Structure

Physi-Chem Properties

Molecular Weight:  418.13
Volume:  404.123
LogP:  1.24
LogD:  0.774
LogS:  -4.13
# Rotatable Bonds:  6
TPSA:  156.91
# H-Bond Aceptor:  9
# H-Bond Donor:  6
# Rings:  3
# Heavy Atoms:  9

MedChem Properties

QED Drug-Likeness Score:  0.284
Synthetic Accessibility Score:  3.647
Fsp3:  0.286
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.741
MDCK Permeability:  6.582420155609725e-06
Pgp-inhibitor:  0.002
Pgp-substrate:  0.02
Human Intestinal Absorption (HIA):  0.454
20% Bioavailability (F20%):  0.212
30% Bioavailability (F30%):  0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.173
Plasma Protein Binding (PPB):  96.32495880126953%
Volume Distribution (VD):  0.692
Pgp-substrate:  1.6396890878677368%

ADMET: Metabolism

CYP1A2-inhibitor:  0.512
CYP1A2-substrate:  0.026
CYP2C19-inhibitor:  0.078
CYP2C19-substrate:  0.054
CYP2C9-inhibitor:  0.041
CYP2C9-substrate:  0.808
CYP2D6-inhibitor:  0.472
CYP2D6-substrate:  0.338
CYP3A4-inhibitor:  0.652
CYP3A4-substrate:  0.061

ADMET: Excretion

Clearance (CL):  6.134
Half-life (T1/2):  0.69

ADMET: Toxicity

hERG Blockers:  0.275
Human Hepatotoxicity (H-HT):  0.026
Drug-inuced Liver Injury (DILI):  0.582
AMES Toxicity:  0.719
Rat Oral Acute Toxicity:  0.211
Maximum Recommended Daily Dose:  0.006
Skin Sensitization:  0.918
Carcinogencity:  0.871
Eye Corrosion:  0.003
Eye Irritation:  0.683
Respiratory Toxicity:  0.035

