Structure

Physi-Chem Properties

Molecular Weight:  216.08
Volume:  226.843
LogP:  3.808
LogD:  2.918
LogS:  -3.612
# Rotatable Bonds:  2
TPSA:  50.44
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  3

MedChem Properties

QED Drug-Likeness Score:  0.783
Synthetic Accessibility Score:  2.641
Fsp3:  0.154
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.8
MDCK Permeability:  1.623463504074607e-05
Pgp-inhibitor:  0.011
Pgp-substrate:  0.005
Human Intestinal Absorption (HIA):  0.006
20% Bioavailability (F20%):  0.028
30% Bioavailability (F30%):  0.762

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.013
Plasma Protein Binding (PPB):  90.13874816894531%
Volume Distribution (VD):  0.98
Pgp-substrate:  14.90678596496582%

ADMET: Metabolism

CYP1A2-inhibitor:  0.982
CYP1A2-substrate:  0.759
CYP2C19-inhibitor:  0.804
CYP2C19-substrate:  0.07
CYP2C9-inhibitor:  0.552
CYP2C9-substrate:  0.694
CYP2D6-inhibitor:  0.567
CYP2D6-substrate:  0.614
CYP3A4-inhibitor:  0.355
CYP3A4-substrate:  0.169

ADMET: Excretion

Clearance (CL):  5.673
Half-life (T1/2):  0.711

ADMET: Toxicity

hERG Blockers:  0.02
Human Hepatotoxicity (H-HT):  0.154
Drug-inuced Liver Injury (DILI):  0.771
AMES Toxicity:  0.058
Rat Oral Acute Toxicity:  0.071
Maximum Recommended Daily Dose:  0.869
Skin Sensitization:  0.542
Carcinogencity:  0.542
Eye Corrosion:  0.058
Eye Irritation:  0.952
Respiratory Toxicity:  0.629

Download Data

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

  Natural Product: NPC28337

Natural Product ID:  NPC28337
Common Name*:   Euparin
IUPAC Name:   1-(6-hydroxy-2-prop-1-en-2-yl-1-benzofuran-5-yl)ethanone
Synonyms:   Euparin
Standard InCHIKey:  OPUFDNZTKHPZHM-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C13H12O3/c1-7(2)12-5-9-4-10(8(3)14)11(15)6-13(9)16-12/h4-6,15H,1H2,2-3H3
SMILES:  C=C(C)c1cc2cc(C(=O)C)c(cc2o1)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL503938
PubChem CID:   119039
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000301] Benzofurans

