Structure

Physi-Chem Properties

Molecular Weight:  416.15
Volume:  406.709
LogP:  2.257
LogD:  2.656
LogS:  -4.049
# Rotatable Bonds:  7
TPSA:  92.68
# H-Bond Aceptor:  8
# H-Bond Donor:  1
# Rings:  4
# Heavy Atoms:  8

MedChem Properties

QED Drug-Likeness Score:  0.689
Synthetic Accessibility Score:  3.544
Fsp3:  0.409
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.829
MDCK Permeability:  5.4700863984180614e-05
Pgp-inhibitor:  0.874
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.002
20% Bioavailability (F20%):  0.006
30% Bioavailability (F30%):  0.026

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.759
Plasma Protein Binding (PPB):  90.54247283935547%
Volume Distribution (VD):  1.153
Pgp-substrate:  10.647164344787598%

ADMET: Metabolism

CYP1A2-inhibitor:  0.292
CYP1A2-substrate:  0.9
CYP2C19-inhibitor:  0.895
CYP2C19-substrate:  0.865
CYP2C9-inhibitor:  0.801
CYP2C9-substrate:  0.808
CYP2D6-inhibitor:  0.752
CYP2D6-substrate:  0.885
CYP3A4-inhibitor:  0.954
CYP3A4-substrate:  0.904

ADMET: Excretion

Clearance (CL):  11.542
Half-life (T1/2):  0.364

ADMET: Toxicity

hERG Blockers:  0.258
Human Hepatotoxicity (H-HT):  0.2
Drug-inuced Liver Injury (DILI):  0.518
AMES Toxicity:  0.029
Rat Oral Acute Toxicity:  0.014
Maximum Recommended Daily Dose:  0.52
Skin Sensitization:  0.424
Carcinogencity:  0.601
Eye Corrosion:  0.003
Eye Irritation:  0.048
Respiratory Toxicity:  0.314

Download Data

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Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC56184

Natural Product ID:  NPC56184
Common Name*:   Podorhizol
IUPAC Name:   (3S,4R)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(S)-hydroxy-(3,4,5-trimethoxyphenyl)methyl]oxolan-2-one
Synonyms:   Podorhizol
Standard InCHIKey:  UNWCWBJEKCTIML-PNHOKKKMSA-N
Standard InCHI:  InChI=1S/C22H24O8/c1-25-17-8-13(9-18(26-2)21(17)27-3)20(23)19-14(10-28-22(19)24)6-12-4-5-15-16(7-12)30-11-29-15/h4-5,7-9,14,19-20,23H,6,10-11H2,1-3H3/t14-,19-,20+/m0/s1
SMILES:  COc1cc(cc(c1OC)OC)[C@H]([C@@H]1[C@@H](Cc2ccc3c(c2)OCO3)COC1=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL512541
PubChem CID:   9931715
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0001392] Lignans, neolignans and related compounds
      • [CHEMONTID:0003686] Furanoid lignans
        • [CHEMONTID:0001604] Tetrahydrofuran lignans
          • [CHEMONTID:0003424] 9,9'-epoxylignans
            • [CHEMONTID:0001613] Dibenzylbutyrolactone lignans

