8167 Intermediate Similarity NPC144547
0.8151 Intermediate Similarity NPC476645
0.8125 Intermediate Similarity NPC185763
0.8125 Intermediate Similarity NPC83409
0.812 Intermediate Similarity NPC135730
0.8115 Intermediate Similarity NPC375356
0.8113 Intermediate Similarity NPC289883
0.8103 Intermediate Similarity NPC471721
0.8095 Intermediate Similarity NPC27659
0.8091 Intermediate Similarity NPC304873
0.8091 Intermediate Similarity NPC244427
0.8091 Intermediate Similarity NPC222390
0.8087 Intermediate Similarity NPC79496
0.8087 Intermediate Similarity NPC292834
0.8083 Intermediate Similarity NPC289432
0.8083 Intermediate Similarity NPC988
0.808 Intermediate Similarity NPC282923
0.8073 Intermediate Similarity NPC217621
0.8056 Intermediate Similarity NPC289201
0.8053 Intermediate Similarity NPC112903
0.8051 Intermediate Similarity NPC212891
0.8049 Intermediate Similarity NPC173978
0.8049 Intermediate Similarity NPC295664
0.8034 Intermediate Similarity NPC474095
0.8034 Intermediate Similarity NPC228936
0.8033 Intermediate Similarity NPC65627
0.8031 Intermediate Similarity NPC471851
0.8019 Intermediate Similarity NPC128645
0.8018 Intermediate Similarity NPC247976
0.8018 Intermediate Similarity NPC329556
0.8017 Intermediate Similarity NPC93287
0.8 Intermediate Similarity NPC475002
0.8 Intermediate Similarity NPC210089
0.8 Intermediate Similarity NPC95126
0.8 Intermediate Similarity NPC202015
0.8 Intermediate Similarity NPC19256
0.7984 Intermediate Similarity NPC103540
0.7983 Intermediate Similarity NPC228318
0.7982 Intermediate Similarity NPC229242
0.7967 Intermediate Similarity NPC318067
0.7967 Intermediate Similarity NPC228739
0.7949 Intermediate Similarity NPC67377
0.7937 Intermediate Similarity NPC48248
0.7937 Intermediate Similarity NPC96024
0.7937 Intermediate Similarity NPC234175
0.7934 Intermediate Similarity NPC133389
0.7934 Intermediate Similarity NPC183339
0.7934 Intermediate Similarity NPC234337
0.7934 Intermediate Similarity NPC133302
0.7934 Intermediate Similarity NPC232958
0.7928 Intermediate Similarity NPC284477
0.792 Intermediate Similarity NPC474106
0.792 Intermediate Similarity NPC96915
0.7907 Intermediate Similarity NPC78307
0.7907 Intermediate Similarity NPC225051
0.7903 Intermediate Similarity NPC152525
0.7903 Intermediate Similarity NPC68756
0.7895 Intermediate Similarity NPC203732
0.7891 Intermediate Similarity NPC205992
0.789 Intermediate Similarity NPC253423
0.789 Intermediate Similarity NPC156021
0.7886 Intermediate Similarity NPC307174
0.7886 Intermediate Similarity NPC223351
0.7881 Intermediate Similarity NPC93181
0.7874 Intermediate Similarity NPC34414
0.7874 Intermediate Similarity NPC276238
0.7874 Intermediate Similarity NPC99731
0.7874 Intermediate Similarity NPC262819
0.7874 Intermediate Similarity NPC146647
0.7869 Intermediate Similarity NPC216216
0.7857 Intermediate Similarity NPC69424
0.7857 Intermediate Similarity NPC19856
0.7857 Intermediate Similarity NPC176130
0.7857 Intermediate Similarity NPC78364
0.7857 Intermediate Similarity NPC84672
0.7851 Intermediate Similarity NPC472708
0.7846 Intermediate Similarity NPC202225
0.7846 Intermediate Similarity NPC23894
0.7846 Intermediate Similarity NPC288089
