Structure

Physi-Chem Properties

Molecular Weight:  126.03
Volume:  122.237
LogP:  0.3
LogD:  0.507
LogS:  -0.029
# Rotatable Bonds:  0
TPSA:  60.69
# H-Bond Aceptor:  3
# H-Bond Donor:  3
# Rings:  1
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.356
Synthetic Accessibility Score:  1.843
Fsp3:  0.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.735
MDCK Permeability:  1.0793613910209388e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.01
Human Intestinal Absorption (HIA):  0.022
20% Bioavailability (F20%):  0.977
30% Bioavailability (F30%):  0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.025
Plasma Protein Binding (PPB):  55.248355865478516%
Volume Distribution (VD):  0.596
Pgp-substrate:  39.559608459472656%

ADMET: Metabolism

CYP1A2-inhibitor:  0.179
CYP1A2-substrate:  0.343
CYP2C19-inhibitor:  0.068
CYP2C19-substrate:  0.058
CYP2C9-inhibitor:  0.1
CYP2C9-substrate:  0.871
CYP2D6-inhibitor:  0.139
CYP2D6-substrate:  0.694
CYP3A4-inhibitor:  0.157
CYP3A4-substrate:  0.126

ADMET: Excretion

Clearance (CL):  19.614
Half-life (T1/2):  0.929

ADMET: Toxicity

hERG Blockers:  0.015
Human Hepatotoxicity (H-HT):  0.074
Drug-inuced Liver Injury (DILI):  0.048
AMES Toxicity:  0.702
Rat Oral Acute Toxicity:  0.697
Maximum Recommended Daily Dose:  0.068
Skin Sensitization:  0.944
Carcinogencity:  0.46
Eye Corrosion:  0.972
Eye Irritation:  0.968
Respiratory Toxicity:  0.701

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  Natural Product: NPC288923

Natural Product ID:  NPC288923
Common Name*:   Benzene-1,2,4-Triol
IUPAC Name:   benzene-1,2,4-triol
Synonyms:  
Standard InCHIKey:  GGNQRNBDZQJCCN-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C6H6O3/c7-4-1-2-5(8)6(9)3-4/h1-3,7-9H
SMILES:  Oc1ccc(c(c1)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL3092389
PubChem CID:   10787
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0000134] Phenols
        • [CHEMONTID:0001310] Benzenetriols and derivatives
          • [CHEMONTID:0000380] Hydroxyquinols and derivatives

*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
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. DOI[10.1172/JCI16309]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. DOI[10.1371/journal.pone.0115359]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[10557354]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[11034610]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[11419736]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[11530998]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[1175644]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[12391014]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[12812989]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[12840027]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[12878451]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[15084647]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[1521032]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[15230696]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[15314235]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[16112079]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota Fruits n.a. n.a. PMID[16309325]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota n.a. Seoul, Korea 2000-Jun PMID[16643034]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[16770722]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[1687010]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[17116739]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[17190852]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[17875433]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[18311922]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota fruit n.a. n.a. PMID[18505286]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[18544912]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. rhizome n.a. PMID[18787781]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[18799520]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[19425150]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota fruit n.a. n.a. PMID[19650637]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[19961175]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[20506249]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[20601097]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. faeces n.a. PMID[20708442]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. bile n.a. PMID[20708442]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. urine n.a. PMID[20708442]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[20876113]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[21302967]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[21798258]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[2268561]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[22711758]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota fruits n.a. n.a. PMID[23305920]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[23315938]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[23717534]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[23752203]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[23810710]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[23811455]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[23868375]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[23919613]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[24101735]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[24399466]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[24494566]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[24558969]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[24816727]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[25114169]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[25181601]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[25293588]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[25644343]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[26236990]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[27228227]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[27471436]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[3179836]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[32141747]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[347637]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[4696527]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[5432584]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[6121420]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[6780563]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[8600370]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[8987136]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[9192820]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[9544564]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. PMID[9800648]
NPO12584 Atractylodes chinensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. Database[MetaboLights]
NPO12584 Atractylodes chinensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12584 Atractylodes chinensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12584 Atractylodes chinensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20338 Mus musculus Species Muridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12584 Atractylodes chinensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16087 Atractylodes lancea Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9518 Gardenia jasminoides Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT1078 Individual Protein Indoleamine 2,3-dioxygenase Homo sapiens Inhibition = 56.0 % PMID[529997]
NPT233 Individual Protein Carbonic anhydrase II Homo sapiens Ki > 100000.0 nM PMID[529998]
NPT2 Others Unspecified Ratio Ki >= 13.5 n.a. PMID[529998]
NPT2 Others Unspecified Ki = 7400.0 nM PMID[529998]
NPT947 Individual Protein Carbonic anhydrase I Homo sapiens Ki > 100000.0 nM PMID[529998]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC > 100000.0 nM PMID[529999]
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC > 100000.0 nM PMID[529999]
NPT25083 SINGLE PROTEIN Arginase-1 Bos taurus IC50 = 360000.0 nM PMID[530000]

