Structure

Physi-Chem Properties

Molecular Weight:  164.08
Volume:  179.994
LogP:  1.12
LogD:  1.197
LogS:  -1.176
# Rotatable Bonds:  3
TPSA:  37.3
# H-Bond Aceptor:  2
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.741
Synthetic Accessibility Score:  1.649
Fsp3:  0.3
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.46
MDCK Permeability:  2.4384778953390196e-05
Pgp-inhibitor:  0.001
Pgp-substrate:  0.545
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.009
30% Bioavailability (F30%):  0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.118
Plasma Protein Binding (PPB):  68.5809097290039%
Volume Distribution (VD):  0.847
Pgp-substrate:  25.46982765197754%

ADMET: Metabolism

CYP1A2-inhibitor:  0.772
CYP1A2-substrate:  0.918
CYP2C19-inhibitor:  0.823
CYP2C19-substrate:  0.482
CYP2C9-inhibitor:  0.263
CYP2C9-substrate:  0.925
CYP2D6-inhibitor:  0.438
CYP2D6-substrate:  0.89
CYP3A4-inhibitor:  0.035
CYP3A4-substrate:  0.305

ADMET: Excretion

Clearance (CL):  14.92
Half-life (T1/2):  0.887

ADMET: Toxicity

hERG Blockers:  0.051
Human Hepatotoxicity (H-HT):  0.145
Drug-inuced Liver Injury (DILI):  0.043
AMES Toxicity:  0.024
Rat Oral Acute Toxicity:  0.107
Maximum Recommended Daily Dose:  0.076
Skin Sensitization:  0.404
Carcinogencity:  0.496
Eye Corrosion:  0.919
Eye Irritation:  0.987
Respiratory Toxicity:  0.026

Download Data

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

  Natural Product: NPC260000

Natural Product ID:  NPC260000
Common Name*:   Raspberryketone
IUPAC Name:   4-(4-hydroxyphenyl)butan-2-one
Synonyms:   Raspberry Ketone; Raspberryketone
Standard InCHIKey:  NJGBTKGETPDVIK-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C10H12O2/c1-8(11)2-3-9-4-6-10(12)7-5-9/h4-7,12H,2-3H2,1H3
SMILES:  CC(=O)CCc1ccc(cc1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL105912
PubChem CID:   21648
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000134] Phenols
        • [CHEMONTID:0004646] 1-hydroxy-2-unsubstituted benzenoids

