Structure

Physi-Chem Properties

Molecular Weight:  366.11
Volume:  360.64
LogP:  5.232
LogD:  3.776
LogS:  -5.217
# Rotatable Bonds:  1
TPSA:  82.04
# H-Bond Aceptor:  6
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.499
Synthetic Accessibility Score:  3.033
Fsp3:  0.286
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:  -4.799
MDCK Permeability:  3.295511851320043e-05
Pgp-inhibitor:  0.655
Pgp-substrate:  0.002
Human Intestinal Absorption (HIA):  0.014
20% Bioavailability (F20%):  0.008
30% Bioavailability (F30%):  0.044

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.011
Plasma Protein Binding (PPB):  90.58792877197266%
Volume Distribution (VD):  0.557
Pgp-substrate:  11.256524085998535%

ADMET: Metabolism

CYP1A2-inhibitor:  0.881
CYP1A2-substrate:  0.938
CYP2C19-inhibitor:  0.876
CYP2C19-substrate:  0.163
CYP2C9-inhibitor:  0.836
CYP2C9-substrate:  0.948
CYP2D6-inhibitor:  0.357
CYP2D6-substrate:  0.883
CYP3A4-inhibitor:  0.328
CYP3A4-substrate:  0.125

ADMET: Excretion

Clearance (CL):  4.929
Half-life (T1/2):  0.178

ADMET: Toxicity

hERG Blockers:  0.008
Human Hepatotoxicity (H-HT):  0.932
Drug-inuced Liver Injury (DILI):  0.98
AMES Toxicity:  0.267
Rat Oral Acute Toxicity:  0.539
Maximum Recommended Daily Dose:  0.842
Skin Sensitization:  0.32
Carcinogencity:  0.332
Eye Corrosion:  0.003
Eye Irritation:  0.113
Respiratory Toxicity:  0.213

Download Data

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

  Natural Product: NPC155640

Natural Product ID:  NPC155640
Common Name*:   Isoglycyrol
IUPAC Name:   n.a.
Synonyms:   Isoglycyrol
Standard InCHIKey:  CFWLRXJPRRCJTI-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C21H18O6/c1-21(2)7-6-12-14(27-21)9-15-17(18(12)24-3)19-16(20(23)26-15)11-5-4-10(22)8-13(11)25-19/h4-5,8-9,22H,6-7H2,1-3H3
SMILES:  COc1c2CCC(Oc2cc2c1c1oc3c(c1c(=O)o2)ccc(c3)O)(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL495063
PubChem CID:   124050
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0002506] Isoflavonoids
        • [CHEMONTID:0000354] Coumestans

*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]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
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]
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
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 18356.4 nM PMID[547478]
NPT135 Individual Protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 3981.1 nM PMID[547478]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 46.1 nM PMID[547478]
NPT156 Individual Protein Sphingomyelin phosphodiesterase Homo sapiens Potency n.a. 25118.9 nM PMID[547478]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 2909.3 nM PMID[547478]
NPT157 Individual Protein Breast cancer type 1 susceptibility protein Homo sapiens Potency n.a. 8912.5 nM PMID[547478]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 16360.1 nM PMID[547478]
NPT535 Individual Protein Parathyroid hormone receptor Homo sapiens Potency n.a. 7079.5 nM PMID[547478]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens FC = 3.32 n.a. PMID[547480]
NPT878 Organism Streptococcus mutans Streptococcus mutans Activity = 500.0 ug ml-1 PMID[547476]
NPT2 Others Unspecified IC50 = 92400.0 nM PMID[547477]
NPT2 Others Unspecified Ki = 77500.0 nM PMID[547477]
NPT2 Others Unspecified EC50 = 274.0 nM PMID[547478]
NPT2 Others Unspecified EC50 = 3131.0 nM PMID[547478]
NPT2 Others Unspecified Potency n.a. 1995.3 nM PMID[547478]
NPT878 Organism Streptococcus mutans Streptococcus mutans MBC > 200.0 ug ml-1 PMID[547479]
NPT878 Organism Streptococcus mutans Streptococcus mutans MIC > 200.0 ug.mL-1 PMID[547479]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. MBC = 200.0 ug ml-1 PMID[547479]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. MIC = 200.0 ug.mL-1 PMID[547479]
NPT2 Others Unspecified Potency n.a. 28183.8 nM PMID[547478]