*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
NPO17839 Machaerium mucronulatum Species Dolichopodidae Eukaryota n.a. n.a. n.a. DOI[10.1016/S0031-9422(00)94598-9]
NPO14144 Hernandia peltata Species Hernandiaceae Eukaryota n.a. stem n.a. DOI[10.1021/np960034d]
NPO25454 Plumbago europaea Species Plumbaginaceae Eukaryota n.a. root n.a. DOI[10.2225/vol5-issue3-fulltext-4]
NPO14144 Hernandia peltata Species Hernandiaceae Eukaryota n.a. n.a. n.a. DOI[10.3987/R-1980-04-0397]
NPO21302 Cladosporium herbarum Species Cladosporiaceae Eukaryota n.a. n.a. n.a. PMID[11325242]
NPO7174 Callyspongia truncata Species Callyspongiidae Eukaryota n.a. n.a. n.a. PMID[12088440]
NPO7174 Callyspongia truncata Species Callyspongiidae Eukaryota n.a. n.a. n.a. PMID[12713420]
NPO14144 Hernandia peltata Species Hernandiaceae Eukaryota n.a. n.a. n.a. PMID[14987061]
NPO7090 Ammi majus Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[15009205]
NPO21302 Cladosporium herbarum Species Cladosporiaceae Eukaryota n.a. n.a. n.a. PMID[16038560]
NPO1338 Arcangelisia gusanlung Species Menispermaceae Eukaryota n.a. stem n.a. PMID[21500777]
NPO9604 Amycolatopsis lurida Species Pseudonocardiaceae Bacteria n.a. n.a. n.a. PMID[25323720]
NPO16653 Matteuccia struthiopteris Species Onocleaceae Eukaryota rhizomes Liaoning province, China 2011-SEP PMID[25927664]
NPO16966 Leptospermum scoparium Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[26731565]
NPO18983 Cleidion brevipetiolatum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[31419126]
NPO16653 Matteuccia struthiopteris Species Onocleaceae Eukaryota n.a. n.a. Database[FooDB]
NPO19127 Citrus tankan Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16653 Matteuccia struthiopteris Species Onocleaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7090 Ammi majus Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25454 Plumbago europaea Species Plumbaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16293 Babylonia japonica Species Buccinidae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18306 Juniperus thurifera Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17385 Magnolia acuminata Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO13963 Laurencia elata Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14144 Hernandia peltata Species Hernandiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25454 Plumbago europaea Species Plumbaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17831 Millettia racemosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18306 Juniperus thurifera Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13963 Laurencia elata Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7090 Ammi majus Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16293 Babylonia japonica Species Buccinidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16653 Matteuccia struthiopteris Species Onocleaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15358 Entandrophragma cylindricum Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19127 Citrus tankan Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5764 Ophioglossum vulgatum Species Ophioglossaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17385 Magnolia acuminata Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7090 Ammi majus Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO19127 Citrus tankan Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16653 Matteuccia struthiopteris Species Onocleaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17385 Magnolia acuminata Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16293 Babylonia japonica Species Buccinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18575 Ochtodes crockeri Species Rhizophyllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18173 Pyrocystis lunula Species Pyrocystaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19189 Brickellia pendula Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3050 Cladonia pseudodidyma Species Cladoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17831 Millettia racemosa Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1338 Arcangelisia gusanlung Species Menispermaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19057 Lentinellus omphalodes