☑ 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 NPC288923 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
0.9647 High Similarity NPC280254
0.8941 High Similarity NPC270094
0.8824 High Similarity NPC4154
0.8824 High Similarity NPC204932
0.8586 High Similarity NPC124712
0.8471 Intermediate Similarity NPC65517
0.82 Intermediate Similarity NPC307875
0.8119 Intermediate Similarity NPC232654
0.8039 Intermediate Similarity NPC176527
0.8 Intermediate Similarity NPC100980
0.7981 Intermediate Similarity NPC247871
0.7961 Intermediate Similarity NPC105727
0.7961 Intermediate Similarity NPC114392
0.7961 Intermediate Similarity NPC58427
0.7961 Intermediate Similarity NPC34864
0.7835 Intermediate Similarity NPC16649
0.7736 Intermediate Similarity NPC268032
0.7732 Intermediate Similarity NPC295295
0.7653 Intermediate Similarity NPC114325
0.7636 Intermediate Similarity NPC76915
0.7636 Intermediate Similarity NPC151617
0.76 Intermediate Similarity NPC291789
0.7576 Intermediate Similarity NPC107522
0.7525 Intermediate Similarity NPC80027
0.75 Intermediate Similarity NPC157213
0.75 Intermediate Similarity NPC214289
0.7451 Intermediate Similarity NPC248573
0.7451 Intermediate Similarity NPC166761
0.7451 Intermediate Similarity NPC10588
0.7451 Intermediate Similarity NPC161571
0.7451 Intermediate Similarity NPC275053
0.7426 Intermediate Similarity NPC109955
0.7404 Intermediate Similarity NPC12278
0.7391 Intermediate Similarity NPC474864
0.7379 Intermediate Similarity NPC143659
0.7379 Intermediate Similarity NPC284011
0.7379 Intermediate Similarity NPC100340
0.7379 Intermediate Similarity NPC72947
0.7368 Intermediate Similarity NPC205850
0.7353 Intermediate Similarity NPC131587
0.7353 Intermediate Similarity NPC314803
0.7321 Intermediate Similarity NPC259638
0.7308 Intermediate Similarity NPC24404
0.7308 Intermediate Similarity NPC222522
0.7308 Intermediate Similarity NPC313030
0.7308 Intermediate Similarity NPC242342
0.7308 Intermediate Similarity NPC249828
0.7308 Intermediate Similarity NPC168303
0.7308 Intermediate Similarity NPC106396
0.7308 Intermediate Similarity NPC71002
0.7308 Intermediate Similarity NPC94351
0.7308 Intermediate Similarity NPC53051
0.7308 Intermediate Similarity NPC85479
0.7308 Intermediate Similarity NPC302219
0.7308 Intermediate Similarity NPC146798
0.7297 Intermediate Similarity NPC472893
0.7282 Intermediate Similarity NPC223393
0.7281 Intermediate Similarity NPC472071
0.7265 Intermediate Similarity NPC221090
0.7265 Intermediate Similarity NPC183446
0.7257 Intermediate Similarity NPC144343
0.7255 Intermediate Similarity NPC88420
0.7245 Intermediate Similarity NPC302546
0.7241 Intermediate Similarity NPC135414
0.7241 Intermediate Similarity NPC228875
0.7241 Intermediate Similarity NPC126216
0.7241 Intermediate Similarity NPC105147
0.7241 Intermediate Similarity NPC246967
0.7238 Intermediate Similarity NPC102216
0.7238 Intermediate Similarity NPC30506
0.7238 Intermediate Similarity NPC241891
0.7238 Intermediate Similarity NPC119860
0.7232 Intermediate Similarity NPC193067
0.7222 Intermediate Similarity NPC71266
0.7212 Intermediate Similarity NPC110764
0.7212 Intermediate Similarity NPC137415
0.7212 Intermediate Similarity NPC166313
0.7212 Intermediate Similarity NPC294186
0.7212 Intermediate Similarity NPC147310
0.7212 Intermediate Similarity NPC24407
0.7212 Intermediate Similarity NPC11280
0.7212 Intermediate Similarity NPC192032
0.7203 Intermediate Similarity NPC33654
0.72 Intermediate Similarity NPC29373
0.7193 Intermediate Similarity NPC20674
0.7193 Intermediate Similarity NPC226629
0.7193 Intermediate Similarity NPC217174
0.7179 Intermediate Similarity NPC192810
0.7179 Intermediate Similarity NPC318777
0.7172 Intermediate Similarity NPC300478
0.7172 Intermediate Similarity NPC47950
0.717 Intermediate Similarity NPC474839
0.717 Intermediate Similarity NPC134829
0.717 Intermediate Similarity NPC292452
0.7168 Intermediate Similarity NPC277588
0.7159 Intermediate Similarity NPC215445