Download Data

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

  Natural Product: NPC259767

Natural Product ID:  NPC259767
Common Name*:   Isoliquiritin
IUPAC Name:   (E)-1-(2,4-dihydroxyphenyl)-3-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-en-1-one
Synonyms:   Isoliquiritin
Standard InCHIKey:  YNWXJFQOCHMPCK-LXGDFETPSA-N
Standard InCHI:  InChI=1S/C21H22O9/c22-10-17-18(26)19(27)20(28)21(30-17)29-13-5-1-11(2-6-13)3-8-15(24)14-7-4-12(23)9-16(14)25/h1-9,17-23,25-28H,10H2/b8-3+/t17-,18-,19+,20-,21-/m1/s1
SMILES:  c1cc(ccc1/C=C/C(=O)c1ccc(cc1O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL599763
PubChem CID:   5318591
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0001111] Flavonoid glycosides
          • [CHEMONTID:0001583] Flavonoid O-glycosides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[11551759]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota Leaves n.a. n.a. PMID[12713396]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root n.a. PMID[16441081]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[16675659]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota roots n.a. n.a. PMID[20022509]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[21123068]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. whole plant n.a. PMID[21214467]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[21866899]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[22074222]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root n.a. PMID[22074222]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[23325115]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota Roots n.a. n.a. PMID[23541646]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root n.a. PMID[23867078]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. rhizome n.a. PMID[23867078]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[24479468]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota roots n.a. n.a. PMID[24957203]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[25445757]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[25744461]
NPO4640 Portulaca oleracea Species Portulacaceae Eukaryota n.a. n.a. n.a. PMID[26562741]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[26841168]
NPO26395 Siegesbeckia pubescens Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[28009521]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[28140583]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[28522265]
NPO4640 Portulaca oleracea Species Portulacaceae Eukaryota n.a. n.a. n.a. PMID[29517238]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[29641206]
NPO4640 Portulaca oleracea Species Portulacaceae Eukaryota n.a. n.a. n.a. PMID[31625751]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[32196343]
NPO4640 Portulaca oleracea Species Portulacaceae Eukaryota n.a. Along the Valencian coast, Spain 2020-Jun&Jul PMID[35161358]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[7381508]
NPO4640 Portulaca oleracea Species Portulacaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO7960 Cicer arietinum Species Fabaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO7960 Cicer arietinum Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO4640 Portulaca oleracea Species Portulacaceae Eukaryota n.a. n.a. Database[FooDB]
NPO7960 Cicer arietinum Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO4640 Portulaca oleracea Species Portulacaceae Eukaryota Herb n.a. n.a. Database[FooDB]
NPO4640 Portulaca oleracea Species Portulacaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO4640 Portulaca oleracea Species Portulacaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO20183 Dalbergia sericea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14379 Onobrychis viciifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22336 Glycyrrhiza aspera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12465 Glycyrrhiza yunnanensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23019 Glycyrrhiza kansuensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7960 Cicer arietinum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO227 Sophora tomentosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7960 Cicer arietinum Species Fabaceae Eukaryota Seeds n.a. Database[Phenol-Explorer]
NPO22336 Glycyrrhiza aspera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO20183 Dalbergia sericea Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15124 Herba sedi sarmentosi n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO12465 Glycyrrhiza yunnanensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO227 Sophora tomentosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26604 Aralia subcapitata Species Araliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4640 Portulaca oleracea Species Portulacaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23019 Glycyrrhiza kansuensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7960 Cicer arietinum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15711 Radix glycyrrhizae preparata Species Lymnaeidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14379 Onobrychis viciifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22336 Glycyrrhiza aspera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12465 Glycyrrhiza yunnanensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23019 Glycyrrhiza kansuensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4640 Portulaca oleracea Species Portulacaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7960 Cicer arietinum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO227 Sophora tomentosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26395 Siegesbeckia pubescens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4640 Portulaca oleracea Species Portulacaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28940 Sigesbeckia glabrescens Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO12465 Glycyrrhiza yunnanensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26604 Aralia subcapitata Species Araliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7786 Lentinus tigrinus Species Lentinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO227 Sophora tomentosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10026 Mitracarpus scaber Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22336 Glycyrrhiza aspera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14379 Onobrychis viciifolia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20183 Dalbergia sericea Species Fabaceae 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
NPT41 Individual Protein Aldose reductase Homo sapiens IC50 = 720.0 nM PMID[514309]
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens Inhibition < 50.0 % PMID[514310]
NPT1592 Individual Protein Dipeptidyl peptidase IV Homo sapiens IC50 = 26920.0 nM PMID[514311]
NPT2 Others Unspecified IC50 = 124000.0 nM PMID[514308]
NPT2 Others Unspecified Ki = 94000.0 nM PMID[514308]

