Structure

Physi-Chem Properties

Molecular Weight:  256.07
Volume:  259.033
LogP:  2.5
LogD:  2.504
LogS:  -3.892
# Rotatable Bonds:  1
TPSA:  66.76
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.823
Synthetic Accessibility Score:  2.657
Fsp3:  0.133
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  1
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.627
MDCK Permeability:  9.933270121109672e-06
Pgp-inhibitor:  0.007
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.012
20% Bioavailability (F20%):  0.373
30% Bioavailability (F30%):  0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.078
Plasma Protein Binding (PPB):  91.86725616455078%
Volume Distribution (VD):  0.445
Pgp-substrate:  6.27425479888916%

ADMET: Metabolism

CYP1A2-inhibitor:  0.867
CYP1A2-substrate:  0.196
CYP2C19-inhibitor:  0.927
CYP2C19-substrate:  0.065
CYP2C9-inhibitor:  0.823
CYP2C9-substrate:  0.958
CYP2D6-inhibitor:  0.775
CYP2D6-substrate:  0.882
CYP3A4-inhibitor:  0.768
CYP3A4-substrate:  0.207

ADMET: Excretion

Clearance (CL):  17.718
Half-life (T1/2):  0.793

ADMET: Toxicity

hERG Blockers:  0.034
Human Hepatotoxicity (H-HT):  0.104
Drug-inuced Liver Injury (DILI):  0.651
AMES Toxicity:  0.582
Rat Oral Acute Toxicity:  0.319
Maximum Recommended Daily Dose:  0.207
Skin Sensitization:  0.73
Carcinogencity:  0.777
Eye Corrosion:  0.01
Eye Irritation:  0.937
Respiratory Toxicity:  0.164

Download Data

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Structure MOL file  
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Similar NPs/Drugs  

  Natural Product: NPC329225

Natural Product ID:  NPC329225
Common Name*:   7-Hydroxy-2-(4-Hydroxyphenyl)-2,3-Dihydrochromen-4-One
IUPAC Name:   7-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
Synonyms:  
Standard InCHIKey:  FURUXTVZLHCCNA-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C15H12O4/c16-10-3-1-9(2-4-10)14-8-13(18)12-6-5-11(17)7-15(12)19-14/h1-7,14,16-17H,8H2
SMILES:  Oc1ccc(cc1)C1CC(=O)c2c(O1)cc(cc2)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL271939
PubChem CID:   1889
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0000337] Flavans
          • [CHEMONTID:0001632] Flavanones

