Structure

Physi-Chem Properties

Molecular Weight:  436.1
Volume:  398.488
LogP:  0.345
LogD:  -0.021
LogS:  -3.505
# Rotatable Bonds:  3
TPSA:  190.28
# H-Bond Aceptor:  11
# H-Bond Donor:  7
# Rings:  4
# Heavy Atoms:  11

MedChem Properties

QED Drug-Likeness Score:  0.209
Synthetic Accessibility Score:  4.048
Fsp3:  0.35
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -6.259
MDCK Permeability:  6.142502570583019e-06
Pgp-inhibitor:  0.011
Pgp-substrate:  0.995
Human Intestinal Absorption (HIA):  0.913
20% Bioavailability (F20%):  0.092
30% Bioavailability (F30%):  0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.038
Plasma Protein Binding (PPB):  81.8006591796875%
Volume Distribution (VD):  0.967
Pgp-substrate:  25.316051483154297%

ADMET: Metabolism

CYP1A2-inhibitor:  0.102
CYP1A2-substrate:  0.133
CYP2C19-inhibitor:  0.014
CYP2C19-substrate:  0.063
CYP2C9-inhibitor:  0.013
CYP2C9-substrate:  0.359
CYP2D6-inhibitor:  0.02
CYP2D6-substrate:  0.176
CYP3A4-inhibitor:  0.022
CYP3A4-substrate:  0.014

ADMET: Excretion

Clearance (CL):  4.213
Half-life (T1/2):  0.83

ADMET: Toxicity

hERG Blockers:  0.074
Human Hepatotoxicity (H-HT):  0.159
Drug-inuced Liver Injury (DILI):  0.964
AMES Toxicity:  0.713
Rat Oral Acute Toxicity:  0.028
Maximum Recommended Daily Dose:  0.028
Skin Sensitization:  0.856
Carcinogencity:  0.021
Eye Corrosion:  0.003
Eye Irritation:  0.288
Respiratory Toxicity:  0.044

Download Data

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Similar NPs/Drugs  

  Natural Product: NPC220912

Natural Product ID:  NPC220912
Common Name*:   Mangiferin Methyl Ether
IUPAC Name:   1,6,7-trihydroxy-3-methoxy-2-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]xanthen-9-one
Synonyms:  
Standard InCHIKey:  HDPSXKXQSOVYLL-PQSJUMPYSA-N
Standard InCHI:  InChI=1S/C20H20O11/c1-29-10-4-11-13(15(24)6-2-7(22)8(23)3-9(6)30-11)17(26)14(10)20-19(28)18(27)16(25)12(5-21)31-20/h2-4,12,16,18-23,25-28H,5H2,1H3/t12-,16-,18+,19-,20+/m1/s1
SMILES:  COc1cc2c(c(=O)c3cc(c(cc3o2)O)O)c(c1[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3233510
PubChem CID:   5491388
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
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]
NPO29381 Trichilia rubescens Species Meliaceae Eukaryota leaves Kibale National Park, Uganda 2000-2001 PMID[19299148]
NPO28864 Nauclea officinalis Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO33051 mango tree n.a. n.a. n.a. stem bark n.a. n.a. PMID[24613627]
NPO27743 Aaptos aaptos Species Suberitidae Eukaryota n.a. South China Sea n.a. PMID[25211032]
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]
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]
NPO29314 Mangifera indica Species Anacardiaceae Eukaryota Flower 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]
NPO29530 Kaempferia marginata Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29344 Parabenzoin trilobum n.a. n.a. n.a. 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
NPT3084 Individual Protein Neuraminidase Influenza A virus Inhibition = 27.7 % PMID[547104]
NPT24971 SINGLE PROTEIN Genome polyprotein Coxsackievirus B3 (strain Nancy) Inhibition = 13.3 % PMID[547104]

