Structure

Physi-Chem Properties

Molecular Weight:  352.09
Volume:  349.264
LogP:  4.054
LogD:  2.944
LogS:  -3.636
# Rotatable Bonds:  1
TPSA:  100.13
# H-Bond Aceptor:  6
# H-Bond Donor:  3
# Rings:  4
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.616
Synthetic Accessibility Score:  3.045
Fsp3:  0.15
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.882
MDCK Permeability:  1.665659510763362e-05
Pgp-inhibitor:  0.007
Pgp-substrate:  0.041
Human Intestinal Absorption (HIA):  0.025
20% Bioavailability (F20%):  0.013
30% Bioavailability (F30%):  0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.007
Plasma Protein Binding (PPB):  98.89598846435547%
Volume Distribution (VD):  0.533
Pgp-substrate:  1.64247727394104%

ADMET: Metabolism

CYP1A2-inhibitor:  0.95
CYP1A2-substrate:  0.298
CYP2C19-inhibitor:  0.515
CYP2C19-substrate:  0.053
CYP2C9-inhibitor:  0.837
CYP2C9-substrate:  0.899
CYP2D6-inhibitor:  0.874
CYP2D6-substrate:  0.279
CYP3A4-inhibitor:  0.665
CYP3A4-substrate:  0.107

ADMET: Excretion

Clearance (CL):  3.954
Half-life (T1/2):  0.741

ADMET: Toxicity

hERG Blockers:  0.065
Human Hepatotoxicity (H-HT):  0.587
Drug-inuced Liver Injury (DILI):  0.242
AMES Toxicity:  0.052
Rat Oral Acute Toxicity:  0.603
Maximum Recommended Daily Dose:  0.913
Skin Sensitization:  0.904
Carcinogencity:  0.552
Eye Corrosion:  0.003
Eye Irritation:  0.691
Respiratory Toxicity:  0.431

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

  Natural Product: NPC74178

Natural Product ID:  NPC74178
Common Name*:   5,7-Dihydroxy-3-(8-Hydroxy-2,2-Dimethylchromen-6-Yl)Chromen-4-One
IUPAC Name:   5,7-dihydroxy-3-(8-hydroxy-2,2-dimethylchromen-6-yl)chromen-4-one
Synonyms:  
Standard InCHIKey:  LWZACZCRAUQSLH-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C20H16O6/c1-20(2)4-3-10-5-11(6-15(23)19(10)26-20)13-9-25-16-8-12(21)7-14(22)17(16)18(13)24/h3-9,21-23H,1-2H3
SMILES:  Oc1cc(O)c2c(c1)occ(c2=O)c1cc(O)c2c(c1)C=CC(O2)(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1864439
PubChem CID:   5481948
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0002506] Isoflavonoids
        • [CHEMONTID:0003530] Pyranoisoflavonoids

*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]
NPO31004 Glycyrrhiza sp Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
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]
NPO22336 Glycyrrhiza aspera Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16193 Glycyrrhiza sp. Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
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]
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[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]
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]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
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]

