Structure

Physi-Chem Properties

Molecular Weight:  344.09
Volume:  334.655
LogP:  2.331
LogD:  0.704
LogS:  -2.934
# Rotatable Bonds:  2
TPSA:  117.97
# H-Bond Aceptor:  7
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  7

MedChem Properties

QED Drug-Likeness Score:  0.616
Synthetic Accessibility Score:  4.248
Fsp3:  0.333
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.859
MDCK Permeability:  2.2225880456971936e-05
Pgp-inhibitor:  0.02
Pgp-substrate:  0.994
Human Intestinal Absorption (HIA):  0.033
20% Bioavailability (F20%):  0.009
30% Bioavailability (F30%):  0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.028
Plasma Protein Binding (PPB):  94.35194396972656%
Volume Distribution (VD):  0.412
Pgp-substrate:  3.0327212810516357%

ADMET: Metabolism

CYP1A2-inhibitor:  0.028
CYP1A2-substrate:  0.798
CYP2C19-inhibitor:  0.029
CYP2C19-substrate:  0.868
CYP2C9-inhibitor:  0.094
CYP2C9-substrate:  0.94
CYP2D6-inhibitor:  0.007
CYP2D6-substrate:  0.117
CYP3A4-inhibitor:  0.301
CYP3A4-substrate:  0.881

ADMET: Excretion

Clearance (CL):  8.598
Half-life (T1/2):  0.455

ADMET: Toxicity

hERG Blockers:  0.007
Human Hepatotoxicity (H-HT):  0.28
Drug-inuced Liver Injury (DILI):  0.864
AMES Toxicity:  0.009
Rat Oral Acute Toxicity:  0.65
Maximum Recommended Daily Dose:  0.126
Skin Sensitization:  0.309
Carcinogencity:  0.656
Eye Corrosion:  0.047
Eye Irritation:  0.885
Respiratory Toxicity:  0.697

Download Data

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

  Natural Product: NPC289660

Natural Product ID:  NPC289660
Common Name*:   Usnic Acid
IUPAC Name:   2,6-diacetyl-3,7,9-trihydroxy-8,9b-dimethyldibenzofuran-1-one
Synonyms:  
Standard InCHIKey:  WEYVVCKOOFYHRW-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C18H16O7/c1-6-14(22)12(8(3)20)16-13(15(6)23)18(4)10(25-16)5-9(21)11(7(2)19)17(18)24/h5,21-23H,1-4H3
SMILES:  CC(=O)C1=C(O)C=C2C(C1=O)(C)c1c(O)c(C)c(c(c1O2)C(=O)C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL242022
PubChem CID:   24211
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000119] Acetophenones