☑ 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 NPC220912 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
0.9935 High Similarity NPC228383
0.9551 High Similarity NPC134783
0.9497 High Similarity NPC477154
0.9497 High Similarity NPC6588
0.9497 High Similarity NPC117854
0.9497 High Similarity NPC14662
0.9494 High Similarity NPC50960
0.949 High Similarity NPC474034
0.949 High Similarity NPC474033
0.9487 High Similarity NPC174953
0.9487 High Similarity NPC471976
0.9484 High Similarity NPC223787
0.9484 High Similarity NPC36852
0.9484 High Similarity NPC262286
0.9481 High Similarity NPC113906
0.9441 High Similarity NPC271848
0.9441 High Similarity NPC81332
0.9441 High Similarity NPC262580
0.9441 High Similarity NPC289396
0.9441 High Similarity NPC212038
0.9437 High Similarity NPC326877
0.9437 High Similarity NPC183036
0.9434 High Similarity NPC207575
0.9434 High Similarity NPC13481
0.9427 High Similarity NPC471211
0.9427 High Similarity NPC26326
0.9427 High Similarity NPC266314
0.9427 High Similarity NPC3629
0.9427 High Similarity NPC471212
0.9427 High Similarity NPC472632
0.9427 High Similarity NPC142252
0.9423 High Similarity NPC250214
0.9423 High Similarity NPC117418
0.9423 High Similarity NPC95936
0.9423 High Similarity NPC53545
0.9423 High Similarity NPC473990
0.9419 High Similarity NPC138243
0.9379 High Similarity NPC103307
0.9379 High Similarity NPC74559
0.9379 High Similarity NPC474434
0.9375 High Similarity NPC243877
0.9371 High Similarity NPC470457
0.9367 High Similarity NPC261470
0.9367 High Similarity NPC81679
0.9367 High Similarity NPC472448
0.9367 High Similarity NPC476247
0.9367 High Similarity NPC83922
0.9363 High Similarity NPC472630
0.9363 High Similarity NPC472631
0.9363 High Similarity NPC470326
0.9359 High Similarity NPC210084
0.9359 High Similarity NPC475267
0.9359 High Similarity NPC78103
0.9359 High Similarity NPC474208
0.9359 High Similarity NPC474055
0.9359 High Similarity NPC291508
0.9359 High Similarity NPC471209
0.9359 High Similarity NPC99597
0.9359 High Similarity NPC162869
0.9359 High Similarity NPC156057
0.9359 High Similarity NPC474836
0.9359 High Similarity NPC472598
0.9359 High Similarity NPC78225
0.9359 High Similarity NPC48208
0.9355 High Similarity NPC477503
0.9355 High Similarity NPC45849
0.9355 High Similarity NPC470327
0.9355 High Similarity NPC200761
0.9355 High Similarity NPC321779
0.9351 High Similarity NPC106976
0.9321 High Similarity NPC121333
0.9317 High Similarity NPC242395
0.9317 High Similarity NPC177480
0.9317 High Similarity NPC95855
0.9317 High Similarity NPC210042
0.9313 High Similarity NPC471213
0.9313 High Similarity NPC128293
0.9308 High Similarity NPC248638
0.9308 High Similarity NPC473313
0.9308 High Similarity NPC470459
0.9308 High Similarity NPC124038
0.9308 High Similarity NPC273959
0.9308 High Similarity NPC7483
0.9308 High Similarity NPC236521
0.9308 High Similarity NPC152659
0.9308 High Similarity NPC472278
0.9308 High Similarity NPC329669
0.9308 High Similarity NPC41301
0.9304 High Similarity NPC289771
0.9304 High Similarity NPC29876
0.9304 High Similarity NPC474038
0.9304 High Similarity NPC167678
0.9304 High Similarity NPC198829
0.9304 High Similarity NPC472634
0.9304 High Similarity NPC471499
0.9304 High Similarity NPC308992
0.9304 High Similarity NPC471210
0.9299 High Similarity NPC469658
