Structure

Physi-Chem Properties

Molecular Weight:  274.08
Volume:  270.459
LogP:  1.722
LogD:  2.002
LogS:  -2.676
# Rotatable Bonds:  1
TPSA:  90.15
# H-Bond Aceptor:  5
# H-Bond Donor:  4
# Rings:  3
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.637
Synthetic Accessibility Score:  3.185
Fsp3:  0.2
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.876
MDCK Permeability:  4.4217931645107456e-06
Pgp-inhibitor:  0.006
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.015
20% Bioavailability (F20%):  0.996
30% Bioavailability (F30%):  0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.035
Plasma Protein Binding (PPB):  92.1573257446289%
Volume Distribution (VD):  0.919
Pgp-substrate:  9.153082847595215%

ADMET: Metabolism

CYP1A2-inhibitor:  0.532
CYP1A2-substrate:  0.193
CYP2C19-inhibitor:  0.097
CYP2C19-substrate:  0.062
CYP2C9-inhibitor:  0.407
CYP2C9-substrate:  0.954
CYP2D6-inhibitor:  0.46
CYP2D6-substrate:  0.597
CYP3A4-inhibitor:  0.564
CYP3A4-substrate:  0.22

ADMET: Excretion

Clearance (CL):  14.423
Half-life (T1/2):  0.852

ADMET: Toxicity

hERG Blockers:  0.04
Human Hepatotoxicity (H-HT):  0.089
Drug-inuced Liver Injury (DILI):  0.049
AMES Toxicity:  0.304
Rat Oral Acute Toxicity:  0.373
Maximum Recommended Daily Dose:  0.096
Skin Sensitization:  0.928
Carcinogencity:  0.3
Eye Corrosion:  0.004
Eye Irritation:  0.873
Respiratory Toxicity:  0.13

Download Data

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

  Natural Product: NPC278552

Natural Product ID:  NPC278552
Common Name*:   Epiafzelechin (2R,3R)(-)
IUPAC Name:   (2R,3R)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
Synonyms:   (-)-Epiafzelechin
Standard InCHIKey:  RSYUFYQTACJFML-UKRRQHHQSA-N
Standard InCHI:  InChI=1S/C15H14O5/c16-9-3-1-8(2-4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-6,13,15-19H,7H2/t13-,15-/m1/s1
SMILES:  Oc1ccc(cc1)[C@H]1Oc2cc(O)cc(c2C[C@H]1O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL159303
PubChem CID:   443639
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000334] Flavonoids
        • [CHEMONTID:0000337] Flavans
          • [CHEMONTID:0003012] Flavan-3-ols

