Structure

Physi-Chem Properties

Molecular Weight:  432.21
Volume:  443.704
LogP:  3.112
LogD:  3.131
LogS:  -3.439
# Rotatable Bonds:  6
TPSA:  75.61
# H-Bond Aceptor:  7
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.742
Synthetic Accessibility Score:  3.444
Fsp3:  0.5
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:  -4.7
MDCK Permeability:  2.8004447813145816e-05
Pgp-inhibitor:  0.967
Pgp-substrate:  0.004
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.002
30% Bioavailability (F30%):  0.093

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.054
Plasma Protein Binding (PPB):  65.71683502197266%
Volume Distribution (VD):  0.639
Pgp-substrate:  34.39697265625%

ADMET: Metabolism

CYP1A2-inhibitor:  0.075
CYP1A2-substrate:  0.988
CYP2C19-inhibitor:  0.13
CYP2C19-substrate:  0.931
CYP2C9-inhibitor:  0.043
CYP2C9-substrate:  0.859
CYP2D6-inhibitor:  0.003
CYP2D6-substrate:  0.914
CYP3A4-inhibitor:  0.625
CYP3A4-substrate:  0.872

ADMET: Excretion

Clearance (CL):  6.298
Half-life (T1/2):  0.137

ADMET: Toxicity

hERG Blockers:  0.365
Human Hepatotoxicity (H-HT):  0.06
Drug-inuced Liver Injury (DILI):  0.155
AMES Toxicity:  0.063
Rat Oral Acute Toxicity:  0.203
Maximum Recommended Daily Dose:  0.041
Skin Sensitization:  0.196
Carcinogencity:  0.044
Eye Corrosion:  0.003
Eye Irritation:  0.044
Respiratory Toxicity:  0.035