0.9299 High Similarity NPC329091
0.9299 High Similarity NPC22192
0.9295 High Similarity NPC195796
0.9295 High Similarity NPC209614
0.9295 High Similarity NPC68093
0.9295 High Similarity NPC472916
0.9295 High Similarity NPC291878
0.9295 High Similarity NPC191146
0.9295 High Similarity NPC470328
0.9295 High Similarity NPC255106
0.9295 High Similarity NPC235165
0.9295 High Similarity NPC472626
0.9295 High Similarity NPC35038
0.9295 High Similarity NPC278778
0.9295 High Similarity NPC470600
0.929 High Similarity NPC192083
0.929 High Similarity NPC298692
0.929 High Similarity NPC74924
0.929 High Similarity NPC213896
0.9286 High Similarity NPC171010
0.9273 High Similarity NPC185275
0.9259 High Similarity NPC224462
0.9259 High Similarity NPC22195
0.9259 High Similarity NPC34287
0.9259 High Similarity NPC472276
0.9259 High Similarity NPC21190
0.9259 High Similarity NPC44558
0.9259 High Similarity NPC471416
0.9259 High Similarity NPC183357
0.9255 High Similarity NPC8965
0.9255 High Similarity NPC474024
0.9255 High Similarity NPC260266
0.9255 High Similarity NPC158761
0.9255 High Similarity NPC477502
0.9255 High Similarity NPC93099
0.9255 High Similarity NPC470456
0.925 High Similarity NPC234052
0.925 High Similarity NPC224280
0.925 High Similarity NPC326520
0.925 High Similarity NPC62261
0.925 High Similarity NPC471788
0.9245 High Similarity NPC472635
0.9245 High Similarity NPC25152
0.9241 High Similarity NPC192686
0.9241 High Similarity NPC475784
0.9241 High Similarity NPC14353
0.9241 High Similarity NPC118256
0.9241 High Similarity NPC228785
0.9241 High Similarity NPC263449
0.9241 High Similarity NPC476980
0.9241 High Similarity NPC119209
0.9241 High Similarity NPC282009
0.9241 High Similarity NPC56085
0.9241 High Similarity NPC204290
0.9241 High Similarity NPC287328
0.9236 High Similarity NPC222814
0.9236 High Similarity NPC472910
0.9236 High Similarity NPC245758
0.9236 High Similarity NPC470402
0.9236 High Similarity NPC469584
0.9236 High Similarity NPC27337
0.9236 High Similarity NPC52889
0.9236 High Similarity NPC472911
0.9236 High Similarity NPC96167
0.9236 High Similarity NPC472914
0.9236 High Similarity NPC472913
0.9236 High Similarity NPC79053
0.9231 High Similarity NPC230149
0.9231 High Similarity NPC134287
0.9231 High Similarity NPC117992
0.9231 High Similarity NPC168247
0.9231 High Similarity NPC256925
0.9231 High Similarity NPC208197
0.9231 High Similarity NPC152951
0.9231 High Similarity NPC130589
0.9231 High Similarity NPC37392
0.9231 High Similarity NPC57674
0.9231 High Similarity NPC2928
0.9226 High Similarity NPC161277
0.9226 High Similarity NPC39007
0.9226 High Similarity NPC101996
0.9212 High Similarity NPC265380
0.9212 High Similarity NPC471789
0.9202 High Similarity NPC307518
0.9202 High Similarity NPC301683
0.9202 High Similarity NPC48773
0.9202 High Similarity NPC205076
0.9198 High Similarity NPC112755
0.9198 High Similarity NPC229687
0.9198 High Similarity NPC170675
0.9198 High Similarity NPC471457
0.9198 High Similarity NPC472381
0.9198 High Similarity NPC472383
0.9198 High Similarity NPC152477
0.9193 High Similarity NPC170245
0.9193 High Similarity NPC119589
0.9193 High Similarity NPC120593
0.9193 High Similarity NPC173292
0.9193 High Similarity NPC470462
0.9187 High Similarity NPC306321
0.9187 High Similarity NPC18100
0.9187 High Similarity NPC472625