*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
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. DOI[10.1016/j.foodchem.2013.08.121]
NPO6349 Celastrus orbiculatus Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[10346948]
NPO6349 Celastrus orbiculatus Species Celastraceae Eukaryota n.a. root n.a. PMID[10346948]
NPO11740 Sagenomella striatispora Species Trichocomaceae Eukaryota n.a. n.a. n.a. PMID[10869218]
NPO6349 Celastrus orbiculatus Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[11170672]
NPO6349 Celastrus orbiculatus Species Celastraceae Eukaryota n.a. root n.a. PMID[11809076]
NPO10498 Artocarpus dadah Species Moraceae Eukaryota bark and twigs Tewah, Central Kalimantan, Indonesia (N 38 57.003; W 094 44.767) 1999-Oct PMID[11858749]
NPO11740 Sagenomella striatispora Species Trichocomaceae Eukaryota n.a. n.a. n.a. PMID[15217294]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Flowers n.a. n.a. PMID[16180814]
NPO8258 Camellia sinensis Species Theaceae Eukaryota seeds Shizuoka prefecture, Japan n.a. PMID[16499314]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. PMID[18068204]
NPO6349 Celastrus orbiculatus Species Celastraceae Eukaryota Seeds n.a. n.a. PMID[18507472]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. root n.a. PMID[18975262]
NPO11205 Cassia sieberiana Species Fabaceae Eukaryota n.a. root n.a. PMID[21070009]
NPO24093 Drynaria fortunei Species Polypodiaceae Eukaryota n.a. n.a. n.a. PMID[21377852]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. PMID[21434603]
NPO28125 Ephedra equisetina Species Ephedraceae Eukaryota n.a. n.a. n.a. PMID[21465337]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. flower n.a. PMID[21922925]
NPO8258 Camellia sinensis Species Theaceae Eukaryota flower buds n.a. n.a. PMID[21925888]
NPO9537 Bauhinia racemosa Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[22348826]
NPO8258 Camellia sinensis Species Theaceae Eukaryota leaves n.a. n.a. PMID[22377672]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. leaf n.a. PMID[23265489]
NPO6349 Celastrus orbiculatus Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[23421714]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Leaves Bandung, West Java, Indonesia PMID[23621359]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. PMID[24333010]
NPO6349 Celastrus orbiculatus Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[27791375]
NPO6349 Celastrus orbiculatus Species Celastraceae Eukaryota n.a. root n.a. PMID[9461657]
NPO6349 Celastrus orbiculatus Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[9461657]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Cotyledon n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Leaf Essent. Oil n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Seed Oil n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Shoot n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. Database[FooDB]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21507 Ephedra intermedia Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24093 Drynaria fortunei Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10498 Artocarpus dadah Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23538 Ephedra distachya Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6349 Celastrus orbiculatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28125 Ephedra equisetina Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7976 Ephedra gerardiana Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18715 Ephedra minuta Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8352 Canthium berberidifolium Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6349 Celastrus orbiculatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28125 Ephedra equisetina Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23538 Ephedra distachya Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24093 Drynaria fortunei Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10498 Artocarpus dadah Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7976 Ephedra gerardiana Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1334 Senegalia catechu Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21507 Ephedra intermedia Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11205 Cassia sieberiana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18715 Ephedra minuta Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21507 Ephedra intermedia Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11205 Cassia sieberiana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23538 Ephedra distachya Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24093 Drynaria fortunei Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18715 Ephedra minuta Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28125 Ephedra equisetina Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO6349 Celastrus orbiculatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7976 Ephedra gerardiana Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21507 Ephedra intermedia Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1334 Senegalia catechu Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24093 Drynaria fortunei Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28125 Ephedra equisetina Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO6349 Celastrus orbiculatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9537 Bauhinia racemosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24093 Drynaria fortunei Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10498 Artocarpus dadah Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11205 Cassia sieberiana Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11740 Sagenomella striatispora Species Trichocomaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8352 Canthium berberidifolium Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1334 Senegalia catechu Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8258 Camellia sinensis Species Theaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28125 Ephedra equisetina Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7976 Ephedra gerardiana Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23538 Ephedra distachya Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18715 Ephedra minuta Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21507 Ephedra intermedia Species Ephedraceae 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
NPO8258 NPC278552 Tea Or Coffee Leaf 0.6 0.6 0.6 mg/100g Database [DUKE]