0.7845 Intermediate Similarity NPC133308
0.7838 Intermediate Similarity NPC282895
0.7823 Intermediate Similarity NPC328107
0.782 Intermediate Similarity NPC190457
0.7818 Intermediate Similarity NPC317280
0.7818 Intermediate Similarity NPC329387
0.7815 Intermediate Similarity NPC322197
0.7812 Intermediate Similarity NPC55949
0.781 Intermediate Similarity NPC267262
0.7807 Intermediate Similarity NPC100767
0.7807 Intermediate Similarity NPC142326
0.7807 Intermediate Similarity NPC94751
0.7805 Intermediate Similarity NPC293831
0.7805 Intermediate Similarity NPC18785
0.7805 Intermediate Similarity NPC295034
0.7805 Intermediate Similarity NPC369
0.7798 Intermediate Similarity NPC61944
0.7797 Intermediate Similarity NPC326664
0.7797 Intermediate Similarity NPC196075
0.7787 Intermediate Similarity NPC238861
0.7787 Intermediate Similarity NPC77000
0.7786 Intermediate Similarity NPC80035
0.7786 Intermediate Similarity NPC258502
0.7778 Intermediate Similarity NPC160499
0.7778 Intermediate Similarity NPC158282
0.7778 Intermediate Similarity NPC471189
0.7778 Intermediate Similarity NPC280789
0.7778 Intermediate Similarity NPC254492
0.7769 Intermediate Similarity NPC477139
0.7769 Intermediate Similarity NPC115458
0.7769 Intermediate Similarity NPC314048
0.7769 Intermediate Similarity NPC249435
0.776 Intermediate Similarity NPC199273
0.776 Intermediate Similarity NPC236189
0.776 Intermediate Similarity NPC74507
0.776 Intermediate Similarity NPC234890
0.775 Intermediate Similarity NPC469843
0.7748 Intermediate Similarity NPC228435
0.7742 Intermediate Similarity NPC282577
0.7739 Intermediate Similarity NPC141523
0.7739 Intermediate Similarity NPC249811
0.7736 Intermediate Similarity NPC199567
0.7731 Intermediate Similarity NPC221275
0.7727 Intermediate Similarity NPC155211
0.7717 Intermediate Similarity NPC478165
0.7717 Intermediate Similarity NPC72667
0.7717 Intermediate Similarity NPC478162
0.7712 Intermediate Similarity NPC272524
0.771 Intermediate Similarity NPC474659
0.771 Intermediate Similarity NPC50924
0.7706 Intermediate Similarity NPC172925
0.7705 Intermediate Similarity NPC204784
0.7705 Intermediate Similarity NPC473767
0.7704 Intermediate Similarity NPC204045
0.7704 Intermediate Similarity NPC305845
0.7698 Intermediate Similarity NPC236405
0.7698 Intermediate Similarity NPC275576
0.7692 Intermediate Similarity NPC137315
0.7692 Intermediate Similarity NPC167504
0.7692 Intermediate Similarity NPC260818
0.7692 Intermediate Similarity NPC58685
0.7687 Intermediate Similarity NPC26924
0.7686 Intermediate Similarity NPC45794
0.768 Intermediate Similarity NPC51079
0.7679 Intermediate Similarity NPC469481
0.7674 Intermediate Similarity NPC108129
0.7672 Intermediate Similarity NPC85493
0.7672 Intermediate Similarity NPC17525
0.7669 Intermediate Similarity NPC53206
0.7669 Intermediate Similarity NPC53414
0.7669 Intermediate Similarity NPC305060
0.7669 Intermediate Similarity NPC475957
0.7669 Intermediate Similarity NPC264022
0.7664 Intermediate Similarity NPC79627
0.7664 Intermediate Similarity NPC277277
0.7664 Intermediate Similarity NPC173413

  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 NPC196673 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