☑ 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 NPC259767 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
1.0 High Similarity NPC88484
0.9864 High Similarity NPC99233
0.9863 High Similarity NPC121001
0.9863 High Similarity NPC259182
0.9797 High Similarity NPC265480
0.9797 High Similarity NPC149368
0.9797 High Similarity NPC170475
0.9796 High Similarity NPC83283
0.9796 High Similarity NPC106625
0.9796 High Similarity NPC39360
0.9796 High Similarity NPC29763
0.9796 High Similarity NPC143851
0.9796 High Similarity NPC210003
0.9732 High Similarity NPC161749
0.9732 High Similarity NPC197896
0.9732 High Similarity NPC23817
0.9732 High Similarity NPC258035
0.9732 High Similarity NPC43638
0.9732 High Similarity NPC313163
0.9732 High Similarity NPC156457
0.973 High Similarity NPC95090
0.973 High Similarity NPC97052
0.973 High Similarity NPC39351
0.973 High Similarity NPC27408
0.973 High Similarity NPC72649
0.973 High Similarity NPC26195
0.973 High Similarity NPC169248
0.9667 High Similarity NPC73511
0.9664 High Similarity NPC127406
0.9664 High Similarity NPC203500
0.9664 High Similarity NPC307938
0.9664 High Similarity NPC323593
0.9664 High Similarity NPC206378
0.9603 High Similarity NPC200708
0.9603 High Similarity NPC271479
0.9603 High Similarity NPC472320
0.96 High Similarity NPC108831
0.96 High Similarity NPC129827
0.96 High Similarity NPC77672
0.96 High Similarity NPC65003
0.96 High Similarity NPC54802
0.96 High Similarity NPC60966
0.96 High Similarity NPC197304
0.96 High Similarity NPC78263
0.96 High Similarity NPC122809
0.96 High Similarity NPC133671
0.96 High Similarity NPC44931
0.96 High Similarity NPC473512
0.96 High Similarity NPC135391
0.96 High Similarity NPC182634
0.96 High Similarity NPC6985
0.9592 High Similarity NPC191154
0.9592 High Similarity NPC213723
0.9589 High Similarity NPC199335
0.9539 High Similarity NPC195685
0.9539 High Similarity NPC210961
0.9539 High Similarity NPC472994
0.9539 High Similarity NPC477628
0.9539 High Similarity NPC303913
0.9539 High Similarity NPC477629
0.9539 High Similarity NPC270675
0.9536 High Similarity NPC472459
0.9536 High Similarity NPC111929
0.9536 High Similarity NPC320283
0.9536 High Similarity NPC308265
0.9536 High Similarity NPC22062
0.9536 High Similarity NPC138811
0.9536 High Similarity NPC473634
0.9536 High Similarity NPC41121
0.9533 High Similarity NPC261866
0.9533 High Similarity NPC45165
0.9527 High Similarity NPC134819
0.9521 High Similarity NPC23084
0.9521 High Similarity NPC218685
0.9477 High Similarity NPC472876
0.9474 High Similarity NPC471079
0.9474 High Similarity NPC136761
0.9474 High Similarity NPC470405
0.9474 High Similarity NPC187379
0.9474 High Similarity NPC271270
0.9474 High Similarity NPC153342
0.9474 High Similarity NPC473623
0.9474 High Similarity NPC142860
0.9474 High Similarity NPC246469
0.9474 High Similarity NPC304741
0.9474 High Similarity NPC97285
0.947 High Similarity NPC288084
0.9459 High Similarity NPC214454
0.9459 High Similarity NPC106025
0.9459 High Similarity NPC477240
0.9416 High Similarity NPC80068
0.9416 High Similarity NPC168822
0.9416 High Similarity NPC88043
0.9412 High Similarity NPC470125
0.9412 High Similarity NPC473438
0.9412 High Similarity NPC265885
0.9412 High Similarity NPC276377
0.9412 High Similarity NPC224530