*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
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[10654410]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[10843587]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[11551759]
NPO23024 Epimedium koreanum Species Berberidaceae Eukaryota n.a. n.a. n.a. PMID[12081149]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota Leaves n.a. n.a. PMID[12713396]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota Roots n.a. n.a. PMID[15568770]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[16392664]
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]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[16933887]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota roots Hualien Hsien, Taiwan 2003-JUL PMID[16933887]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. PMID[17951038]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[18175961]
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]
NPO23024 Epimedium koreanum Species Berberidaceae Eukaryota n.a. root n.a. PMID[22051934]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root n.a. PMID[22074222]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. 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]
NPO18117 Dalbergia odorifera Species Fabaceae Eukaryota heartwood n.a. n.a. PMID[23743282]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. rhizome n.a. PMID[23867078]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root n.a. PMID[23867078]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[24295087]
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]
NPO23024 Epimedium koreanum Species Berberidaceae Eukaryota aerial parts herbal garden of Chungbuk National University, Cheongju, Korea 2012-Oct PMID[24963714]
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]
NPO25653 Spatholobus suberectus Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[26690274]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[26841168]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[27575476]
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]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[29641206]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota Roots n.a. n.a. PMID[30298740]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[32196343]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[7381508]
NPO18117 Dalbergia odorifera Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[9525107]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota Roots n.a. n.a. PMID[9868163]
NPO23024 Epimedium koreanum Species Berberidaceae Eukaryota n.a. aerial part n.a. Database[Article]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. root n.a. Database[Article]
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]
NPO7960 Cicer arietinum Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18117 Dalbergia odorifera 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]
NPO25653 Spatholobus suberectus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7154 Glycyrrhiza uralensis 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]
NPO23024 Epimedium koreanum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7960 Cicer arietinum Species Fabaceae Eukaryota Seeds n.a. Database[Phenol-Explorer]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19231 Sophora flavescens 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]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23024 Epimedium koreanum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25653 Spatholobus suberectus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18117 Dalbergia odorifera 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]
NPO25653 Spatholobus suberectus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12354 Sargassum pallidum Species Sargassaceae 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]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18117 Dalbergia odorifera Species Fabaceae 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]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23024 Epimedium koreanum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19231 Sophora flavescens 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]
NPO23024 Epimedium koreanum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18117 Dalbergia odorifera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25653 Spatholobus suberectus 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]
NPO12354 Sargassum pallidum Species Sargassaceae 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]
NPO19231 Sophora flavescens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO19231 Sophora flavescens 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]
NPO3634 Robinia pseudoacacia Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12354 Sargassum pallidum Species Sargassaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23024 Epimedium koreanum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18117 Dalbergia odorifera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25653 Spatholobus suberectus 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
NPT65 Cell Line HepG2 Homo sapiens Potency n.a. 562.3 nM PMID[537459]
NPT886 Cell Line NIH3T3 Mus musculus Survival = 74.14 % PMID[537461]
NPT886 Cell Line NIH3T3 Mus musculus Survival = 88.44 % PMID[537461]
NPT886 Cell Line NIH3T3 Mus musculus Survival = 110.7 % PMID[537461]
NPT886 Cell Line NIH3T3 Mus musculus Survival = 125.52 % PMID[537461]
NPT886 Cell Line NIH3T3 Mus musculus Activity = 18.42 % PMID[537461]
NPT886 Cell Line NIH3T3 Mus musculus Activity = 7.85 % PMID[537461]
NPT886 Cell Line NIH3T3 Mus musculus Activity = 5.51 % PMID[537461]
NPT886 Cell Line NIH3T3 Mus musculus Activity = 2.63 % PMID[537461]
NPT21 Organism Aspergillus niger Aspergillus niger MIC > 800000.0 nM PMID[537458]
NPT2 Others Unspecified Potency n.a. 501.2 nM PMID[537459]
NPT35 Others n.a. LogD7.4 n.a. 2.4 n.a. PMID[537460]
NPT2 Others Unspecified Potency n.a. 39810.7 nM PMID[537459]
NPT20904 CELL-LINE Hep 3B2 Homo sapiens Activity = 100.18 % PMID[537461]
NPT20904 CELL-LINE Hep 3B2 Homo sapiens Activity = 103.79 % PMID[537461]
NPT20904 CELL-LINE Hep 3B2 Homo sapiens Activity = 111.93 % PMID[537461]
NPT20904 CELL-LINE Hep 3B2 Homo sapiens Activity = 134.54 % PMID[537461]
NPT20904 CELL-LINE Hep 3B2 Homo sapiens Survival = 70.66 % PMID[537461]
NPT20904 CELL-LINE Hep 3B2 Homo sapiens Survival = 88.42 % PMID[537461]
NPT20904 CELL-LINE Hep 3B2 Homo sapiens Survival = 98.79 % PMID[537461]
NPT20904 CELL-LINE Hep 3B2 Homo sapiens Survival = 112.22 % PMID[537461]
NPT20904 CELL-LINE Hep 3B2 Homo sapiens Activity = 11.57 % PMID[537461]
NPT20904 CELL-LINE Hep 3B2 Homo sapiens Activity = 6.83 % PMID[537461]
NPT20904 CELL-LINE Hep 3B2 Homo sapiens Activity = 4.93 % PMID[537461]
NPT20904 CELL-LINE Hep 3B2 Homo sapiens Activity = 3.82 % PMID[537461]