0.7155 Intermediate Similarity NPC285289
0.7143 Intermediate Similarity NPC477802
0.7143 Intermediate Similarity NPC477801
0.7143 Intermediate Similarity NPC196479
0.7143 Intermediate Similarity NPC112596
0.7143 Intermediate Similarity NPC47422
0.7143 Intermediate Similarity NPC476006
0.713 Intermediate Similarity NPC10932
0.713 Intermediate Similarity NPC61516
0.713 Intermediate Similarity NPC247364
0.713 Intermediate Similarity NPC229401
0.713 Intermediate Similarity NPC232084
0.7115 Intermediate Similarity NPC130103
0.7103 Intermediate Similarity NPC473653
0.7103 Intermediate Similarity NPC109691
0.7103 Intermediate Similarity NPC39664
0.7103 Intermediate Similarity NPC118286
0.7103 Intermediate Similarity NPC248904
0.7103 Intermediate Similarity NPC302681
0.7103 Intermediate Similarity NPC39097
0.7103 Intermediate Similarity NPC470700
0.7094 Intermediate Similarity NPC152722
0.7083 Intermediate Similarity NPC33756
0.7083 Intermediate Similarity NPC124436
0.7083 Intermediate Similarity NPC38459
0.7083 Intermediate Similarity NPC319826
0.7083 Intermediate Similarity NPC265146
0.7083 Intermediate Similarity NPC37074
0.7083 Intermediate Similarity NPC50368
0.7075 Intermediate Similarity NPC218879
0.7075 Intermediate Similarity NPC244513
0.7075 Intermediate Similarity NPC471511
0.7075 Intermediate Similarity NPC79672
0.7075 Intermediate Similarity NPC120719
0.7075 Intermediate Similarity NPC227458
0.7075 Intermediate Similarity NPC52087
0.7069 Intermediate Similarity NPC24125
0.7065 Intermediate Similarity NPC322285
0.7043 Intermediate Similarity NPC191866
0.7037 Intermediate Similarity NPC204901
0.7037 Intermediate Similarity NPC305603
0.7037 Intermediate Similarity NPC232523
0.7037 Intermediate Similarity NPC61033
0.7037 Intermediate Similarity NPC158253
0.7037 Intermediate Similarity NPC54844
0.7025 Intermediate Similarity NPC266691
0.7025 Intermediate Similarity NPC19694
0.701 Intermediate Similarity NPC150837
0.701 Intermediate Similarity NPC248817
0.701 Intermediate Similarity NPC286904
0.701 Intermediate Similarity NPC175313
0.7009 Intermediate Similarity NPC246056
0.7009 Intermediate Similarity NPC37802
0.7009 Intermediate Similarity NPC237667
0.7009 Intermediate Similarity NPC239291
0.7 Intermediate Similarity NPC245060
0.7 Intermediate Similarity NPC110677
0.7 Intermediate Similarity NPC298845
0.7 Intermediate Similarity NPC312304
0.7 Intermediate Similarity NPC469622
0.7 Intermediate Similarity NPC189589
0.6972 Remote Similarity NPC61885
0.6972 Remote Similarity NPC174981
0.6972 Remote Similarity NPC63698
0.697 Remote Similarity NPC104216
0.6967 Remote Similarity NPC158477
0.6967 Remote Similarity NPC58164
0.6967 Remote Similarity NPC10225
0.6964 Remote Similarity NPC471485
0.6949 Remote Similarity NPC225710
0.6949 Remote Similarity NPC262253
0.6949 Remote Similarity NPC71579
0.6949 Remote Similarity NPC41562
0.6949 Remote Similarity NPC473411
0.6944 Remote Similarity NPC164576
0.6944 Remote Similarity NPC477814
0.6944 Remote Similarity NPC67250
0.6944 Remote Similarity NPC12640
0.6944 Remote Similarity NPC1075
0.6944 Remote Similarity NPC1786
0.6944 Remote Similarity NPC99836
0.6944 Remote Similarity NPC201662
0.6944 Remote Similarity NPC19149
0.6944 Remote Similarity NPC294902
0.6942 Remote Similarity NPC216836
0.6939 Remote Similarity NPC155393
0.6939 Remote Similarity NPC197783
0.6923 Remote Similarity NPC475078
0.6923 Remote Similarity NPC276195
0.6923 Remote Similarity NPC152097
0.6916 Remote Similarity NPC130817
0.6911 Remote Similarity NPC220935
0.6911 Remote Similarity NPC51840
0.6911 Remote Similarity NPC234488
0.6911 Remote Similarity NPC311680
0.6911 Remote Similarity NPC299221
0.6909 Remote Similarity NPC202647
0.6909 Remote Similarity NPC473524
0.6909 Remote Similarity NPC19808
0.6909 Remote Similarity NPC33728
0.6907 Remote Similarity NPC23837
0.6893 Remote Similarity NPC313650
0.6891 Remote Similarity NPC84086
0.6891 Remote Similarity NPC197757