Species Auriscalpiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9535 Cortinarius basirubescens Species Cortinariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25454 Plumbago europaea Species Plumbaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18983 Cleidion brevipetiolatum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21302 Cladosporium herbarum Species Cladosporiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15608 Tanacetum santolina Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18306 Juniperus thurifera Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12801 Aglaia meridionalis Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7807 Polyporus sulphureus Species Polyporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18520 Helipterum strictum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17385 Magnolia acuminata Species Magnoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13963 Laurencia elata Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18792 Crotalaria lechnaultii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17709 Timonius kaniensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17275 Chamaemelum scariosum Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16966 Leptospermum scoparium Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17802 Simmondsia chinensis Species Simmondsiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7174 Callyspongia truncata Species Callyspongiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16653 Matteuccia struthiopteris Species Onocleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3746 Hesperocyparis nevadensis Species Cupressaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18061 Anacystis cyanea n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO12282 Parmelia conspersa Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18847 Copaifera paupera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9604 Amycolatopsis lurida Species Pseudonocardiaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO18707 Allium ursinum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19127 Citrus tankan Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17190 Senecio erraticus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12072 Escallonia philippiana Species Escalloniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13594 Hippocratea indica Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18242 Gleichenia glauca Species Gleicheniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17068 Talaromyces wortmanni Species Trichocomaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5764 Ophioglossum vulgatum Species Ophioglossaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17596 Ficus maxima Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11603 Lathyrus macrorrhizus Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7090 Ammi majus Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18377 Chaetomium retardatum Species Chaetomiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11677 Lactobacillus acidophilus Species Lactobacillaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO10712 Tabebuia rosea Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21938 Coleus carnosus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16829 Dunaliella acidophila Species Dunaliellaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17839 Machaerium mucronulatum Species Dolichopodidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15358 Entandrophragma cylindricum Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17718 Artemisia schmidtiana 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
NPT1081 Cell Line BXPC-3 Homo sapiens ED50 = 3.8 ug ml-1 PMID[460177]
NPT83 Cell Line MCF7 Homo sapiens ED50 = 6.6 ug ml-1 PMID[460177]
NPT168 Cell Line P388 Mus musculus ED50 > 1.0 ug ml-1 PMID[460177]
NPT395 Cell Line SF-268 Homo sapiens ED50 > 10.0 ug ml-1 PMID[460177]
NPT397 Cell Line NCI-H460 Homo sapiens ED50 > 10.0 ug ml-1 PMID[460177]
NPT575 Cell Line KM-20L2 Homo sapiens ED50 > 10.0 ug ml-1 PMID[460177]
NPT90 Cell Line DU-145 Homo sapiens ED50 > 10.0 ug ml-1 PMID[460177]
NPT1522 Organism Neisseria gonorrhoeae Neisseria gonorrhoeae MIC = 32.0 ug.mL-1 PMID[460177]