☑ 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
NPT65 Cell Line HepG2 Homo sapiens Potency n.a. 10000.0 nM PMID[467963]
NPT10 Individual Protein Geminin Homo sapiens Potency n.a. 14581.0 nM PMID[467963]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 29092.9 nM PMID[467963]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 23109.3 nM PMID[467963]
NPT161 Individual Protein Rap guanine nucleotide exchange factor 4 Homo sapiens Potency n.a. 2818.4 nM PMID[467963]
NPT83 Cell Line MCF7 Homo sapiens GI = 15.0 % PMID[467964]
NPT660 Cell Line SW480 Homo sapiens GI = 29.0 % PMID[467964]
NPT65 Cell Line HepG2 Homo sapiens GI = 5.0 % PMID[467964]
NPT2615 Cell Line HEK-293T Homo sapiens GI = 0.0 % PMID[467964]
NPT113 Cell Line RAW264.7 Mus musculus Inhibition = 14.0 % PMID[467964]
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens Inhibition = 58.0 % PMID[467964]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens FC = 1.13 n.a. PMID[467965]
NPT178 Individual Protein Protein-tyrosine phosphatase 1B Homo sapiens Inhibition > 60.0 % PMID[467966]
NPT65 Cell Line HepG2 Homo sapiens Activity = 80.0 % PMID[467966]
NPT2 Others Unspecified AbsAC40_uM n.a. 4.93 uM PMID[467963]
NPT2 Others Unspecified Potency n.a. 11220.2 nM PMID[467963]
NPT21742 CELL-LINE L02 Homo sapiens GI = 7.0 % PMID[467964]
NPT2 Others Unspecified Inhibition = 8.0 % PMID[467964]
NPT2 Others Unspecified Inhibition = 95.0 % PMID[467964]
NPT2 Others Unspecified IC50 = 250.0 nM PMID[467964]
NPT2 Others Unspecified Inhibition > 40.0 % PMID[467966]