☑ 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 NPC155640 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
0.9805 High Similarity NPC115432
0.9805 High Similarity NPC260296
0.974 High Similarity NPC244750
0.9441 High Similarity NPC120220
0.9423 High Similarity NPC65504
0.9416 High Similarity NPC41326
0.9383 High Similarity NPC472584
0.9355 High Similarity NPC1477
0.9355 High Similarity NPC213608
0.9317 High Similarity NPC320789
0.9299 High Similarity NPC260902
0.9299 High Similarity NPC296957
0.929 High Similarity NPC5871
0.9255 High Similarity NPC323137
0.9236 High Similarity NPC247677
0.9236 High Similarity NPC13879
0.9236 High Similarity NPC160015
0.9221 High Similarity NPC37226
0.9221 High Similarity NPC226644
0.9212 High Similarity NPC164384
0.9207 High Similarity NPC261471
0.9193 High Similarity NPC204088
0.9193 High Similarity NPC329215
0.9193 High Similarity NPC259007
0.9156 High Similarity NPC135325
0.913 High Similarity NPC38591
0.9119 High Similarity NPC476350
0.9119 High Similarity NPC476349
0.9119 High Similarity NPC40583
0.9108 High Similarity NPC472462
0.9103 High Similarity NPC170169
0.9097 High Similarity NPC37208
0.9097 High Similarity NPC221868
0.9091 High Similarity NPC130581
0.9091 High Similarity NPC37606
0.9091 High Similarity NPC12148
0.9085 High Similarity NPC218533
0.9085 High Similarity NPC78830
0.9057 High Similarity NPC268360
0.9051 High Similarity NPC148938
0.9048 High Similarity NPC97523
0.9045 High Similarity NPC67654
0.9038 High Similarity NPC230713
0.9038 High Similarity NPC78335
0.9032 High Similarity NPC272194
0.9026 High Similarity NPC300267
0.9026 High Similarity NPC210826
0.9026 High Similarity NPC51641
0.8987 High Similarity NPC235333
0.8987 High Similarity NPC122365
0.8981 High Similarity NPC156244
0.8981 High Similarity NPC312549
0.8981 High Similarity NPC209142
0.8974 High Similarity NPC39929
0.8974 High Similarity NPC178202
0.8974 High Similarity NPC296030
0.8968 High Similarity NPC140120
0.8963 High Similarity NPC86477
0.8961 High Similarity NPC230943
0.8938 High Similarity NPC246647
0.8938 High Similarity NPC212967
0.8938 High Similarity NPC164110
0.8938 High Similarity NPC269495
0.8938 High Similarity NPC96342
0.8938 High Similarity NPC270044
0.8931 High Similarity NPC99199
0.8931 High Similarity NPC297531
0.8931 High Similarity NPC213936
0.8931 High Similarity NPC198490
0.8924 High Similarity NPC207624
0.8917 High Similarity NPC29777
0.8917 High Similarity NPC471115
0.891 High Similarity NPC39195
0.8909 High Similarity NPC53252
0.8903 High Similarity NPC477955
0.8896 High Similarity NPC166138
0.8896 High Similarity NPC159508
0.8896 High Similarity NPC225884
0.8896 High Similarity NPC106985
0.8896 High Similarity NPC302181
0.8896 High Similarity NPC472581
0.8896 High Similarity NPC18585
0.8889 High Similarity NPC30655
0.8889 High Similarity NPC74854
0.8889 High Similarity NPC92589
0.8889 High Similarity NPC45124
0.8875 High Similarity NPC180924
0.8868 High Similarity NPC183874
0.8868 High Similarity NPC72370
0.8861 High Similarity NPC316960
0.8861 High Similarity NPC115324
0.8861 High Similarity NPC148945
0.8861 High Similarity NPC204561
0.8861 High Similarity NPC193976
0.8861 High Similarity NPC106372
0.8861 High Similarity NPC317715
0.8861 High Similarity NPC78835
0.8861 High Similarity NPC290671