Download Data

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

  Natural Product: NPC102256

Natural Product ID:  NPC102256
Common Name*:   Schizandrin
IUPAC Name:   n.a.
Synonyms:   Schisandrin
Standard InCHIKey:  YEFOAORQXAOVJQ-RZFZLAGVSA-N
Standard InCHI:  InChI=1S/C24H32O7/c1-13-9-14-10-16(26-3)20(28-5)22(30-7)18(14)19-15(12-24(13,2)25)11-17(27-4)21(29-6)23(19)31-8/h10-11,13,25H,9,12H2,1-8H3/t13-,24-/m0/s1
SMILES:  COc1c(OC)cc2c(c1OC)c1c(cc(c(c1OC)OC)OC)C[C@@H]([C@@](C2)(C)O)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL253688
PubChem CID:   3001664
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000238] Tannins
        • [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[11599360]
NPO24804 Schisandra rubriflora Species Schisandraceae Eukaryota n.a. leaf n.a. PMID[16494492]
NPO24804 Schisandra rubriflora Species Schisandraceae Eukaryota n.a. stem n.a. PMID[16494492]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. PMID[16562834]
NPO24804 Schisandra rubriflora Species Schisandraceae Eukaryota fruits n.a. n.a. PMID[17190445]
NPO24804 Schisandra rubriflora Species Schisandraceae Eukaryota n.a. fruit n.a. PMID[17190445]
NPO24804 Schisandra rubriflora Species Schisandraceae Eukaryota n.a. n.a. n.a. PMID[17489633]
NPO18146 Kadsura angustifolia Species Schisandraceae Eukaryota stems Honghe Prefecture of Yunnan Province, China 2005-Oct PMID[18278869]
NPO24804 Schisandra rubriflora Species Schisandraceae Eukaryota leaves and stems n.a. n.a. PMID[20146529]
NPO18146 Kadsura angustifolia Species Schisandraceae Eukaryota n.a. n.a. n.a. PMID[21232955]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota n.a. seed n.a. PMID[21381697]
NPO33401 schisandra sphenathera Species Schisandraceae Eukaryota stems n.a. n.a. PMID[23237974]
NPO7385 Schisandra sphenanthera Species Schisandraceae Eukaryota fruits n.a. n.a. PMID[23265871]
NPO29191 Schisandra neglecta Species Schisandraceae Eukaryota Stems Luoji Mountain Village, Xichang County, Sicuan Province, China 2011-Sep PMID[23738539]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. fruit n.a. PMID[24155209]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. PMID[24959987]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. PMID[25302569]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota Plant n.a. n.a. Database[FooDB]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota n.a. n.a. Database[FooDB]
NPO7385 Schisandra sphenanthera Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4582 Baphicacanthus cusia Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24804 Schisandra rubriflora Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4593 Lagerstroemia indica Species Lythraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO433 Geranium sibiricum Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota n.a. n.a. Database[Phenol-Explorer]
NPO7385 Schisandra sphenanthera Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24804 Schisandra rubriflora Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4593 Lagerstroemia indica Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4582 Baphicacanthus cusia Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18146 Kadsura angustifolia Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO433 Geranium sibiricum Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24804 Schisandra rubriflora Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4593 Lagerstroemia indica Species Lythraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7385 Schisandra sphenanthera Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4582 Baphicacanthus cusia Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7385 Schisandra sphenanthera Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO433 Geranium sibiricum Species Geraniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8210 Trigonella foenum-graecum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24804 Schisandra rubriflora Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8075 Cacospongia scalaris Species Thorectidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2263 