Structure

Physi-Chem Properties

Molecular Weight:  424.1
Volume:  389.748
LogP:  0.137
LogD:  -0.123
LogS:  -2.216
# Rotatable Bonds:  4
TPSA:  208.37
# H-Bond Aceptor:  11
# H-Bond Donor:  9
# Rings:  3
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.214
Synthetic Accessibility Score:  3.983
Fsp3:  0.316
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.514
MDCK Permeability:  3.679592509797658e-06
Pgp-inhibitor:  0.019
Pgp-substrate:  0.602
Human Intestinal Absorption (HIA):  0.931
20% Bioavailability (F20%):  0.987
30% Bioavailability (F30%):  1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.02
Plasma Protein Binding (PPB):  95.1823959350586%
Volume Distribution (VD):  0.612
Pgp-substrate:  6.6492767333984375%

ADMET: Metabolism

CYP1A2-inhibitor:  0.135
CYP1A2-substrate:  0.023
CYP2C19-inhibitor:  0.018
CYP2C19-substrate:  0.045
CYP2C9-inhibitor:  0.061
CYP2C9-substrate:  0.149
CYP2D6-inhibitor:  0.011
CYP2D6-substrate:  0.136
CYP3A4-inhibitor:  0.067
CYP3A4-substrate:  0.014

ADMET: Excretion

Clearance (CL):  8.226
Half-life (T1/2):  0.854

ADMET: Toxicity

hERG Blockers:  0.161
Human Hepatotoxicity (H-HT):  0.082
Drug-inuced Liver Injury (DILI):  0.974
AMES Toxicity:  0.81
Rat Oral Acute Toxicity:  0.023
Maximum Recommended Daily Dose:  0.016
Skin Sensitization:  0.921
Carcinogencity:  0.045
Eye Corrosion:  0.003
Eye Irritation:  0.783
Respiratory Toxicity:  0.029

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  Natural Product: NPC227485

Natural Product ID:  NPC227485
Common Name*:   VYGJDASIWDWDAM-ZJKJAXBQSA-N
IUPAC Name:   n.a.
Synonyms:  
Standard InCHIKey:  VYGJDASIWDWDAM-ZJKJAXBQSA-N
Standard InCHI:  InChI=1S/C19H20O11/c20-5-11-15(26)17(28)18(29)19(30-11)13-10(24)4-9(23)12(16(13)27)14(25)6-1-2-7(21)8(22)3-6/h1-4,11,15,17-24,26-29H,5H2/t11-,15-,17+,18-,19+/m1/s1
SMILES:  c1cc(c(cc1C(=O)c1c(cc(c(c1O)[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3358631
PubChem CID:   NA
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0004603] Organic oxygen compounds
      • [CHEMONTID:0000323] Organooxygen compounds
        • [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates
          • [CHEMONTID:0002105] Glycosyl compounds
            • [CHEMONTID:0004165] Phenolic glycosides