☑ 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 NPC329225 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 NPC147686
1.0 High Similarity NPC472460
0.9924 High Similarity NPC79943
0.9924 High Similarity NPC287246
0.9924 High Similarity NPC84585
0.9924 High Similarity NPC296490
0.9924 High Similarity NPC13768
0.9924 High Similarity NPC243083
0.9924 High Similarity NPC32441
0.9924 High Similarity NPC476480
0.9924 High Similarity NPC295261
0.9924 High Similarity NPC107586
0.9924 High Similarity NPC12296
0.9776 High Similarity NPC20709
0.9776 High Similarity NPC310135
0.9776 High Similarity NPC150648
0.9776 High Similarity NPC225153
0.9776 High Similarity NPC265871
0.9776 High Similarity NPC274784
0.9776 High Similarity NPC329203
0.9776 High Similarity NPC261234
0.9776 High Similarity NPC222342
0.9774 High Similarity NPC275055
0.9774 High Similarity NPC290291
0.9773 High Similarity NPC9985
0.9773 High Similarity NPC239495
0.9704 High Similarity NPC110228
0.9704 High Similarity NPC6407
0.9704 High Similarity NPC188243
0.9701 High Similarity NPC118813
0.9701 High Similarity NPC280284
0.9701 High Similarity NPC188947
0.9701 High Similarity NPC99333
0.9635 High Similarity NPC310130
0.9635 High Similarity NPC149026
0.9635 High Similarity NPC68104
0.9635 High Similarity NPC257097
0.9635 High Similarity NPC91560
0.9635 High Similarity NPC175504
0.9635 High Similarity NPC75049
0.9635 High Similarity NPC39329
0.9635 High Similarity NPC150408
0.9635 High Similarity NPC143896
0.9635 High Similarity NPC164980
0.9635 High Similarity NPC221432
0.9635 High Similarity NPC169591
0.9632 High Similarity NPC3188
0.9632 High Similarity NPC213322
0.9632 High Similarity NPC324386
0.9632 High Similarity NPC4743
0.9632 High Similarity NPC312391
0.963 High Similarity NPC316480
0.963 High Similarity NPC140890
0.9565 High Similarity NPC473015
0.9565 High Similarity NPC236766
0.9565 High Similarity NPC209040
0.9565 High Similarity NPC197252
0.9565 High Similarity NPC473013
0.9562 High Similarity NPC148757
0.9562 High Similarity NPC37496
0.9562 High Similarity NPC125855
0.9562 High Similarity NPC296917
0.9562 High Similarity NPC1089
0.9562 High Similarity NPC194432
0.9562 High Similarity NPC76338
0.9562 High Similarity NPC306829
0.9562 High Similarity NPC166934
0.9562 High Similarity NPC32739
0.9562 High Similarity NPC177354
0.9562 High Similarity NPC228504
0.9562 High Similarity NPC107572
0.9562 High Similarity NPC227579
0.9562 High Similarity NPC78
0.9562 High Similarity NPC166482
0.9562 High Similarity NPC182852
0.9562 High Similarity NPC223500
0.9562 High Similarity NPC161506
0.9562 High Similarity NPC64915
0.9562 High Similarity NPC328164
0.9562 High Similarity NPC265040
0.9562 High Similarity NPC167624
0.9562 High Similarity NPC324436
0.9562 High Similarity NPC220998
0.9562 High Similarity NPC66515
0.9562 High Similarity NPC202981
0.9562 High Similarity NPC324134
0.9562 High Similarity NPC10937
0.9562 High Similarity NPC40833
0.9562 High Similarity NPC76372
0.9559 High Similarity NPC284550
0.9559 High Similarity NPC129853
0.9559 High Similarity NPC76445
0.9559 High Similarity NPC182421
0.9556 High Similarity NPC124269
0.9549 High Similarity NPC172262
0.9496 High Similarity NPC1940
0.9496 High Similarity NPC148011
0.9493 High Similarity NPC125894
0.9493 High Similarity NPC81697