0.9412 High Similarity NPC135846
0.9412 High Similarity NPC216496
0.9412 High Similarity NPC215710
0.9412 High Similarity NPC159579
0.9412 High Similarity NPC64305
0.9412 High Similarity NPC249281
0.9412 High Similarity NPC47923
0.9412 High Similarity NPC173582
0.9412 High Similarity NPC116458
0.9412 High Similarity NPC170052
0.9412 High Similarity NPC139320
0.9412 High Similarity NPC297987
0.9412 High Similarity NPC282169
0.9412 High Similarity NPC476215
0.9412 High Similarity NPC101636
0.9412 High Similarity NPC253788
0.9412 High Similarity NPC85707
0.9412 High Similarity NPC181465
0.9412 High Similarity NPC259957
0.9412 High Similarity NPC246943
0.9412 High Similarity NPC48093
0.9412 High Similarity NPC163242
0.9412 High Similarity NPC129217
0.9408 High Similarity NPC43761
0.9404 High Similarity NPC295613
0.9404 High Similarity NPC473657
0.94 High Similarity NPC108706
0.94 High Similarity NPC87304
0.94 High Similarity NPC78021
0.94 High Similarity NPC211158
0.94 High Similarity NPC268950
0.9396 High Similarity NPC190217
0.9396 High Similarity NPC23253
0.9388 High Similarity NPC302989
0.9355 High Similarity NPC19240
0.9355 High Similarity NPC85751
0.9355 High Similarity NPC129264
0.9355 High Similarity NPC165720
0.9355 High Similarity NPC139060
0.9355 High Similarity NPC205824
0.9351 High Similarity NPC77660
0.9351 High Similarity NPC475382
0.9351 High Similarity NPC189142
0.9351 High Similarity NPC150164
0.9351 High Similarity NPC240306
0.9351 High Similarity NPC190450
0.9351 High Similarity NPC44947
0.9351 High Similarity NPC127782
0.9351 High Similarity NPC259834
0.9351 High Similarity NPC131745
0.9351 High Similarity NPC298171
0.9351 High Similarity NPC27942
0.9351 High Similarity NPC300537
0.9338 High Similarity NPC470603
0.9338 High Similarity NPC470605
0.9338 High Similarity NPC470604
0.9295 High Similarity NPC260504
0.9295 High Similarity NPC473278
0.9295 High Similarity NPC89809
0.929 High Similarity NPC473644
0.929 High Similarity NPC29830
0.929 High Similarity NPC66087
0.929 High Similarity NPC121703
0.929 High Similarity NPC270335
0.929 High Similarity NPC243930
0.929 High Similarity NPC311850
0.929 High Similarity NPC19709
0.929 High Similarity NPC183672
0.929 High Similarity NPC88023
0.929 High Similarity NPC179198
0.929 High Similarity NPC278419
0.929 High Similarity NPC191306
0.929 High Similarity NPC309025
0.929 High Similarity NPC257566
0.929 High Similarity NPC124155
0.9281 High Similarity NPC104677
0.9236 High Similarity NPC229729
0.9236 High Similarity NPC116745
0.9236 High Similarity NPC48640
0.9236 High Similarity NPC45400
0.9236 High Similarity NPC149244
0.9231 High Similarity NPC22832
0.9231 High Similarity NPC277205
0.9231 High Similarity NPC311830
0.9231 High Similarity NPC287889
0.9231 High Similarity NPC135358
0.9231 High Similarity NPC72016
0.9231 High Similarity NPC76831
0.9231 High Similarity NPC289667
0.9231 High Similarity NPC292929
0.9226 High Similarity NPC473043
0.9221 High Similarity NPC306978
0.9216 High Similarity NPC470606
0.92 High Similarity NPC38775
0.9189 High Similarity NPC1940
0.9189 High Similarity NPC148011
0.9177 High Similarity NPC229687
0.9177 High Similarity NPC222455
0.9172 High Similarity NPC118284
0.9172 High Similarity NPC179950
0.9172 High Similarity NPC142142
0.9172 High Similarity NPC70441