*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
NPO851 Eupatorium lindleyanum Species Asteraceae Eukaryota Whole plant Songyang County, Zhejiang Province, China n.a. PMID[15387644]
NPO451 Dracaena deisteliana Species Teiidae Eukaryota stems Yaound, village of Bangoua, near Bangangt 2007-APR PMID[20553003]
NPO6414 Eupatorium cannabinum Species Asteraceae Eukaryota n.a. aerial part n.a. PMID[21391659]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. whole plant n.a. PMID[21428416]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[22870812]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[23435948]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[25737008]
NPO6414 Eupatorium cannabinum Species Asteraceae Eukaryota Aerial Parts n.a. n.a. PMID[30653318]
NPO13981 Helianthella quinquenervis Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[8882437]
NPO851 Eupatorium lindleyanum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO21343 Eupatorium fortunei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26664 Senecio nudicaulis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6414 Eupatorium cannabinum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6401 Ligularia stenocephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22160 Polygonatum cyrtonema Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26664 Senecio nudicaulis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6401 Ligularia stenocephala Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO851 Eupatorium lindleyanum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21343 Eupatorium fortunei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6414 Eupatorium cannabinum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22160 Polygonatum cyrtonema Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO851 Eupatorium lindleyanum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO6414 Eupatorium cannabinum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22160 Polygonatum cyrtonema Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21343 Eupatorium fortunei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO851 Eupatorium lindleyanum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22160 Polygonatum cyrtonema Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7123 Aria intermedia Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25827 Echinops giganteus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO851 Eupatorium lindleyanum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26546 Gnaphalium obtusifolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10328 Sida hermaphrodita Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11100 Artemisia capillaris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6035 Streptomyces flavofungini Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO7124 Ophiorrhiza acuminata Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13143 Musineon divaricatum Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9831 Acacia catechuoides Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21343 Eupatorium fortunei Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13981 Helianthella quinquenervis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9205 Hartwrightia floridana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6206 Ursinia nudicaulis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6414 Eupatorium cannabinum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22160 Polygonatum cyrtonema Species Asparagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1282 Haminoea fusari Species Haminoeidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6897 Petersianthus macrocarpus Species Lecythidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26225 Solanum hindsianum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO451 Dracaena deisteliana Species Teiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25771 Magnolia stellata Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26664 Senecio nudicaulis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6401 Ligularia stenocephala Species Asteraceae 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
NPT83 Cell Line MCF7 Homo sapiens ED50 = 6.0 ug ml-1 PMID[525446]
NPT139 Cell Line HT-29 Homo sapiens ED50 = 6.0 ug ml-1 PMID[525446]
NPT81 Cell Line A549 Homo sapiens ED50 = 22.0 ug ml-1 PMID[525446]
NPT483 Individual Protein Prelamin-A/C Homo sapiens Potency = 14125.4 nM PMID[525449]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 17782.8 nM PMID[525449]
NPT531 Individual Protein Nuclear receptor ROR-gamma Mus musculus Potency = 446.7 nM PMID[525449]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Potency = 31622.8 nM PMID[525449]
NPT140 Organism Artemia Artemia LC50 = 44.0 ug.mL-1 PMID[525446]
NPT117 Organism Echinochloa crus-galli Echinochloa crus-galli IC50 = 252.0 ug.mL-1 PMID[525446]
NPT965 Organism Amaranthus hypochondriacus Amaranthus hypochondriacus IC50 = 111.0 ug.mL-1 PMID[525446]
NPT330 Organism Trichophyton mentagrophytes Trichophyton mentagrophytes MIC = 29.0 ug.mL-1 PMID[525446]
NPT454 Organism Tenebrio molitor Tenebrio molitor Activity = 83.0 % PMID[525447]
NPT454 Organism Tenebrio molitor Tenebrio molitor Activity = 10.5 day PMID[525447]
NPT2 Others Unspecified Potency = 6309.6 nM PMID[525449]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 13.7 % PMID[525450]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. Inhibition = 12.6 % PMID[525450]
NPT776 Organism Spodoptera littoralis Spodoptera littoralis FR50 = 0.42 n.a. PMID[525451]
NPT176 Organism Artemia salina Artemia salina LC50 = 58.9 ppm PMID[525451]
NPT1175 Organism Spodoptera litura Spodoptera litura pED50 = 5.92 n.a. PMID[525452]
NPT35 Others n.a. Rf = 0.76 n.a. PMID[525452]
NPT1175 Organism Spodoptera litura Spodoptera litura ED50 = 1.2 10'-9mol/cm2 PMID[525452]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 94.93 % PMID[525453]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 98.85 % PMID[525453]
NPT2 Others Unspecified Potency n.a. 35481.3 nM PMID[525449]
NPT2 Others Unspecified Potency n.a. 4466.8 nM PMID[525449]
NPT2 Others Unspecified Potency n.a. 3162.3 nM PMID[525449]