☑ 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 NPC74178 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 NPC184755
0.9867 High Similarity NPC170026
0.9867 High Similarity NPC282307
0.9801 High Similarity NPC52889
0.98 High Similarity NPC234255
0.9737 High Similarity NPC204879
0.9735 High Similarity NPC471985
0.9735 High Similarity NPC472455
0.9677 High Similarity NPC303174
0.9675 High Similarity NPC261470
0.9673 High Similarity NPC119209
0.9673 High Similarity NPC192686
0.9673 High Similarity NPC118256
0.9673 High Similarity NPC28241
0.9671 High Similarity NPC474681
0.9671 High Similarity NPC218313
0.9671 High Similarity NPC78071
0.9669 High Similarity NPC472280
0.9667 High Similarity NPC237994
0.961 High Similarity NPC259456
0.961 High Similarity NPC474038
0.9608 High Similarity NPC187792
0.9605 High Similarity NPC133970
0.9605 High Similarity NPC5322
0.9605 High Similarity NPC6633
0.9603 High Similarity NPC170492
0.96 High Similarity NPC154345
0.96 High Similarity NPC256406
0.9551 High Similarity NPC50960
0.9548 High Similarity NPC474033
0.9548 High Similarity NPC474034
0.9548 High Similarity NPC472448
0.9548 High Similarity NPC474150
0.9548 High Similarity NPC83922
0.9548 High Similarity NPC474162
0.9545 High Similarity NPC475784
0.9545 High Similarity NPC328102
0.9545 High Similarity NPC476980
0.9545 High Similarity NPC474960
0.9542 High Similarity NPC284820
0.9542 High Similarity NPC27337
0.9542 High Similarity NPC473272
0.9542 High Similarity NPC291508
0.9539 High Similarity NPC117992
0.9539 High Similarity NPC256925
0.9539 High Similarity NPC57674
0.9539 High Similarity NPC168247
0.9539 High Similarity NPC152951
0.9539 High Similarity NPC200246
0.9539 High Similarity NPC230149
0.9536 High Similarity NPC471982
0.9533 High Similarity NPC189270
0.9533 High Similarity NPC5840
0.9487 High Similarity NPC472625
0.9487 High Similarity NPC186686
0.9484 High Similarity NPC134783
0.9484 High Similarity NPC167678
0.9484 High Similarity NPC471210
0.9484 High Similarity NPC26326
0.9484 High Similarity NPC198829
0.9484 High Similarity NPC29876
0.9484 High Similarity NPC234644
0.9484 High Similarity NPC472632
0.9484 High Similarity NPC57715
0.9477 High Similarity NPC278778
0.9477 High Similarity NPC195796
0.9477 High Similarity NPC470600
0.9477 High Similarity NPC291878
0.9477 High Similarity NPC35038
0.9477 High Similarity NPC276444
0.9474 High Similarity NPC273462
0.9474 High Similarity NPC70433
0.9474 High Similarity NPC49402
0.9474 High Similarity NPC33051
0.9474 High Similarity NPC227337
0.9467 High Similarity NPC38545
0.9467 High Similarity NPC171916
0.9427 High Similarity NPC470773
0.9423 High Similarity NPC476247
0.9423 High Similarity NPC78332
0.9423 High Similarity NPC194427
0.9419 High Similarity NPC188433
0.9419 High Similarity NPC471973
0.9419 High Similarity NPC204290
0.9419 High Similarity NPC472624
0.9419 High Similarity NPC174953
0.9416 High Similarity NPC474055
0.9416 High Similarity NPC237418
0.9416 High Similarity NPC476630
0.9416 High Similarity NPC472598
0.9416 High Similarity NPC67876
0.9416 High Similarity NPC471209
0.9416 High Similarity NPC476981
0.9416 High Similarity NPC218871
0.9412 High Similarity NPC45849
0.9412 High Similarity NPC200761
0.9412 High Similarity NPC470327
0.9412 High Similarity NPC477503