  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 NPC288923 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
0.9647 High Similarity NPD9094 Approved
0.8941 High Similarity NPD9089 Approved
0.8824 High Similarity NPD9093 Approved
0.8471 Intermediate Similarity NPD9088 Approved
0.8 Intermediate Similarity NPD9087 Approved
0.7653 Intermediate Similarity NPD9296 Approved
0.75 Intermediate Similarity NPD9295 Approved
0.7451 Intermediate Similarity NPD1242 Phase 1
0.7379 Intermediate Similarity NPD940 Approved
0.7379 Intermediate Similarity NPD846 Approved
0.7156 Intermediate Similarity NPD9280 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD9073 Approved
0.7083 Intermediate Similarity NPD111 Approved
0.6949 Remote Similarity NPD9269 Phase 2
0.6923 Remote Similarity NPD68 Approved
0.6923 Remote Similarity NPD9097 Approved
0.6923 Remote Similarity NPD9096 Approved
0.6923 Remote Similarity NPD9095 Approved
0.6887 Remote Similarity NPD291 Approved
0.6792 Remote Similarity NPD289 Clinical (unspecified phase)
0.6762 Remote Similarity NPD9273 Approved
0.6757 Remote Similarity NPD4750 Phase 3
0.6757 Remote Similarity NPD3022 Approved
0.6757 Remote Similarity NPD3021 Approved
0.6748 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6694 Remote Similarity NPD3027 Phase 3
0.6667 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6667 Remote Similarity NPD9365 Approved
0.6637 Remote Similarity NPD228 Approved
0.6635 Remote Similarity NPD2933 Approved
0.6635 Remote Similarity NPD2934 Approved
0.661 Remote Similarity NPD9268 Approved
0.6579 Remote Similarity NPD9377 Approved
0.6579 Remote Similarity NPD9379 Approved
0.6571 Remote Similarity NPD2860 Approved
0.6571 Remote Similarity NPD2859 Approved
0.6555 Remote Similarity NPD9381 Approved
0.6555 Remote Similarity NPD9384 Approved
0.6535 Remote Similarity NPD1613 Approved
0.6535 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6486 Remote Similarity NPD968 Approved
0.6476 Remote Similarity NPD1432 Clinical (unspecified phase)
0.6466 Remote Similarity NPD9299 Approved
0.6415 Remote Similarity NPD844 Approved
0.6406 Remote Similarity NPD943 Approved
0.6389 Remote Similarity NPD3020 Approved
0.6387 Remote Similarity NPD1548 Phase 1
0.6381 Remote Similarity NPD845 Approved
0.6357 Remote Similarity NPD230 Phase 1
0.6355 Remote Similarity NPD288 Approved
0.6341 Remote Similarity NPD9622 Approved
0.6336 Remote Similarity NPD651 Clinical (unspecified phase)
0.6316 Remote Similarity NPD556 Approved
0.6303 Remote Similarity NPD1408 Clinical (unspecified phase)
0.6283 Remote Similarity NPD9265 Clinical (unspecified phase)
0.625 Remote Similarity NPD7533 Approved
0.625 Remote Similarity NPD7534 Approved
0.6228 Remote Similarity NPD74 Approved
0.6228 Remote Similarity NPD9266 Approved
0.619 Remote Similarity NPD9620 Approved