  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 NPC220912 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
0.929 High Similarity NPD2393 Clinical (unspecified phase)
0.913 High Similarity NPD6168 Clinical (unspecified phase)
0.913 High Similarity NPD6166 Phase 2
0.913 High Similarity NPD6167 Clinical (unspecified phase)
0.9103 High Similarity NPD1934 Approved
0.9045 High Similarity NPD2801 Approved
0.9 High Similarity NPD5494 Approved
0.8974 High Similarity NPD4380 Phase 2
0.8931 High Similarity NPD4868 Clinical (unspecified phase)
0.8909 High Similarity NPD7074 Phase 3
0.8848 High Similarity NPD7054 Approved
0.8795 High Similarity NPD7472 Approved
0.8788 High Similarity NPD3818 Discontinued
0.875 High Similarity NPD4338 Clinical (unspecified phase)
0.8743 High Similarity NPD6797 Phase 2
0.8696 High Similarity NPD3882 Suspended
0.869 High Similarity NPD7251 Discontinued
0.8642 High Similarity NPD7075 Discontinued
0.8642 High Similarity NPD4381 Clinical (unspecified phase)
0.8631 High Similarity NPD7993 Clinical (unspecified phase)
0.8598 High Similarity NPD6959 Discontinued
0.859 High Similarity NPD1511 Approved
0.8529 High Similarity NPD7808 Phase 3
0.8512 High Similarity NPD7804 Clinical (unspecified phase)
0.8512 High Similarity NPD5844 Phase 1
0.8509 High Similarity NPD6801 Discontinued
0.8481 Intermediate Similarity NPD1512 Approved
0.8457 Intermediate Similarity NPD1465 Phase 2
0.8457 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8418 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8405 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8405 Intermediate Similarity NPD5402 Approved
0.8405 Intermediate Similarity NPD3817 Phase 2
0.8387 Intermediate Similarity NPD1549 Phase 2
0.8344 Intermediate Similarity NPD7819 Suspended
0.8333 Intermediate Similarity NPD7411 Suspended
0.8323 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8323 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8302 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8256 Intermediate Similarity NPD6559 Discontinued
0.8214 Intermediate Similarity NPD6232 Discontinued
0.8176 Intermediate Similarity NPD7473 Discontinued
0.8141 Intermediate Similarity NPD2796 Approved
0.8077 Intermediate Similarity NPD1510 Phase 2
0.8047 Intermediate Similarity NPD1247 Approved
0.8012 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8012 Intermediate Similarity NPD6799 Approved
0.7975 Intermediate Similarity NPD5403 Approved
0.7944 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7935 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7935 Intermediate Similarity NPD1613 Approved
0.7935 Intermediate Similarity NPD943 Approved
0.7935 Intermediate Similarity NPD1240 Approved
0.7933 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7911 Intermediate Similarity NPD2935 Discontinued
0.7875 Intermediate Similarity NPD2800 Approved
0.7853 Intermediate Similarity NPD5401 Approved
0.7834 Intermediate Similarity NPD1607 Approved
0.7831 Intermediate Similarity NPD6599 Discontinued
0.7811 Intermediate Similarity NPD7768 Phase 2
0.7771 Intermediate Similarity NPD230 Phase 1
0.7753 Intermediate Similarity NPD8312 Approved
0.7753 Intermediate Similarity NPD8313 Approved
0.7746 Intermediate Similarity NPD3926 Phase 2
0.7744 Intermediate Similarity NPD2533 Approved
0.7744 Intermediate Similarity NPD2532 Approved
0.7744 Intermediate Similarity NPD2534 Approved
0.7727 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7719 Intermediate Similarity NPD919 Approved
0.7714 Intermediate Similarity NPD7228 Approved
0.7714 Intermediate Similarity NPD3751 Discontinued
0.7711 Intermediate Similarity NPD1653 Approved
0.7677 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7669 Intermediate Similarity NPD6190 Approved
0.7667 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7661 Intermediate Similarity NPD3749 Approved
0.7654 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7651 Intermediate Similarity NPD920 Approved
0.7647 Intermediate Similarity NPD6777 Approved
0.7647 Intermediate Similarity NPD6781 Approved
0.7647 Intermediate Similarity NPD6778 Approved
0.7647 Intermediate Similarity NPD6779 Approved
0.7647 Intermediate Similarity NPD6776 Approved
0.7647 Intermediate Similarity NPD6782 Approved
0.7647 Intermediate Similarity NPD6780 Approved
0.7647 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7628 Intermediate Similarity NPD3027 Phase 3
0.7616 Intermediate Similarity NPD6234 Discontinued
0.761 Intermediate Similarity NPD6651 Approved
0.7607 Intermediate Similarity NPD3750 Approved
0.7607 Intermediate Similarity NPD4628 Phase 3
0.7604 Intermediate Similarity NPD8151 Discontinued
0.7593 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7586 Intermediate Similarity NPD3787 Discontinued
0.7584 Intermediate Similarity NPD5953 Discontinued
0.7571 Intermediate Similarity NPD7286 Phase 2