0.8673 High Similarity NPD5951 Approved
0.8611 High Similarity NPD1237 Approved
0.8235 Intermediate Similarity NPD7163 Clinical (unspecified phase)
0.8018 Intermediate Similarity NPD1929 Approved
0.8018 Intermediate Similarity NPD1930 Approved
0.8018 Intermediate Similarity NPD1931 Clinical (unspecified phase)
0.8016 Intermediate Similarity NPD7008 Discontinued
0.8016 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD4141 Clinical (unspecified phase)
0.7984 Intermediate Similarity NPD1470 Approved
0.7951 Intermediate Similarity NPD1201 Approved
0.7928 Intermediate Similarity NPD1932 Approved
0.7886 Intermediate Similarity NPD4878 Approved
0.7787 Intermediate Similarity NPD3412 Clinical (unspecified phase)
0.7706 Intermediate Similarity NPD688 Clinical (unspecified phase)
0.7672 Intermediate Similarity NPD6831 Clinical (unspecified phase)
0.7627 Intermediate Similarity NPD1609 Clinical (unspecified phase)
0.7594 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7589 Intermediate Similarity NPD2066 Phase 3
0.7581 Intermediate Similarity NPD4879 Approved
0.7544 Intermediate Similarity NPD5700 Clinical (unspecified phase)
0.7521 Intermediate Similarity NPD2329 Discontinued
0.75 Intermediate Similarity NPD9258 Approved
0.75 Intermediate Similarity NPD9256 Approved
0.7459 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7455 Intermediate Similarity NPD1202 Approved
0.7434 Intermediate Similarity NPD1238 Approved
0.7431 Intermediate Similarity NPD1239 Approved
0.7411 Intermediate Similarity NPD3495 Discontinued
0.7402 Intermediate Similarity NPD5158 Clinical (unspecified phase)
0.7402 Intermediate Similarity NPD5157 Phase 1
0.7402 Intermediate Similarity NPD5159 Phase 2
0.7383 Intermediate Similarity NPD650 Approved
0.7355 Intermediate Similarity NPD4869 Clinical (unspecified phase)
0.7345 Intermediate Similarity NPD9495 Approved
0.7328 Intermediate Similarity NPD164 Approved
0.7279 Intermediate Similarity NPD5406 Approved
0.7279 Intermediate Similarity NPD5405 Approved
0.7279 Intermediate Similarity NPD5408 Approved
0.7279 Intermediate Similarity NPD5404 Approved
0.7273 Intermediate Similarity NPD7609 Phase 3
0.7266 Intermediate Similarity NPD182 Clinical (unspecified phase)
0.7258 Intermediate Similarity NPD7610 Discontinued
0.725 Intermediate Similarity NPD2181 Clinical (unspecified phase)
0.7231 Intermediate Similarity NPD4980 Approved
0.7231 Intermediate Similarity NPD6007 Clinical (unspecified phase)
0.7227 Intermediate Similarity NPD2182 Approved
0.7222 Intermediate Similarity NPD3019 Approved
0.7207 Intermediate Similarity NPD1508 Approved
0.7207 Intermediate Similarity NPD7631 Approved
0.7197 Intermediate Similarity NPD6966 Discovery
0.7194 Intermediate Similarity NPD7003 Approved
0.7154 Intermediate Similarity NPD1164 Approved
0.7154 Intermediate Similarity NPD2629 Approved
0.7143 Intermediate Similarity NPD3764 Approved
0.7143 Intermediate Similarity NPD942 Approved
0.7143 Intermediate Similarity NPD2342 Discontinued
0.7143 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.713 Intermediate Similarity NPD9257 Approved
0.713 Intermediate Similarity NPD9259 Approved
0.7105 Intermediate Similarity NPD1566 Phase 3
0.7105 Intermediate Similarity NPD1565 Approved