0.619 Remote Similarity NPD9621 Approved
0.619 Remote Similarity NPD9619 Approved
0.6179 Remote Similarity NPD1610 Phase 2
0.6179 Remote Similarity NPD422 Phase 1
0.6174 Remote Similarity NPD9380 Clinical (unspecified phase)
0.614 Remote Similarity NPD9267 Approved
0.614 Remote Similarity NPD9552 Approved
0.614 Remote Similarity NPD290 Approved
0.614 Remote Similarity NPD9263 Approved
0.614 Remote Similarity NPD9264 Approved
0.6111 Remote Similarity NPD1809 Phase 2
0.6098 Remote Similarity NPD915 Approved
0.6082 Remote Similarity NPD9294 Approved
0.608 Remote Similarity NPD2983 Phase 2
0.608 Remote Similarity NPD2982 Phase 2
0.6048 Remote Similarity NPD1091 Approved
0.6028 Remote Similarity NPD1653 Approved
0.6018 Remote Similarity NPD9610 Approved
0.6018 Remote Similarity NPD9608 Approved
0.6018 Remote Similarity NPD9501 Approved
0.6017 Remote Similarity NPD7635 Approved
0.6 Remote Similarity NPD6671 Approved
0.6 Remote Similarity NPD2981 Phase 2
0.6 Remote Similarity NPD598 Approved
0.6 Remote Similarity NPD9507 Approved
0.6 Remote Similarity NPD2337 Clinical (unspecified phase)
0.6 Remote Similarity NPD597 Approved
0.6 Remote Similarity NPD601 Approved
0.5971 Remote Similarity NPD1511 Approved
0.5954 Remote Similarity NPD1136 Approved
0.5954 Remote Similarity NPD1130 Approved
0.5954 Remote Similarity NPD1132 Approved
0.5952 Remote Similarity NPD4379 Clinical (unspecified phase)
0.5952 Remote Similarity NPD4749 Approved
0.5942 Remote Similarity NPD302 Approved
0.5938 Remote Similarity NPD602 Approved
0.5938 Remote Similarity NPD858 Approved
0.5938 Remote Similarity NPD599 Approved
0.5938 Remote Similarity NPD859 Approved
0.5929 Remote Similarity NPD9500 Approved
0.5917 Remote Similarity NPD1476 Clinical (unspecified phase)
0.5913 Remote Similarity NPD1444 Approved
0.5913 Remote Similarity NPD1445 Approved
0.5909 Remote Similarity NPD3059 Approved
0.5909 Remote Similarity NPD3061 Approved
0.5909 Remote Similarity NPD3062 Approved
0.5906 Remote Similarity NPD5310 Approved
0.5906 Remote Similarity NPD5311 Approved
0.5906 Remote Similarity NPD9634 Clinical (unspecified phase)
0.5891 Remote Similarity NPD3018 Phase 2
0.5887 Remote Similarity NPD1512 Approved
0.5859 Remote Similarity NPD3053 Approved
0.5859 Remote Similarity NPD3055 Approved
0.5846 Remote Similarity NPD4908 Phase 1
0.5827 Remote Similarity NPD6190 Approved
0.5822 Remote Similarity NPD2801 Approved
0.5821 Remote Similarity NPD817 Approved
0.5821 Remote Similarity NPD823 Approved
0.5821 Remote Similarity NPD5314 Approved
0.582 Remote Similarity NPD9493 Approved
0.5814 Remote Similarity NPD258 Approved
0.5814 Remote Similarity NPD257 Approved
0.5812 Remote Similarity NPD2684 Approved
0.5809 Remote Similarity NPD9570 Approved
0.5806 Remote Similarity NPD1357 Approved
0.5802 Remote Similarity NPD4625 Phase 3
0.5789 Remote Similarity NPD1558 Phase 1