  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 NPC259767 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
0.9732 High Similarity NPD4381 Clinical (unspecified phase)
0.9114 High Similarity NPD3818 Discontinued
0.9073 High Similarity NPD4380 Phase 2
0.9057 High Similarity NPD7804 Clinical (unspecified phase)
0.9057 High Similarity NPD7054 Approved
0.9 High Similarity NPD7074 Phase 3
0.9 High Similarity NPD7472 Approved
0.8973 High Similarity NPD1549 Phase 2
0.8944 High Similarity NPD6797 Phase 2
0.8904 High Similarity NPD1552 Clinical (unspecified phase)
0.8904 High Similarity NPD1550 Clinical (unspecified phase)
0.8889 High Similarity NPD7251 Discontinued
0.8846 High Similarity NPD7075 Discontinued
0.8834 High Similarity NPD4338 Clinical (unspecified phase)
0.8834 High Similarity NPD7808 Phase 3
0.8773 High Similarity NPD6559 Discontinued
0.871 High Similarity NPD1934 Approved
0.871 High Similarity NPD6801 Discontinued
0.8675 High Similarity NPD6799 Approved
0.8654 High Similarity NPD7096 Clinical (unspecified phase)
0.8654 High Similarity NPD2393 Clinical (unspecified phase)
0.8627 High Similarity NPD5403 Approved
0.8526 High Similarity NPD7411 Suspended
0.8519 High Similarity NPD6167 Clinical (unspecified phase)
0.8519 High Similarity NPD6168 Clinical (unspecified phase)
0.8519 High Similarity NPD6166 Phase 2
0.8514 High Similarity NPD1510 Phase 2
0.8497 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8497 Intermediate Similarity NPD5401 Approved
0.8456 Intermediate Similarity NPD2796 Approved
0.8431 Intermediate Similarity NPD1511 Approved
0.8428 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8418 Intermediate Similarity NPD2801 Approved
0.8377 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8367 Intermediate Similarity NPD1240 Approved
0.8365 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8365 Intermediate Similarity NPD5402 Approved
0.8365 Intermediate Similarity NPD3817 Phase 2
0.8344 Intermediate Similarity NPD6599 Discontinued
0.8323 Intermediate Similarity NPD1512 Approved
0.8313 Intermediate Similarity NPD3882 Suspended
0.8302 Intermediate Similarity NPD7819 Suspended
0.8255 Intermediate Similarity NPD1607 Approved
0.8117 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.8092 Intermediate Similarity NPD1551 Phase 2
0.8072 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8047 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8012 Intermediate Similarity NPD8313 Approved
0.8012 Intermediate Similarity NPD8312 Approved
0.8 Intermediate Similarity NPD4628 Phase 3
0.8 Intermediate Similarity NPD6959 Discontinued
0.8 Intermediate Similarity NPD3750 Approved
0.8 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7987 Intermediate Similarity NPD1653 Approved
0.7987 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7976 Intermediate Similarity NPD3751 Discontinued
0.7939 Intermediate Similarity NPD5494 Approved
0.7935 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7927 Intermediate Similarity NPD3749 Approved
0.7923 Intermediate Similarity NPD7584 Approved
0.7866 Intermediate Similarity NPD7768 Phase 2
0.7862 Intermediate Similarity NPD1091 Approved
0.7853 Intermediate Similarity NPD8455 Phase 2
0.7844 Intermediate Similarity NPD3787 Discontinued
0.7829 Intermediate Similarity NPD1933 Approved
0.7824 Intermediate Similarity NPD5844 Phase 1
0.7812 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.777 Intermediate Similarity NPD1203 Approved
0.7756 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7744 Intermediate Similarity NPD1465 Phase 2
0.774 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7738 Intermediate Similarity NPD6232 Discontinued
0.7733 Intermediate Similarity NPD6832 Phase 2
0.7706 Intermediate Similarity NPD7473 Discontinued
0.7692 Intermediate Similarity NPD6782 Approved
0.7692 Intermediate Similarity NPD6778 Approved
0.7692 Intermediate Similarity NPD6779 Approved
0.7692 Intermediate Similarity NPD6776 Approved
0.7692 Intermediate Similarity NPD6780 Approved
0.7692 Intermediate Similarity NPD6777 Approved
0.7692 Intermediate Similarity NPD6781 Approved
0.7679 Intermediate Similarity NPD7199 Phase 2
0.7677 Intermediate Similarity NPD3748 Approved
0.7647 Intermediate Similarity NPD1613 Approved
0.7647 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.763 Intermediate Similarity NPD5953 Discontinued
0.7628 Intermediate Similarity NPD2935 Discontinued
0.7624 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7616 Intermediate Similarity NPD7286 Phase 2
0.7595 Intermediate Similarity NPD2800 Approved
0.7593 Intermediate Similarity NPD920 Approved
0.7586 Intermediate Similarity NPD7685 Pre-registration
0.7578 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7568 Intermediate Similarity NPD7435 Discontinued
0.7564 Intermediate Similarity NPD7033 Discontinued