☑ 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
NPT759 Cell Line H9 Homo sapiens IC50 = 100.0 ug.mL-1 PMID[462936]
NPT30 Individual Protein Cyclooxygenase-1 Homo sapiens IC50 = 15000.0 nM PMID[462938]
NPT30 Individual Protein Cyclooxygenase-1 Homo sapiens IC50 = 6400.0 nM PMID[462939]
NPT31 Individual Protein Cyclooxygenase-2 Homo sapiens IC50 = 69700.0 nM PMID[462939]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 = 70.0 ug.mL-1 PMID[462936]
NPT27 Others Unspecified Therapeutic index = 1.4 n.a. PMID[462936]
NPT1 Others Radical scavenging activity IC50 = 7.5 ug.mL-1 PMID[462937]
NPT2 Others Unspecified Inhibition = 81.5 % PMID[462939]
NPT2 Others Unspecified Inhibition = 17.0 % PMID[462940]
NPT1 Others Radical scavenging activity IC50 = 9.25 ug.mL-1 PMID[462941]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 493.43 uM/L PMID[462941]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 977.98 uM/L PMID[462941]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Activity = 1506.89 uM/L PMID[462941]
NPT1593 Tissue Liver Rattus norvegicus Activity = 14.4 nM/ml PMID[462941]
NPT1593 Tissue Liver Rattus norvegicus Inhibition = 81.76 % PMID[462941]
NPT138 Organism Brugia malayi Brugia malayi Inhibition = 50.0 % PMID[462942]
NPT138 Organism Brugia malayi Brugia malayi Inhibition = 59.0 % PMID[462942]
NPT138 Organism Brugia malayi Brugia malayi Inhibition = 14.8 % PMID[462942]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 48.25 % PMID[462943]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 26.68 % PMID[462943]
NPT21995 SINGLE PROTEIN Synaptojanin-2 Homo sapiens IC50 = 15900.0 nM PMID[462944]
NPT21994 SINGLE PROTEIN Synaptojanin-1 Homo sapiens IC50 <= 15900.0 nM PMID[462944]
NPT21995 SINGLE PROTEIN Synaptojanin-2 Homo sapiens IC50 = 15900.0 nM PMID[462945]
NPT21994 SINGLE PROTEIN Synaptojanin-1 Homo sapiens IC50 <= 15900.0 nM PMID[462945]
NPT21995 SINGLE PROTEIN Synaptojanin-2 Homo sapiens IC50 = 15900.0 nM PMID[462946]