☑ 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 NPC56184 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
0.9792 High Similarity NPC477698
0.9728 High Similarity NPC136757
0.9658 High Similarity NPC164082
0.9592 High Similarity NPC477699
0.9396 High Similarity NPC473236
0.9388 High Similarity NPC145569
0.9388 High Similarity NPC474965
0.9388 High Similarity NPC216223
0.9388 High Similarity NPC477695
0.9388 High Similarity NPC125570
0.9388 High Similarity NPC668
0.9388 High Similarity NPC174512
0.9388 High Similarity NPC293757
0.9338 High Similarity NPC32373
0.9338 High Similarity NPC237946
0.9315 High Similarity NPC3982
0.9306 High Similarity NPC176586
0.9306 High Similarity NPC210354
0.9306 High Similarity NPC40237
0.9306 High Similarity NPC287124
0.9306 High Similarity NPC151423
0.9276 High Similarity NPC19947
0.9276 High Similarity NPC207584
0.9262 High Similarity NPC477700
0.9241 High Similarity NPC474288
0.9221 High Similarity NPC288149
0.9211 High Similarity NPC478055
0.9184 High Similarity NPC212890
0.9178 High Similarity NPC475000
0.9178 High Similarity NPC477701
0.9178 High Similarity NPC141569
0.9178 High Similarity NPC191158
0.9178 High Similarity NPC177644
0.9178 High Similarity NPC166884
0.9178 High Similarity NPC92693
0.9178 High Similarity NPC218841
0.9156 High Similarity NPC96593
0.9156 High Similarity NPC119910
0.9156 High Similarity NPC91634
0.9156 High Similarity NPC150943
0.9156 High Similarity NPC268718
0.9145 High Similarity NPC186316
0.9139 High Similarity NPC245948
0.9133 High Similarity NPC32079
0.9116 High Similarity NPC223185
0.9116 High Similarity NPC477702
0.9054 High Similarity NPC193779
0.9048 High Similarity NPC27159
0.9007 High Similarity NPC13985
0.9007 High Similarity NPC210642
0.9007 High Similarity NPC303519
0.8986 High Similarity NPC474158
0.8981 High Similarity NPC116759
0.8981 High Similarity NPC14294
0.898 High Similarity NPC106920
0.898 High Similarity NPC477696
0.898 High Similarity NPC477697
0.898 High Similarity NPC470811
0.898 High Similarity NPC273657
0.8974 High Similarity NPC115624
0.8974 High Similarity NPC100465
0.8974 High Similarity NPC152424
0.8958 High Similarity NPC209229
0.8958 High Similarity NPC11453
0.8954 High Similarity NPC103197
0.8954 High Similarity NPC30009
0.894 High Similarity NPC473989
0.894 High Similarity NPC229882
0.894 High Similarity NPC158635
0.8933 High Similarity NPC304821
0.8917 High Similarity NPC76687
0.8912 High Similarity NPC52664
0.891 High Similarity NPC218471
0.891 High Similarity NPC239818
0.8904 High Similarity NPC46591
0.8903 High Similarity NPC181168
0.8903 High Similarity NPC163527
0.8903 High Similarity NPC115281
0.8897 High Similarity NPC185908
0.8897 High Similarity NPC283949
0.8889 High Similarity NPC150534
0.8889 High Similarity NPC245615
0.8889 High Similarity NPC299706
0.8889 High Similarity NPC72796
0.8889 High Similarity NPC61604
0.8889 High Similarity NPC211386
0.8889 High Similarity NPC44245
0.8889 High Similarity NPC115466
0.8867 High Similarity NPC80230
0.8867 High Similarity NPC304687
0.8867 High Similarity NPC101755
0.8867 High Similarity NPC104024
0.8867 High Similarity NPC65574
0.8844 High Similarity NPC470991
0.8844 High Similarity NPC100675
0.8844 High Similarity NPC166137
0.8844 High Similarity NPC282291
0.8834 High Similarity NPC23593