0.8861 High Similarity NPC309512
0.8861 High Similarity NPC58668
0.8861 High Similarity NPC23668
0.8854 High Similarity NPC473016
0.8854 High Similarity NPC317492
0.8848 High Similarity NPC476459
0.8846 High Similarity NPC308200
0.8846 High Similarity NPC180477
0.8846 High Similarity NPC17816
0.8841 High Similarity NPC136641
0.8839 High Similarity NPC311741
0.8839 High Similarity NPC469953
0.8839 High Similarity NPC234629
0.8834 High Similarity NPC143402
0.8834 High Similarity NPC219861
0.8831 High Similarity NPC144499
0.8831 High Similarity NPC53192
0.8827 High Similarity NPC49009
0.8812 High Similarity NPC279218
0.8812 High Similarity NPC474542
0.8812 High Similarity NPC108937
0.8812 High Similarity NPC469934
0.8805 High Similarity NPC263676
0.8805 High Similarity NPC473996
0.8805 High Similarity NPC142308
0.8797 High Similarity NPC167576
0.8797 High Similarity NPC151973
0.8797 High Similarity NPC470107
0.8797 High Similarity NPC155882
0.8797 High Similarity NPC191104
0.879 High Similarity NPC145467
0.879 High Similarity NPC266572
0.879 High Similarity NPC296869
0.879 High Similarity NPC161864
0.879 High Similarity NPC168085
0.879 High Similarity NPC208303
0.8788 High Similarity NPC277480
0.8782 High Similarity NPC470322
0.8782 High Similarity NPC154217
0.8782 High Similarity NPC299011
0.8782 High Similarity NPC57470
0.8782 High Similarity NPC25844
0.878 High Similarity NPC109180
0.8774 High Similarity NPC295696
0.8774 High Similarity NPC38219
0.8774 High Similarity NPC219915
0.8774 High Similarity NPC17262
0.8773 High Similarity NPC14822
0.8758 High Similarity NPC475797
0.8758 High Similarity NPC469936
0.8758 High Similarity NPC129053
0.8758 High Similarity NPC321372
0.8758 High Similarity NPC109967
0.8758 High Similarity NPC137100
0.8758 High Similarity NPC474609
0.8758 High Similarity NPC474738
0.8758 High Similarity NPC78554
0.875 High Similarity NPC310794
0.8742 High Similarity NPC116604
0.8742 High Similarity NPC472580
0.8742 High Similarity NPC472636
0.8735 High Similarity NPC50394
0.8734 High Similarity NPC266499
0.8734 High Similarity NPC19238
0.8734 High Similarity NPC88445
0.8734 High Similarity NPC469932
0.8734 High Similarity NPC164205
0.8734 High Similarity NPC471114
0.8734 High Similarity NPC104236
0.8727 High Similarity NPC29411
0.8727 High Similarity NPC37183
0.8726 High Similarity NPC473077
0.8726 High Similarity NPC237635
0.8726 High Similarity NPC296998
0.8726 High Similarity NPC104406
0.8726 High Similarity NPC23728
0.8726 High Similarity NPC79469
0.8726 High Similarity NPC110303
0.8726 High Similarity NPC24673
0.8726 High Similarity NPC297886
0.8726 High Similarity NPC249942
0.8726 High Similarity NPC97716
0.8726 High Similarity NPC201731
0.8718 High Similarity NPC311144
0.8718 High Similarity NPC196137
0.8718 High Similarity NPC209040
0.8718 High Similarity NPC184649
0.8718 High Similarity NPC155144
0.8718 High Similarity NPC271288
0.8718 High Similarity NPC303185
0.8718 High Similarity NPC1886
0.8718 High Similarity NPC98926
0.8712 High Similarity NPC239270
0.8712 High Similarity NPC303210
0.8712 High Similarity NPC114147
0.8712 High Similarity NPC169
0.8712 High Similarity NPC304839
0.8712 High Similarity NPC95472
0.8712 High Similarity NPC220582
0.871 High Similarity NPC470636
0.871 High Similarity NPC96791
0.871 High Similarity NPC11561