*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
NPO30586 Cyclopia genistoides Species Fabaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s00217-002-0644-5]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota n.a. n.a. n.a. DOI[10.1246/bcsj.30.618]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. root n.a. PMID[14727919]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. leaf n.a. PMID[14727919]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. bark n.a. PMID[14727919]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. xylem n.a. PMID[14727919]
NPO29530 Kaempferia marginata Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[16309313]
NPO27743 Aaptos aaptos Species Suberitidae Eukaryota n.a. n.a. n.a. PMID[17716892]
NPO28864 Nauclea officinalis Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO29381 Trichilia rubescens Species Meliaceae Eukaryota leaves Kibale National Park, Uganda 2000-2001 PMID[19299148]
NPO27743 Aaptos aaptos Species Suberitidae Eukaryota n.a. South China Sea n.a. PMID[25211032]
NPO30586 Cyclopia genistoides Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[25419864]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota n.a. n.a. n.a. PMID[27466882]
NPO4055 Aspergillus unguis Species Aspergillaceae Eukaryota n.a. n.a. n.a. PMID[31117521]
NPO29530 Kaempferia marginata Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[31873014]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota Flower n.a. n.a. Database[FooDB]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota Pericarp n.a. n.a. Database[FooDB]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. n.a. Database[FooDB]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota n.a. n.a. Database[FooDB]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota Essential Oil n.a. n.a. Database[FooDB]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28949 Croton cumingii Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29004 Ruta pinnata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28864 Nauclea officinalis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota Fruits n.a. Database[Phenol-Explorer]
NPO29344 Parabenzoin trilobum n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO29530 Kaempferia marginata Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4055 Aspergillus unguis Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28805 Thymus piperella Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28949 Croton cumingii Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28864 Nauclea officinalis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29004 Ruta pinnata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28864 Nauclea officinalis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28949 Croton cumingii Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28824 Forsteronia refracta Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28898 Grewia mollis Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29363 Aconitum nevadense Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29004 Ruta pinnata Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29400 Conocephalum japonicum Species Conocephalaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26192 Cordylanthus kingii Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29510 Aulacocephalus temmincki Species Serranidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29446 Stevia polycephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28918 Ophiolepis superba Species Ophiolepididae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29530 Kaempferia marginata Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29154 Heliotropium floridum Species Heliotropiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29047 Disynaphia halimifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28864 Nauclea officinalis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29292 Teucrium depressum Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29276 Juglans nigra Species Juglandaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28971 Bersama yangambiensis Species Melianthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27269 Annona impressivenia Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29189 Castanopsis sclerophylla Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4055 Aspergillus unguis Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29415 Hovenia acerba Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25981 Crinipellis scabella Species Marasmiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13818 Narcissus concolor Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27743 Aaptos aaptos Species Suberitidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3744 Polycephalomyces nipponicus Species Ophiocordycipitaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28784 Alseodaphne corneri Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29203 Gymnocarpium robertianum Species Cystopteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9157 Rubrivivax gelatinosus Species n.a. Bacteria n.a. n.a. n.a. Database[UNPD]
NPO4244 Doodia picta Species Blechnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29488 Sophora angustifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29142 Kaunia saltensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29450 Streptomyces parvisporogenes Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO29344 Parabenzoin trilobum n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO28805 Thymus piperella Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3340 Fridericia chica Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29068 Papilio phorcas Species Papilionidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28937 Heterotheca grandiflora Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1245 Eunicella cavolinii Species Gorgoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29242 Salvia dorrii Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28845 Eragrostis viscosa Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29127 Cystophora scalaris Species Sargassaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29225 Oncoba echinata Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29381 Trichilia rubescens Species Meliaceae 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
NPT2 Others Unspecified Inhibition = 54.0 % PMID[513103]