0.9408 High Similarity NPC60972
0.9408 High Similarity NPC257648
0.9408 High Similarity NPC39732
0.9408 High Similarity NPC477231
0.9408 High Similarity NPC472912
0.9404 High Similarity NPC88804
0.9404 High Similarity NPC3825
0.94 High Similarity NPC254702
0.94 High Similarity NPC166036
0.94 High Similarity NPC139364
0.94 High Similarity NPC203077
0.94 High Similarity NPC194653
0.94 High Similarity NPC203747
0.94 High Similarity NPC238279
0.94 High Similarity NPC80710
0.9371 High Similarity NPC288813
0.9371 High Similarity NPC165456
0.9367 High Similarity NPC43319
0.9363 High Similarity NPC124038
0.9363 High Similarity NPC470772
0.9359 High Similarity NPC472634
0.9359 High Similarity NPC258331
0.9359 High Similarity NPC471212
0.9359 High Similarity NPC40037
0.9359 High Similarity NPC471211
0.9355 High Similarity NPC53545
0.9355 High Similarity NPC117418
0.9355 High Similarity NPC473990
0.9355 High Similarity NPC469658
0.9351 High Similarity NPC209614
0.9351 High Similarity NPC472626
0.9351 High Similarity NPC470328
0.9346 High Similarity NPC74924
0.9346 High Similarity NPC213896
0.9346 High Similarity NPC18727
0.9346 High Similarity NPC469550
0.9346 High Similarity NPC192083
0.9342 High Similarity NPC31363
0.9338 High Similarity NPC48479
0.9338 High Similarity NPC137062
0.9338 High Similarity NPC139293
0.9338 High Similarity NPC183950
0.9338 High Similarity NPC195763
0.9338 High Similarity NPC69430
0.9338 High Similarity NPC177298
0.9338 High Similarity NPC264550
0.9338 High Similarity NPC264289
0.9338 High Similarity NPC52005
0.9338 High Similarity NPC200060
0.9338 High Similarity NPC223579
0.9338 High Similarity NPC40290
0.9338 High Similarity NPC333691
0.9338 High Similarity NPC287101
0.9338 High Similarity NPC142876
0.9333 High Similarity NPC79469
0.9333 High Similarity NPC24673
0.9333 High Similarity NPC97716
0.9333 High Similarity NPC201731
0.9333 High Similarity NPC104406
0.9333 High Similarity NPC237635
0.9308 High Similarity NPC218226
0.9304 High Similarity NPC293319
0.9304 High Similarity NPC300053
0.9304 High Similarity NPC239752
0.9304 High Similarity NPC108433
0.9304 High Similarity NPC472450
0.9304 High Similarity NPC275780
0.9304 High Similarity NPC62261
0.9299 High Similarity NPC81679
0.9299 High Similarity NPC472635
0.9295 High Similarity NPC36217
0.9295 High Similarity NPC472630
0.9295 High Similarity NPC472631
0.9295 High Similarity NPC287328
0.9295 High Similarity NPC282009
0.929 High Similarity NPC219867
0.929 High Similarity NPC136674
0.929 High Similarity NPC180011
0.929 High Similarity NPC36852
0.929 High Similarity NPC472963
0.929 High Similarity NPC299520
0.929 High Similarity NPC129684
0.929 High Similarity NPC161960
0.929 High Similarity NPC78225
0.929 High Similarity NPC304008
0.929 High Similarity NPC262286
0.929 High Similarity NPC223787
0.929 High Similarity NPC187745
0.9286 High Similarity NPC130589
0.9286 High Similarity NPC321779
0.9286 High Similarity NPC39184
0.9286 High Similarity NPC213622
0.9286 High Similarity NPC134287
0.9286 High Similarity NPC256612
0.9286 High Similarity NPC470681
0.9286 High Similarity NPC226025
0.9286 High Similarity NPC20830
0.9286 High Similarity NPC133392
0.9281 High Similarity NPC55205
0.9281 High Similarity NPC323626
0.9281 High Similarity NPC260979
0.9281 High Similarity NPC63187