*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
NPO15003 Streptomyces lydicus Species Streptomycetaceae Bacteria n.a. n.a. n.a. DOI[10.1021/ja107190w]
NPO30634 Acer nikoense Species Sapindaceae Eukaryota n.a. Japan n.a. PMID[12542351]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. whole plant n.a. PMID[16755060]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. aerial part n.a. PMID[17666848]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[18177011]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. aerial part n.a. PMID[18239311]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[19271742]
NPO16422 Teclea gerrardii Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[19299148]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[19785430]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[19962306]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[20078074]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[20590154]
NPO1103 Dioscorea japonica Species Dioscoreaceae Eukaryota rhizomes n.a. n.a. PMID[21353549]
NPO30634 Acer nikoense Species Sapindaceae Eukaryota n.a. n.a. n.a. PMID[21550801]
NPO14409 Dioscorea nipponica Species Dioscoreaceae Eukaryota rhizomes n.a. n.a. PMID[23707257]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota whole plants Nanning District, Guangxi Province, China 2012-Sep PMID[25647077]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota aerial parts Seoul, Korea n.a. PMID[26331882]
NPO16509 Avena sativa Species Poaceae Eukaryota n.a. n.a. n.a. PMID[6705789]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. rhizome n.a. PMID[8064299]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[8064299]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO16509 Avena sativa Species Poaceae Eukaryota n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. Database[FooDB]
NPO16509 Avena sativa Species Poaceae Eukaryota Hay n.a. n.a. Database[FooDB]
NPO16509 Avena sativa Species Poaceae Eukaryota Hull Husk n.a. n.a. Database[FooDB]
NPO16509 Avena sativa Species Poaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO16509 Avena sativa Species Poaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota Resin, Exudate, Sap n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota Rhizome n.a. n.a. Database[FooDB]
NPO16509 Avena sativa Species Poaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO16509 Avena sativa Species Poaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO16509 Avena sativa Species Poaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO16509 Avena sativa Species Poaceae Eukaryota n.a. n.a. Database[FooDB]
NPO1631 Amomum xanthioides Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11820 Amomum villosum Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30634 Acer nikoense Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16509 Avena sativa Species Poaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1103 Dioscorea japonica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1479 Amomum longiligulare Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16750 Salvia castanea Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12120 Thalictrum flavum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14409 Dioscorea nipponica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11820 Amomum villosum Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16750 Salvia castanea Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1479 Amomum longiligulare Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14409 Dioscorea nipponica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1103 Dioscorea japonica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1631 Amomum xanthioides Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16509 Avena sativa Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12120 Thalictrum flavum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13983 Acer maximowiczianum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17351 Tropicoporus linteus Species Hymenochaetaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1631 Amomum xanthioides Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14409 Dioscorea nipponica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16509 Avena sativa Species Poaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1631 Amomum xanthioides Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14409 Dioscorea nipponica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1479 Amomum longiligulare Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11820 Amomum villosum Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20553 Zingiber officinale Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25238 Rheum coreanum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1103 Dioscorea japonica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO17351 Tropicoporus linteus Species Hymenochaetaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13983 Acer maximowiczianum Species Sapindaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16039 Scutellaria barbata Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16509 Avena sativa Species Poaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1631 Amomum xanthioides Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4216 Dalbergia assamica Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1103 Dioscorea japonica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22207 Polyporus pini Species Polyporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15260 Senecio suaveolens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15502 Muscari botryoides Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14409 Dioscorea nipponica Species Dioscoreaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15639 Dasycladus vermicularis Species Dasycladaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7988.1 Fraxinus angustifolia subsp. oxycarpa Subspecies Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28024 Rheum palmatum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12120 Thalictrum flavum Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8435 Hedysarum theinum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16750 Salvia castanea Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11820 Amomum villosum Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13700 Streptomyces nobilis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO25238 Rheum coreanum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9125 Haemanthus amarylloides Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20881 Rheum officinale Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15384 Olearia pimeleoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15003 Streptomyces lydicus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO2318 Stellaria holostea Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16422 Teclea gerrardii Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14543 Mycena sanguinolenta Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13210 Echinops transiliensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7632 Rheum tanguticum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14851 Lantana montevidensis Species Verbenaceae 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
NPT111 Cell Line K562 Homo sapiens IC50 > 100000.0 nM PMID[545228]
NPT153 Individual Protein Androgen Receptor Homo sapiens IC50 = 252000.0 nM PMID[545229]
NPT153 Individual Protein Androgen Receptor Homo sapiens IC50 = 251188.64 nM PMID[545229]
NPT76 Cell Line C6 Rattus norvegicus Activity = 106.8 % PMID[545230]
NPT76 Cell Line C6 Rattus norvegicus Activity = 100.9 % PMID[545230]
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 6164.5 nM PubChem BioAssay data set
NPT29 Organism Rattus norvegicus Rattus norvegicus Drug uptake = 4000.0 ng/ml PMID[545229]
NPT2 Others Unspecified Potency n.a. 2730.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 54482.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 15355.3 nM PubChem BioAssay data set