☑ 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 NPC28337 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.9556 High Similarity NPC29638
0.9496 High Similarity NPC225884
0.9362 High Similarity NPC51641
0.9362 High Similarity NPC300267
0.9362 High Similarity NPC210826
0.9296 High Similarity NPC12148
0.9296 High Similarity NPC130581
0.9286 High Similarity NPC53192
0.9231 High Similarity NPC272194
0.9231 High Similarity NPC135325
0.922 High Similarity NPC302181
0.9209 High Similarity NPC37206
0.9209 High Similarity NPC137009
0.9172 High Similarity NPC116604
0.9167 High Similarity NPC296030
0.9167 High Similarity NPC226644
0.9167 High Similarity NPC37226
0.9167 High Similarity NPC178202
0.9167 High Similarity NPC39929
0.9167 High Similarity NPC37208
0.9167 High Similarity NPC221868
0.9155 High Similarity NPC230943
0.911 High Similarity NPC253872
0.911 High Similarity NPC263676
0.9103 High Similarity NPC230713
0.9103 High Similarity NPC78335
0.9078 High Similarity NPC171870
0.9071 High Similarity NPC262635
0.9058 High Similarity NPC151113
0.9051 High Similarity NPC108113
0.9051 High Similarity NPC93756
0.9041 High Similarity NPC170169
0.9028 High Similarity NPC17816
0.9021 High Similarity NPC155144
0.8986 High Similarity NPC125920
0.898 High Similarity NPC5871
0.8958 High Similarity NPC190572
0.8944 High Similarity NPC254010
0.8929 High Similarity NPC228661
0.8921 High Similarity NPC163029
0.8921 High Similarity NPC60667
0.8919 High Similarity NPC183874
0.8919 High Similarity NPC122365
0.8919 High Similarity NPC472462
0.8919 High Similarity NPC235333
0.8919 High Similarity NPC213608
0.8919 High Similarity NPC1477
0.8913 High Similarity NPC247743
0.8897 High Similarity NPC198427
0.8889 High Similarity NPC98926
0.8881 High Similarity NPC144499
0.8881 High Similarity NPC313036
0.8873 High Similarity NPC307990
0.8873 High Similarity NPC305355
0.8873 High Similarity NPC172986
0.8873 High Similarity NPC261227
0.8873 High Similarity NPC16455
0.8873 High Similarity NPC69769
0.8873 High Similarity NPC475680
0.8873 High Similarity NPC270883
0.8865 High Similarity NPC470671
0.8865 High Similarity NPC131130
0.8865 High Similarity NPC474487
0.8865 High Similarity NPC474504
0.8865 High Similarity NPC470672
0.8865 High Similarity NPC201395
0.8859 High Similarity NPC297531
0.8859 High Similarity NPC198490
0.8859 High Similarity NPC148938
0.8859 High Similarity NPC213936
0.8857 High Similarity NPC222633
0.8857 High Similarity NPC156910
0.8857 High Similarity NPC174999
0.8844 High Similarity NPC167576
0.8836 High Similarity NPC168085
0.8832 High Similarity NPC270369
0.8832 High Similarity NPC5515
0.8824 High Similarity NPC230818
0.8819 High Similarity NPC166138
0.8819 High Similarity NPC18585
0.8819 High Similarity NPC172182
0.8819 High Similarity NPC262935
0.8819 High Similarity NPC251182
0.8819 High Similarity NPC106985
0.8819 High Similarity NPC17262
0.8811 High Similarity NPC64908
0.8811 High Similarity NPC205006
0.8811 High Similarity NPC156590
0.8811 High Similarity NPC118840
0.8811 High Similarity NPC147688
0.8811 High Similarity NPC110969
0.8811 High Similarity NPC3188
0.8803 High Similarity NPC18260
0.8803 High Similarity NPC78913
0.8803 High Similarity NPC301217
0.8803 High Similarity NPC55018
0.8803 High Similarity NPC96565
0.8803 High Similarity NPC216978