0.756 Intermediate Similarity NPD3226 Approved
0.7545 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7529 Intermediate Similarity NPD37 Approved
0.7527 Intermediate Similarity NPD8150 Discontinued
0.7526 Intermediate Similarity NPD7696 Phase 3
0.7526 Intermediate Similarity NPD7697 Approved
0.7526 Intermediate Similarity NPD7698 Approved
0.7526 Intermediate Similarity NPD7435 Discontinued
0.7516 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD4966 Approved
0.75 Intermediate Similarity NPD4965 Approved
0.75 Intermediate Similarity NPD4967 Phase 2
0.7487 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.747 Intermediate Similarity NPD7390 Discontinued
0.7469 Intermediate Similarity NPD1551 Phase 2
0.7461 Intermediate Similarity NPD7701 Phase 2
0.7444 Intermediate Similarity NPD7685 Pre-registration
0.7439 Intermediate Similarity NPD1243 Approved
0.7438 Intermediate Similarity NPD447 Suspended
0.7436 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD7783 Phase 2
0.7432 Intermediate Similarity NPD8434 Phase 2
0.7429 Intermediate Similarity NPD7199 Phase 2
0.7427 Intermediate Similarity NPD6844 Discontinued
0.7425 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7425 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD2346 Discontinued
0.7409 Intermediate Similarity NPD7584 Approved
0.7407 Intermediate Similarity NPD2799 Discontinued
0.7407 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7396 Intermediate Similarity NPD7870 Phase 2
0.7396 Intermediate Similarity NPD7871 Phase 2
0.7394 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7382 Intermediate Similarity NPD6823 Phase 2
0.738 Intermediate Similarity NPD6534 Approved
0.738 Intermediate Similarity NPD4363 Phase 3
0.738 Intermediate Similarity NPD4360 Phase 2
0.738 Intermediate Similarity NPD6535 Approved
0.7362 Intermediate Similarity NPD6099 Approved
0.7362 Intermediate Similarity NPD6100 Approved
0.7358 Intermediate Similarity NPD2313 Discontinued
0.7358 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7354 Intermediate Similarity NPD7700 Phase 2
0.7354 Intermediate Similarity NPD7699 Phase 2
0.7317 Intermediate Similarity NPD7266 Discontinued
0.7317 Intermediate Similarity NPD2344 Approved
0.7305 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7301 Intermediate Similarity NPD3748 Approved
0.7296 Intermediate Similarity NPD7874 Approved
0.7296 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7289 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7288 Intermediate Similarity NPD5710 Approved
0.7288 Intermediate Similarity NPD5711 Approved
0.7283 Intermediate Similarity NPD8455 Phase 2
0.7278 Intermediate Similarity NPD9494 Approved
0.7259 Intermediate Similarity NPD7801 Approved
0.7253 Intermediate Similarity NPD7240 Approved
0.7251 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7247 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7233 Intermediate Similarity NPD4908 Phase 1
0.7226 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD1933 Approved
0.7219 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7169 Intermediate Similarity NPD2424 Discontinued
0.7168 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD6212 Phase 3
0.7143 Intermediate Similarity NPD5353 Approved
0.7143 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD2309 Approved
0.7143 Intermediate Similarity NPD6213 Phase 3
0.7134 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD6832 Phase 2
0.7117 Intermediate Similarity NPD5124 Phase 1
0.7117 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD7033 Discontinued
0.707 Intermediate Similarity NPD9269 Phase 2
0.7063 Intermediate Similarity NPD2861 Phase 2
0.7056 Intermediate Similarity NPD5242 Approved
0.7052 Intermediate Similarity NPD7458 Discontinued
0.7044 Intermediate Similarity NPD1203 Approved
0.7041 Intermediate Similarity NPD8319 Approved
0.7041 Intermediate Similarity NPD8320 Phase 1
0.7039 Intermediate Similarity NPD8127 Discontinued
0.702 Intermediate Similarity NPD7585 Approved
0.7017 Intermediate Similarity NPD2403 Approved
0.7012 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD3823 Discontinued
0.7006 Intermediate Similarity NPD1610 Phase 2
0.7 Intermediate Similarity NPD7229 Phase 3
0.6994 Remote Similarity NPD6233 Phase 2
0.6979 Remote Similarity NPD4361 Phase 2
0.6979 Remote Similarity NPD4362 Clinical (unspecified phase)
0.6975 Remote Similarity NPD4625 Phase 3
0.697 Remote Similarity NPD7583 Approved
0.6959 Remote Similarity NPD7237 Clinical (unspecified phase)
0.6957 Remote Similarity NPD1729 Discontinued
0.6942 Remote Similarity NPD8155 Clinical (unspecified phase)
0.6942 Remote Similarity NPD7907 Approved
0.6935 Remote Similarity NPD7549 Discontinued
0.6933 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6933 Remote Similarity NPD6798 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