*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
NPO29118 Euonymus alatus Species Celastraceae Eukaryota leaves and twigs n.a. n.a. PMID[21435874]
NPO29118 Euonymus alatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29118 Euonymus alatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29118 Euonymus alatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29118 Euonymus alatus Species Celastraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29118 Euonymus alatus Species Celastraceae 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
NPT3967 Individual Protein Fructose-1,6-bisphosphatase Sus scrofa IC50 = 930000.0 nM PMID[552027]
NPT2266 Individual Protein Fructose-1,6-bisphosphatase Homo sapiens IC50 = 371000.0 nM PMID[552027]
NPT790 Organism Mycobacterium tuberculosis H37Rv Mycobacterium tuberculosis H37Rv MIC = 12.5 ug.mL-1 PMID[552026]
NPT87 Organism Aspergillus fumigatus Aspergillus fumigatus MIC = 34.9 10'-2mmol/ml PMID[552028]
NPT87 Organism Aspergillus fumigatus Aspergillus fumigatus MFC = 69.8 10'-2mmol/ml PMID[552028]
NPT3650 Organism Aspergillus versicolor Aspergillus versicolor MFC = 8.8 10'-2mmol/ml PMID[552028]
NPT3650 Organism Aspergillus versicolor Aspergillus versicolor MIC = 4.4 10'-2mmol/ml PMID[552028]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 0.2 10'-2mmol/ml PMID[552028]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 4.28 10'-2mmol/ml PMID[552028]
NPT314 Organism Bacillus cereus Bacillus cereus MIC = 1.07 10'-2mmol/ml PMID[552028]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC = 0.15 10'-2mmol/ml PMID[552028]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC = 3.21 10'-2mmol/ml PMID[552028]
NPT19 Organism Escherichia coli Escherichia coli MIC = 0.15 10'-2mmol/ml PMID[552028]
NPT19 Organism Escherichia coli Escherichia coli MIC = 3.21 10'-2mmol/ml PMID[552028]
NPT1033 Organism Enterobacter cloacae Enterobacter cloacae MIC = 0.03 10'-2mmol/ml PMID[552028]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MBC = 0.3 10'-2mmol/ml PMID[552028]
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MBC = 10.68 10'-2mmol/ml PMID[552028]
NPT314 Organism Bacillus cereus Bacillus cereus MBC = 2.18 10'-2mmol/ml PMID[552028]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MBC = 0.3 10'-2mmol/ml PMID[552028]
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MBC = 6.54 10'-2mmol/ml PMID[552028]
NPT19 Organism Escherichia coli Escherichia coli MBC = 0.3 10'-2mmol/ml PMID[552028]
NPT19 Organism Escherichia coli Escherichia coli MBC = 6.54 10'-2mmol/ml PMID[552028]
NPT1033 Organism Enterobacter cloacae Enterobacter cloacae MBC = 0.06 10'-2mmol/ml PMID[552028]
NPT3176 Organism Aspergillus ochraceus Aspergillus ochraceus MIC = 3.2 10'-2mmol/ml PMID[552028]
NPT3176 Organism Aspergillus ochraceus Aspergillus ochraceus MFC = 4.4 10'-2mmol/ml PMID[552028]
NPT21 Organism Aspergillus niger Aspergillus niger MIC = 6.4 10'-2mmol/ml PMID[552028]
NPT21 Organism Aspergillus niger Aspergillus niger MFC = 8.8 10'-2mmol/ml PMID[552028]
NPT2567 Organism Trichoderma viride Hypocrea rufa MIC = 3.2 10'-2mmol/ml PMID[552028]
NPT2567 Organism Trichoderma viride Hypocrea rufa MFC = 4.4 10'-2mmol/ml PMID[552028]
NPT3695 Organism Penicillium funiculosum Penicillium funiculosum MIC = 6.4 10'-2mmol/ml PMID[552028]
NPT3695 Organism Penicillium funiculosum Penicillium funiculosum MFC = 8.8 10'-2mmol/ml PMID[552028]
NPT6344 Organism Penicillium ochrochloron Penicillium ochrochloron MIC = 6.4 10'-2mmol/ml PMID[552028]
NPT6344 Organism Penicillium ochrochloron Penicillium ochrochloron MFC = 8.8 10'-2mmol/ml PMID[552028]
NPT23783 ORGANISM Penicillium cyclopium Penicillium cyclopium MIC = 6.4 10'-2mmol/ml PMID[552028]
NPT23783 ORGANISM Penicillium cyclopium Penicillium cyclopium MFC = 8.8 10'-2mmol/ml PMID[552028]
NPT88 Organism Mycobacterium tuberculosis Mycobacterium tuberculosis MIC = 35600.0 nM PMID[552029]