Croton megistocarpus Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8187 Schisandra chinensis Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7385 Schisandra sphenanthera Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4582 Baphicacanthus cusia Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29191 Schisandra neglecta Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14100 Persea kusanoi Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4593 Lagerstroemia indica Species Lythraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18146 Kadsura angustifolia Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7639 Senecio isatideus 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
NPT82 Cell Line MDA-MB-231 Homo sapiens IC50 = 61500.0 nM PMID[506901]
NPT1086 Cell Line SK-HEP1 Homo sapiens IC50 = 71300.0 nM PMID[506901]
NPT2548 Cell Line SNU-638 Homo sapiens IC50 = 21100.0 nM PMID[506901]
NPT396 Cell Line T47D Homo sapiens IC50 = 19800.0 nM PMID[506901]
NPT148 Cell Line HCT-15 Homo sapiens IC50 = 50200.0 nM PMID[506901]
NPT111 Cell Line K562 Homo sapiens IC50 = 25000.0 nM PMID[506901]
NPT81 Cell Line A549 Homo sapiens IC50 = 20700.0 nM PMID[506901]
NPT759 Cell Line H9 Homo sapiens IC50 > 58000.0 nM PMID[506902]
NPT54 Individual Protein Nonstructural protein 1 Influenza A virus Potency = 3981.1 nM PMID[506905]
NPT1594 Individual Protein Multidrug resistance-associated protein 1 Homo sapiens IC50 = 0.0005 ug.mL-1 PMID[506907]
NPT1594 Individual Protein Multidrug resistance-associated protein 1 Homo sapiens IC50 = 1.401 ug.mL-1 PMID[506907]
NPT1594 Individual Protein Multidrug resistance-associated protein 1 Homo sapiens IC50 = 0.0035 ug.mL-1 PMID[506907]
NPT1594 Individual Protein Multidrug resistance-associated protein 1 Homo sapiens IC50 = 3.135 ug.mL-1 PMID[506907]
NPT1594 Individual Protein Multidrug resistance-associated protein 1 Homo sapiens IC50 = 0.054 ug.mL-1 PMID[506907]
NPT1594 Individual Protein Multidrug resistance-associated protein 1 Homo sapiens IC50 = 0.094 ug.mL-1 PMID[506907]
NPT165 Cell Line HeLa Homo sapiens IC50 > 100000.0 nM PMID[506908]
NPT659 Cell Line SMMC-7721 Homo sapiens IC50 > 100000.0 nM PMID[506908]
NPT71 Cell Line HEK293 Homo sapiens Inhibition = 6.2 % PMID[506909]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Drug metabolism >= 30.0 pmol/min PMID[506912]
NPT4023 Individual Protein Cytochrome P450 3A5 Homo sapiens Drug metabolism = 1.0 pmol/min PMID[506912]
NPT71 Cell Line HEK293 Homo sapiens IC50 = 81740.0 nM PMID[506913]
NPT90 Cell Line DU-145 Homo sapiens IC50 = 13090.0 nM PMID[506913]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 32560.0 nM PMID[506913]
NPT81 Cell Line A549 Homo sapiens IC50 = 21650.0 nM PMID[506913]
NPT165 Cell Line HeLa Homo sapiens IC50 = 28560.0 nM PMID[506913]
NPT81 Cell Line A549 Homo sapiens IC50 = 8500.0 nM PMID[506915]
NPT90 Cell Line DU-145 Homo sapiens IC50 = 5380.0 nM PMID[506915]
NPT165 Cell Line HeLa Homo sapiens IC50 = 5060.0 nM PMID[506915]
NPT71 Cell Line HEK293 Homo sapiens IC50 = 80470.0 nM PMID[506915]
NPT27 Others Unspecified CC50 > 200.0 ug.mL-1 PMID[506906]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 = 15.8 ug.mL-1 PMID[506906]
NPT27 Others Unspecified Ratio CC50/EC50 > 12.66 n.a. PMID[506906]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 18526.0 nM PMID[506905]
NPT20798 PROTEIN COMPLEX GTP-binding nuclear protein Ran/Importin subunit beta-1/Snurportin-1 Homo sapiens Potency n.a. 2909.3 nM PMID[506905]
NPT2 Others Unspecified Potency n.a. 3981.1 nM PMID[506905]
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Potency n.a. 7375.3 nM PMID[506905]
NPT176 Organism Artemia salina Artemia salina LC50 > 100.0 ug.mL-1 PMID[506908]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IC50 > 100000.0 nM PMID[506908]
NPT21742 CELL-LINE L02 Homo sapiens Survival = 43.3 % PMID[506910]
NPT2 Others Unspecified Activity = 125.0 % PMID[506911]
NPT2 Others Unspecified Ratio IC50 = 6.244 n.a. PMID[506913]
NPT2 Others Unspecified Ratio IC50 = 3.8 n.a. PMID[506914]
NPT2 Others Unspecified IC50 = 5360.0 nM PMID[506915]

