Structure

Physi-Chem Properties

Molecular Weight:  370.18
Volume:  388.895
LogP:  5.183
LogD:  3.775
LogS:  -3.513
# Rotatable Bonds:  5
TPSA:  68.15
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  5

MedChem Properties

QED Drug-Likeness Score:  0.766
Synthetic Accessibility Score:  3.321
Fsp3:  0.364
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.832
MDCK Permeability:  1.3454870895657223e-05
Pgp-inhibitor:  0.219
Pgp-substrate:  0.622
Human Intestinal Absorption (HIA):  0.012
20% Bioavailability (F20%):  0.878
30% Bioavailability (F30%):  0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.021
Plasma Protein Binding (PPB):  98.23041534423828%
Volume Distribution (VD):  1.859
Pgp-substrate:  2.977855682373047%

ADMET: Metabolism

CYP1A2-inhibitor:  0.629
CYP1A2-substrate:  0.939
CYP2C19-inhibitor:  0.918
CYP2C19-substrate:  0.636
CYP2C9-inhibitor:  0.787
CYP2C9-substrate:  0.953
CYP2D6-inhibitor:  0.704
CYP2D6-substrate:  0.888
CYP3A4-inhibitor:  0.614
CYP3A4-substrate:  0.51

ADMET: Excretion

Clearance (CL):  11.94
Half-life (T1/2):  0.456

ADMET: Toxicity

hERG Blockers:  0.192
Human Hepatotoxicity (H-HT):  0.696
Drug-inuced Liver Injury (DILI):  0.097
AMES Toxicity:  0.099
Rat Oral Acute Toxicity:  0.22
Maximum Recommended Daily Dose:  0.947
Skin Sensitization:  0.938
Carcinogencity:  0.089
Eye Corrosion:  0.003
Eye Irritation:  0.734
Respiratory Toxicity:  0.862

Download Data

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

  Natural Product: NPC38664

Natural Product ID:  NPC38664
Common Name*:   Glyasperin D
IUPAC Name:   4-[(3R)-5,7-dimethoxy-6-(3-methylbut-2-enyl)-3,4-dihydro-2H-chromen-3-yl]benzene-1,3-diol
Synonyms:   Glyasperin D
Standard InCHIKey:  DDMAUIOCNQXFHL-AWEZNQCLSA-N
Standard InCHI:  InChI=1S/C22H26O5/c1-13(2)5-7-17-20(25-3)11-21-18(22(17)26-4)9-14(12-27-21)16-8-6-15(23)10-19(16)24/h5-6,8,10-11,14,23-24H,7,9,12H2,1-4H3/t14-/m0/s1
SMILES:  CC(=CCc1c(cc2c(C[C@@H](CO2)c2ccc(cc2O)O)c1OC)OC)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1563332
PubChem CID:   480860
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0002506] Isoflavonoids
        • [CHEMONTID:0002586] O-methylated isoflavonoids
          • [CHEMONTID:0002602] 7-O-methylated isoflavonoids