☑ 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 NPC227485 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
0.9342 High Similarity NPC117418
0.9342 High Similarity NPC53545
0.929 High Similarity NPC471788
0.9276 High Similarity NPC291508
0.9276 High Similarity NPC474055
0.9276 High Similarity NPC472598
0.9272 High Similarity NPC321779
0.9267 High Similarity NPC323626
0.9267 High Similarity NPC324233
0.9226 High Similarity NPC124038
0.9221 High Similarity NPC471499
0.9221 High Similarity NPC289771
0.9221 High Similarity NPC228383
0.9221 High Similarity NPC472634
0.9221 High Similarity NPC26326
0.9221 High Similarity NPC142252
0.9216 High Similarity NPC22192
0.9211 High Similarity NPC278778
0.9211 High Similarity NPC35038
0.9211 High Similarity NPC291878
0.9211 High Similarity NPC195796
0.9205 High Similarity NPC192083
0.9205 High Similarity NPC213896
0.9195 High Similarity NPC89442
0.9172 High Similarity NPC260266
0.9161 High Similarity NPC476247
0.9161 High Similarity NPC474034
0.9161 High Similarity NPC472635
0.9161 High Similarity NPC220912
0.9161 High Similarity NPC474033
0.9156 High Similarity NPC470326
0.9156 High Similarity NPC287328
0.9156 High Similarity NPC282009
0.9156 High Similarity NPC472631
0.9156 High Similarity NPC472630
0.915 High Similarity NPC78103
0.915 High Similarity NPC27337
0.9145 High Similarity NPC470327
0.9145 High Similarity NPC230149
0.9145 High Similarity NPC168247
0.9145 High Similarity NPC117992
0.9145 High Similarity NPC45849
0.9145 High Similarity NPC200761
0.9145 High Similarity NPC57674
0.9145 High Similarity NPC477503
0.9145 High Similarity NPC152951
0.9139 High Similarity NPC106976
0.9133 High Similarity NPC177308
0.9133 High Similarity NPC124478
0.9108 High Similarity NPC119589
0.9108 High Similarity NPC13481
0.9108 High Similarity NPC207575
0.9097 High Similarity NPC134783
0.9097 High Similarity NPC472632
0.9097 High Similarity NPC474038
0.9097 High Similarity NPC266314
0.9091 High Similarity NPC250214
0.9091 High Similarity NPC95936
0.9085 High Similarity NPC472626
0.9085 High Similarity NPC470328
0.9085 High Similarity NPC209614
0.9079 High Similarity NPC33051
0.9079 High Similarity NPC70433
0.9079 High Similarity NPC246328
0.9079 High Similarity NPC74924
0.9079 High Similarity NPC227337
0.9079 High Similarity NPC18727
0.9079 High Similarity NPC27532
0.9079 High Similarity NPC298692
0.9079 High Similarity NPC325028
0.9079 High Similarity NPC273462
0.9079 High Similarity NPC49402
0.9079 High Similarity NPC256346
0.9073 High Similarity NPC256406
0.9067 High Similarity NPC1612
0.9067 High Similarity NPC183959
0.9067 High Similarity NPC38545
0.9067 High Similarity NPC171916
0.9048 High Similarity NPC121573
0.9048 High Similarity NPC190587
0.9048 High Similarity NPC22176
0.9048 High Similarity NPC226738
0.9045 High Similarity NPC108433
0.9045 High Similarity NPC472277
0.9045 High Similarity NPC165720
0.9045 High Similarity NPC300053
0.9032 High Similarity NPC36217
0.9032 High Similarity NPC118256
0.9032 High Similarity NPC174953
0.9032 High Similarity NPC192686
0.9032 High Similarity NPC328102
0.9032 High Similarity NPC475784
0.9032 High Similarity NPC321399
0.9032 High Similarity NPC119209
0.9032 High Similarity NPC472624
0.9026 High Similarity NPC471209
0.9026 High Similarity NPC99597
0.9026 High Similarity NPC36852