0.8803 High Similarity NPC220062
0.8803 High Similarity NPC303633
0.88 High Similarity NPC180924
0.88 High Similarity NPC160015
0.88 High Similarity NPC247677
0.8794 High Similarity NPC254841
0.8794 High Similarity NPC62735
0.8792 High Similarity NPC473194
0.8786 High Similarity NPC9985
0.8786 High Similarity NPC239495
0.8784 High Similarity NPC193976
0.8784 High Similarity NPC106372
0.8784 High Similarity NPC156244
0.8784 High Similarity NPC115324
0.8784 High Similarity NPC58668
0.8784 High Similarity NPC23668
0.8777 High Similarity NPC57601
0.8776 High Similarity NPC317492
0.8768 High Similarity NPC31872
0.8768 High Similarity NPC473584
0.8768 High Similarity NPC475589
0.8768 High Similarity NPC313618
0.8768 High Similarity NPC27490
0.8759 High Similarity NPC311741
0.8759 High Similarity NPC84772
0.8759 High Similarity NPC234629
0.8759 High Similarity NPC470857
0.8759 High Similarity NPC297788
0.8758 High Similarity NPC219861
0.8758 High Similarity NPC193998
0.875 High Similarity NPC473042
0.875 High Similarity NPC186098
0.875 High Similarity NPC80694
0.875 High Similarity NPC11561
0.875 High Similarity NPC226636
0.8742 High Similarity NPC164110
0.8742 High Similarity NPC246647
0.8742 High Similarity NPC296957
0.8742 High Similarity NPC65504
0.8742 High Similarity NPC96342
0.8742 High Similarity NPC268360
0.8742 High Similarity NPC260902
0.8742 High Similarity NPC212967
0.8741 High Similarity NPC159275
0.8741 High Similarity NPC477272
0.8741 High Similarity NPC241100
0.8741 High Similarity NPC235239
0.8732 High Similarity NPC21350
0.8732 High Similarity NPC57380
0.8732 High Similarity NPC470668
0.8732 High Similarity NPC124269
0.8732 High Similarity NPC470669
0.8725 High Similarity NPC67654
0.8725 High Similarity NPC207624
0.8725 High Similarity NPC142308
0.8723 High Similarity NPC150399
0.8723 High Similarity NPC477242
0.8723 High Similarity NPC477243
0.8723 High Similarity NPC41461
0.8723 High Similarity NPC168105
0.8723 High Similarity NPC25287
0.8723 High Similarity NPC66349
0.8723 High Similarity NPC249606
0.8723 High Similarity NPC274109
0.8723 High Similarity NPC12165
0.8723 High Similarity NPC186838
0.8723 High Similarity NPC477244
0.8723 High Similarity NPC1486
0.8723 High Similarity NPC240593
0.8723 High Similarity NPC98115
0.8716 High Similarity NPC472421
0.8716 High Similarity NPC472406
0.8716 High Similarity NPC135303
0.8716 High Similarity NPC148423
0.8716 High Similarity NPC155882
0.8714 High Similarity NPC144027
0.8714 High Similarity NPC236974
0.8714 High Similarity NPC164136
0.8714 High Similarity NPC172262
0.8707 High Similarity NPC306788
0.8705 High Similarity NPC10971
0.8705 High Similarity NPC203817
0.8705 High Similarity NPC25937
0.8705 High Similarity NPC285054
0.8701 High Similarity NPC109180
0.8701 High Similarity NPC472581
0.8699 High Similarity NPC477955
0.8696 High Similarity NPC324482
0.8693 High Similarity NPC304387
0.869 High Similarity NPC219915
0.869 High Similarity NPC149026
0.869 High Similarity NPC143896
0.869 High Similarity NPC310130
0.869 High Similarity NPC293053
0.869 High Similarity NPC24821
0.869 High Similarity NPC221432
0.869 High Similarity NPC9117
0.869 High Similarity NPC164980
0.869 High Similarity NPC175504
0.869 High Similarity NPC169591
0.869 High Similarity NPC68104
0.869 High Similarity NPC11700