*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
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota Leaves n.a. n.a. PMID[12713396]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root n.a. PMID[16441081]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[16675659]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota roots n.a. n.a. PMID[20022509]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[21123068]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[21866899]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root n.a. PMID[22074222]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[22074222]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[23325115]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota Roots n.a. n.a. PMID[23541646]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. rhizome n.a. PMID[23867078]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root n.a. PMID[23867078]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[24479468]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota roots n.a. n.a. PMID[24957203]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[25445757]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[25744461]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[26841168]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[28140583]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[28522265]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[29641206]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[32196343]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[7381508]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22336 Glycyrrhiza aspera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22336 Glycyrrhiza aspera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22336 Glycyrrhiza aspera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO10026 Mitracarpus scaber Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22336 Glycyrrhiza aspera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7786 Lentinus tigrinus Species Lentinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ 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
NPT532 Individual Protein Lysine-specific demethylase 4A Homo sapiens Potency n.a. 56234.1 nM PMID[447476]
NPT65 Cell Line HepG2 Homo sapiens Potency n.a. 25118.9 nM PMID[447476]
NPT154 Individual Protein Mothers against decapentaplegic homolog 3 Homo sapiens Potency n.a. 22387.2 nM PMID[447476]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 16360.1 nM PMID[447476]
NPT478 Individual Protein Ataxin-2 Homo sapiens Potency n.a. 39810.7 nM PMID[447476]
NPT101 Individual Protein Glucagon-like peptide 1 receptor Homo sapiens Potency n.a. 22387.2 nM PMID[447476]
NPT159 Individual Protein Aberrant vpr protein Human immunodeficiency virus 1 Potency n.a. 63095.7 nM PMID[447476]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 29092.9 nM PMID[447476]
NPT65 Cell Line HepG2 Homo sapiens Activity = 99.0 % PMID[447479]
NPT660 Cell Line SW480 Homo sapiens Activity = 78.0 % PMID[447479]
NPT81 Cell Line A549 Homo sapiens Activity = 25.0 % PMID[447479]
NPT83 Cell Line MCF7 Homo sapiens Activity = 98.0 % PMID[447479]
NPT65 Cell Line HepG2 Homo sapiens IC50 = 3800.0 nM PMID[447479]
NPT660 Cell Line SW480 Homo sapiens IC50 = 7200.0 nM PMID[447479]
NPT81 Cell Line A549 Homo sapiens IC50 = 12900.0 nM PMID[447479]
NPT83 Cell Line MCF7 Homo sapiens IC50 = 6700.0 nM PMID[447479]
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens Inhibition > 60.0 % PMID[447480]
NPT65 Cell Line HepG2 Homo sapiens Activity = 80.0 % PMID[447480]
NPT2 Others Unspecified Inhibition = 20.0 % PMID[447475]
NPT2 Others Unspecified CC50 = 15280.0 nM PMID[447476]
NPT27 Others Unspecified CC50 = 68100.0 nM PMID[447477]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. EC50 = 17600.0 nM PMID[447477]
NPT2 Others Unspecified Ratio CC50/EC50 = 5.7 n.a. PMID[447477]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. EC50 = 42000.0 nM PMID[447477]
NPT2 Others Unspecified Ratio CC50/EC50 = 1.6 n.a. PMID[447477]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. MIC = 17200.0 nM PMID[447477]
NPT803 Individual Protein Flap endonuclease 1 Homo sapiens Potency n.a. 79432.8 nM PMID[447476]
NPT2 Others Unspecified Potency n.a. 10000.0 nM PMID[447476]
NPT920 Individual Protein Alpha-synuclein Homo sapiens Potency n.a. 35481.3 nM PMID[447476]
NPT741 Individual Protein Tyrosinase Homo sapiens Inhibition > 95.0 % PMID[447479]
NPT741 Individual Protein Tyrosinase Homo sapiens IC50 = 154.0 nM PMID[447479]
NPT2 Others Unspecified Inhibition > 40.0 % PMID[447480]