  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 NPC74178 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
0.9346 High Similarity NPD2393 Clinical (unspecified phase)
0.9281 High Similarity NPD1934 Approved
0.9221 High Similarity NPD2801 Approved
0.9103 High Similarity NPD3882 Suspended
0.9007 High Similarity NPD1511 Approved
0.8944 High Similarity NPD6166 Phase 2
0.8944 High Similarity NPD6168 Clinical (unspecified phase)
0.8944 High Similarity NPD6167 Clinical (unspecified phase)
0.8903 High Similarity NPD4380 Phase 2
0.8889 High Similarity NPD1512 Approved
0.8834 High Similarity NPD3818 Discontinued
0.8824 High Similarity NPD4378 Clinical (unspecified phase)
0.8824 High Similarity NPD7410 Clinical (unspecified phase)
0.8797 High Similarity NPD3817 Phase 2
0.878 High Similarity NPD7054 Approved
0.8727 High Similarity NPD7074 Phase 3
0.8727 High Similarity NPD7472 Approved
0.8696 High Similarity NPD5494 Approved
0.8688 High Similarity NPD7075 Discontinued
0.8625 High Similarity NPD4868 Clinical (unspecified phase)
0.8616 High Similarity NPD7096 Clinical (unspecified phase)
0.86 High Similarity NPD1510 Phase 2
0.8571 High Similarity NPD4381 Clinical (unspecified phase)
0.8563 High Similarity NPD6797 Phase 2
0.8553 High Similarity NPD6801 Discontinued
0.8553 High Similarity NPD1549 Phase 2
0.8543 High Similarity NPD2796 Approved
0.8512 High Similarity NPD7251 Discontinued
0.85 High Similarity NPD7819 Suspended
0.8491 Intermediate Similarity NPD7411 Suspended
0.8487 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8487 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8462 Intermediate Similarity NPD7808 Phase 3
0.8462 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.8447 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8397 Intermediate Similarity NPD6799 Approved
0.8364 Intermediate Similarity NPD6232 Discontinued
0.8333 Intermediate Similarity NPD1240 Approved
0.8333 Intermediate Similarity NPD5844 Phase 1
0.8333 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8323 Intermediate Similarity NPD7473 Discontinued
0.8293 Intermediate Similarity NPD919 Approved
0.8239 Intermediate Similarity NPD5403 Approved
0.8224 Intermediate Similarity NPD1607 Approved
0.8221 Intermediate Similarity NPD5402 Approved
0.8212 Intermediate Similarity NPD943 Approved
0.8199 Intermediate Similarity NPD6599 Discontinued
0.8193 Intermediate Similarity NPD6959 Discontinued
0.8193 Intermediate Similarity NPD1247 Approved
0.8171 Intermediate Similarity NPD7768 Phase 2
0.816 Intermediate Similarity NPD1465 Phase 2
0.8155 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.8129 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.8113 Intermediate Similarity NPD5401 Approved
0.8089 Intermediate Similarity NPD3750 Approved
0.8081 Intermediate Similarity NPD6559 Discontinued
0.8025 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7988 Intermediate Similarity NPD3926 Phase 2
0.7962 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7949 Intermediate Similarity NPD2935 Discontinued
0.7904 Intermediate Similarity NPD3749 Approved
0.7901 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7857 Intermediate Similarity NPD1613 Approved
0.7857 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7834 Intermediate Similarity NPD1551 Phase 2
0.7829 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7806 Intermediate Similarity NPD230 Phase 1
0.7799 Intermediate Similarity NPD1243 Approved
0.7799 Intermediate Similarity NPD2800 Approved
0.7791 Intermediate Similarity NPD920 Approved
0.7778 Intermediate Similarity NPD2533 Approved
0.7778 Intermediate Similarity NPD3027 Phase 3
0.7778 Intermediate Similarity NPD2534 Approved
0.7778 Intermediate Similarity NPD2532 Approved
0.7772 Intermediate Similarity NPD7501 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD3748 Approved
0.7765 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7764 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7763 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.775 Intermediate Similarity NPD4628 Phase 3
0.7727 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7727 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7714 Intermediate Similarity NPD5953 Discontinued
0.7692 Intermediate Similarity NPD447 Suspended
0.7669 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7661 Intermediate Similarity NPD7199 Phase 2
0.7658 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7658 Intermediate Similarity NPD2799 Discontinued
0.7647 Intermediate Similarity NPD9494 Approved
0.7643 Intermediate Similarity NPD6651 Approved
0.764 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7616 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7613 Intermediate Similarity NPD2313 Discontinued
0.7613 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.761 Intermediate Similarity NPD6100 Approved
0.761 Intermediate Similarity NPD6099 Approved
0.7609 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7607 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.76 Intermediate Similarity NPD7286 Phase 2