0.7105 Intermediate Similarity NPD1564 Approved
0.7101 Intermediate Similarity NPD2346 Discontinued
0.7087 Intermediate Similarity NPD2932 Approved
0.708 Intermediate Similarity NPD1693 Approved
0.7077 Intermediate Similarity NPD1283 Approved
0.7077 Intermediate Similarity NPD1876 Approved
0.7063 Intermediate Similarity NPD7009 Phase 2
0.7059 Intermediate Similarity NPD6817 Clinical (unspecified phase)
0.7054 Intermediate Similarity NPD3972 Approved
0.7049 Intermediate Similarity NPD9508 Approved
0.7034 Intermediate Similarity NPD3226 Approved
0.7034 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7031 Intermediate Similarity NPD7457 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD1089 Approved
0.7027 Intermediate Similarity NPD1086 Approved
0.7027 Intermediate Similarity NPD1090 Approved
0.7018 Intermediate Similarity NPD1989 Approved
0.7018 Intermediate Similarity NPD1843 Approved
0.7008 Intermediate Similarity NPD1651 Approved
0.6977 Remote Similarity NPD6287 Discontinued
0.6972 Remote Similarity NPD7236 Approved
0.696 Remote Similarity NPD3317 Approved
0.6953 Remote Similarity NPD2345 Approved
0.6937 Remote Similarity NPD800 Approved
0.6934 Remote Similarity NPD3528 Clinical (unspecified phase)
0.6923 Remote Similarity NPD7390 Discontinued
0.6918 Remote Similarity NPD6591 Clinical (unspecified phase)
0.6918 Remote Similarity NPD7458 Discontinued
0.6903 Remote Similarity NPD1088 Approved
0.6891 Remote Similarity NPD5909 Discontinued
0.6889 Remote Similarity NPD2313 Discontinued
0.6885 Remote Similarity NPD1317 Discontinued
0.6879 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6875 Remote Similarity NPD7422 Clinical (unspecified phase)
0.686 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6857 Remote Similarity NPD7702 Clinical (unspecified phase)
0.6857 Remote Similarity NPD2343 Clinical (unspecified phase)
0.6852 Remote Similarity NPD9491 Approved
0.6849 Remote Similarity NPD7239 Suspended
0.6846 Remote Similarity NPD1281 Approved
0.6846 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6842 Remote Similarity NPD1563 Approved
0.6842 Remote Similarity NPD2798 Approved
0.6842 Remote Similarity NPD5122 Clinical (unspecified phase)
0.6838 Remote Similarity NPD7714 Approved
0.6838 Remote Similarity NPD7715 Approved
0.6838 Remote Similarity NPD7961 Discontinued
0.6838 Remote Similarity NPD7713 Phase 3
0.6835 Remote Similarity NPD1510 Phase 2
0.6831 Remote Similarity NPD4628 Phase 3
0.6828 Remote Similarity NPD6273 Approved
0.6812 Remote Similarity NPD1607 Approved
0.6807 Remote Similarity NPD6647 Phase 2
0.6806 Remote Similarity NPD8165 Discontinued
0.6797 Remote Similarity NPD9545 Approved
0.6769 Remote Similarity NPD3023 Approved
0.6769 Remote Similarity NPD3026 Approved
0.6762 Remote Similarity NPD9294 Approved
0.6757 Remote Similarity NPD1087 Approved
0.6746 Remote Similarity NPD690 Clinical (unspecified phase)
0.6744 Remote Similarity NPD3025 Approved
0.6744 Remote Similarity NPD3024 Approved
0.6729 Remote Similarity NPD1507 Clinical (unspecified phase)
0.6721 Remote Similarity NPD9267 Approved
0.6721 Remote Similarity NPD9264 Approved
0.6721 Remote Similarity NPD9263 Approved
0.672 Remote Similarity NPD6858 Approved