0.8831 High Similarity NPC312763
0.8831 High Similarity NPC348849
0.8831 High Similarity NPC178195
0.8831 High Similarity NPC273578
0.8828 High Similarity NPC143895
0.8824 High Similarity NPC476434
0.8816 High Similarity NPC149505
0.8812 High Similarity NPC185498
0.8808 High Similarity NPC325720
0.8808 High Similarity NPC316676
0.8805 High Similarity NPC222531
0.879 High Similarity NPC474770
0.8776 High Similarity NPC177868
0.8776 High Similarity NPC226547
0.8776 High Similarity NPC56091
0.8774 High Similarity NPC38699
0.8774 High Similarity NPC238834
0.8773 High Similarity NPC107739
0.8767 High Similarity NPC14022
0.8766 High Similarity NPC308555
0.8766 High Similarity NPC178574
0.8766 High Similarity NPC65591
0.8758 High Similarity NPC62354
0.875 High Similarity NPC177476
0.875 High Similarity NPC196937
0.875 High Similarity NPC262455
0.875 High Similarity NPC306475
0.875 High Similarity NPC205915
0.875 High Similarity NPC136750
0.875 High Similarity NPC266848
0.8727 High Similarity NPC236089
0.8726 High Similarity NPC76211
0.8725 High Similarity NPC298317
0.8725 High Similarity NPC185071
0.8725 High Similarity NPC255566
0.8725 High Similarity NPC12728
0.8725 High Similarity NPC474808
0.872 High Similarity NPC263955
0.8718 High Similarity NPC163635
0.871 High Similarity NPC473425
0.8704 High Similarity NPC179240
0.8701 High Similarity NPC151425
0.8696 High Similarity NPC471180
0.8688 High Similarity NPC475738
0.8681 High Similarity NPC147616
0.8681 High Similarity NPC261812
0.8681 High Similarity NPC259742
0.8681 High Similarity NPC219671
0.8681 High Similarity NPC65183
0.8681 High Similarity NPC72046
0.8681 High Similarity NPC104077
0.8667 High Similarity NPC29587
0.8667 High Similarity NPC15743
0.8654 High Similarity NPC254163
0.8645 High Similarity NPC24562
0.8645 High Similarity NPC474606
0.8645 High Similarity NPC474514
0.8639 High Similarity NPC474039
0.8639 High Similarity NPC308976
0.8636 High Similarity NPC474975
0.8636 High Similarity NPC475756
0.863 High Similarity NPC189474
0.863 High Similarity NPC148893
0.863 High Similarity NPC18576
0.863 High Similarity NPC25333
0.863 High Similarity NPC49235
0.863 High Similarity NPC236522
0.8627 High Similarity NPC51328
0.8627 High Similarity NPC55158
0.8627 High Similarity NPC286235
0.8625 High Similarity NPC475865
0.8611 High Similarity NPC192255
0.8609 High Similarity NPC475868
0.8609 High Similarity NPC180953
0.8608 High Similarity NPC173726
0.8608 High Similarity NPC241600
0.859 High Similarity NPC287504
0.859 High Similarity NPC25127
0.859 High Similarity NPC198461
0.8581 High Similarity NPC246566
0.8581 High Similarity NPC95498
0.8581 High Similarity NPC471154
0.8581 High Similarity NPC302610
0.858 High Similarity NPC79322
0.8571 High Similarity NPC25695
0.8571 High Similarity NPC121651
0.8571 High Similarity NPC172818
0.8562 High Similarity NPC262804
0.8562 High Similarity NPC40654
0.8562 High Similarity NPC110958
0.8562 High Similarity NPC19890
0.8562 High Similarity NPC248132
0.8562 High Similarity NPC47181
0.8562 High Similarity NPC130449
0.8562 High Similarity NPC31530
0.8553 High Similarity NPC321696
0.8553 High Similarity NPC321958
0.8544 High Similarity NPC474990
0.8544 High Similarity NPC472860
0.8543 High Similarity NPC239254
0.8543 High Similarity NPC172171
0.8543 High Similarity NPC187774