☑ 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 NPC38664 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC53986
0.9918 High Similarity NPC93962
0.9835 High Similarity NPC230479
0.9835 High Similarity NPC50315
0.9835 High Similarity NPC26879
0.9835 High Similarity NPC283049
0.9758 High Similarity NPC236014
0.9758 High Similarity NPC268917
0.9758 High Similarity NPC17343
0.9758 High Similarity NPC68205
0.9758 High Similarity NPC207892
0.9758 High Similarity NPC150011
0.9758 High Similarity NPC211413
0.9758 High Similarity NPC280653
0.9758 High Similarity NPC300875
0.9758 High Similarity NPC206224
0.9758 High Similarity NPC293203
0.9758 High Similarity NPC118114
0.9758 High Similarity NPC164804
0.9758 High Similarity NPC196765
0.9758 High Similarity NPC129106
0.9758 High Similarity NPC118683
0.9758 High Similarity NPC12875
0.9758 High Similarity NPC228369
0.9758 High Similarity NPC164574
0.9758 High Similarity NPC244888
0.9758 High Similarity NPC476166
0.9758 High Similarity NPC129784
0.968 High Similarity NPC13005
0.9677 High Similarity NPC27187
0.9677 High Similarity NPC470225
0.9675 High Similarity NPC274717
0.9603 High Similarity NPC77196
0.96 High Similarity NPC181497
0.96 High Similarity NPC271945
0.959 High Similarity NPC285040
0.959 High Similarity NPC188022
0.959 High Similarity NPC17809
0.959 High Similarity NPC102540
0.959 High Similarity NPC103420
0.9528 High Similarity NPC296915
0.9528 High Similarity NPC198154
0.9528 High Similarity NPC115335
0.9528 High Similarity NPC223008
0.9528 High Similarity NPC225696
0.9528 High Similarity NPC97834
0.9516 High Similarity NPC39064
0.9516 High Similarity NPC47283
0.9512 High Similarity NPC276212
0.9508 High Similarity NPC134195
0.9508 High Similarity NPC86502
0.9508 High Similarity NPC197351
0.9508 High Similarity NPC106914
0.9508 High Similarity NPC246648
0.9449 High Similarity NPC85435
0.9449 High Similarity NPC92805
0.9444 High Similarity NPC103799
0.944 High Similarity NPC134360
0.9426 High Similarity NPC38761
0.9426 High Similarity NPC76465
0.9421 High Similarity NPC54972
0.9421 High Similarity NPC193364
0.9375 High Similarity NPC117048
0.9375 High Similarity NPC473107
0.9375 High Similarity NPC124085
0.9355 High Similarity NPC262573
0.9355 High Similarity NPC471215
0.9344 High Similarity NPC100099
0.9344 High Similarity NPC36016
0.9308 High Similarity NPC474687
0.9291 High Similarity NPC162801
0.928 High Similarity NPC149796
0.9237 High Similarity NPC260741
0.9237 High Similarity NPC475836
0.9237 High Similarity NPC70682
0.9231 High Similarity NPC471522
0.9231 High Similarity NPC18189
0.9231 High Similarity NPC3049
0.9231 High Similarity NPC262585
0.9231 High Similarity NPC20829
0.9206 High Similarity NPC222572
0.9206 High Similarity NPC87224
0.9194 High Similarity NPC256015
0.9194 High Similarity NPC294156
0.916 High Similarity NPC470308
0.916 High Similarity NPC470307
0.9154 High Similarity NPC473413
0.912 High Similarity NPC81641
0.9106 High Similarity NPC476633
0.9098 High Similarity NPC35216
0.9098 High Similarity NPC93398
0.9098 High Similarity NPC8283
0.9098 High Similarity NPC5155
0.9098 High Similarity NPC258979
0.9091 High Similarity NPC131118
0.9091 High Similarity NPC32630
0.9084 High Similarity NPC265433
0.9084 High Similarity NPC173660
0.9084 High Similarity NPC162659