  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 NPC28337 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
0.9071 High Similarity NPD1243 Approved
0.8768 High Similarity NPD1240 Approved
0.8643 High Similarity NPD1607 Approved
0.863 High Similarity NPD4378 Clinical (unspecified phase)
0.8621 High Similarity NPD643 Clinical (unspecified phase)
0.8601 High Similarity NPD1549 Phase 2
0.8542 High Similarity NPD2800 Approved
0.8531 High Similarity NPD1552 Clinical (unspecified phase)
0.8531 High Similarity NPD1550 Clinical (unspecified phase)
0.8531 High Similarity NPD2344 Approved
0.8521 High Similarity NPD1510 Phase 2
0.8514 High Similarity NPD920 Approved
0.8503 High Similarity NPD642 Clinical (unspecified phase)
0.8503 High Similarity NPD7410 Clinical (unspecified phase)
0.8411 Intermediate Similarity NPD7411 Suspended
0.8377 Intermediate Similarity NPD3749 Approved
0.8366 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD2796 Approved
0.8299 Intermediate Similarity NPD2309 Approved
0.8217 Intermediate Similarity NPD1247 Approved
0.8188 Intermediate Similarity NPD1511 Approved
0.8182 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8176 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8141 Intermediate Similarity NPD7075 Discontinued
0.8105 Intermediate Similarity NPD4380 Phase 2
0.8095 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.8089 Intermediate Similarity NPD919 Approved
0.8079 Intermediate Similarity NPD1512 Approved
0.8077 Intermediate Similarity NPD3882 Suspended
0.8065 Intermediate Similarity NPD7819 Suspended
0.8065 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8041 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8013 Intermediate Similarity NPD2532 Approved
0.8013 Intermediate Similarity NPD2533 Approved
0.8013 Intermediate Similarity NPD2534 Approved
0.8 Intermediate Similarity NPD1934 Approved
0.7987 Intermediate Similarity NPD3750 Approved
0.7962 Intermediate Similarity NPD7768 Phase 2
0.7959 Intermediate Similarity NPD1551 Phase 2
0.7947 Intermediate Similarity NPD6799 Approved
0.7885 Intermediate Similarity NPD6801 Discontinued
0.7879 Intermediate Similarity NPD6559 Discontinued
0.7877 Intermediate Similarity NPD6651 Approved
0.7875 Intermediate Similarity NPD6959 Discontinued
0.7834 Intermediate Similarity NPD2801 Approved
0.7799 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7786 Intermediate Similarity NPD9717 Approved
0.7785 Intermediate Similarity NPD1471 Phase 3
0.777 Intermediate Similarity NPD2799 Discontinued
0.777 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7758 Intermediate Similarity NPD1729 Discontinued
0.7756 Intermediate Similarity NPD6599 Discontinued
0.7746 Intermediate Similarity NPD1203 Approved
0.7718 Intermediate Similarity NPD2935 Discontinued
0.7702 Intermediate Similarity NPD5494 Approved
0.7692 Intermediate Similarity NPD3226 Approved
0.7673 Intermediate Similarity NPD2296 Approved
0.7669 Intermediate Similarity NPD3926 Phase 2
0.7651 Intermediate Similarity NPD3748 Approved
0.7636 Intermediate Similarity NPD3818 Discontinued
0.7632 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7619 Intermediate Similarity NPD943 Approved
0.7605 Intermediate Similarity NPD5953 Discontinued
0.7603 Intermediate Similarity NPD2313 Discontinued
0.7603 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.759 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7589 Intermediate Similarity NPD422 Phase 1
0.7566 Intermediate Similarity NPD2654 Approved
0.755 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD6166 Phase 2
0.7515 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6232 Discontinued
0.7485 Intermediate Similarity NPD7286 Phase 2
0.7483 Intermediate Similarity NPD6100 Approved
0.7483 Intermediate Similarity NPD6099 Approved
0.747 Intermediate Similarity NPD7473 Discontinued
0.7465 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD3817 Phase 2
0.7429 Intermediate Similarity NPD9545 Approved
0.7425 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.741 Intermediate Similarity NPD9493 Approved
0.7407 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD1465 Phase 2
0.7379 Intermediate Similarity NPD1164 Approved
0.7372 Intermediate Similarity NPD7390 Discontinued
0.7365 Intermediate Similarity NPD411 Approved
0.7365 Intermediate Similarity NPD3268 Approved
0.7356 Intermediate Similarity NPD4287 Approved
0.7343 Intermediate Similarity NPD1610 Phase 2
0.7342 Intermediate Similarity NPD5403 Approved
0.7337 Intermediate Similarity NPD7074 Phase 3
0.7333 Intermediate Similarity NPD447 Suspended
0.7333 Intermediate Similarity NPD230 Phase 1
0.7329 Intermediate Similarity NPD2798 Approved
0.7325 Intermediate Similarity NPD5401 Approved
0.732 Intermediate Similarity NPD2346 Discontinued