0.9493 High Similarity NPC85162
0.9493 High Similarity NPC278249
0.9493 High Similarity NPC77794
0.9493 High Similarity NPC223812
0.9493 High Similarity NPC107177
0.9493 High Similarity NPC478086
0.9493 High Similarity NPC185276
0.9493 High Similarity NPC214166
0.9493 High Similarity NPC316816
0.9489 High Similarity NPC110038
0.9489 High Similarity NPC166689
0.9489 High Similarity NPC17170
0.9489 High Similarity NPC258630
0.9489 High Similarity NPC156190
0.9489 High Similarity NPC248372
0.9489 High Similarity NPC96408
0.9489 High Similarity NPC279650
0.9481 High Similarity NPC266597
0.9481 High Similarity NPC188879
0.9481 High Similarity NPC250266
0.9478 High Similarity NPC39426
0.9478 High Similarity NPC234560
0.9474 High Similarity NPC78540
0.9474 High Similarity NPC50898
0.9474 High Similarity NPC274121
0.9474 High Similarity NPC213216
0.9474 High Similarity NPC57601
0.9429 High Similarity NPC23728
0.9429 High Similarity NPC110303
0.9424 High Similarity NPC4152
0.9424 High Similarity NPC279417
0.9424 High Similarity NPC39045
0.9424 High Similarity NPC142731
0.9424 High Similarity NPC306607
0.9424 High Similarity NPC303185
0.9424 High Similarity NPC473014
0.9424 High Similarity NPC131568
0.9424 High Similarity NPC49130
0.9424 High Similarity NPC62290
0.9424 High Similarity NPC470135
0.9424 High Similarity NPC208176
0.9424 High Similarity NPC326506
0.9424 High Similarity NPC184649
0.9424 High Similarity NPC470136
0.9424 High Similarity NPC131579
0.9424 High Similarity NPC235217
0.942 High Similarity NPC147145
0.942 High Similarity NPC73028
0.9416 High Similarity NPC69769
0.9407 High Similarity NPC234133
0.9407 High Similarity NPC240593
0.9407 High Similarity NPC47815
0.9407 High Similarity NPC29353
0.9407 High Similarity NPC124784
0.9407 High Similarity NPC235428
0.9407 High Similarity NPC473887
0.9407 High Similarity NPC231772
0.9407 High Similarity NPC87545
0.9407 High Similarity NPC127447
0.9407 High Similarity NPC194281
0.9362 High Similarity NPC132592
0.9362 High Similarity NPC160821
0.9357 High Similarity NPC267375
0.9357 High Similarity NPC88964
0.9357 High Similarity NPC470647
0.9357 High Similarity NPC229190
0.9357 High Similarity NPC470134
0.9357 High Similarity NPC312973
0.9357 High Similarity NPC176229
0.9357 High Similarity NPC142405
0.9357 High Similarity NPC301276
0.9357 High Similarity NPC54577
0.9357 High Similarity NPC473078
0.9357 High Similarity NPC67805
0.9357 High Similarity NPC475052
0.9357 High Similarity NPC83357
0.9357 High Similarity NPC246948
0.9357 High Similarity NPC109183
0.9357 High Similarity NPC299011
0.9357 High Similarity NPC470133
0.9357 High Similarity NPC472629
0.9357 High Similarity NPC470132
0.9357 High Similarity NPC111786
0.9357 High Similarity NPC20488
0.9357 High Similarity NPC195621
0.9357 High Similarity NPC285630
0.9357 High Similarity NPC214774
0.9357 High Similarity NPC127059
0.9357 High Similarity NPC470131
0.9353 High Similarity NPC166138
0.9353 High Similarity NPC106985
0.9353 High Similarity NPC113770
0.9353 High Similarity NPC18585
0.9348 High Similarity NPC110969
0.9343 High Similarity NPC78913
0.9343 High Similarity NPC18260
0.9338 High Similarity NPC294409
0.9338 High Similarity NPC162680
0.9338 High Similarity NPC181124
0.9338 High Similarity NPC116632
0.9338 High Similarity NPC212767