0.9084 High Similarity NPC270456
0.9084 High Similarity NPC248727
0.9077 High Similarity NPC476615
0.9077 High Similarity NPC476617
0.9077 High Similarity NPC476616
0.904 High Similarity NPC159132
0.9032 High Similarity NPC150026
0.903 High Similarity NPC59841
0.903 High Similarity NPC2613
0.903 High Similarity NPC204347
0.903 High Similarity NPC475891
0.9023 High Similarity NPC259519
0.9016 High Similarity NPC295259
0.9016 High Similarity NPC59561
0.9016 High Similarity NPC172253
0.9008 High Similarity NPC195022
0.9008 High Similarity NPC125579
0.9 High Similarity NPC11060
0.8992 High Similarity NPC160623
0.8992 High Similarity NPC472590
0.8976 High Similarity NPC473134
0.8968 High Similarity NPC278552
0.8968 High Similarity NPC167571
0.8968 High Similarity NPC207179
0.896 High Similarity NPC474160
0.8955 High Similarity NPC265075
0.8955 High Similarity NPC100482
0.8955 High Similarity NPC277331
0.8952 High Similarity NPC97432
0.8952 High Similarity NPC190454
0.8947 High Similarity NPC127218
0.8947 High Similarity NPC471388
0.8947 High Similarity NPC25966
0.8947 High Similarity NPC319647
0.8947 High Similarity NPC245207
0.8939 High Similarity NPC470802
0.8939 High Similarity NPC234952
0.8934 High Similarity NPC74821
0.8931 High Similarity NPC317380
0.8926 High Similarity NPC85292
0.8926 High Similarity NPC229147
0.8926 High Similarity NPC54507
0.8923 High Similarity NPC472798
0.8897 High Similarity NPC93323
0.8897 High Similarity NPC280092
0.8897 High Similarity NPC475492
0.8897 High Similarity NPC12641
0.8897 High Similarity NPC473108
0.8897 High Similarity NPC45257
0.8881 High Similarity NPC184797
0.8881 High Similarity NPC309124
0.8881 High Similarity NPC27495
0.8872 High Similarity NPC477938
0.8872 High Similarity NPC276490
0.8864 High Similarity NPC112246
0.8864 High Similarity NPC94750
0.8864 High Similarity NPC112939
0.8864 High Similarity NPC474206
0.8864 High Similarity NPC151224
0.8864 High Similarity NPC470356
0.8864 High Similarity NPC121812
0.8864 High Similarity NPC61946
0.8855 High Similarity NPC215037
0.8855 High Similarity NPC177712
0.8855 High Similarity NPC469610
0.8855 High Similarity NPC24913
0.8846 High Similarity NPC8899
0.8843 High Similarity NPC464
0.8843 High Similarity NPC185541
0.8837 High Similarity NPC96719
0.8837 High Similarity NPC16577
0.8837 High Similarity NPC472795
0.8837 High Similarity NPC472797
0.8837 High Similarity NPC472796
0.8837 High Similarity NPC222108
0.8832 High Similarity NPC469557
0.8828 High Similarity NPC46978
0.8824 High Similarity NPC85264
0.8824 High Similarity NPC102044
0.8824 High Similarity NPC47633
0.8819 High Similarity NPC105031
0.8819 High Similarity NPC113495
0.8815 High Similarity NPC471389
0.8815 High Similarity NPC263261
0.8815 High Similarity NPC87725
0.8806 High Similarity NPC473739
0.8806 High Similarity NPC236306
0.8806 High Similarity NPC232164
0.8797 High Similarity NPC227503
0.8797 High Similarity NPC474639
0.8797 High Similarity NPC230734
0.8797 High Similarity NPC141717
0.8797 High Similarity NPC16435
0.8797 High Similarity NPC306441
0.8797 High Similarity NPC472800
0.8788 High Similarity NPC131950
0.8779 High Similarity NPC86655
0.8779 High Similarity NPC202762
0.8779 High Similarity NPC127624
0.8779 High Similarity NPC469611
0.8769 High Similarity NPC254000