☑ 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 NPC102256 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
0.968 High Similarity NPC207702
0.968 High Similarity NPC149008
0.968 High Similarity NPC283114
0.9612 High Similarity NPC180602
0.9612 High Similarity NPC214853
0.9612 High Similarity NPC55239
0.9612 High Similarity NPC240279
0.9535 High Similarity NPC289258
0.9535 High Similarity NPC188378
0.9535 High Similarity NPC7515
0.9535 High Similarity NPC276026
0.9535 High Similarity NPC555
0.9535 High Similarity NPC56764
0.9535 High Similarity NPC206737
0.9535 High Similarity NPC469659
0.9453 High Similarity NPC184928
0.9453 High Similarity NPC141493
0.9394 High Similarity NPC53722
0.9394 High Similarity NPC471183
0.9394 High Similarity NPC201404
0.9394 High Similarity NPC290714
0.9389 High Similarity NPC133025
0.9318 High Similarity NPC156948
0.9318 High Similarity NPC86605
0.9318 High Similarity NPC301765
0.9318 High Similarity NPC3072
0.9318 High Similarity NPC46277
0.9118 High Similarity NPC469630
0.9091 High Similarity NPC256776
0.9091 High Similarity NPC145722
0.9091 High Similarity NPC185680
0.9077 High Similarity NPC126836
0.9077 High Similarity NPC224157
0.9077 High Similarity NPC192687
0.9062 High Similarity NPC223953
0.9044 High Similarity NPC229172
0.9044 High Similarity NPC184684
0.9044 High Similarity NPC230538
0.9044 High Similarity NPC133934
0.9044 High Similarity NPC103637
0.9044 High Similarity NPC36531
0.9044 High Similarity NPC184641
0.9044 High Similarity NPC470917
0.903 High Similarity NPC865
0.9015 High Similarity NPC32778
0.9 High Similarity NPC190144
0.8993 High Similarity NPC295297
0.8993 High Similarity NPC137352
0.8993 High Similarity NPC183083
0.8992 High Similarity NPC242032
0.8992 High Similarity NPC189248
0.8992 High Similarity NPC471986
0.8992 High Similarity NPC202904
0.8984 High Similarity NPC105925
0.8978 High Similarity NPC324962
0.8968 High Similarity NPC477886
0.8955 High Similarity NPC32189
0.8955 High Similarity NPC202846
0.8955 High Similarity NPC143139
0.8955 High Similarity NPC205442
0.8947 High Similarity NPC209199
0.8947 High Similarity NPC125649
0.8939 High Similarity NPC475856
0.8939 High Similarity NPC6451
0.8923 High Similarity NPC154866
0.8921 High Similarity NPC474054
0.8915 High Similarity NPC76451
0.8915 High Similarity NPC82299
0.8913 High Similarity NPC121661
0.8913 High Similarity NPC172171
0.8913 High Similarity NPC239254
0.8913 High Similarity NPC87883
0.8913 High Similarity NPC73467
0.8889 High Similarity NPC266006
0.8881 High Similarity NPC200557
0.8881 High Similarity NPC10314
0.8881 High Similarity NPC294884
0.8881 High Similarity NPC69029
0.8881 High Similarity NPC108198
0.8881 High Similarity NPC313081
0.8881 High Similarity NPC158142
0.8864 High Similarity NPC474356
0.8864 High Similarity NPC45715
0.8864 High Similarity NPC15543
0.8864 High Similarity NPC12275
0.8864 High Similarity NPC232275
0.8849 High Similarity NPC189239
0.8849 High Similarity NPC197352
0.8849 High Similarity NPC110763
0.8849 High Similarity NPC166506
0.8849 High Similarity NPC475868
0.8846 High Similarity NPC74817
0.8846 High Similarity NPC127587
0.8846 High Similarity NPC246620
0.8846 High Similarity NPC473221
0.8846 High Similarity NPC124452
0.8846 High Similarity NPC282000
0.8846 High Similarity NPC169474