  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 NPC329225 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
1.0 High Similarity NPD1549 Phase 2
0.9924 High Similarity NPD1550 Clinical (unspecified phase)
0.9924 High Similarity NPD1552 Clinical (unspecified phase)
0.9478 High Similarity NPD1510 Phase 2
0.9323 High Similarity NPD1240 Approved
0.9185 High Similarity NPD1607 Approved
0.9124 High Similarity NPD2796 Approved
0.9014 High Similarity NPD4378 Clinical (unspecified phase)
0.8973 High Similarity NPD1934 Approved
0.8966 High Similarity NPD4380 Phase 2
0.8912 High Similarity NPD2393 Clinical (unspecified phase)
0.8904 High Similarity NPD7411 Suspended
0.8881 High Similarity NPD7410 Clinical (unspecified phase)
0.8859 High Similarity NPD4381 Clinical (unspecified phase)
0.8859 High Similarity NPD7075 Discontinued
0.8851 High Similarity NPD8443 Clinical (unspecified phase)
0.8811 High Similarity NPD1511 Approved
0.8784 High Similarity NPD7096 Clinical (unspecified phase)
0.8714 High Similarity NPD1551 Phase 2
0.869 High Similarity NPD1512 Approved
0.8681 High Similarity NPD6799 Approved
0.8658 High Similarity NPD7819 Suspended
0.8636 High Similarity NPD1547 Clinical (unspecified phase)
0.8601 High Similarity NPD3750 Approved
0.8591 High Similarity NPD6801 Discontinued
0.8487 Intermediate Similarity NPD3749 Approved
0.8456 Intermediate Similarity NPD6599 Discontinued
0.8421 Intermediate Similarity NPD3882 Suspended
0.8411 Intermediate Similarity NPD2801 Approved
0.8403 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8397 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8397 Intermediate Similarity NPD6166 Phase 2
0.8397 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8397 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8382 Intermediate Similarity NPD1203 Approved
0.8378 Intermediate Similarity NPD5403 Approved
0.8367 Intermediate Similarity NPD5401 Approved
0.8345 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8323 Intermediate Similarity NPD6959 Discontinued
0.8301 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8301 Intermediate Similarity NPD7768 Phase 2
0.8291 Intermediate Similarity NPD3818 Discontinued
0.8252 Intermediate Similarity NPD3748 Approved
0.8239 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8231 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.8222 Intermediate Similarity NPD1610 Phase 2
0.8195 Intermediate Similarity NPD1548 Phase 1
0.8187 Intermediate Similarity NPD7074 Phase 3
0.8151 Intermediate Similarity NPD1243 Approved
0.8151 Intermediate Similarity NPD2800 Approved
0.8141 Intermediate Similarity NPD5494 Approved
0.8138 Intermediate Similarity NPD2344 Approved
0.8133 Intermediate Similarity NPD920 Approved
0.8125 Intermediate Similarity NPD7054 Approved
0.8121 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.8117 Intermediate Similarity NPD3817 Phase 2
0.8099 Intermediate Similarity NPD943 Approved
0.8095 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.8075 Intermediate Similarity NPD7472 Approved
0.8029 Intermediate Similarity NPD9717 Approved
0.8025 Intermediate Similarity NPD6797 Phase 2
0.8 Intermediate Similarity NPD5402 Approved
0.7986 Intermediate Similarity NPD6651 Approved
0.7975 Intermediate Similarity NPD7251 Discontinued
0.7975 Intermediate Similarity NPD6559 Discontinued
0.7973 Intermediate Similarity NPD4628 Phase 3
0.7958 Intermediate Similarity NPD2313 Discontinued
0.7945 Intermediate Similarity NPD2935 Discontinued
0.7943 Intermediate Similarity NPD6832 Phase 2
0.7943 Intermediate Similarity NPD4908 Phase 1
0.7927 Intermediate Similarity NPD7808 Phase 3
0.7927 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7919 Intermediate Similarity NPD2309 Approved
0.7914 Intermediate Similarity NPD5953 Discontinued
0.7901 Intermediate Similarity NPD7286 Phase 2
0.7877 Intermediate Similarity NPD7033 Discontinued
0.7877 Intermediate Similarity NPD2799 Discontinued
0.7877 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7847 Intermediate Similarity NPD1613 Approved
0.7847 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7832 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7826 Intermediate Similarity NPD422 Phase 1
0.7823 Intermediate Similarity NPD6099 Approved
0.7823 Intermediate Similarity NPD6100 Approved
0.7821 Intermediate Similarity NPD1465 Phase 2
0.7818 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7805 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7794 Intermediate Similarity NPD9545 Approved
0.7791 Intermediate Similarity NPD5844 Phase 1
0.7763 Intermediate Similarity NPD2534 Approved
0.7763 Intermediate Similarity NPD2532 Approved
0.7763 Intermediate Similarity NPD2533 Approved
0.7736 Intermediate Similarity NPD919 Approved
0.7708 Intermediate Similarity NPD3268 Approved
0.7702 Intermediate Similarity NPD6232 Discontinued
0.7692 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7687 Intermediate Similarity NPD1241 Discontinued
0.7677 Intermediate Similarity NPD3226 Approved