☑ 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 NPC260000 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
0.9891 High Similarity NPC280869
0.9468 High Similarity NPC245561
0.9368 High Similarity NPC52472
0.9278 High Similarity NPC261573
0.9278 High Similarity NPC120693
0.9278 High Similarity NPC8931
0.9192 High Similarity NPC228737
0.9192 High Similarity NPC226699
0.9184 High Similarity NPC13495
0.91 High Similarity NPC317305
0.9091 High Similarity NPC70843
0.9091 High Similarity NPC69332
0.9091 High Similarity NPC95178
0.9091 High Similarity NPC29989
0.9091 High Similarity NPC188677
0.9091 High Similarity NPC6984
0.9011 High Similarity NPC23167
0.901 High Similarity NPC95172
0.8936 High Similarity NPC181709
0.8913 High Similarity NPC113460
0.8913 High Similarity NPC25493
0.8911 High Similarity NPC31274
0.8901 High Similarity NPC197783
0.8878 High Similarity NPC472585
0.8824 High Similarity NPC88141
0.8817 High Similarity NPC318325
0.8817 High Similarity NPC177420
0.8817 High Similarity NPC242240
0.8817 High Similarity NPC123273
0.8817 High Similarity NPC280347
0.8817 High Similarity NPC258219
0.8812 High Similarity NPC34715
0.8791 High Similarity NPC175313
0.8791 High Similarity NPC248817
0.8788 High Similarity NPC13426
0.8738 High Similarity NPC252544
0.8738 High Similarity NPC21162
0.8738 High Similarity NPC321252
0.8737 High Similarity NPC138117
0.8737 High Similarity NPC325292
0.8725 High Similarity NPC224584
0.8725 High Similarity NPC17525
0.8723 High Similarity NPC300017
0.8723 High Similarity NPC55561
0.8681 High Similarity NPC265146
0.8681 High Similarity NPC124436
0.8667 High Similarity NPC242136
0.8667 High Similarity NPC11824
0.8654 High Similarity NPC177576
0.8654 High Similarity NPC114682
0.8654 High Similarity NPC212718
0.8641 High Similarity NPC326187
0.8632 High Similarity NPC45040
0.8632 High Similarity NPC304541
0.8627 High Similarity NPC141523
0.8602 High Similarity NPC307235
0.8602 High Similarity NPC407
0.8602 High Similarity NPC184169
0.86 High Similarity NPC298224
0.8571 High Similarity NPC17693
0.8571 High Similarity NPC48525
0.8571 High Similarity NPC286222
0.8571 High Similarity NPC231717
0.8558 High Similarity NPC222905
0.8558 High Similarity NPC116842
0.8558 High Similarity NPC222084
0.8557 High Similarity NPC26244
0.8557 High Similarity NPC313650
0.8529 High Similarity NPC317592
0.8515 High Similarity NPC38209
0.8511 High Similarity NPC27974
0.8511 High Similarity NPC104216
0.8505 High Similarity NPC23402
0.8495 Intermediate Similarity NPC155393
0.8491 Intermediate Similarity NPC148969
0.8476 Intermediate Similarity NPC268388
0.8469 Intermediate Similarity NPC473388
0.8462 Intermediate Similarity NPC234639
0.8454 Intermediate Similarity NPC316301
0.8454 Intermediate Similarity NPC81010
0.8454 Intermediate Similarity NPC151715
0.8454 Intermediate Similarity NPC32977
0.8454 Intermediate Similarity NPC128062
0.8454 Intermediate Similarity NPC27323
0.8438 Intermediate Similarity NPC270547
0.8438 Intermediate Similarity NPC204210
0.8438 Intermediate Similarity NPC155908
0.8426 Intermediate Similarity NPC28951
0.8426 Intermediate Similarity NPC325646
0.8426 Intermediate Similarity NPC19290
0.8421 Intermediate Similarity NPC98772
0.8416 Intermediate Similarity NPC68269
0.8416 Intermediate Similarity NPC135784
0.8411 Intermediate Similarity NPC285350
0.8387 Intermediate Similarity NPC286904
0.8384 Intermediate Similarity NPC201967
0.8367 Intermediate Similarity NPC274678
0.8367 Intermediate Similarity NPC286006
0.8367 Intermediate Similarity NPC8392
0.8349 Intermediate Similarity NPC150919
0.8333 Intermediate Similarity NPC300478
0.8333 Intermediate Similarity NPC322197
0.8318 Intermediate Similarity NPC309808
0.83 Intermediate Similarity NPC171843
0.83 Intermediate Similarity NPC80027
0.83 Intermediate Similarity NPC130193