0.8846 High Similarity NPC293054
0.8846 High Similarity NPC236791
0.8846 High Similarity NPC266555
0.8846 High Similarity NPC159968
0.8846 High Similarity NPC82679
0.8846 High Similarity NPC324112
0.8828 High Similarity NPC282496
0.8828 High Similarity NPC233526
0.8824 High Similarity NPC184613
0.8824 High Similarity NPC29868
0.8824 High Similarity NPC212942
0.8824 High Similarity NPC6300
0.8824 High Similarity NPC230124
0.8824 High Similarity NPC114171
0.8824 High Similarity NPC79622
0.8806 High Similarity NPC160697
0.8803 High Similarity NPC470916
0.8797 High Similarity NPC161958
0.8797 High Similarity NPC14224
0.8794 High Similarity NPC477879
0.8788 High Similarity NPC299221
0.8788 High Similarity NPC237169
0.8788 High Similarity NPC470624
0.8788 High Similarity NPC311680
0.8788 High Similarity NPC234488
0.8788 High Similarity NPC51840
0.8786 High Similarity NPC154971
0.8786 High Similarity NPC252286
0.8779 High Similarity NPC28765
0.8769 High Similarity NPC103823
0.8769 High Similarity NPC9891
0.8769 High Similarity NPC28730
0.8769 High Similarity NPC186845
0.8769 High Similarity NPC44748
0.8769 High Similarity NPC18924
0.8769 High Similarity NPC214406
0.8769 High Similarity NPC78974
0.8769 High Similarity NPC88297
0.8769 High Similarity NPC223136
0.8759 High Similarity NPC12668
0.8759 High Similarity NPC308768
0.875 High Similarity NPC242715
0.875 High Similarity NPC22902
0.875 High Similarity NPC56329
0.8741 High Similarity NPC111655
0.8741 High Similarity NPC224472
0.8741 High Similarity NPC256262
0.8741 High Similarity NPC241241
0.8732 High Similarity NPC474393
0.8732 High Similarity NPC474347
0.873 High Similarity NPC15805
0.873 High Similarity NPC475961
0.873 High Similarity NPC254625
0.8722 High Similarity NPC149337
0.8722 High Similarity NPC469907
0.8722 High Similarity NPC474017
0.8722 High Similarity NPC471983
0.8712 High Similarity NPC469963
0.8712 High Similarity NPC58164
0.8712 High Similarity NPC469951
0.8712 High Similarity NPC10225
0.8702 High Similarity NPC252131
0.8692 High Similarity NPC233410
0.8692 High Similarity NPC116907
0.8692 High Similarity NPC57490
0.8692 High Similarity NPC117214
0.8692 High Similarity NPC193544
0.8692 High Similarity NPC208950
0.8692 High Similarity NPC299584
0.8692 High Similarity NPC221077
0.8692 High Similarity NPC203133
0.8692 High Similarity NPC234400
0.8692 High Similarity NPC475169
0.8692 High Similarity NPC472093
0.8692 High Similarity NPC82483
0.8692 High Similarity NPC251855
0.8692 High Similarity NPC17943
0.8692 High Similarity NPC60885
0.8692 High Similarity NPC298757
0.8692 High Similarity NPC265483
0.8686 High Similarity NPC218131
0.8686 High Similarity NPC243759
0.8686 High Similarity NPC105847
0.8686 High Similarity NPC243996
0.8686 High Similarity NPC275061
0.8686 High Similarity NPC220344
0.8686 High Similarity NPC132804
0.8676 High Similarity NPC173660
0.8676 High Similarity NPC265433
0.8676 High Similarity NPC30632
0.8676 High Similarity NPC162659
0.8676 High Similarity NPC248727
0.8676 High Similarity NPC197166
0.8676 High Similarity NPC270456
0.8672 High Similarity NPC75713
0.8671 High Similarity NPC477381
0.8662 High Similarity NPC325720
0.8662 High Similarity NPC316676
0.8657 High Similarity NPC204215
0.8657 High Similarity NPC175067
0.8657 High Similarity NPC127624
0.8643 High Similarity NPC326144