0.7305 Intermediate Similarity NPD1548 Phase 1
0.7292 Intermediate Similarity NPD1608 Approved
0.729 Intermediate Similarity NPD4628 Phase 3
0.7289 Intermediate Similarity NPD5710 Approved
0.7289 Intermediate Similarity NPD5711 Approved
0.7278 Intermediate Similarity NPD7054 Approved
0.7278 Intermediate Similarity NPD5844 Phase 1
0.7248 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7235 Intermediate Similarity NPD7472 Approved
0.723 Intermediate Similarity NPD6832 Phase 2
0.7222 Intermediate Similarity NPD6280 Approved
0.7222 Intermediate Similarity NPD6279 Approved
0.7202 Intermediate Similarity NPD2403 Approved
0.7194 Intermediate Similarity NPD1241 Discontinued
0.7193 Intermediate Similarity NPD6797 Phase 2
0.719 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD4308 Phase 3
0.7186 Intermediate Similarity NPD6808 Phase 2
0.7181 Intermediate Similarity NPD4625 Phase 3
0.7151 Intermediate Similarity NPD7251 Discontinued
0.7151 Intermediate Similarity NPD3658 Clinical (unspecified phase)
0.7151 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7151 Intermediate Similarity NPD4361 Phase 2
0.7143 Intermediate Similarity NPD3266 Approved
0.7143 Intermediate Similarity NPD2797 Approved
0.7143 Intermediate Similarity NPD3267 Approved
0.7134 Intermediate Similarity NPD5402 Approved
0.7133 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD1296 Phase 2
0.7133 Intermediate Similarity NPD3764 Approved
0.7125 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7114 Intermediate Similarity NPD4908 Phase 1
0.711 Intermediate Similarity NPD7808 Phase 3
0.7103 Intermediate Similarity NPD1201 Approved
0.7095 Intermediate Similarity NPD1019 Discontinued
0.7083 Intermediate Similarity NPD17 Approved
0.7078 Intermediate Similarity NPD7033 Discontinued
0.7075 Intermediate Similarity NPD3225 Approved
0.7055 Intermediate Similarity NPD3972 Approved
0.7047 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD4288 Approved
0.7027 Intermediate Similarity NPD1470 Approved
0.7011 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD4749 Approved
0.7 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD4363 Phase 3
0.7 Intermediate Similarity NPD4360 Phase 2
0.6995 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6994 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6993 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6982 Remote Similarity NPD7229 Phase 3
0.6962 Remote Similarity NPD7003 Approved
0.6959 Remote Similarity NPD1876 Approved
0.6957 Remote Similarity NPD74 Approved
0.6957 Remote Similarity NPD9266 Approved
0.6949 Remote Similarity NPD8434 Phase 2
0.6933 Remote Similarity NPD9494 Approved
0.6928 Remote Similarity NPD4307 Phase 2
0.6923 Remote Similarity NPD8090 Clinical (unspecified phase)
0.6923 Remote Similarity NPD5408 Approved
0.6923 Remote Similarity NPD5404 Approved
0.6923 Remote Similarity NPD5406 Approved
0.6923 Remote Similarity NPD5405 Approved
0.6901 Remote Similarity NPD4575 Clinical (unspecified phase)
0.6897 Remote Similarity NPD1252 Clinical (unspecified phase)
0.6894 Remote Similarity NPD7004 Clinical (unspecified phase)
0.689 Remote Similarity NPD6585 Discontinued
0.6884 Remote Similarity NPD9263 Approved
0.6884 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6884 Remote Similarity NPD9264 Approved
0.6884 Remote Similarity NPD9267 Approved
0.6883 Remote Similarity NPD5124 Phase 1
0.6883 Remote Similarity NPD1933 Approved
0.6883 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6879 Remote Similarity NPD6004 Phase 3
0.6879 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6879 Remote Similarity NPD6002 Phase 3
0.6879 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6879 Remote Similarity NPD6005 Phase 3
0.6867 Remote Similarity NPD5760 Phase 2
0.6867 Remote Similarity NPD5761 Phase 2
0.6857 Remote Similarity NPD6104 Discontinued
0.6848 Remote Similarity NPD5890 Approved
0.6848 Remote Similarity NPD5889 Approved
0.6848 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6846 Remote Similarity NPD1283 Approved
0.6832 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6829 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6829 Remote Similarity NPD7458 Discontinued
0.6824 Remote Similarity NPD9269 Phase 2
0.6824 Remote Similarity NPD1481 Phase 2
0.6821 Remote Similarity NPD2163 Approved
0.6818 Remote Similarity NPD1613 Approved
0.6818 Remote Similarity NPD1612 Clinical (unspecified phase)
0.6813 Remote Similarity NPD2354 Approved
0.6806 Remote Similarity NPD405 Clinical (unspecified phase)
0.6797 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6797 Remote Similarity NPD1699 Clinical (unspecified phase)
0.6781 Remote Similarity NPD1651 Approved
0.6781 Remote Similarity NPD9268 Approved
0.6776 Remote Similarity NPD1008 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