0.83 Intermediate Similarity NPC128723
0.83 Intermediate Similarity NPC92730
0.8269 Intermediate Similarity NPC29883
0.8257 Intermediate Similarity NPC299252
0.8257 Intermediate Similarity NPC277394
0.8257 Intermediate Similarity NPC61062
0.8252 Intermediate Similarity NPC303141
0.8252 Intermediate Similarity NPC219913
0.8247 Intermediate Similarity NPC306074
0.8241 Intermediate Similarity NPC118288
0.8241 Intermediate Similarity NPC221870
0.8241 Intermediate Similarity NPC276111
0.8235 Intermediate Similarity NPC470202
0.8229 Intermediate Similarity NPC70436
0.8218 Intermediate Similarity NPC253746
0.82 Intermediate Similarity NPC109955
0.82 Intermediate Similarity NPC77492
0.82 Intermediate Similarity NPC107619
0.82 Intermediate Similarity NPC225464
0.8198 Intermediate Similarity NPC79933
0.8198 Intermediate Similarity NPC473974
0.8198 Intermediate Similarity NPC161617
0.8198 Intermediate Similarity NPC473767
0.8198 Intermediate Similarity NPC299406
0.8198 Intermediate Similarity NPC258366
0.8198 Intermediate Similarity NPC31296
0.8191 Intermediate Similarity NPC150837
0.8182 Intermediate Similarity NPC246679
0.8173 Intermediate Similarity NPC184658
0.8173 Intermediate Similarity NPC1065
0.8165 Intermediate Similarity NPC4665
0.8165 Intermediate Similarity NPC161304
0.8165 Intermediate Similarity NPC240163
0.8163 Intermediate Similarity NPC94139
0.8163 Intermediate Similarity NPC210497
0.8163 Intermediate Similarity NPC147284
0.8163 Intermediate Similarity NPC55903
0.8163 Intermediate Similarity NPC306884
0.8163 Intermediate Similarity NPC162314
0.8163 Intermediate Similarity NPC3358
0.8155 Intermediate Similarity NPC52087
0.8155 Intermediate Similarity NPC79672
0.8148 Intermediate Similarity NPC62546
0.8148 Intermediate Similarity NPC109241
0.8148 Intermediate Similarity NPC162113
0.8144 Intermediate Similarity NPC192
0.8125 Intermediate Similarity NPC190501
0.8125 Intermediate Similarity NPC318552
0.8119 Intermediate Similarity NPC51333
0.8119 Intermediate Similarity NPC78119
0.8119 Intermediate Similarity NPC132078
0.8119 Intermediate Similarity NPC252821
0.8119 Intermediate Similarity NPC122005
0.8119 Intermediate Similarity NPC216468
0.8113 Intermediate Similarity NPC259554
0.8108 Intermediate Similarity NPC40649
0.8108 Intermediate Similarity NPC249435
0.8108 Intermediate Similarity NPC161943
0.8108 Intermediate Similarity NPC328694
0.8108 Intermediate Similarity NPC209486
0.8108 Intermediate Similarity NPC273282
0.8108 Intermediate Similarity NPC474890
0.81 Intermediate Similarity NPC132271
0.81 Intermediate Similarity NPC292730
0.81 Intermediate Similarity NPC283711
0.81 Intermediate Similarity NPC202986
0.81 Intermediate Similarity NPC216520
0.81 Intermediate Similarity NPC82664
0.8091 Intermediate Similarity NPC188867
0.8091 Intermediate Similarity NPC471928
0.8091 Intermediate Similarity NPC128249
0.8091 Intermediate Similarity NPC281686
0.8091 Intermediate Similarity NPC471925
0.8091 Intermediate Similarity NPC477453
0.8091 Intermediate Similarity NPC471924
0.8091 Intermediate Similarity NPC106551
0.8091 Intermediate Similarity NPC131192
0.8081 Intermediate Similarity NPC152415
0.8081 Intermediate Similarity NPC245187
0.8077 Intermediate Similarity NPC243677
0.8061 Intermediate Similarity NPC231150
0.8058 Intermediate Similarity NPC304638
0.8058 Intermediate Similarity NPC196479
0.8053 Intermediate Similarity NPC190971
0.8053 Intermediate Similarity NPC259703
0.8053 Intermediate Similarity NPC98305
0.8053 Intermediate Similarity NPC32322
0.8039 Intermediate Similarity NPC225506
0.8039 Intermediate Similarity NPC213730
0.8036 Intermediate Similarity NPC42657
0.8036 Intermediate Similarity NPC319950
0.8036 Intermediate Similarity NPC182240
0.8036 Intermediate Similarity NPC158222
0.802 Intermediate Similarity NPC152097