  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 NPC155640 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
0.9177 High Similarity NPD3749 Approved
0.8742 High Similarity NPD7411 Suspended
0.8614 High Similarity NPD7852 Clinical (unspecified phase)
0.8608 High Similarity NPD920 Approved
0.8599 High Similarity NPD4378 Clinical (unspecified phase)
0.8599 High Similarity NPD7410 Clinical (unspecified phase)
0.8528 High Similarity NPD7768 Phase 2
0.8519 High Similarity NPD7819 Suspended
0.8516 High Similarity NPD1243 Approved
0.8506 High Similarity NPD2344 Approved
0.8481 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.8476 Intermediate Similarity NPD7075 Discontinued
0.8466 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8405 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.8354 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.8333 Intermediate Similarity NPD1549 Phase 2
0.8333 Intermediate Similarity NPD4380 Phase 2
0.8323 Intermediate Similarity NPD6959 Discontinued
0.8314 Intermediate Similarity NPD6559 Discontinued
0.8293 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8291 Intermediate Similarity NPD2309 Approved
0.828 Intermediate Similarity NPD2800 Approved
0.8274 Intermediate Similarity NPD6232 Discontinued
0.8269 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8269 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8263 Intermediate Similarity NPD5494 Approved
0.8235 Intermediate Similarity NPD7473 Discontinued
0.8228 Intermediate Similarity NPD3750 Approved
0.8165 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.8144 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8141 Intermediate Similarity NPD1510 Phase 2
0.814 Intermediate Similarity NPD5844 Phase 1
0.8137 Intermediate Similarity NPD2534 Approved
0.8137 Intermediate Similarity NPD2533 Approved
0.8137 Intermediate Similarity NPD2532 Approved
0.8121 Intermediate Similarity NPD6801 Discontinued
0.8117 Intermediate Similarity NPD1240 Approved
0.809 Intermediate Similarity NPD4287 Approved
0.8089 Intermediate Similarity NPD2796 Approved
0.8084 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8075 Intermediate Similarity NPD6799 Approved
0.8049 Intermediate Similarity NPD3226 Approved
0.8038 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.8035 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8025 Intermediate Similarity NPD2799 Discontinued
0.8013 Intermediate Similarity NPD1607 Approved
0.8012 Intermediate Similarity NPD3926 Phase 2
0.8012 Intermediate Similarity NPD1934 Approved
0.8 Intermediate Similarity NPD6599 Discontinued
0.7988 Intermediate Similarity NPD919 Approved
0.7976 Intermediate Similarity NPD3882 Suspended
0.7975 Intermediate Similarity NPD2935 Discontinued
0.7965 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7965 Intermediate Similarity NPD6166 Phase 2
0.7965 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7964 Intermediate Similarity NPD1465 Phase 2
0.7964 Intermediate Similarity NPD2801 Approved
0.7943 Intermediate Similarity NPD5953 Discontinued
0.7911 Intermediate Similarity NPD3748 Approved
0.7875 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7874 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7874 Intermediate Similarity NPD3818 Discontinued
0.7871 Intermediate Similarity NPD2313 Discontinued
0.7862 Intermediate Similarity NPD1551 Phase 2
0.7853 Intermediate Similarity NPD1511 Approved
0.7829 Intermediate Similarity NPD7286 Phase 2
0.7812 Intermediate Similarity NPD2346 Discontinued
0.7811 Intermediate Similarity NPD3817 Phase 2
0.7784 Intermediate Similarity NPD7074 Phase 3
0.7778 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7758 Intermediate Similarity NPD1512 Approved
0.7756 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.774 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD7054 Approved
0.7711 Intermediate Similarity NPD5403 Approved
0.7706 Intermediate Similarity NPD5402 Approved
0.7706 Intermediate Similarity NPD2296 Approved
0.7688 Intermediate Similarity NPD1247 Approved
0.7684 Intermediate Similarity NPD7472 Approved
0.7669 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7662 Intermediate Similarity NPD1203 Approved
0.7654 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7654 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7644 Intermediate Similarity NPD6808 Phase 2
0.7644 Intermediate Similarity NPD5710 Approved
0.7644 Intermediate Similarity NPD5711 Approved
0.7644 Intermediate Similarity NPD7229 Phase 3
0.7643 Intermediate Similarity NPD3764 Approved
0.7643 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.764 Intermediate Similarity NPD6797 Phase 2
0.7609 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7598 Intermediate Similarity NPD7251 Discontinued
0.759 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.759 Intermediate Similarity NPD5401 Approved
0.7582 Intermediate Similarity NPD8434 Phase 2
0.7578 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7562 Intermediate Similarity NPD6651 Approved