☑ 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 NPC278552 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 NPC207179
1.0 High Similarity NPC167571
0.9661 High Similarity NPC97432
0.9661 High Similarity NPC190454
0.959 High Similarity NPC222572
0.959 High Similarity NPC87224
0.9516 High Similarity NPC103799
0.9492 High Similarity NPC258979
0.9492 High Similarity NPC8283
0.9492 High Similarity NPC93398
0.944 High Similarity NPC78770
0.944 High Similarity NPC261619
0.944 High Similarity NPC126029
0.944 High Similarity NPC61477
0.944 High Similarity NPC15658
0.944 High Similarity NPC185604
0.944 High Similarity NPC219876
0.936 High Similarity NPC268266
0.936 High Similarity NPC220825
0.936 High Similarity NPC42760
0.936 High Similarity NPC268342
0.9339 High Similarity NPC76465
0.9339 High Similarity NPC38761
0.9274 High Similarity NPC274717
0.9268 High Similarity NPC276212
0.9268 High Similarity NPC471215
0.9268 High Similarity NPC262573
0.9256 High Similarity NPC100099
0.9256 High Similarity NPC36016
0.9219 High Similarity NPC61946
0.9219 High Similarity NPC164787
0.9206 High Similarity NPC162801
0.9187 High Similarity NPC17809
0.9187 High Similarity NPC285040
0.9187 High Similarity NPC102540
0.9187 High Similarity NPC103420
0.9187 High Similarity NPC188022
0.9174 High Similarity NPC193364
0.9174 High Similarity NPC54972
0.916 High Similarity NPC74821
0.9147 High Similarity NPC16435
0.9147 High Similarity NPC302701
0.9147 High Similarity NPC306441
0.9147 High Similarity NPC269091
0.9141 High Similarity NPC124085
0.9141 High Similarity NPC117048
0.912 High Similarity NPC226331
0.912 High Similarity NPC39064
0.912 High Similarity NPC46274
0.912 High Similarity NPC47283
0.9113 High Similarity NPC283049
0.9113 High Similarity NPC50315
0.9113 High Similarity NPC26879
0.9113 High Similarity NPC230479
0.9106 High Similarity NPC106914
0.9106 High Similarity NPC246648
0.9106 High Similarity NPC197351
0.9106 High Similarity NPC86502
0.9106 High Similarity NPC134195
0.9083 High Similarity NPC295259
0.9077 High Similarity NPC87777
0.9077 High Similarity NPC262328
0.907 High Similarity NPC112939
0.907 High Similarity NPC112246
0.907 High Similarity NPC474206
0.907 High Similarity NPC470356
0.907 High Similarity NPC260898
0.907 High Similarity NPC234333
0.907 High Similarity NPC94750
0.907 High Similarity NPC47398
0.907 High Similarity NPC151224
0.907 High Similarity NPC121812
0.9062 High Similarity NPC85435
0.9062 High Similarity NPC92805
0.9062 High Similarity NPC11060
0.9062 High Similarity NPC215037
0.9062 High Similarity NPC263064
0.904 High Similarity NPC250432
0.904 High Similarity NPC5447
0.9024 High Similarity NPC474160
0.9008 High Similarity NPC475836
0.9 High Similarity NPC20829
0.9 High Similarity NPC262585
0.9 High Similarity NPC474639
0.9 High Similarity NPC230734
0.9 High Similarity NPC18189
0.9 High Similarity NPC3049
0.9 High Similarity NPC227503
0.9 High Similarity NPC470802
0.8984 High Similarity NPC86655
0.8984 High Similarity NPC202762
0.8968 High Similarity NPC53986
0.8968 High Similarity NPC38664
0.8931 High Similarity NPC102904
0.8931 High Similarity NPC107551
0.8931 High Similarity NPC326797
0.8931 High Similarity NPC211549
0.8931 High Similarity NPC103976
0.8931 High Similarity NPC176051