  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 NPC260000 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
0.8681 High Similarity NPD111 Approved
0.8646 High Similarity NPD2933 Approved
0.8646 High Similarity NPD2934 Approved
0.8557 High Similarity NPD2860 Approved
0.8557 High Similarity NPD2859 Approved
0.8454 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD256 Approved
0.8333 Intermediate Similarity NPD255 Approved
0.83 Intermediate Similarity NPD3020 Approved
0.8269 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.8137 Intermediate Similarity NPD846 Approved
0.8137 Intermediate Similarity NPD940 Approved
0.8125 Intermediate Similarity NPD2932 Approved
0.8125 Intermediate Similarity NPD3019 Approved
0.8091 Intermediate Similarity NPD9568 Approved
0.8 Intermediate Similarity NPD1809 Phase 2
0.8 Intermediate Similarity NPD844 Approved
0.798 Intermediate Similarity NPD845 Approved
0.7946 Intermediate Similarity NPD9545 Approved
0.7921 Intermediate Similarity NPD288 Approved
0.7876 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7864 Intermediate Similarity NPD289 Clinical (unspecified phase)
0.785 Intermediate Similarity NPD9266 Approved
0.785 Intermediate Similarity NPD74 Approved
0.7818 Intermediate Similarity NPD1241 Discontinued
0.781 Intermediate Similarity NPD9608 Approved
0.781 Intermediate Similarity NPD9610 Approved
0.7768 Intermediate Similarity NPD9493 Approved
0.7768 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7757 Intermediate Similarity NPD9267 Approved
0.7757 Intermediate Similarity NPD9263 Approved
0.7757 Intermediate Similarity NPD9264 Approved
0.7692 Intermediate Similarity NPD1242 Phase 1
0.7684 Intermediate Similarity NPD9491 Approved
0.7672 Intermediate Similarity NPD1535 Discovery
0.767 Intermediate Similarity NPD9495 Approved
0.7632 Intermediate Similarity NPD1759 Phase 1
0.7615 Intermediate Similarity NPD3021 Approved
0.7615 Intermediate Similarity NPD3022 Approved
0.7607 Intermediate Similarity NPD1481 Phase 2
0.7544 Intermediate Similarity NPD1758 Phase 1
0.7542 Intermediate Similarity NPD1755 Approved
0.7524 Intermediate Similarity NPD3028 Approved
0.7521 Intermediate Similarity NPD1201 Approved
0.75 Intermediate Similarity NPD257 Approved
0.75 Intermediate Similarity NPD258 Approved
0.75 Intermediate Similarity NPD9258 Approved
0.75 Intermediate Similarity NPD9256 Approved
0.7478 Intermediate Similarity NPD1894 Discontinued
0.7477 Intermediate Similarity NPD228 Approved
0.7477 Intermediate Similarity NPD1237 Approved
0.7474 Intermediate Similarity NPD226 Approved
0.7473 Intermediate Similarity NPD9087 Approved
0.7455 Intermediate Similarity NPD9380 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD3026 Approved
0.7436 Intermediate Similarity NPD3023 Approved
0.7417 Intermediate Similarity NPD1164 Approved
0.7414 Intermediate Similarity NPD1651 Approved
0.7414 Intermediate Similarity NPD3024 Approved
0.7414 Intermediate Similarity NPD3025 Approved
0.74 Intermediate Similarity NPD800 Approved
0.7383 Intermediate Similarity NPD9261 Approved
0.7379 Intermediate Similarity NPD1693 Approved
0.7345 Intermediate Similarity NPD2228 Approved
0.7345 Intermediate Similarity NPD2229 Approved