0.9026 High Similarity NPC474836
0.9026 High Similarity NPC299520
0.9026 High Similarity NPC475267
0.9026 High Similarity NPC129684
0.9026 High Similarity NPC156057
0.9026 High Similarity NPC474208
0.9026 High Similarity NPC162869
0.9026 High Similarity NPC48208
0.9026 High Similarity NPC210084
0.9026 High Similarity NPC223787
0.9026 High Similarity NPC262286
0.9026 High Similarity NPC78225
0.9026 High Similarity NPC52530
0.902 High Similarity NPC39184
0.902 High Similarity NPC256925
0.902 High Similarity NPC226025
0.902 High Similarity NPC113906
0.902 High Similarity NPC134287
0.902 High Similarity NPC130589
0.9013 High Similarity NPC61506
0.9013 High Similarity NPC246162
0.9013 High Similarity NPC36835
0.9013 High Similarity NPC240476
0.9013 High Similarity NPC260491
0.9013 High Similarity NPC257648
0.9013 High Similarity NPC219582
0.9013 High Similarity NPC302950
0.9013 High Similarity NPC19721
0.9013 High Similarity NPC477231
0.9013 High Similarity NPC236637
0.9013 High Similarity NPC9743
0.9007 High Similarity NPC472279
0.9 High Similarity NPC188679
0.9 High Similarity NPC81332
0.9 High Similarity NPC203077
0.9 High Similarity NPC166036
0.9 High Similarity NPC262580
0.9 High Similarity NPC289396
0.9 High Similarity NPC321011
0.9 High Similarity NPC294852
0.9 High Similarity NPC212038
0.9 High Similarity NPC271848
0.9 High Similarity NPC238279
0.8987 High Similarity NPC471213
0.8981 High Similarity NPC205265
0.8981 High Similarity NPC472281
0.8981 High Similarity NPC472625
0.8981 High Similarity NPC18100
0.8981 High Similarity NPC88043
0.8974 High Similarity NPC471212
0.8974 High Similarity NPC471210
0.8974 High Similarity NPC158188
0.8974 High Similarity NPC308992
0.8974 High Similarity NPC471211
0.8968 High Similarity NPC204879
0.8968 High Similarity NPC210459
0.8968 High Similarity NPC473990
0.8961 High Similarity NPC471500
0.8961 High Similarity NPC472916
0.8961 High Similarity NPC201837
0.8961 High Similarity NPC474638
0.8961 High Similarity NPC78492
0.8961 High Similarity NPC255106
0.8961 High Similarity NPC472455
0.8961 High Similarity NPC208152
0.8961 High Similarity NPC138243
0.8961 High Similarity NPC250922
0.8961 High Similarity NPC191146
0.8961 High Similarity NPC13858
0.8961 High Similarity NPC68093
0.8961 High Similarity NPC320825
0.8961 High Similarity NPC235165
0.8961 High Similarity NPC326037
0.8954 High Similarity NPC250557
0.8954 High Similarity NPC124714
0.8954 High Similarity NPC141212
0.8947 High Similarity NPC209846
0.8947 High Similarity NPC477897
0.8947 High Similarity NPC263384
0.8947 High Similarity NPC289774
0.8947 High Similarity NPC471676
0.8947 High Similarity NPC244577
0.8947 High Similarity NPC204515
0.8947 High Similarity NPC472420
0.8947 High Similarity NPC31363
0.8947 High Similarity NPC472422
0.8947 High Similarity NPC328740
0.894 High Similarity NPC139293
0.894 High Similarity NPC142876
0.894 High Similarity NPC333691
0.894 High Similarity NPC40290
0.894 High Similarity NPC105512
0.894 High Similarity NPC264550
0.894 High Similarity NPC195763
0.894 High Similarity NPC264289
0.894 High Similarity NPC69430
0.894 High Similarity NPC200060
0.8933 High Similarity NPC476463
0.8933 High Similarity NPC188074
0.8933 High Similarity NPC95864
0.8933 High Similarity NPC125449
0.8931 High Similarity NPC243877