  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 NPC38664 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
0.9677 High Similarity NPD4907 Clinical (unspecified phase)
0.9516 High Similarity NPD4908 Phase 1
0.9421 High Similarity NPD1610 Phase 2
0.8934 High Similarity NPD1548 Phase 1
0.8837 High Similarity NPD4625 Phase 3
0.8682 High Similarity NPD2861 Phase 2
0.8661 High Similarity NPD4749 Approved
0.8636 High Similarity NPD1613 Approved
0.8636 High Similarity NPD1612 Clinical (unspecified phase)
0.8626 High Similarity NPD6410 Clinical (unspecified phase)
0.8615 High Similarity NPD1529 Clinical (unspecified phase)
0.8538 High Similarity NPD1530 Clinical (unspecified phase)
0.8296 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.8296 Intermediate Similarity NPD5124 Phase 1
0.8271 Intermediate Similarity NPD3027 Phase 3
0.8239 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8209 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.8143 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.8112 Intermediate Similarity NPD7447 Phase 1
0.8108 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8092 Intermediate Similarity NPD3600 Clinical (unspecified phase)
0.8088 Intermediate Similarity NPD4060 Phase 1
0.8077 Intermediate Similarity NPD422 Phase 1
0.8045 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.8042 Intermediate Similarity NPD7213 Phase 3
0.8042 Intermediate Similarity NPD7212 Phase 2
0.8041 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.803 Intermediate Similarity NPD8651 Approved
0.8027 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7953 Intermediate Similarity NPD6671 Approved
0.7943 Intermediate Similarity NPD1549 Phase 2
0.7929 Intermediate Similarity NPD6100 Approved
0.7929 Intermediate Similarity NPD6099 Approved
0.7914 Intermediate Similarity NPD4536 Approved
0.7914 Intermediate Similarity NPD4537 Clinical (unspecified phase)
0.7914 Intermediate Similarity NPD4538 Approved
0.7838 Intermediate Similarity NPD4380 Phase 2
0.7832 Intermediate Similarity NPD3750 Approved
0.7832 Intermediate Similarity NPD7466 Approved
0.7832 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7815 Intermediate Similarity NPD7768 Phase 2
0.7805 Intermediate Similarity NPD968 Approved
0.7803 Intermediate Similarity NPD1091 Approved
0.78 Intermediate Similarity NPD7819 Suspended
0.7785 Intermediate Similarity NPD7411 Suspended
0.7769 Intermediate Similarity NPD940 Approved
0.7769 Intermediate Similarity NPD846 Approved
0.7763 Intermediate Similarity NPD7075 Discontinued
0.774 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7733 Intermediate Similarity NPD1934 Approved
0.773 Intermediate Similarity NPD5588 Approved
0.773 Intermediate Similarity NPD1510 Phase 2
0.773 Intermediate Similarity NPD5960 Phase 3
0.7708 Intermediate Similarity NPD3892 Phase 2
0.7704 Intermediate Similarity NPD2797 Approved
0.7687 Intermediate Similarity NPD6582 Phase 2
0.7687 Intermediate Similarity NPD6583 Phase 3
0.7682 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.768 Intermediate Similarity NPD2684 Approved
0.7676 Intermediate Similarity NPD2796 Approved
0.7674 Intermediate Similarity NPD7157 Approved
0.7647 Intermediate Similarity NPD6584 Phase 3
0.7639 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7639 Intermediate Similarity NPD1652 Phase 2
0.763 Intermediate Similarity NPD6696 Suspended
0.7619 Intermediate Similarity NPD4750 Phase 3
0.7613 Intermediate Similarity NPD6959 Discontinued
0.7603 Intermediate Similarity NPD6666 Approved
0.7603 Intermediate Similarity NPD6667 Approved
0.7603 Intermediate Similarity NPD3020 Approved
0.7603 Intermediate Similarity NPD5058 Phase 3
0.7591 Intermediate Similarity NPD3018 Phase 2
0.758 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7578 Intermediate Similarity NPD5535 Approved
0.7578 Intermediate Similarity NPD7843 Approved
0.7571 Intermediate Similarity NPD1240 Approved
0.7564 Intermediate Similarity NPD7229 Phase 3
0.7554 Intermediate Similarity NPD3268 Approved
0.7535 Intermediate Similarity NPD2200 Suspended
0.7532 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7519 Intermediate Similarity NPD5283 Phase 1
0.7518 Intermediate Similarity NPD6355 Discontinued
0.7518 Intermediate Similarity NPD3691 Phase 2
0.7518 Intermediate Similarity NPD3690 Phase 2
0.7517 Intermediate Similarity NPD6674 Discontinued
0.75 Intermediate Similarity NPD6002 Phase 3
0.75 Intermediate Similarity NPD6005 Phase 3
0.75 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6004 Phase 3
0.75 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7483 Intermediate Similarity NPD3748 Approved
0.7483 Intermediate Similarity NPD7033 Discontinued
0.7481 Intermediate Similarity NPD7340 Approved
0.7468 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7465 Intermediate Similarity NPD1607 Approved
0.7465 Intermediate Similarity NPD4097 Suspended