0.7562 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7553 Intermediate Similarity NPD8151 Discontinued
0.7548 Intermediate Similarity NPD6651 Approved
0.7532 Intermediate Similarity NPD943 Approved
0.7516 Intermediate Similarity NPD2313 Discontinued
0.75 Intermediate Similarity NPD7585 Approved
0.75 Intermediate Similarity NPD7458 Discontinued
0.7485 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD1243 Approved
0.7484 Intermediate Similarity NPD1652 Phase 2
0.7483 Intermediate Similarity NPD2798 Approved
0.7473 Intermediate Similarity NPD7697 Approved
0.7473 Intermediate Similarity NPD7698 Approved
0.7473 Intermediate Similarity NPD7696 Phase 3
0.747 Intermediate Similarity NPD37 Approved
0.7469 Intermediate Similarity NPD2532 Approved
0.7469 Intermediate Similarity NPD2534 Approved
0.7469 Intermediate Similarity NPD2533 Approved
0.7468 Intermediate Similarity NPD2344 Approved
0.7468 Intermediate Similarity NPD7266 Discontinued
0.7466 Intermediate Similarity NPD1548 Phase 1
0.7457 Intermediate Similarity NPD7228 Approved
0.7456 Intermediate Similarity NPD6234 Discontinued
0.7452 Intermediate Similarity NPD2799 Discontinued
0.745 Intermediate Similarity NPD9717 Approved
0.7447 Intermediate Similarity NPD7583 Approved
0.7443 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.744 Intermediate Similarity NPD4965 Approved
0.744 Intermediate Similarity NPD4967 Phase 2
0.744 Intermediate Similarity NPD4966 Approved
0.7433 Intermediate Similarity NPD7871 Phase 2
0.7433 Intermediate Similarity NPD7870 Phase 2
0.7419 Intermediate Similarity NPD6823 Phase 2
0.7418 Intermediate Similarity NPD6534 Approved
0.7418 Intermediate Similarity NPD6535 Approved
0.7407 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD7701 Phase 2
0.7403 Intermediate Similarity NPD6798 Discontinued
0.7394 Intermediate Similarity NPD3226 Approved
0.7391 Intermediate Similarity NPD6190 Approved
0.7389 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD4908 Phase 1
0.7384 Intermediate Similarity NPD3926 Phase 2
0.7383 Intermediate Similarity NPD1610 Phase 2
0.7382 Intermediate Similarity NPD7783 Phase 2
0.7382 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7372 Intermediate Similarity NPD230 Phase 1
0.7362 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD6233 Phase 2
0.7353 Intermediate Similarity NPD919 Approved
0.7341 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD7874 Approved
0.7322 Intermediate Similarity NPD4360 Phase 2
0.7322 Intermediate Similarity NPD4363 Phase 3
0.732 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7318 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7305 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD7700 Phase 2
0.7297 Intermediate Similarity NPD7699 Phase 2
0.7296 Intermediate Similarity NPD6100 Approved
0.7296 Intermediate Similarity NPD6099 Approved
0.7292 Intermediate Similarity NPD7801 Approved
0.729 Intermediate Similarity NPD3268 Approved
0.729 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7284 Intermediate Similarity NPD2309 Approved
0.7278 Intermediate Similarity NPD8434 Phase 2
0.7267 Intermediate Similarity NPD1247 Approved
0.7267 Intermediate Similarity NPD422 Phase 1
0.7261 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7261 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7261 Intermediate Similarity NPD447 Suspended
0.7261 Intermediate Similarity NPD5124 Phase 1
0.7256 Intermediate Similarity NPD4662 Approved
0.7256 Intermediate Similarity NPD4661 Approved
0.725 Intermediate Similarity NPD2346 Discontinued
0.7237 Intermediate Similarity NPD3225 Approved
0.723 Intermediate Similarity NPD9545 Approved
0.7226 Intermediate Similarity NPD3027 Phase 3
0.7222 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD2797 Approved
0.7186 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7174 Intermediate Similarity NPD6212 Phase 3
0.7174 Intermediate Similarity NPD6213 Phase 3
0.7174 Intermediate Similarity NPD6214 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD2654 Approved
0.716 Intermediate Similarity NPD6844 Discontinued
0.7158 Intermediate Similarity NPD8320 Phase 1
0.7158 Intermediate Similarity NPD8319 Approved
0.7152 Intermediate Similarity NPD6355 Discontinued
0.7143 Intermediate Similarity NPD1019 Discontinued
0.7128 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD4308 Phase 3
0.7099 Intermediate Similarity NPD2424 Discontinued
0.7095 Intermediate Similarity NPD7240 Approved
0.7095 Intermediate Similarity NPD9493 Approved
0.7091 Intermediate Similarity NPD7390 Discontinued
0.7088 Intermediate Similarity NPD8150 Discontinued
0.7076 Intermediate Similarity NPD4288 Approved
0.7073 Intermediate Similarity NPD3887 Approved
0.7073 Intermediate Similarity NPD2354 Approved
0.7063 Intermediate Similarity NPD7097 Phase 1

  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