0.7598 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.759 Intermediate Similarity NPD3226 Approved
0.7582 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.758 Intermediate Similarity NPD1933 Approved
0.7572 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7562 Intermediate Similarity NPD2344 Approved
0.7547 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7544 Intermediate Similarity NPD6234 Discontinued
0.7543 Intermediate Similarity NPD3751 Discontinued
0.7531 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.753 Intermediate Similarity NPD1653 Approved
0.75 Intermediate Similarity NPD7390 Discontinued
0.7485 Intermediate Similarity NPD6190 Approved
0.7484 Intermediate Similarity NPD4908 Phase 1
0.7472 Intermediate Similarity NPD7685 Pre-registration
0.7468 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD5124 Phase 1
0.7453 Intermediate Similarity NPD2346 Discontinued
0.7438 Intermediate Similarity NPD7033 Discontinued
0.7435 Intermediate Similarity NPD7584 Approved
0.7414 Intermediate Similarity NPD3787 Discontinued
0.7405 Intermediate Similarity NPD4360 Phase 2
0.7405 Intermediate Similarity NPD4363 Phase 3
0.7403 Intermediate Similarity NPD1203 Approved
0.7389 Intermediate Similarity NPD8313 Approved
0.7389 Intermediate Similarity NPD8312 Approved
0.7381 Intermediate Similarity NPD7458 Discontinued
0.7378 Intermediate Similarity NPD2309 Approved
0.7372 Intermediate Similarity NPD6832 Phase 2
0.7368 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7355 Intermediate Similarity NPD2798 Approved
0.7353 Intermediate Similarity NPD37 Approved
0.7349 Intermediate Similarity NPD7422 Clinical (unspecified phase)
0.7345 Intermediate Similarity NPD7228 Approved
0.7333 Intermediate Similarity NPD1548 Phase 1
0.7329 Intermediate Similarity NPD4308 Phase 3
0.7326 Intermediate Similarity NPD4965 Approved
0.7326 Intermediate Similarity NPD4966 Approved
0.7326 Intermediate Similarity NPD4967 Phase 2
0.7325 Intermediate Similarity NPD4625 Phase 3
0.7302 Intermediate Similarity NPD6779 Approved
0.7302 Intermediate Similarity NPD6777 Approved
0.7302 Intermediate Similarity NPD6782 Approved
0.7302 Intermediate Similarity NPD6776 Approved
0.7302 Intermediate Similarity NPD6780 Approved
0.7302 Intermediate Similarity NPD6778 Approved
0.7302 Intermediate Similarity NPD6781 Approved
0.7278 Intermediate Similarity NPD3268 Approved
0.7278 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD5242 Approved
0.7273 Intermediate Similarity NPD4361 Phase 2
0.7273 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7268 Intermediate Similarity NPD8434 Phase 2
0.7268 Intermediate Similarity NPD8150 Discontinued
0.7255 Intermediate Similarity NPD1610 Phase 2
0.725 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7232 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7226 Intermediate Similarity NPD3225 Approved
0.7216 Intermediate Similarity NPD5711 Approved
0.7216 Intermediate Similarity NPD5710 Approved
0.7208 Intermediate Similarity NPD9717 Approved
0.7188 Intermediate Similarity NPD4060 Phase 1
0.7188 Intermediate Similarity NPD7435 Discontinued
0.7179 Intermediate Similarity NPD2797 Approved
0.7179 Intermediate Similarity NPD8151 Discontinued
0.7178 Intermediate Similarity NPD5408 Approved
0.7178 Intermediate Similarity NPD5406 Approved
0.7178 Intermediate Similarity NPD5404 Approved
0.7178 Intermediate Similarity NPD5405 Approved
0.717 Intermediate Similarity NPD6798 Discontinued
0.7168 Intermediate Similarity NPD4288 Approved
0.7167 Intermediate Similarity NPD1729 Discontinued
0.7152 Intermediate Similarity NPD5536 Phase 2
0.7151 Intermediate Similarity NPD6844 Discontinued
0.7143 Intermediate Similarity NPD7549 Discontinued
0.7143 Intermediate Similarity NPD422 Phase 1
0.7119 Intermediate Similarity NPD7229 Phase 3
0.7108 Intermediate Similarity NPD8166 Discontinued
0.7101 Intermediate Similarity NPD5049 Phase 3
0.7098 Intermediate Similarity NPD7696 Phase 3
0.7098 Intermediate Similarity NPD7697 Approved
0.7098 Intermediate Similarity NPD7698 Approved
0.7097 Intermediate Similarity NPD1608 Approved
0.7097 Intermediate Similarity NPD9269 Phase 2
0.7093 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7093 Intermediate Similarity NPD5890 Approved
0.7093 Intermediate Similarity NPD5889 Approved
0.7093 Intermediate Similarity NPD6385 Approved
0.7093 Intermediate Similarity NPD6386 Approved
0.7091 Intermediate Similarity NPD2424 Discontinued
0.7089 Intermediate Similarity NPD3018 Phase 2
0.7083 Intermediate Similarity NPD4357 Discontinued
0.7081 Intermediate Similarity NPD4307 Phase 2
0.707 Intermediate Similarity NPD1470 Approved
0.7069 Intermediate Similarity NPD5353 Approved
0.7066 Intermediate Similarity NPD2354 Approved
0.7063 Intermediate Similarity NPD411 Approved
0.7063 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD8127 Discontinued
0.7062 Intermediate Similarity NPD7871 Phase 2

  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