0.7345 Intermediate Similarity NPD2234 Approved
0.734 Intermediate Similarity NPD9088 Approved
0.7339 Intermediate Similarity NPD1445 Approved
0.7339 Intermediate Similarity NPD1444 Approved
0.7333 Intermediate Similarity NPD1283 Approved
0.7333 Intermediate Similarity NPD9273 Approved
0.7327 Intermediate Similarity NPD1089 Approved
0.7327 Intermediate Similarity NPD1086 Approved
0.7327 Intermediate Similarity NPD1090 Approved
0.7295 Intermediate Similarity NPD9569 Approved
0.7288 Intermediate Similarity NPD3847 Discontinued
0.7281 Intermediate Similarity NPD9281 Approved
0.728 Intermediate Similarity NPD1240 Approved
0.7273 Intermediate Similarity NPD1470 Approved
0.7263 Intermediate Similarity NPD9490 Approved
0.7257 Intermediate Similarity NPD9377 Approved
0.7257 Intermediate Similarity NPD9379 Approved
0.7234 Intermediate Similarity NPD9294 Approved
0.7207 Intermediate Similarity NPD2684 Approved
0.72 Intermediate Similarity NPD6663 Approved
0.72 Intermediate Similarity NPD259 Phase 1
0.719 Intermediate Similarity NPD196 Phase 1
0.7184 Intermediate Similarity NPD1088 Approved
0.7182 Intermediate Similarity NPD968 Approved
0.7168 Intermediate Similarity NPD6124 Clinical (unspecified phase)
0.7167 Intermediate Similarity NPD1608 Approved
0.7167 Intermediate Similarity NPD3972 Approved
0.7167 Intermediate Similarity NPD9717 Approved
0.7165 Intermediate Similarity NPD1607 Approved
0.7158 Intermediate Similarity NPD227 Approved
0.7158 Intermediate Similarity NPD225 Approved
0.7154 Intermediate Similarity NPD9494 Approved
0.7154 Intermediate Similarity NPD5736 Approved
0.7143 Intermediate Similarity NPD943 Approved
0.7143 Intermediate Similarity NPD4750 Phase 3
0.7143 Intermediate Similarity NPD825 Approved
0.7143 Intermediate Similarity NPD826 Approved
0.7143 Intermediate Similarity NPD1792 Phase 2
0.7131 Intermediate Similarity NPD2797 Approved
0.712 Intermediate Similarity NPD3764 Approved
0.7115 Intermediate Similarity NPD5122 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD821 Approved
0.7103 Intermediate Similarity NPD2066 Phase 3
0.71 Intermediate Similarity NPD9257 Approved
0.71 Intermediate Similarity NPD9259 Approved
0.7094 Intermediate Similarity NPD856 Approved
0.7094 Intermediate Similarity NPD16 Approved
0.7094 Intermediate Similarity NPD318 Approved
0.7094 Intermediate Similarity NPD317 Approved
0.7087 Intermediate Similarity NPD274 Approved
0.7087 Intermediate Similarity NPD275 Approved
0.7087 Intermediate Similarity NPD555 Phase 2
0.7087 Intermediate Similarity NPD1239 Approved
0.7083 Intermediate Similarity NPD1281 Approved
0.7083 Intermediate Similarity NPD422 Phase 1
0.7064 Intermediate Similarity NPD9500 Approved
0.7059 Intermediate Similarity NPD5346 Phase 2
0.7059 Intermediate Similarity NPD5347 Phase 2
0.7054 Intermediate Similarity NPD6831 Clinical (unspecified phase)
0.7049 Intermediate Similarity NPD1876 Approved
0.7043 Intermediate Similarity NPD7159 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD9089 Approved
0.704 Intermediate Similarity NPD9537 Phase 1
0.704 Intermediate Similarity NPD9536 Phase 1
0.704 Intermediate Similarity NPD3136 Phase 2