0.7561 Intermediate Similarity NPD4628 Phase 3
0.7556 Intermediate Similarity NPD7808 Phase 3
0.7532 Intermediate Similarity NPD3268 Approved
0.753 Intermediate Similarity NPD7390 Discontinued
0.7516 Intermediate Similarity NPD6832 Phase 2
0.7516 Intermediate Similarity NPD4908 Phase 1
0.7515 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7514 Intermediate Similarity NPD8313 Approved
0.7514 Intermediate Similarity NPD8312 Approved
0.75 Intermediate Similarity NPD5124 Phase 1
0.75 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD6280 Approved
0.7485 Intermediate Similarity NPD1471 Phase 3
0.7485 Intermediate Similarity NPD6279 Approved
0.7469 Intermediate Similarity NPD4308 Phase 3
0.7469 Intermediate Similarity NPD7033 Discontinued
0.7468 Intermediate Similarity NPD9717 Approved
0.7455 Intermediate Similarity NPD7003 Approved
0.7436 Intermediate Similarity NPD2797 Approved
0.7427 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7423 Intermediate Similarity NPD5404 Approved
0.7423 Intermediate Similarity NPD6099 Approved
0.7423 Intermediate Similarity NPD6100 Approved
0.7423 Intermediate Similarity NPD5406 Approved
0.7423 Intermediate Similarity NPD5408 Approved
0.7423 Intermediate Similarity NPD5405 Approved
0.7405 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7385 Intermediate Similarity NPD8151 Discontinued
0.7374 Intermediate Similarity NPD3751 Discontinued
0.7354 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7341 Intermediate Similarity NPD8455 Phase 2
0.734 Intermediate Similarity NPD4363 Phase 3
0.734 Intermediate Similarity NPD4360 Phase 2
0.731 Intermediate Similarity NPD7783 Phase 2
0.731 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.731 Intermediate Similarity NPD7458 Discontinued
0.7299 Intermediate Similarity NPD4288 Approved
0.729 Intermediate Similarity NPD422 Phase 1
0.7284 Intermediate Similarity NPD447 Suspended
0.7284 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7278 Intermediate Similarity NPD2798 Approved
0.7261 Intermediate Similarity NPD3225 Approved
0.725 Intermediate Similarity NPD4625 Phase 3
0.7243 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD5760 Phase 2
0.7241 Intermediate Similarity NPD5761 Phase 2
0.7222 Intermediate Similarity NPD943 Approved
0.7222 Intermediate Similarity NPD4307 Phase 2
0.7219 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7216 Intermediate Similarity NPD7435 Discontinued
0.7215 Intermediate Similarity NPD3266 Approved
0.7215 Intermediate Similarity NPD1164 Approved
0.7215 Intermediate Similarity NPD3267 Approved
0.7211 Intermediate Similarity NPD4361 Phase 2
0.7211 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7198 Intermediate Similarity NPD1729 Discontinued
0.7191 Intermediate Similarity NPD7199 Phase 2
0.7182 Intermediate Similarity NPD7177 Discontinued
0.7179 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD1610 Phase 2
0.7178 Intermediate Similarity NPD230 Phase 1
0.7178 Intermediate Similarity NPD1933 Approved
0.7175 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.7168 Intermediate Similarity NPD6585 Discontinued
0.7151 Intermediate Similarity NPD3787 Discontinued
0.715 Intermediate Similarity NPD6780 Approved
0.715 Intermediate Similarity NPD6778 Approved
0.715 Intermediate Similarity NPD6782 Approved
0.715 Intermediate Similarity NPD6777 Approved
0.715 Intermediate Similarity NPD6781 Approved
0.715 Intermediate Similarity NPD6776 Approved
0.715 Intermediate Similarity NPD6779 Approved
0.7135 Intermediate Similarity NPD6273 Approved
0.7134 Intermediate Similarity NPD1608 Approved
0.7128 Intermediate Similarity NPD7697 Approved
0.7128 Intermediate Similarity NPD7696 Phase 3
0.7128 Intermediate Similarity NPD7698 Approved
0.7126 Intermediate Similarity NPD5890 Approved
0.7126 Intermediate Similarity NPD5889 Approved
0.7112 Intermediate Similarity NPD8150 Discontinued
0.7111 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7107 Intermediate Similarity NPD7584 Approved
0.7099 Intermediate Similarity NPD411 Approved
0.7092 Intermediate Similarity NPD7870 Phase 2
0.7092 Intermediate Similarity NPD7871 Phase 2
0.7088 Intermediate Similarity NPD7228 Approved
0.7086 Intermediate Similarity NPD37 Approved
0.7083 Intermediate Similarity NPD2654 Approved
0.7079 Intermediate Similarity NPD6234 Discontinued
0.7072 Intermediate Similarity NPD2403 Approved
0.7066 Intermediate Similarity NPD6002 Phase 3
0.7066 Intermediate Similarity NPD6004 Phase 3
0.7066 Intermediate Similarity NPD6005 Phase 3
0.7066 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7066 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD1019 Discontinued
0.7062 Intermediate Similarity NPD4967 Phase 2
0.7062 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD4966 Approved
0.7062 Intermediate Similarity NPD4965 Approved
0.7032 Intermediate Similarity NPD9545 Approved
0.7025 Intermediate Similarity NPD3972 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