  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 NPC56184 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
0.9338 High Similarity NPD4966 Approved
0.9338 High Similarity NPD4965 Approved
0.9338 High Similarity NPD4967 Phase 2
0.9139 High Similarity NPD37 Approved
0.9091 High Similarity NPD6234 Discontinued
0.8812 High Similarity NPD7228 Approved
0.8616 High Similarity NPD7199 Phase 2
0.8485 Intermediate Similarity NPD7240 Approved
0.8395 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.8366 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.8354 Intermediate Similarity NPD3818 Discontinued
0.8205 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.8095 Intermediate Similarity NPD3027 Phase 3
0.8036 Intermediate Similarity NPD7074 Phase 3
0.8012 Intermediate Similarity NPD7090 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7976 Intermediate Similarity NPD7054 Approved
0.7929 Intermediate Similarity NPD7472 Approved
0.7892 Intermediate Similarity NPD6232 Discontinued
0.7877 Intermediate Similarity NPD7237 Clinical (unspecified phase)
0.7861 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7857 Intermediate Similarity NPD7473 Discontinued
0.7853 Intermediate Similarity NPD3817 Phase 2
0.784 Intermediate Similarity NPD1934 Approved
0.7836 Intermediate Similarity NPD6559 Discontinued
0.7805 Intermediate Similarity NPD3882 Suspended
0.7805 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7802 Intermediate Similarity NPD7680 Approved
0.7791 Intermediate Similarity NPD7808 Phase 3
0.7778 Intermediate Similarity NPD6797 Phase 2
0.7771 Intermediate Similarity NPD5494 Approved
0.7758 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7733 Intermediate Similarity NPD7685 Pre-registration
0.7733 Intermediate Similarity NPD7251 Discontinued
0.7707 Intermediate Similarity NPD4109 Clinical (unspecified phase)
0.7707 Intermediate Similarity NPD4110 Phase 3
0.7702 Intermediate Similarity NPD1653 Approved
0.7692 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD6166 Phase 2
0.7692 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7683 Intermediate Similarity NPD2801 Approved
0.7683 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7682 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7671 Intermediate Similarity NPD3705 Approved
0.7661 Intermediate Similarity NPD5844 Phase 1
0.7628 Intermediate Similarity NPD7266 Discontinued
0.7582 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7582 Intermediate Similarity NPD1613 Approved
0.7547 Intermediate Similarity NPD6190 Approved
0.7532 Intermediate Similarity NPD6355 Discontinued
0.753 Intermediate Similarity NPD5402 Approved
0.7516 Intermediate Similarity NPD2532 Approved
0.7516 Intermediate Similarity NPD2534 Approved
0.7516 Intermediate Similarity NPD2533 Approved
0.75 Intermediate Similarity NPD4380 Phase 2
0.7484 Intermediate Similarity NPD4628 Phase 3
0.7484 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7471 Intermediate Similarity NPD3787 Discontinued
0.747 Intermediate Similarity NPD7819 Suspended
0.747 Intermediate Similarity NPD8455 Phase 2
0.7468 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7466 Intermediate Similarity NPD1357 Approved
0.7457 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7444 Intermediate Similarity NPD7296 Approved
0.744 Intermediate Similarity NPD7075 Discontinued
0.7419 Intermediate Similarity NPD230 Phase 1
0.7412 Intermediate Similarity NPD8127 Discontinued
0.741 Intermediate Similarity NPD6801 Discontinued
0.7407 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7405 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7405 Intermediate Similarity NPD6002 Phase 3
0.7405 Intermediate Similarity NPD6005 Phase 3
0.7405 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7405 Intermediate Similarity NPD6004 Phase 3
0.7394 Intermediate Similarity NPD7028 Phase 2
0.7389 Intermediate Similarity NPD7033 Discontinued
0.7383 Intermediate Similarity NPD1608 Approved
0.7371 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD7229 Phase 3
0.7366 Intermediate Similarity NPD5006 Approved
0.7366 Intermediate Similarity NPD5005 Approved
0.7365 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD1465 Phase 2
0.7349 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7346 Intermediate Similarity NPD1511 Approved
0.7346 Intermediate Similarity NPD6799 Approved
0.7342 Intermediate Similarity NPD2935 Discontinued
0.7342 Intermediate Similarity NPD2438 Suspended
0.7333 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD2983 Phase 2
0.7333 Intermediate Similarity NPD2982 Phase 2
0.7326 Intermediate Similarity NPD3926 Phase 2
0.7326 Intermediate Similarity NPD5242 Approved
0.732 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD5403 Approved
0.7308 Intermediate Similarity NPD447 Suspended
0.7303 Intermediate Similarity NPD5647 Approved