0.672 Remote Similarity NPD7635 Approved
0.672 Remote Similarity NPD7094 Approved
0.6715 Remote Similarity NPD6663 Approved
0.6694 Remote Similarity NPD5048 Discontinued
0.6693 Remote Similarity NPD4198 Discontinued
0.6692 Remote Similarity NPD5126 Approved
0.6692 Remote Similarity NPD5125 Phase 3
0.6692 Remote Similarity NPD1888 Phase 1
0.6667 Remote Similarity NPD3091 Approved
0.6667 Remote Similarity NPD4452 Approved
0.6667 Remote Similarity NPD943 Approved
0.6667 Remote Similarity NPD5736 Approved
0.6667 Remote Similarity NPD74 Approved
0.6667 Remote Similarity NPD4445 Approved
0.6667 Remote Similarity NPD226 Approved
0.6667 Remote Similarity NPD9266 Approved
0.6667 Remote Similarity NPD1240 Approved
0.6667 Remote Similarity NPD4453 Approved
0.6641 Remote Similarity NPD4106 Approved
0.6641 Remote Similarity NPD4135 Approved
0.6641 Remote Similarity NPD9493 Approved
0.6641 Remote Similarity NPD4136 Approved
0.6639 Remote Similarity NPD1616 Discontinued
0.6638 Remote Similarity NPD9260 Approved
0.6621 Remote Similarity NPD3300 Phase 2
0.662 Remote Similarity NPD1471 Phase 3
0.662 Remote Similarity NPD2344 Approved
0.6615 Remote Similarity NPD1710 Approved
0.6615 Remote Similarity NPD1245 Approved
0.6597 Remote Similarity NPD3750 Approved
0.6597 Remote Similarity NPD8166 Discontinued
0.6596 Remote Similarity NPD2799 Discontinued
0.6596 Remote Similarity NPD3299 Clinical (unspecified phase)
0.6596 Remote Similarity NPD4308 Phase 3
0.6587 Remote Similarity NPD5277 Phase 2
0.6573 Remote Similarity NPD1549 Phase 2
0.6567 Remote Similarity NPD1574 Approved
0.6565 Remote Similarity NPD5305 Approved
0.6565 Remote Similarity NPD2286 Discontinued
0.6565 Remote Similarity NPD5306 Approved
0.6565 Remote Similarity NPD1362 Clinical (unspecified phase)
0.6556 Remote Similarity NPD7011 Discontinued
0.6555 Remote Similarity NPD3020 Approved
0.6549 Remote Similarity NPD2935 Discontinued
0.6538 Remote Similarity NPD2227 Clinical (unspecified phase)
0.6538 Remote Similarity NPD7741 Discontinued
0.6535 Remote Similarity NPD1241 Discontinued
0.6535 Remote Similarity NPD6010 Discontinued
0.6533 Remote Similarity NPD4380 Phase 2
0.6522 Remote Similarity NPD5422 Clinical (unspecified phase)
0.6519 Remote Similarity NPD1593 Approved
0.6513 Remote Similarity NPD7819 Suspended
0.6503 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6503 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6496 Remote Similarity NPD6049 Phase 2
0.6496 Remote Similarity NPD6048 Clinical (unspecified phase)
0.6489 Remote Similarity NPD4102 Approved
0.6489 Remote Similarity NPD4105 Approved
0.6484 Remote Similarity NPD1246 Approved
0.6481 Remote Similarity NPD9490 Approved
0.6479 Remote Similarity NPD7305 Phase 1
0.6471 Remote Similarity NPD5740 Clinical (unspecified phase)
0.6471 Remote Similarity NPD6085 Phase 2
0.6467 Remote Similarity NPD5086 Approved
0.6466 Remote Similarity NPD3092 Approved
0.6466 Remote Similarity NPD4806 Approved
0.6466 Remote Similarity NPD4807 Approved
0.6449 Remote Similarity NPD6039 Approved
0.6441 Remote Similarity NPD2859 Approved
0.6441 Remote Similarity NPD2860 Approved
0.6439 Remote Similarity NPD7725 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