  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 NPC227485 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
0.9205 High Similarity NPD2393 Clinical (unspecified phase)
0.9133 High Similarity NPD4380 Phase 2
0.9013 High Similarity NPD1934 Approved
0.8812 High Similarity NPD3818 Discontinued
0.8805 High Similarity NPD6167 Clinical (unspecified phase)
0.8805 High Similarity NPD6166 Phase 2
0.8805 High Similarity NPD6168 Clinical (unspecified phase)
0.8718 High Similarity NPD4868 Clinical (unspecified phase)
0.871 High Similarity NPD2801 Approved
0.8681 High Similarity NPD943 Approved
0.8609 High Similarity NPD1511 Approved
0.8599 High Similarity NPD3882 Suspended
0.8589 High Similarity NPD7074 Phase 3
0.8544 High Similarity NPD7075 Discontinued
0.8544 High Similarity NPD4381 Clinical (unspecified phase)
0.8528 High Similarity NPD7054 Approved
0.8497 Intermediate Similarity NPD1512 Approved
0.8476 Intermediate Similarity NPD7472 Approved
0.8438 Intermediate Similarity NPD5494 Approved
0.8434 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8424 Intermediate Similarity NPD6797 Phase 2
0.84 Intermediate Similarity NPD1549 Phase 2
0.8373 Intermediate Similarity NPD7251 Discontinued
0.8354 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD6232 Discontinued
0.8333 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8322 Intermediate Similarity NPD1510 Phase 2
0.8313 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8312 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8302 Intermediate Similarity NPD3817 Phase 2
0.8293 Intermediate Similarity NPD7473 Discontinued
0.8291 Intermediate Similarity NPD6801 Discontinued
0.8243 Intermediate Similarity NPD230 Phase 1
0.8239 Intermediate Similarity NPD7819 Suspended
0.8235 Intermediate Similarity NPD6190 Approved
0.8214 Intermediate Similarity NPD7808 Phase 3
0.8193 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8187 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8155 Intermediate Similarity NPD6559 Discontinued
0.8113 Intermediate Similarity NPD7411 Suspended
0.8084 Intermediate Similarity NPD5844 Phase 1
0.8079 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.8077 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8075 Intermediate Similarity NPD5402 Approved
0.8054 Intermediate Similarity NPD1240 Approved
0.8049 Intermediate Similarity NPD6959 Discontinued
0.8026 Intermediate Similarity NPD2796 Approved
0.8012 Intermediate Similarity NPD1465 Phase 2
0.7961 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7947 Intermediate Similarity NPD1607 Approved
0.7933 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7933 Intermediate Similarity NPD1613 Approved
0.7898 Intermediate Similarity NPD6799 Approved
0.7862 Intermediate Similarity NPD5403 Approved
0.7816 Intermediate Similarity NPD8150 Discontinued
0.7798 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7792 Intermediate Similarity NPD2935 Discontinued
0.7785 Intermediate Similarity NPD7390 Discontinued
0.774 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7736 Intermediate Similarity NPD5401 Approved
0.7736 Intermediate Similarity NPD2533 Approved
0.7736 Intermediate Similarity NPD2532 Approved
0.7736 Intermediate Similarity NPD2534 Approved
0.7736 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7733 Intermediate Similarity NPD3027 Phase 3
0.7727 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7725 Intermediate Similarity NPD1247 Approved
0.7716 Intermediate Similarity NPD6599 Discontinued
0.7667 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.764 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7633 Intermediate Similarity NPD3926 Phase 2
0.7628 Intermediate Similarity NPD7266 Discontinued
0.7619 Intermediate Similarity NPD9269 Phase 2
0.7605 Intermediate Similarity NPD6234 Discontinued
0.7605 Intermediate Similarity NPD919 Approved
0.76 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.759 Intermediate Similarity NPD7768 Phase 2
0.758 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7557 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7556 Intermediate Similarity NPD6534 Approved
0.7556 Intermediate Similarity NPD6535 Approved
0.7545 Intermediate Similarity NPD3749 Approved
0.7543 Intermediate Similarity NPD8313 Approved
0.7543 Intermediate Similarity NPD8312 Approved
0.7541 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD2800 Approved
0.7515 Intermediate Similarity NPD37 Approved
0.75 Intermediate Similarity NPD7228 Approved
0.75 Intermediate Similarity NPD3751 Discontinued
0.7485 Intermediate Similarity NPD4965 Approved
0.7485 Intermediate Similarity NPD4966 Approved
0.7485 Intermediate Similarity NPD4967 Phase 2
0.7485 Intermediate Similarity NPD1653 Approved
0.7484 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD3750 Approved