0.5789 Remote Similarity NPD9261 Approved
0.5785 Remote Similarity NPD9281 Approved
0.5785 Remote Similarity NPD9618 Approved
0.5785 Remote Similarity NPD9614 Approved
0.5772 Remote Similarity NPD318 Approved
0.5772 Remote Similarity NPD856 Approved
0.5772 Remote Similarity NPD317 Approved
0.5772 Remote Similarity NPD16 Approved
0.5769 Remote Similarity NPD9569 Approved
0.5769 Remote Similarity NPD9494 Approved
0.5766 Remote Similarity NPD7266 Discontinued
0.5763 Remote Similarity NPD1792 Phase 2
0.5758 Remote Similarity NPD4907 Clinical (unspecified phase)
0.5752 Remote Similarity NPD3028 Approved
0.5736 Remote Similarity NPD3094 Phase 2
0.5726 Remote Similarity NPD9545 Approved
0.5726 Remote Similarity NPD1759 Phase 1
0.5726 Remote Similarity NPD2342 Discontinued
0.5725 Remote Similarity NPD3537 Clinical (unspecified phase)
0.5714 Remote Similarity NPD9376 Approved
0.5704 Remote Similarity NPD2568 Approved
0.5702 Remote Similarity NPD2234 Approved
0.5702 Remote Similarity NPD2228 Approved
0.5702 Remote Similarity NPD2229 Approved
0.5693 Remote Similarity NPD3454 Phase 3
0.5692 Remote Similarity NPD6917 Clinical (unspecified phase)
0.568 Remote Similarity NPD1797 Approved
0.568 Remote Similarity NPD1798 Approved
0.5672 Remote Similarity NPD1240 Approved
0.5672 Remote Similarity NPD1555 Discontinued
0.5672 Remote Similarity NPD468 Phase 1
0.5669 Remote Similarity NPD3092 Approved
0.5669 Remote Similarity NPD1535 Discovery
0.5652 Remote Similarity NPD2029 Clinical (unspecified phase)
0.5649 Remote Similarity NPD2861 Phase 2
0.5646 Remote Similarity NPD1934 Approved
0.5645 Remote Similarity NPD9613 Approved
0.5645 Remote Similarity NPD9616 Approved
0.5645 Remote Similarity NPD1758 Phase 1
0.5645 Remote Similarity NPD9615 Approved
0.5639 Remote Similarity NPD2028 Clinical (unspecified phase)
0.5639 Remote Similarity NPD6410 Clinical (unspecified phase)
0.5639 Remote Similarity NPD3145 Approved
0.5639 Remote Similarity NPD3144 Approved
0.5635 Remote Similarity NPD5238 Clinical (unspecified phase)
0.5625 Remote Similarity NPD1481 Phase 2
0.562 Remote Similarity NPD7843 Approved
0.562 Remote Similarity NPD1105 Clinical (unspecified phase)
0.5615 Remote Similarity NPD1133 Approved
0.5615 Remote Similarity NPD1135 Approved
0.5615 Remote Similarity NPD1129 Approved
0.5615 Remote Similarity NPD1134 Approved
0.5615 Remote Similarity NPD1131 Approved
0.5615 Remote Similarity NPD3827 Clinical (unspecified phase)
0.561 Remote Similarity NPD9342 Approved
0.561 Remote Similarity NPD255 Approved
0.561 Remote Similarity NPD256 Approved
0.561 Remote Similarity NPD191 Approved
0.5608 Remote Similarity NPD2393 Clinical (unspecified phase)
0.5603 Remote Similarity NPD2219 Phase 1
0.5603 Remote Similarity NPD9244 Approved
0.56 Remote Similarity NPD316 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