☑ 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 NPC289660 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 NPC82920
1.0 High Similarity NPC164697
0.9926 High Similarity NPC111201
0.9925 High Similarity NPC270913
0.9149 High Similarity NPC96791
0.9149 High Similarity NPC470636
0.9149 High Similarity NPC226942
0.9137 High Similarity NPC268178
0.9137 High Similarity NPC54820
0.9137 High Similarity NPC180501
0.9078 High Similarity NPC316911
0.9078 High Similarity NPC316560
0.9014 High Similarity NPC321629
0.9014 High Similarity NPC323884
0.9014 High Similarity NPC326193
0.9014 High Similarity NPC321148
0.9014 High Similarity NPC325346
0.8973 High Similarity NPC321896
0.8973 High Similarity NPC476185
0.8951 High Similarity NPC262935
0.8951 High Similarity NPC11700
0.8951 High Similarity NPC251182
0.8951 High Similarity NPC172182
0.8944 High Similarity NPC74397
0.8921 High Similarity NPC101752
0.8904 High Similarity NPC471114
0.8889 High Similarity NPC117716
0.8889 High Similarity NPC206212
0.8889 High Similarity NPC470674
0.8889 High Similarity NPC470673
0.8889 High Similarity NPC71184
0.8881 High Similarity NPC472344
0.8873 High Similarity NPC477272
0.8865 High Similarity NPC470671
0.8865 High Similarity NPC131130
0.8865 High Similarity NPC474487
0.8865 High Similarity NPC474504
0.8865 High Similarity NPC470672
0.8865 High Similarity NPC477055
0.8865 High Similarity NPC477056
0.8865 High Similarity NPC183639
0.8865 High Similarity NPC199458
0.8857 High Similarity NPC174999
0.8803 High Similarity NPC241975
0.8803 High Similarity NPC19476
0.8794 High Similarity NPC131782
0.8794 High Similarity NPC474624
0.8794 High Similarity NPC138047
0.8784 High Similarity NPC476162
0.8777 High Similarity NPC108113
0.8777 High Similarity NPC93756
0.8776 High Similarity NPC226644
0.8776 High Similarity NPC178202
0.8776 High Similarity NPC37226
0.8776 High Similarity NPC317492
0.8767 High Similarity NPC300988
0.8767 High Similarity NPC308200
0.8767 High Similarity NPC10990
0.875 High Similarity NPC112829
0.875 High Similarity NPC276565
0.875 High Similarity NPC294432
0.875 High Similarity NPC313368
0.875 High Similarity NPC470556
0.8742 High Similarity NPC196448
0.8741 High Similarity NPC11056
0.8732 High Similarity NPC254168
0.8732 High Similarity NPC470083
0.8732 High Similarity NPC272844
0.8732 High Similarity NPC470669
0.8732 High Similarity NPC248995
0.8732 High Similarity NPC470668
0.8732 High Similarity NPC219584
0.8725 High Similarity NPC470353
0.8725 High Similarity NPC5871
0.8723 High Similarity NPC470983
0.8723 High Similarity NPC470982
0.8723 High Similarity NPC156910
0.8716 High Similarity NPC78335
0.8716 High Similarity NPC476509
0.8716 High Similarity NPC230713
0.8714 High Similarity NPC125920
0.8707 High Similarity NPC39195
0.8707 High Similarity NPC135325
0.8707 High Similarity NPC168085
0.8707 High Similarity NPC145467
0.8705 High Similarity NPC215875
0.8705 High Similarity NPC285054
0.8705 High Similarity NPC15834
0.8705 High Similarity NPC10971
0.8699 High Similarity NPC82534
0.8699 High Similarity NPC210826
0.869 High Similarity NPC184738
0.869 High Similarity NPC470909
0.869 High Similarity NPC473813
0.869 High Similarity NPC470553
0.869 High Similarity NPC293053
0.869 High Similarity NPC24821
0.869 High Similarity NPC9117