0.8931 High Similarity NPC474687
0.8931 High Similarity NPC474282
0.8926 High Similarity NPC172253
0.8926 High Similarity NPC59561
0.8923 High Similarity NPC473413
0.8915 High Similarity NPC475840
0.8906 High Similarity NPC129106
0.8906 High Similarity NPC17343
0.8906 High Similarity NPC268917
0.8906 High Similarity NPC129784
0.8906 High Similarity NPC228369
0.8906 High Similarity NPC476166
0.8906 High Similarity NPC118114
0.8906 High Similarity NPC207892
0.8906 High Similarity NPC164574
0.8906 High Similarity NPC196765
0.8906 High Similarity NPC300875
0.8906 High Similarity NPC12875
0.8906 High Similarity NPC150011
0.8906 High Similarity NPC280653
0.8906 High Similarity NPC236014
0.8906 High Similarity NPC206224
0.8898 High Similarity NPC93962
0.8889 High Similarity NPC149796
0.8872 High Similarity NPC471389
0.8872 High Similarity NPC210192
0.8872 High Similarity NPC100482
0.8872 High Similarity NPC277331
0.8872 High Similarity NPC178054
0.8864 High Similarity NPC236306
0.8864 High Similarity NPC232164
0.8864 High Similarity NPC473739
0.8864 High Similarity NPC471388
0.8855 High Similarity NPC472336
0.8855 High Similarity NPC162659
0.8855 High Similarity NPC248727
0.8855 High Similarity NPC472334
0.8855 High Similarity NPC270456
0.8855 High Similarity NPC265433
0.8855 High Similarity NPC234952
0.8846 High Similarity NPC317380
0.8846 High Similarity NPC170694
0.8837 High Similarity NPC201587
0.8837 High Similarity NPC13005
0.8837 High Similarity NPC253105
0.8837 High Similarity NPC470752
0.8837 High Similarity NPC127624
0.8833 High Similarity NPC301651
0.8833 High Similarity NPC473556
0.8828 High Similarity NPC470225
0.8828 High Similarity NPC27187
0.8828 High Similarity NPC91291
0.8819 High Similarity NPC311293
0.8819 High Similarity NPC148366
0.8806 High Similarity NPC230718
0.8806 High Similarity NPC5253
0.8806 High Similarity NPC472353
0.8806 High Similarity NPC49542
0.8806 High Similarity NPC139976
0.8806 High Similarity NPC84207
0.8806 High Similarity NPC128337
0.8797 High Similarity NPC309124
0.8797 High Similarity NPC184797
0.8788 High Similarity NPC134260
0.8788 High Similarity NPC276490
0.8779 High Similarity NPC472337
0.8779 High Similarity NPC195022
0.8769 High Similarity NPC229442
0.8769 High Similarity NPC168059
0.876 High Similarity NPC472597
0.876 High Similarity NPC121376
0.876 High Similarity NPC250727
0.876 High Similarity NPC211413
0.876 High Similarity NPC244888
0.876 High Similarity NPC68205
0.876 High Similarity NPC271945
0.876 High Similarity NPC309787
0.876 High Similarity NPC118683
0.876 High Similarity NPC164804
0.876 High Similarity NPC293203
0.876 High Similarity NPC181497
0.875 High Similarity NPC470258
0.875 High Similarity NPC285339
0.875 High Similarity NPC273295
0.875 High Similarity NPC202582
0.875 High Similarity NPC3439
0.875 High Similarity NPC222004
0.875 High Similarity NPC226788
0.875 High Similarity NPC218856
0.875 High Similarity NPC134360
0.875 High Similarity NPC190629
0.875 High Similarity NPC210623
0.8722 High Similarity NPC25966
0.8722 High Similarity NPC292487
0.8722 High Similarity NPC245207
0.8722 High Similarity NPC260741
0.8722 High Similarity NPC70682
0.8722 High Similarity NPC32630
0.8722 High Similarity NPC127218
0.8722 High Similarity NPC319647
0.8712 High Similarity NPC173660