  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 NPC102256 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
0.8571 High Similarity NPD3027 Phase 3
0.8284 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.8284 Intermediate Similarity NPD3018 Phase 2
0.8254 Intermediate Similarity NPD5283 Phase 1
0.8222 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.812 Intermediate Similarity NPD2983 Phase 2
0.812 Intermediate Similarity NPD2982 Phase 2
0.8116 Intermediate Similarity NPD1613 Approved
0.8116 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8045 Intermediate Similarity NPD2981 Phase 2
0.8029 Intermediate Similarity NPD4625 Phase 3
0.7956 Intermediate Similarity NPD4908 Phase 1
0.7941 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7881 Intermediate Similarity NPD37 Approved
0.7852 Intermediate Similarity NPD4749 Approved
0.7842 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7836 Intermediate Similarity NPD3705 Approved
0.7836 Intermediate Similarity NPD1610 Phase 2
0.7727 Intermediate Similarity NPD4965 Approved
0.7727 Intermediate Similarity NPD4967 Phase 2
0.7727 Intermediate Similarity NPD4966 Approved
0.7721 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.7714 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7682 Intermediate Similarity NPD4005 Discontinued
0.7677 Intermediate Similarity NPD7975 Clinical (unspecified phase)
0.7673 Intermediate Similarity NPD7473 Discontinued
0.7671 Intermediate Similarity NPD6674 Discontinued
0.7655 Intermediate Similarity NPD3540 Phase 1
0.7635 Intermediate Similarity NPD7124 Phase 2
0.7628 Intermediate Similarity NPD6234 Discontinued
0.76 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.7595 Intermediate Similarity NPD6232 Discontinued
0.7586 Intermediate Similarity NPD3539 Phase 1
0.7569 Intermediate Similarity NPD6111 Discontinued
0.7568 Intermediate Similarity NPD5307 Clinical (unspecified phase)
0.7564 Intermediate Similarity NPD4055 Discovery
0.7538 Intermediate Similarity NPD228 Approved
0.7537 Intermediate Similarity NPD1548 Phase 1
0.7532 Intermediate Similarity NPD7199 Phase 2
0.75 Intermediate Similarity NPD2861 Phase 2
0.7483 Intermediate Similarity NPD4060 Phase 1
0.7483 Intermediate Similarity NPD3620 Phase 2
0.7483 Intermediate Similarity NPD3619 Clinical (unspecified phase)
0.7466 Intermediate Similarity NPD6099 Approved
0.7466 Intermediate Similarity NPD6100 Approved
0.7465 Intermediate Similarity NPD5110 Phase 2
0.7465 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7465 Intermediate Similarity NPD5109 Approved
0.7465 Intermediate Similarity NPD5111 Phase 2
0.7438 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7432 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD1934 Approved
0.7407 Intermediate Similarity NPD7228 Approved
0.7385 Intermediate Similarity NPD3022 Approved
0.7385 Intermediate Similarity NPD3021 Approved
0.7385 Intermediate Similarity NPD4750 Phase 3
0.7383 Intermediate Similarity NPD3892 Phase 2
0.7372 Intermediate Similarity NPD2801 Approved
0.7362 Intermediate Similarity NPD5844 Phase 1
0.7361 Intermediate Similarity NPD2238 Phase 2
0.7355 Intermediate Similarity NPD5090 Approved
0.7355 Intermediate Similarity NPD5089 Approved
0.7338 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD5536 Phase 2
0.7313 Intermediate Similarity NPD6671 Approved
0.7286 Intermediate Similarity NPD6696 Suspended
0.7266 Intermediate Similarity NPD2233 Approved
0.7266 Intermediate Similarity NPD2232 Approved
0.7266 Intermediate Similarity NPD2230 Approved
0.7261 Intermediate Similarity NPD1465 Phase 2
0.7261 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7237 Intermediate Similarity NPD4357 Discontinued
0.7229 Intermediate Similarity NPD7240 Approved
0.7226 Intermediate Similarity NPD6055 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD2219 Phase 1
0.7215 Intermediate Similarity NPD6374 Clinical (unspecified phase)
0.7215 Intermediate Similarity NPD3817 Phase 2
0.72 Intermediate Similarity NPD5177 Phase 3
0.7192 Intermediate Similarity NPD3657 Discovery
0.7185 Intermediate Similarity NPD709 Approved
0.7185 Intermediate Similarity NPD7157 Approved
0.7183 Intermediate Similarity NPD4624 Approved
0.7181 Intermediate Similarity NPD5763 Approved
0.7181 Intermediate Similarity NPD5762 Approved
0.7179 Intermediate Similarity NPD4675 Approved
0.7179 Intermediate Similarity NPD4678 Approved
0.7174 Intermediate Similarity NPD4626 Approved
0.717 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD3882 Suspended
0.7163 Intermediate Similarity NPD8651 Approved
0.7163 Intermediate Similarity NPD1283 Approved
0.716 Intermediate Similarity NPD7229 Phase 3
0.7153 Intermediate Similarity NPD7095 Approved
0.7152 Intermediate Similarity NPD7819 Suspended
0.7152 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD5494 Approved