0.869 High Similarity NPC18886
0.869 High Similarity NPC474939
0.869 High Similarity NPC96216
0.869 High Similarity NPC307895
0.869 High Similarity NPC212932
0.869 High Similarity NPC5990
0.869 High Similarity NPC190637
0.869 High Similarity NPC33653
0.869 High Similarity NPC473812
0.8681 High Similarity NPC171870
0.8675 High Similarity NPC160015
0.8675 High Similarity NPC474386
0.8675 High Similarity NPC247677
0.8671 High Similarity NPC96565
0.8671 High Similarity NPC220062
0.8671 High Similarity NPC55018
0.8671 High Similarity NPC137009
0.8671 High Similarity NPC53181
0.8671 High Similarity NPC139554
0.8671 High Similarity NPC301217
0.8671 High Similarity NPC472343
0.8671 High Similarity NPC37206
0.8671 High Similarity NPC23257
0.8671 High Similarity NPC216978
0.8671 High Similarity NPC303633
0.8671 High Similarity NPC240305
0.8671 High Similarity NPC217186
0.8667 High Similarity NPC213608
0.8667 High Similarity NPC235333
0.8667 High Similarity NPC1477
0.8662 High Similarity NPC322301
0.8662 High Similarity NPC255801
0.8658 High Similarity NPC170169
0.8658 High Similarity NPC473131
0.8658 High Similarity NPC470675
0.8652 High Similarity NPC60667
0.8643 High Similarity NPC16197
0.8639 High Similarity NPC202494
0.8639 High Similarity NPC12148
0.8639 High Similarity NPC130581
0.8633 High Similarity NPC27490
0.863 High Similarity NPC216538
0.863 High Similarity NPC472446
0.863 High Similarity NPC224714
0.863 High Similarity NPC297788
0.863 High Similarity NPC234629
0.863 High Similarity NPC326500
0.863 High Similarity NPC271288
0.863 High Similarity NPC311144
0.863 High Similarity NPC273538
0.863 High Similarity NPC75694
0.863 High Similarity NPC288910
0.863 High Similarity NPC470890
0.863 High Similarity NPC476055
0.863 High Similarity NPC133060
0.863 High Similarity NPC472447
0.863 High Similarity NPC311741
0.863 High Similarity NPC118059
0.863 High Similarity NPC470554
0.8623 High Similarity NPC186628
0.8623 High Similarity NPC84772
0.8621 High Similarity NPC200694
0.8621 High Similarity NPC204469
0.8621 High Similarity NPC473042
0.8621 High Similarity NPC144499
0.8618 High Similarity NPC260902
0.8618 High Similarity NPC270044
0.8618 High Similarity NPC296957
0.8611 High Similarity NPC221173
0.8611 High Similarity NPC270883
0.8611 High Similarity NPC69769
0.8611 High Similarity NPC469818
0.8611 High Similarity NPC241100
0.8611 High Similarity NPC159275
0.8611 High Similarity NPC172986
0.8611 High Similarity NPC261227
0.8611 High Similarity NPC471587
0.8609 High Similarity NPC470344
0.8609 High Similarity NPC148938
0.8609 High Similarity NPC297531
0.8609 High Similarity NPC213936
0.8609 High Similarity NPC471116
0.8601 High Similarity NPC201395
0.8591 High Similarity NPC470908
0.8591 High Similarity NPC472421
0.8591 High Similarity NPC321387
0.8591 High Similarity NPC327059
0.8591 High Similarity NPC29777
0.8591 High Similarity NPC471115
0.8591 High Similarity NPC227122
0.8582 High Similarity NPC144027
0.8582 High Similarity NPC103842
0.8582 High Similarity NPC236974
0.8581 High Similarity NPC475055
0.8581 High Similarity NPC186397
0.8581 High Similarity NPC37135
0.8571 High Similarity NPC299011
0.8571 High Similarity NPC473135
0.8571 High Similarity NPC178343
0.8571 High Similarity NPC220418
0.8571 High Similarity NPC470910
0.8571 High Similarity NPC187282