  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 NPC278552 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
0.944 High Similarity NPD1613 Approved
0.944 High Similarity NPD1612 Clinical (unspecified phase)
0.9174 High Similarity NPD1610 Phase 2
0.916 High Similarity NPD1548 Phase 1
0.912 High Similarity NPD1529 Clinical (unspecified phase)
0.904 High Similarity NPD1530 Clinical (unspecified phase)
0.8819 High Similarity NPD4908 Phase 1
0.8682 High Similarity NPD4907 Clinical (unspecified phase)
0.8605 High Similarity NPD3027 Phase 3
0.856 High Similarity NPD1091 Approved
0.8309 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8309 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8308 Intermediate Similarity NPD2861 Phase 2
0.8248 Intermediate Similarity NPD1549 Phase 2
0.8235 Intermediate Similarity NPD290 Approved
0.8188 Intermediate Similarity NPD1652 Phase 2
0.8125 Intermediate Similarity NPD422 Phase 1
0.8045 Intermediate Similarity NPD4625 Phase 3
0.8017 Intermediate Similarity NPD2684 Approved
0.8014 Intermediate Similarity NPD1934 Approved
0.8 Intermediate Similarity NPD4380 Phase 2
0.8 Intermediate Similarity NPD4749 Approved
0.8 Intermediate Similarity NPD968 Approved
0.7985 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7985 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7958 Intermediate Similarity NPD7213 Phase 3
0.7958 Intermediate Similarity NPD7212 Phase 2
0.7956 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7956 Intermediate Similarity NPD4536 Approved
0.7956 Intermediate Similarity NPD4538 Approved
0.7941 Intermediate Similarity NPD5124 Phase 1
0.7941 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7929 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7919 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7903 Intermediate Similarity NPD7843 Approved
0.7899 Intermediate Similarity NPD5960 Phase 3
0.7899 Intermediate Similarity NPD5588 Approved
0.7862 Intermediate Similarity NPD1653 Approved
0.7838 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7829 Intermediate Similarity NPD5846 Approved
0.7829 Intermediate Similarity NPD6516 Phase 2
0.7803 Intermediate Similarity NPD8651 Approved
0.7778 Intermediate Similarity NPD7447 Phase 1
0.777 Intermediate Similarity NPD1510 Phase 2
0.7733 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7721 Intermediate Similarity NPD6798 Discontinued
0.7717 Intermediate Similarity NPD7157 Approved
0.7708 Intermediate Similarity NPD1511 Approved
0.7682 Intermediate Similarity NPD7075 Discontinued
0.7667 Intermediate Similarity NPD846 Approved
0.7667 Intermediate Similarity NPD940 Approved
0.7655 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7639 Intermediate Similarity NPD5058 Phase 3
0.7622 Intermediate Similarity NPD3750 Approved
0.7613 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7613 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7613 Intermediate Similarity NPD6166 Phase 2
0.7609 Intermediate Similarity NPD4060 Phase 1
0.7609 Intermediate Similarity NPD1240 Approved
0.7603 Intermediate Similarity NPD1512 Approved
0.76 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7584 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7578 Intermediate Similarity NPD6671 Approved
0.7551 Intermediate Similarity NPD5403 Approved
0.7536 Intermediate Similarity NPD6233 Phase 2
0.7534 Intermediate Similarity NPD5401 Approved
0.7533 Intermediate Similarity NPD6801 Discontinued
0.7518 Intermediate Similarity NPD7033 Discontinued
0.75 Intermediate Similarity NPD1607 Approved
0.75 Intermediate Similarity NPD3018 Phase 2
0.7483 Intermediate Similarity NPD2424 Discontinued
0.7483 Intermediate Similarity NPD2801 Approved
0.7468 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7466 Intermediate Similarity NPD6799 Approved
0.7465 Intermediate Similarity NPD2796 Approved
0.7465 Intermediate Similarity NPD1551 Phase 2
0.7463 Intermediate Similarity NPD6582 Phase 2
0.7463 Intermediate Similarity NPD6583 Phase 3
0.7438 Intermediate Similarity NPD1242 Phase 1
0.7434 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7429 Intermediate Similarity NPD6355 Discontinued
0.7429 Intermediate Similarity NPD4340 Discontinued
0.7426 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7421 Intermediate Similarity NPD7074 Phase 3
0.7407 Intermediate Similarity NPD3225 Approved
0.7405 Intermediate Similarity NPD3818 Discontinued
0.7402 Intermediate Similarity NPD228 Approved
0.7379 Intermediate Similarity NPD4628 Phase 3
0.7379 Intermediate Similarity NPD3892 Phase 2
0.7379 Intermediate Similarity NPD4535 Phase 3
0.7368 Intermediate Similarity NPD8455 Phase 2
0.7358 Intermediate Similarity NPD7054 Approved
0.7351 Intermediate Similarity NPD7411 Suspended
0.7344 Intermediate Similarity NPD5535 Approved
0.7343 Intermediate Similarity NPD6099 Approved
0.7343 Intermediate Similarity NPD6100 Approved
0.7333 Intermediate Similarity NPD2983 Phase 2
0.7333 Intermediate Similarity NPD2982 Phase 2