0.7484 Intermediate Similarity NPD6651 Approved
0.7484 Intermediate Similarity NPD4628 Phase 3
0.7471 Intermediate Similarity NPD5953 Discontinued
0.7467 Intermediate Similarity NPD1470 Approved
0.7452 Intermediate Similarity NPD1551 Phase 2
0.7446 Intermediate Similarity NPD6778 Approved
0.7446 Intermediate Similarity NPD6780 Approved
0.7446 Intermediate Similarity NPD6782 Approved
0.7446 Intermediate Similarity NPD6781 Approved
0.7446 Intermediate Similarity NPD6776 Approved
0.7446 Intermediate Similarity NPD6777 Approved
0.7446 Intermediate Similarity NPD6779 Approved
0.7439 Intermediate Similarity NPD3226 Approved
0.7432 Intermediate Similarity NPD7699 Phase 2
0.7432 Intermediate Similarity NPD7700 Phase 2
0.7429 Intermediate Similarity NPD7685 Pre-registration
0.7423 Intermediate Similarity NPD920 Approved
0.7407 Intermediate Similarity NPD8151 Discontinued
0.7407 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD9494 Approved
0.7368 Intermediate Similarity NPD3787 Discontinued
0.7356 Intermediate Similarity NPD7286 Phase 2
0.7347 Intermediate Similarity NPD9268 Approved
0.7342 Intermediate Similarity NPD5404 Approved
0.7342 Intermediate Similarity NPD5405 Approved
0.7342 Intermediate Similarity NPD5406 Approved
0.7342 Intermediate Similarity NPD5408 Approved
0.7338 Intermediate Similarity NPD2313 Discontinued
0.7326 Intermediate Similarity NPD7435 Discontinued
0.7315 Intermediate Similarity NPD1201 Approved
0.731 Intermediate Similarity NPD7199 Phase 2
0.7308 Intermediate Similarity NPD6212 Phase 3
0.7308 Intermediate Similarity NPD6213 Phase 3
0.7308 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD447 Suspended
0.7296 Intermediate Similarity NPD2346 Discontinued
0.7288 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7287 Intermediate Similarity NPD8319 Approved
0.7287 Intermediate Similarity NPD8320 Phase 1
0.7284 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD2799 Discontinued
0.7267 Intermediate Similarity NPD5710 Approved
0.7267 Intermediate Similarity NPD5711 Approved
0.7239 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7234 Intermediate Similarity NPD7697 Approved
0.7234 Intermediate Similarity NPD7696 Phase 3
0.7234 Intermediate Similarity NPD7698 Approved
0.7226 Intermediate Similarity NPD3764 Approved
0.7226 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD8434 Phase 2
0.7219 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD7584 Approved
0.7205 Intermediate Similarity NPD1243 Approved
0.72 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7196 Intermediate Similarity NPD7870 Phase 2
0.7196 Intermediate Similarity NPD7871 Phase 2
0.7188 Intermediate Similarity NPD2344 Approved
0.7181 Intermediate Similarity NPD6823 Phase 2
0.7174 Intermediate Similarity NPD4363 Phase 3
0.7174 Intermediate Similarity NPD4360 Phase 2
0.7173 Intermediate Similarity NPD7701 Phase 2
0.717 Intermediate Similarity NPD3748 Approved
0.7162 Intermediate Similarity NPD9545 Approved
0.716 Intermediate Similarity NPD8166 Discontinued
0.7126 Intermediate Similarity NPD3455 Phase 2
0.7126 Intermediate Similarity NPD5242 Approved
0.7126 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7126 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD6099 Approved
0.7125 Intermediate Similarity NPD6100 Approved
0.7124 Intermediate Similarity NPD1164 Approved
0.7118 Intermediate Similarity NPD5353 Approved
0.7115 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7098 Intermediate Similarity NPD7874 Approved
0.7098 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7089 Intermediate Similarity NPD1933 Approved
0.7062 Intermediate Similarity NPD7801 Approved
0.7059 Intermediate Similarity NPD8455 Phase 2
0.7055 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7039 Intermediate Similarity NPD7240 Approved
0.7037 Intermediate Similarity NPD2424 Discontinued
0.7027 Intermediate Similarity NPD9493 Approved
0.7024 Intermediate Similarity NPD7458 Discontinued
0.7013 Intermediate Similarity NPD1203 Approved
0.7012 Intermediate Similarity NPD2309 Approved
0.7 Intermediate Similarity NPD6844 Discontinued
0.6987 Remote Similarity NPD6832 Phase 2
0.6987 Remote Similarity NPD4908 Phase 1
0.6979 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6975 Remote Similarity NPD2029 Clinical (unspecified phase)
0.6974 Remote Similarity NPD7782 Clinical (unspecified phase)
0.6974 Remote Similarity NPD1610 Phase 2
0.6974 Remote Similarity NPD7783 Phase 2
0.697 Remote Similarity NPD3300 Phase 2
0.6968 Remote Similarity NPD2798 Approved
0.6957 Remote Similarity NPD7033 Discontinued
0.6941 Remote Similarity NPD6385 Approved
0.6941 Remote Similarity NPD6386 Approved
0.6913 Remote Similarity NPD405 Clinical (unspecified phase)
0.6889 Remote Similarity NPD3823 Discontinued

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data