  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 NPC289660 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
0.9925 High Similarity NPD2800 Approved
0.8913 High Similarity NPD6651 Approved
0.863 High Similarity NPD4378 Clinical (unspecified phase)
0.863 High Similarity NPD2532 Approved
0.863 High Similarity NPD2534 Approved
0.863 High Similarity NPD2533 Approved
0.8378 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.8182 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8151 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.8151 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.8129 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.8112 Intermediate Similarity NPD1240 Approved
0.8095 Intermediate Similarity NPD1549 Phase 2
0.8041 Intermediate Similarity NPD1243 Approved
0.8027 Intermediate Similarity NPD2344 Approved
0.8026 Intermediate Similarity NPD920 Approved
0.8014 Intermediate Similarity NPD1510 Phase 2
0.8 Intermediate Similarity NPD1607 Approved
0.7987 Intermediate Similarity NPD4380 Phase 2
0.7987 Intermediate Similarity NPD6959 Discontinued
0.7973 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7962 Intermediate Similarity NPD3882 Suspended
0.7959 Intermediate Similarity NPD2796 Approved
0.7949 Intermediate Similarity NPD7819 Suspended
0.7949 Intermediate Similarity NPD2801 Approved
0.7947 Intermediate Similarity NPD1511 Approved
0.7937 Intermediate Similarity NPD5711 Approved
0.7937 Intermediate Similarity NPD5710 Approved
0.7935 Intermediate Similarity NPD7411 Suspended
0.7911 Intermediate Similarity NPD3749 Approved
0.7911 Intermediate Similarity NPD7075 Discontinued
0.7885 Intermediate Similarity NPD1934 Approved
0.7871 Intermediate Similarity NPD6599 Discontinued
0.7867 Intermediate Similarity NPD3750 Approved
0.7843 Intermediate Similarity NPD1512 Approved
0.7834 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7815 Intermediate Similarity NPD2309 Approved
0.7812 Intermediate Similarity NPD5494 Approved
0.7778 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7771 Intermediate Similarity NPD6801 Discontinued
0.777 Intermediate Similarity NPD2799 Discontinued
0.7748 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7736 Intermediate Similarity NPD7768 Phase 2
0.773 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7718 Intermediate Similarity NPD6099 Approved
0.7718 Intermediate Similarity NPD6100 Approved
0.7712 Intermediate Similarity NPD6799 Approved
0.7688 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7636 Intermediate Similarity NPD3818 Discontinued
0.7619 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7607 Intermediate Similarity NPD6232 Discontinued
0.7603 Intermediate Similarity NPD2313 Discontinued
0.76 Intermediate Similarity NPD2935 Discontinued
0.759 Intermediate Similarity NPD7286 Phase 2
0.759 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD7473 Discontinued
0.7566 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7533 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7533 Intermediate Similarity NPD3748 Approved
0.7516 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD6166 Phase 2
0.7515 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7515 Intermediate Similarity NPD2403 Approved
0.7515 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5953 Discontinued
0.7483 Intermediate Similarity NPD1551 Phase 2
0.7483 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7468 Intermediate Similarity NPD3226 Approved
0.7456 Intermediate Similarity NPD6559 Discontinued
0.7455 Intermediate Similarity NPD3926 Phase 2
0.7453 Intermediate Similarity NPD3817 Phase 2
0.7451 Intermediate Similarity NPD2654 Approved
0.7439 Intermediate Similarity NPD1247 Approved
0.7434 Intermediate Similarity NPD2346 Discontinued
0.7407 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD4628 Phase 3
0.7372 Intermediate Similarity NPD7390 Discontinued
0.7337 Intermediate Similarity NPD7074 Phase 3
0.7317 Intermediate Similarity NPD919 Approved
0.7292 Intermediate Similarity NPD9717 Approved
0.7284 Intermediate Similarity NPD1465 Phase 2
0.7278 Intermediate Similarity NPD7054 Approved
0.7267 Intermediate Similarity NPD943 Approved
0.726 Intermediate Similarity NPD1203 Approved
0.7254 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7239 Intermediate Similarity NPD2296 Approved
0.7235 Intermediate Similarity NPD1729 Discontinued
0.7235 Intermediate Similarity NPD7472 Approved
0.7222 Intermediate Similarity NPD422 Phase 1
0.7219 Intermediate Similarity NPD5124 Phase 1
0.7219 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.7208 Intermediate Similarity NPD1471 Phase 3
0.7208 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD6797 Phase 2
0.7176 Intermediate Similarity NPD5844 Phase 1