0.7329 Intermediate Similarity NPD6559 Discontinued
0.7324 Intermediate Similarity NPD7097 Phase 1
0.732 Intermediate Similarity NPD5402 Approved
0.7313 Intermediate Similarity NPD1535 Discovery
0.7312 Intermediate Similarity NPD7472 Approved
0.731 Intermediate Similarity NPD6674 Discontinued
0.7299 Intermediate Similarity NPD6584 Phase 3
0.7297 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7285 Intermediate Similarity NPD6599 Discontinued
0.7273 Intermediate Similarity NPD3748 Approved
0.7273 Intermediate Similarity NPD3882 Suspended
0.7267 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD6797 Phase 2
0.726 Intermediate Similarity NPD7466 Approved
0.7259 Intermediate Similarity NPD1481 Phase 2
0.7259 Intermediate Similarity NPD2981 Phase 2
0.7255 Intermediate Similarity NPD1465 Phase 2
0.725 Intermediate Similarity NPD5844 Phase 1
0.7236 Intermediate Similarity NPD291 Approved
0.7234 Intermediate Similarity NPD5837 Clinical (unspecified phase)
0.7234 Intermediate Similarity NPD1558 Phase 1
0.7226 Intermediate Similarity NPD2797 Approved
0.7222 Intermediate Similarity NPD7251 Discontinued
0.7214 Intermediate Similarity NPD1296 Phase 2
0.7211 Intermediate Similarity NPD2677 Approved
0.7209 Intermediate Similarity NPD821 Approved
0.7208 Intermediate Similarity NPD3817 Phase 2
0.7206 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7203 Intermediate Similarity NPD9365 Approved
0.7197 Intermediate Similarity NPD7199 Phase 2
0.7194 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.7192 Intermediate Similarity NPD5061 Approved
0.7192 Intermediate Similarity NPD5062 Approved
0.7192 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD37 Approved
0.7185 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7183 Intermediate Similarity NPD5735 Approved
0.7179 Intermediate Similarity NPD6234 Discontinued
0.7178 Intermediate Similarity NPD7808 Phase 3
0.7178 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7172 Intermediate Similarity NPD5762 Approved
0.7172 Intermediate Similarity NPD5763 Approved
0.7172 Intermediate Similarity NPD7266 Discontinued
0.7172 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7163 Intermediate Similarity NPD4062 Phase 3
0.7161 Intermediate Similarity NPD7768 Phase 2
0.7161 Intermediate Similarity NPD4965 Approved
0.7161 Intermediate Similarity NPD4966 Approved
0.7161 Intermediate Similarity NPD4967 Phase 2
0.7154 Intermediate Similarity NPD5283 Phase 1
0.7152 Intermediate Similarity NPD3787 Discontinued
0.7143 Intermediate Similarity NPD1894 Discontinued
0.7143 Intermediate Similarity NPD3179 Approved
0.7143 Intermediate Similarity NPD3180 Approved
0.7143 Intermediate Similarity NPD7819 Suspended
0.7143 Intermediate Similarity NPD7095 Approved
0.7143 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD3054 Approved
0.7133 Intermediate Similarity NPD3052 Approved
0.7132 Intermediate Similarity NPD2231 Phase 2
0.7132 Intermediate Similarity NPD2235 Phase 2
0.7124 Intermediate Similarity NPD6072 Discontinued
0.7113 Intermediate Similarity NPD2238 Phase 2
0.7113 Intermediate Similarity NPD3597 Clinical (unspecified phase)
0.7109 Intermediate Similarity NPD5451 Approved
0.7107 Intermediate Similarity NPD2859 Approved
0.7107 Intermediate Similarity NPD2860 Approved
0.7105 Intermediate Similarity NPD8158 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD1203 Approved
0.7092 Intermediate Similarity NPD3268 Approved
0.7089 Intermediate Similarity NPD6959 Discontinued
0.7083 Intermediate Similarity NPD4978 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD2200 Suspended
0.7081 Intermediate Similarity NPD7228 Approved
0.7081 Intermediate Similarity NPD3751 Discontinued
0.708 Intermediate Similarity NPD3685 Discontinued
0.7075 Intermediate Similarity NPD5177 Phase 3
0.7067 Intermediate Similarity NPD3536 Discontinued
0.7067 Intermediate Similarity NPD3985 Discontinued
0.7059 Intermediate Similarity NPD4675 Approved
0.7059 Intermediate Similarity NPD4678 Approved
0.705 Intermediate Similarity NPD3690 Phase 2
0.705 Intermediate Similarity NPD3691 Phase 2
0.7045 Intermediate Similarity NPD2557 Approved
0.7037 Intermediate Similarity NPD5125 Phase 3
0.7037 Intermediate Similarity NPD5126 Approved
0.7034 Intermediate Similarity NPD3846 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD2934 Approved
0.7025 Intermediate Similarity NPD2933 Approved
0.7025 Intermediate Similarity NPD5494 Approved
0.7015 Intermediate Similarity NPD6580 Approved
0.7015 Intermediate Similarity NPD1182 Approved
0.7015 Intermediate Similarity NPD6581 Approved
0.7007 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD1608 Approved
0.7006 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7006 Intermediate Similarity NPD3749 Approved
0.7 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.6993 Remote Similarity NPD3620 Phase 2
0.6993 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6992 Remote Similarity NPD3596 Phase 2

  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