0.7676 Intermediate Similarity NPD2798 Approved
0.7671 Intermediate Similarity NPD1933 Approved
0.7669 Intermediate Similarity NPD7473 Discontinued
0.766 Intermediate Similarity NPD3225 Approved
0.7651 Intermediate Similarity NPD2346 Discontinued
0.7647 Intermediate Similarity NPD9493 Approved
0.7647 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.764 Intermediate Similarity NPD1247 Approved
0.7635 Intermediate Similarity NPD4308 Phase 3
0.7622 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7616 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7606 Intermediate Similarity NPD2797 Approved
0.7586 Intermediate Similarity NPD1296 Phase 2
0.758 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7572 Intermediate Similarity NPD4360 Phase 2
0.7572 Intermediate Similarity NPD4363 Phase 3
0.7552 Intermediate Similarity NPD1019 Discontinued
0.7551 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7551 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7551 Intermediate Similarity NPD230 Phase 1
0.7551 Intermediate Similarity NPD5124 Phase 1
0.755 Intermediate Similarity NPD2654 Approved
0.7547 Intermediate Similarity NPD4288 Approved
0.7546 Intermediate Similarity NPD3926 Phase 2
0.753 Intermediate Similarity NPD1729 Discontinued
0.7518 Intermediate Similarity NPD3972 Approved
0.7518 Intermediate Similarity NPD1608 Approved
0.7515 Intermediate Similarity NPD3751 Discontinued
0.7486 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD3266 Approved
0.7483 Intermediate Similarity NPD1470 Approved
0.7483 Intermediate Similarity NPD3267 Approved
0.7466 Intermediate Similarity NPD411 Approved
0.7466 Intermediate Similarity NPD3764 Approved
0.7466 Intermediate Similarity NPD6798 Discontinued
0.7452 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7447 Intermediate Similarity NPD1201 Approved
0.7442 Intermediate Similarity NPD4287 Approved
0.744 Intermediate Similarity NPD6104 Discontinued
0.7436 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7432 Intermediate Similarity NPD447 Suspended
0.74 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7394 Intermediate Similarity NPD1481 Phase 2
0.7379 Intermediate Similarity NPD2861 Phase 2
0.7365 Intermediate Similarity NPD4307 Phase 2
0.7361 Intermediate Similarity NPD1164 Approved
0.7355 Intermediate Similarity NPD7390 Discontinued
0.733 Intermediate Similarity NPD4361 Phase 2
0.733 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7329 Intermediate Similarity NPD2296 Approved
0.7324 Intermediate Similarity NPD1535 Discovery
0.732 Intermediate Similarity NPD1652 Phase 2
0.7312 Intermediate Similarity NPD6844 Discontinued
0.7308 Intermediate Similarity NPD4662 Approved
0.7308 Intermediate Similarity NPD4661 Approved
0.7305 Intermediate Similarity NPD17 Approved
0.7303 Intermediate Similarity NPD1471 Phase 3
0.7289 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7286 Intermediate Similarity NPD1894 Discontinued
0.7279 Intermediate Similarity NPD4625 Phase 3
0.7273 Intermediate Similarity NPD5710 Approved
0.7273 Intermediate Similarity NPD3787 Discontinued
0.7273 Intermediate Similarity NPD5711 Approved
0.7263 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7251 Intermediate Similarity NPD8312 Approved
0.7251 Intermediate Similarity NPD8313 Approved
0.725 Intermediate Similarity NPD5889 Approved
0.725 Intermediate Similarity NPD5890 Approved
0.7248 Intermediate Similarity NPD3140 Approved
0.7248 Intermediate Similarity NPD3142 Approved
0.7244 Intermediate Similarity NPD7212 Phase 2
0.7244 Intermediate Similarity NPD7213 Phase 3
0.7233 Intermediate Similarity NPD7458 Discontinued
0.7226 Intermediate Similarity NPD3887 Approved
0.7226 Intermediate Similarity NPD2354 Approved
0.7222 Intermediate Similarity NPD4749 Approved
0.7213 Intermediate Similarity NPD7584 Approved
0.7205 Intermediate Similarity NPD7577 Discontinued
0.72 Intermediate Similarity NPD6355 Discontinued
0.719 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7185 Intermediate Similarity NPD9266 Approved
0.7185 Intermediate Similarity NPD74 Approved
0.7181 Intermediate Similarity NPD6233 Phase 2
0.7179 Intermediate Similarity NPD7440 Discontinued
0.7172 Intermediate Similarity NPD1876 Approved
0.717 Intermediate Similarity NPD1653 Approved
0.7162 Intermediate Similarity NPD3027 Phase 3
0.7143 Intermediate Similarity NPD9494 Approved
0.7134 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7124 Intermediate Similarity NPD5405 Approved
0.7124 Intermediate Similarity NPD5406 Approved
0.7124 Intermediate Similarity NPD5404 Approved
0.7124 Intermediate Similarity NPD5408 Approved
0.7114 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD9263 Approved
0.7111 Intermediate Similarity NPD9267 Approved
0.7111 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7111 Intermediate Similarity NPD9264 Approved
0.7108 Intermediate Similarity NPD7199 Phase 2
0.7101 Intermediate Similarity NPD7893 Clinical (unspecified phase)

  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