0.7172 Intermediate Similarity NPD3972 Approved
0.7151 Intermediate Similarity NPD7251 Discontinued
0.7151 Intermediate Similarity NPD4361 Phase 2
0.7151 Intermediate Similarity NPD4362 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD5402 Approved
0.7133 Intermediate Similarity NPD3268 Approved
0.7133 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD5403 Approved
0.7123 Intermediate Similarity NPD4749 Approved
0.7114 Intermediate Similarity NPD4908 Phase 1
0.711 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.711 Intermediate Similarity NPD7808 Phase 3
0.7105 Intermediate Similarity NPD447 Suspended
0.7105 Intermediate Similarity NPD230 Phase 1
0.7097 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD6002 Phase 3
0.7097 Intermediate Similarity NPD6004 Phase 3
0.7097 Intermediate Similarity NPD6005 Phase 3
0.7097 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD2798 Approved
0.7095 Intermediate Similarity NPD4363 Phase 3
0.7095 Intermediate Similarity NPD4360 Phase 2
0.7083 Intermediate Similarity NPD7229 Phase 3
0.7078 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7075 Intermediate Similarity NPD6696 Suspended
0.7073 Intermediate Similarity NPD5761 Phase 2
0.7073 Intermediate Similarity NPD5760 Phase 2
0.7062 Intermediate Similarity NPD4287 Approved
0.7052 Intermediate Similarity NPD3658 Clinical (unspecified phase)
0.7052 Intermediate Similarity NPD6104 Discontinued
0.7045 Intermediate Similarity NPD8434 Phase 2
0.7027 Intermediate Similarity NPD2797 Approved
0.702 Intermediate Similarity NPD3764 Approved
0.7018 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD5401 Approved
0.7 Intermediate Similarity NPD6832 Phase 2
0.6994 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6986 Remote Similarity NPD1610 Phase 2
0.6968 Remote Similarity NPD7033 Discontinued
0.6954 Remote Similarity NPD4625 Phase 3
0.6951 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6943 Remote Similarity NPD2424 Discontinued
0.6939 Remote Similarity NPD1608 Approved
0.6933 Remote Similarity NPD7458 Discontinued
0.6928 Remote Similarity NPD4288 Approved
0.6914 Remote Similarity NPD6980 Clinical (unspecified phase)
0.6909 Remote Similarity NPD6280 Approved
0.6909 Remote Similarity NPD6279 Approved
0.6908 Remote Similarity NPD411 Approved
0.6908 Remote Similarity NPD1296 Phase 2
0.6871 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6867 Remote Similarity NPD6917 Clinical (unspecified phase)
0.6859 Remote Similarity NPD4308 Phase 3
0.6855 Remote Similarity NPD7003 Approved
0.6831 Remote Similarity NPD1241 Discontinued
0.6828 Remote Similarity NPD9545 Approved
0.6828 Remote Similarity NPD1548 Phase 1
0.6821 Remote Similarity NPD1530 Clinical (unspecified phase)
0.6815 Remote Similarity NPD5408 Approved
0.6815 Remote Similarity NPD5405 Approved
0.6815 Remote Similarity NPD5404 Approved
0.6815 Remote Similarity NPD5406 Approved
0.6811 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6807 Remote Similarity NPD37 Approved
0.6806 Remote Similarity NPD9493 Approved
0.6805 Remote Similarity NPD6234 Discontinued
0.68 Remote Similarity NPD1164 Approved
0.68 Remote Similarity NPD3267 Approved
0.68 Remote Similarity NPD1470 Approved
0.68 Remote Similarity NPD3266 Approved
0.6796 Remote Similarity NPD7879 Clinical (unspecified phase)
0.6786 Remote Similarity NPD4967 Phase 2
0.6786 Remote Similarity NPD4965 Approved
0.6786 Remote Similarity NPD4966 Approved
0.6784 Remote Similarity NPD6808 Phase 2
0.6776 Remote Similarity NPD1529 Clinical (unspecified phase)
0.6774 Remote Similarity NPD1899 Clinical (unspecified phase)
0.6763 Remote Similarity NPD3446 Phase 1
0.6757 Remote Similarity NPD1201 Approved
0.6755 Remote Similarity NPD1019 Discontinued
0.6739 Remote Similarity NPD8090 Clinical (unspecified phase)
0.6735 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6735 Remote Similarity NPD17 Approved
0.6733 Remote Similarity NPD3225 Approved
0.6733 Remote Similarity NPD1876 Approved
0.6733 Remote Similarity NPD8651 Approved
0.6728 Remote Similarity NPD6143 Clinical (unspecified phase)
0.6725 Remote Similarity NPD7199 Phase 2
0.6724 Remote Similarity NPD3751 Discontinued
0.669 Remote Similarity NPD405 Clinical (unspecified phase)
0.6685 Remote Similarity NPD8312 Approved
0.6685 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6685 Remote Similarity NPD8313 Approved
0.6667 Remote Similarity NPD6355 Discontinued
0.6647 Remote Similarity NPD7184 Clinical (unspecified phase)
0.6646 Remote Similarity NPD6273 Approved
0.6646 Remote Similarity NPD5049 Phase 3
0.6627 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6622 Remote Similarity NPD1778 Approved
0.6604 Remote Similarity NPD4477 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