0.7299 Intermediate Similarity NPD3751 Discontinued
0.7294 Intermediate Similarity NPD919 Approved
0.7292 Intermediate Similarity NPD5283 Phase 1
0.729 Intermediate Similarity NPD6233 Phase 2
0.7289 Intermediate Similarity NPD6599 Discontinued
0.7267 Intermediate Similarity NPD2981 Phase 2
0.7261 Intermediate Similarity NPD6653 Approved
0.7256 Intermediate Similarity NPD1512 Approved
0.7255 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7255 Intermediate Similarity NPD3018 Phase 2
0.7253 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7247 Intermediate Similarity NPD8312 Approved
0.7247 Intermediate Similarity NPD8313 Approved
0.7246 Intermediate Similarity NPD7411 Suspended
0.7243 Intermediate Similarity NPD4420 Approved
0.7239 Intermediate Similarity NPD4357 Discontinued
0.7235 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD6798 Discontinued
0.7219 Intermediate Similarity NPD5353 Approved
0.7219 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD7097 Phase 1
0.7208 Intermediate Similarity NPD4908 Phase 1
0.7205 Intermediate Similarity NPD6674 Discontinued
0.7197 Intermediate Similarity NPD1933 Approved
0.7195 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7195 Intermediate Similarity NPD5401 Approved
0.7188 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7188 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7181 Intermediate Similarity NPD17 Approved
0.7176 Intermediate Similarity NPD7768 Phase 2
0.7171 Intermediate Similarity NPD1283 Approved
0.717 Intermediate Similarity NPD1510 Phase 2
0.716 Intermediate Similarity NPD5563 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD3750 Approved
0.7143 Intermediate Similarity NPD1549 Phase 2
0.7134 Intermediate Similarity NPD1240 Approved
0.7134 Intermediate Similarity NPD4060 Phase 1
0.7134 Intermediate Similarity NPD2979 Phase 3
0.7127 Intermediate Similarity NPD8434 Phase 2
0.7125 Intermediate Similarity NPD2796 Approved
0.7125 Intermediate Similarity NPD1551 Phase 2
0.7124 Intermediate Similarity NPD2797 Approved
0.7115 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD7827 Phase 1
0.711 Intermediate Similarity NPD1247 Approved
0.7105 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7086 Intermediate Similarity NPD1091 Approved
0.7086 Intermediate Similarity NPD1610 Phase 2
0.707 Intermediate Similarity NPD4062 Phase 3
0.7063 Intermediate Similarity NPD2799 Discontinued
0.7051 Intermediate Similarity NPD7095 Approved
0.7044 Intermediate Similarity NPD1607 Approved
0.7041 Intermediate Similarity NPD6386 Approved
0.7041 Intermediate Similarity NPD6385 Approved
0.7037 Intermediate Similarity NPD5958 Discontinued
0.7035 Intermediate Similarity NPD3749 Approved
0.7032 Intermediate Similarity NPD2861 Phase 2
0.7024 Intermediate Similarity NPD7458 Discontinued
0.7019 Intermediate Similarity NPD6100 Approved
0.7019 Intermediate Similarity NPD6099 Approved
0.7018 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.7012 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7011 Intermediate Similarity NPD6959 Discontinued
0.7006 Intermediate Similarity NPD3764 Approved
0.7006 Intermediate Similarity NPD920 Approved
0.7006 Intermediate Similarity NPD3268 Approved
0.7006 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD5585 Approved
0.6989 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6981 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6981 Remote Similarity NPD5124 Phase 1
0.698 Remote Similarity NPD5536 Phase 2
0.6975 Remote Similarity NPD5762 Approved
0.6975 Remote Similarity NPD5763 Approved
0.6974 Remote Similarity NPD1281 Approved
0.6971 Remote Similarity NPD7315 Approved
0.6971 Remote Similarity NPD5710 Approved
0.6971 Remote Similarity NPD5711 Approved
0.697 Remote Similarity NPD5058 Phase 3
0.6964 Remote Similarity NPD3687 Approved
0.6964 Remote Similarity NPD3686 Approved
0.6961 Remote Similarity NPD7280 Phase 3
0.6961 Remote Similarity NPD7281 Phase 3
0.6959 Remote Similarity NPD8151 Discontinued
0.6959 Remote Similarity NPD2978 Approved
0.6959 Remote Similarity NPD2977 Approved
0.6957 Remote Similarity NPD3748 Approved
0.6954 Remote Similarity NPD6746 Phase 2
0.6946 Remote Similarity NPD6273 Approved
0.6946 Remote Similarity NPD1940 Clinical (unspecified phase)
0.6933 Remote Similarity NPD1894 Discontinued
0.6933 Remote Similarity NPD4534 Discontinued
0.6923 Remote Similarity NPD3226 Approved
0.6923 Remote Similarity NPD6055 Clinical (unspecified phase)
0.6918 Remote Similarity NPD4140 Approved
0.6918 Remote Similarity NPD3620 Phase 2
0.6918 Remote Similarity NPD3619 Clinical (unspecified phase)
0.6918 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6918 Remote Similarity NPD943 Approved
0.6914 Remote Similarity NPD6032 Approved
0.6908 Remote Similarity NPD3847 Discontinued
0.6906 Remote Similarity NPD7549 Discontinued

  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