0.746 Intermediate Similarity NPD290 Approved
0.7451 Intermediate Similarity NPD2801 Approved
0.7448 Intermediate Similarity NPD2424 Discontinued
0.7447 Intermediate Similarity NPD2238 Phase 2
0.7438 Intermediate Similarity NPD5844 Phase 1
0.7438 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD5494 Approved
0.7434 Intermediate Similarity NPD6072 Discontinued
0.7432 Intermediate Similarity NPD7041 Phase 2
0.7432 Intermediate Similarity NPD1511 Approved
0.7432 Intermediate Similarity NPD7040 Clinical (unspecified phase)
0.7431 Intermediate Similarity NPD1551 Phase 2
0.7431 Intermediate Similarity NPD2935 Discontinued
0.7429 Intermediate Similarity NPD6798 Discontinued
0.7426 Intermediate Similarity NPD5327 Phase 3
0.7426 Intermediate Similarity NPD2983 Phase 2
0.7426 Intermediate Similarity NPD2982 Phase 2
0.7413 Intermediate Similarity NPD7097 Phase 1
0.7398 Intermediate Similarity NPD1242 Phase 1
0.7397 Intermediate Similarity NPD2800 Approved
0.7394 Intermediate Similarity NPD5735 Approved
0.7388 Intermediate Similarity NPD6516 Phase 2
0.7388 Intermediate Similarity NPD4626 Approved
0.7388 Intermediate Similarity NPD5846 Approved
0.7386 Intermediate Similarity NPD6801 Discontinued
0.7386 Intermediate Similarity NPD37 Approved
0.7385 Intermediate Similarity NPD1398 Phase 1
0.7372 Intermediate Similarity NPD3225 Approved
0.7372 Intermediate Similarity NPD6234 Discontinued
0.7361 Intermediate Similarity NPD2799 Discontinued
0.7361 Intermediate Similarity NPD4108 Discontinued
0.7358 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD6166 Phase 2
0.7355 Intermediate Similarity NPD4965 Approved
0.7355 Intermediate Similarity NPD4967 Phase 2
0.7355 Intermediate Similarity NPD2859 Approved
0.7355 Intermediate Similarity NPD4966 Approved
0.7355 Intermediate Similarity NPD2860 Approved
0.7353 Intermediate Similarity NPD1608 Approved
0.7353 Intermediate Similarity NPD2981 Phase 2
0.7351 Intermediate Similarity NPD1653 Approved
0.7347 Intermediate Similarity NPD4535 Phase 3
0.7344 Intermediate Similarity NPD5451 Approved
0.7338 Intermediate Similarity NPD8455 Phase 2
0.7333 Intermediate Similarity NPD3496 Discontinued
0.7333 Intermediate Similarity NPD1512 Approved
0.7329 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7324 Intermediate Similarity NPD4140 Approved
0.7315 Intermediate Similarity NPD6799 Approved
0.7313 Intermediate Similarity NPD5691 Approved
0.7313 Intermediate Similarity NPD3445 Approved
0.7313 Intermediate Similarity NPD3444 Approved
0.7313 Intermediate Similarity NPD3443 Approved
0.731 Intermediate Similarity NPD4477 Approved
0.731 Intermediate Similarity NPD4476 Approved
0.7308 Intermediate Similarity NPD821 Approved
0.7301 Intermediate Similarity NPD6559 Discontinued
0.7279 Intermediate Similarity NPD1611 Approved
0.7278 Intermediate Similarity NPD7199 Phase 2
0.7273 Intermediate Similarity NPD2557 Approved
0.7273 Intermediate Similarity NPD2933 Approved
0.7273 Intermediate Similarity NPD2934 Approved
0.7273 Intermediate Similarity NPD6387 Discontinued
0.7267 Intermediate Similarity NPD2534 Approved
0.7267 Intermediate Similarity NPD2533 Approved
0.7267 Intermediate Similarity NPD2532 Approved
0.726 Intermediate Similarity NPD7030 Discontinued
0.726 Intermediate Similarity NPD5762 Approved
0.726 Intermediate Similarity NPD5763 Approved
0.7259 Intermediate Similarity NPD2668 Approved
0.7259 Intermediate Similarity NPD2667 Approved
0.7256 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7255 Intermediate Similarity NPD6599 Discontinued
0.7254 Intermediate Similarity NPD6233 Phase 2
0.7244 Intermediate Similarity NPD3882 Suspended
0.7241 Intermediate Similarity NPD3846 Clinical (unspecified phase)
0.7239 Intermediate Similarity NPD7741 Discontinued
0.7239 Intermediate Similarity NPD6581 Approved
0.7239 Intermediate Similarity NPD6580 Approved
0.7234 Intermediate Similarity NPD7095 Approved
0.7233 Intermediate Similarity NPD6232 Discontinued
0.723 Intermediate Similarity NPD4628 Phase 3
0.7226 Intermediate Similarity NPD2233 Approved
0.7226 Intermediate Similarity NPD2235 Phase 2
0.7226 Intermediate Similarity NPD5929 Approved
0.7226 Intermediate Similarity NPD2230 Approved
0.7226 Intermediate Similarity NPD2231 Phase 2
0.7226 Intermediate Similarity NPD2232 Approved
0.7222 Intermediate Similarity NPD2157 Approved
0.7222 Intermediate Similarity NPD6353 Approved
0.7218 Intermediate Similarity NPD3596 Phase 2
0.7211 Intermediate Similarity NPD7037 Approved
0.7209 Intermediate Similarity NPD3022 Approved
0.7209 Intermediate Similarity NPD3021 Approved
0.7205 Intermediate Similarity NPD7473 Discontinued
0.7203 Intermediate Similarity NPD5837 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD3749 Approved
0.7194 Intermediate Similarity NPD3267 Approved
0.7194 Intermediate Similarity NPD4098 Discontinued
0.7194 Intermediate Similarity NPD3266 Approved

  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