0.7143 Intermediate Similarity NPD5261 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD4097 Suspended
0.7124 Intermediate Similarity NPD1511 Approved
0.7115 Intermediate Similarity NPD7261 Clinical (unspecified phase)
0.7109 Intermediate Similarity NPD940 Approved
0.7109 Intermediate Similarity NPD846 Approved
0.7105 Intermediate Similarity NPD2677 Approved
0.7101 Intermediate Similarity NPD1651 Approved
0.7097 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD6895 Approved
0.7095 Intermediate Similarity NPD6896 Approved
0.7092 Intermediate Similarity NPD1669 Approved
0.709 Intermediate Similarity NPD7843 Approved
0.709 Intermediate Similarity NPD7635 Approved
0.7083 Intermediate Similarity NPD7549 Discontinued
0.7075 Intermediate Similarity NPD6355 Discontinued
0.7075 Intermediate Similarity NPD5735 Approved
0.7073 Intermediate Similarity NPD6166 Phase 2
0.7073 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7073 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7071 Intermediate Similarity NPD422 Phase 1
0.7067 Intermediate Similarity NPD1375 Discontinued
0.7067 Intermediate Similarity NPD2029 Clinical (unspecified phase)
0.7051 Intermediate Similarity NPD1653 Approved
0.705 Intermediate Similarity NPD2667 Approved
0.705 Intermediate Similarity NPD2668 Approved
0.7047 Intermediate Similarity NPD6029 Clinical (unspecified phase)
0.7047 Intermediate Similarity NPD6028 Clinical (unspecified phase)
0.7045 Intermediate Similarity NPD2684 Approved
0.7044 Intermediate Similarity NPD4585 Approved
0.7042 Intermediate Similarity NPD2922 Phase 1
0.7039 Intermediate Similarity NPD7466 Approved
0.7039 Intermediate Similarity NPD3750 Approved
0.7032 Intermediate Similarity NPD7314 Clinical (unspecified phase)
0.7032 Intermediate Similarity NPD1512 Approved
0.7031 Intermediate Similarity NPD1242 Phase 1
0.7013 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD7340 Approved
0.7007 Intermediate Similarity NPD1240 Approved
0.7007 Intermediate Similarity NPD1558 Phase 1
0.7006 Intermediate Similarity NPD7074 Phase 3
0.7 Intermediate Similarity NPD8054 Approved
0.7 Intermediate Similarity NPD8053 Approved
0.6988 Remote Similarity NPD8099 Discontinued
0.6988 Remote Similarity NPD8252 Approved
0.6988 Remote Similarity NPD8251 Approved
0.6978 Remote Similarity NPD1357 Approved
0.6978 Remote Similarity NPD5691 Approved
0.6974 Remote Similarity NPD4237 Approved
0.6974 Remote Similarity NPD3060 Approved
0.6974 Remote Similarity NPD4236 Phase 3
0.6972 Remote Similarity NPD5327 Phase 3
0.6968 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6968 Remote Similarity NPD7447 Phase 1
0.6966 Remote Similarity NPD5752 Clinical (unspecified phase)
0.6959 Remote Similarity NPD5124 Phase 1
0.6959 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6953 Remote Similarity NPD3020 Approved
0.6951 Remote Similarity NPD3787 Discontinued
0.695 Remote Similarity NPD1091 Approved
0.695 Remote Similarity NPD1281 Approved
0.695 Remote Similarity NPD1611 Approved
0.6946 Remote Similarity NPD7054 Approved
0.6946 Remote Similarity NPD8156 Discontinued
0.6933 Remote Similarity NPD3748 Approved
0.6933 Remote Similarity NPD1510 Phase 2
0.6933 Remote Similarity NPD4108 Discontinued
0.6928 Remote Similarity NPD6658 Clinical (unspecified phase)
0.6928 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6928 Remote Similarity NPD6331 Phase 2
0.6928 Remote Similarity NPD4110 Phase 3
0.6913 Remote Similarity NPD6353 Approved
0.6913 Remote Similarity NPD1607 Approved
0.6909 Remote Similarity NPD3926 Phase 2
0.6908 Remote Similarity NPD4664 Clinical (unspecified phase)
0.6905 Remote Similarity NPD7472 Approved
0.6903 Remote Similarity NPD7040 Clinical (unspecified phase)
0.6903 Remote Similarity NPD7041 Phase 2
0.6901 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6901 Remote Similarity NPD1608 Approved
0.6894 Remote Similarity NPD2563 Approved
0.6894 Remote Similarity NPD2560 Approved
0.6892 Remote Similarity NPD2979 Phase 3
0.689 Remote Similarity NPD6959 Discontinued
0.6887 Remote Similarity NPD2935 Discontinued
0.6887 Remote Similarity NPD2438 Suspended
0.6886 Remote Similarity NPD3818 Discontinued
0.6883 Remote Similarity NPD5084 Clinical (unspecified phase)
0.6883 Remote Similarity NPD5241 Discontinued
0.6871 Remote Similarity NPD5718 Phase 2
0.6867 Remote Similarity NPD4537 Clinical (unspecified phase)
0.6867 Remote Similarity NPD4538 Approved
0.6867 Remote Similarity NPD4536 Approved
0.6866 Remote Similarity NPD5451 Approved
0.6863 Remote Similarity NPD1652 Phase 2
0.6859 Remote Similarity NPD2533 Approved
0.6859 Remote Similarity NPD4584 Approved
0.6859 Remote Similarity NPD4123 Phase 3
0.6859 Remote Similarity NPD2532 Approved
0.6859 Remote Similarity NPD2534 Approved
0.6855 Remote Similarity NPD4380 Phase 2
0.6852 Remote Similarity NPD6788 Approved
0.6842 Remote Similarity NPD7266 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