0.7034 Intermediate Similarity NPD3091 Approved
0.703 Intermediate Similarity NPD4793 Discontinued
0.703 Intermediate Similarity NPD1087 Approved
0.7027 Intermediate Similarity NPD3134 Approved
0.7025 Intermediate Similarity NPD9269 Phase 2
0.7016 Intermediate Similarity NPD454 Approved
0.6992 Remote Similarity NPD1203 Approved
0.6984 Remote Similarity NPD6798 Discontinued
0.6984 Remote Similarity NPD6859 Clinical (unspecified phase)
0.6984 Remote Similarity NPD3268 Approved
0.6983 Remote Similarity NPD690 Clinical (unspecified phase)
0.6983 Remote Similarity NPD475 Phase 2
0.6983 Remote Similarity NPD9614 Approved
0.6983 Remote Similarity NPD9618 Approved
0.6975 Remote Similarity NPD9268 Approved
0.6964 Remote Similarity NPD1358 Approved
0.6964 Remote Similarity NPD2342 Discontinued
0.6964 Remote Similarity NPD290 Approved
0.696 Remote Similarity NPD2614 Approved
0.6957 Remote Similarity NPD5535 Approved
0.6957 Remote Similarity NPD7843 Approved
0.6957 Remote Similarity NPD7635 Approved
0.6952 Remote Similarity NPD1202 Approved
0.6947 Remote Similarity NPD2344 Approved
0.6939 Remote Similarity NPD9093 Approved
0.6935 Remote Similarity NPD2798 Approved
0.693 Remote Similarity NPD9280 Clinical (unspecified phase)
0.6929 Remote Similarity NPD6233 Phase 2
0.6929 Remote Similarity NPD4062 Phase 3
0.6923 Remote Similarity NPD651 Clinical (unspecified phase)
0.6923 Remote Similarity NPD1509 Clinical (unspecified phase)
0.6923 Remote Similarity NPD6671 Approved
0.6923 Remote Similarity NPD1510 Phase 2
0.6917 Remote Similarity NPD4626 Approved
0.6917 Remote Similarity NPD5238 Clinical (unspecified phase)
0.6917 Remote Similarity NPD1778 Approved
0.6917 Remote Similarity NPD4059 Approved
0.6917 Remote Similarity NPD17 Approved
0.6916 Remote Similarity NPD1564 Approved
0.6916 Remote Similarity NPD1566 Phase 3
0.6916 Remote Similarity NPD1565 Approved
0.6909 Remote Similarity NPD1929 Approved
0.6909 Remote Similarity NPD1930 Approved
0.6909 Remote Similarity NPD1931 Clinical (unspecified phase)
0.6905 Remote Similarity NPD9718 Approved
0.6893 Remote Similarity NPD9295 Approved
0.6891 Remote Similarity NPD5304 Approved
0.6891 Remote Similarity NPD1548 Phase 1
0.6891 Remote Similarity NPD5303 Approved
0.6887 Remote Similarity NPD688 Clinical (unspecified phase)
0.687 Remote Similarity NPD2935 Discontinued
0.687 Remote Similarity NPD7450 Phase 2
0.6847 Remote Similarity NPD5909 Discontinued
0.6842 Remote Similarity NPD5451 Approved
0.6838 Remote Similarity NPD2629 Approved
0.6838 Remote Similarity NPD1791 Approved
0.6838 Remote Similarity NPD1476 Clinical (unspecified phase)
0.6838 Remote Similarity NPD1793 Approved
0.6833 Remote Similarity NPD4093 Discontinued
0.6822 Remote Similarity NPD6355 Discontinued
0.6822 Remote Similarity NPD230 Phase 1
0.6818 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6818 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6807 Remote Similarity NPD9613 Approved
0.6807 Remote Similarity NPD9616 Approved
0.6807 Remote Similarity NPD5536 Phase 2
0.6807 Remote Similarity NPD9615 Approved
0.6803 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6803 Remote Similarity NPD3092 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