Natural Product: NPC13495

Natural Product ID:  NPC13495
Common Name:   4-Hydroxyphenylpyruvic Acid
IUPAC Name:   3-(4-hydroxyphenyl)-2-oxopropanoic acid
Synonyms:   4-Hydroxy-Phenylpyruvate; 4-Hydroxyphenylpyruvate
Molecular Formula:   C9H8O4
Standard InCHIKey:  KKADPXVIOXHVKN-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,10H,5H2,(H,12,13)
Canonical SMILES:  Oc1ccc(cc1)CC(=O)C(=O)O
First Find Year:  
Max Developmental Stage:  
Synthetic Gene Cluster:   ;

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO1797 Homo sapiens Species Hominidae Eukaryota blood PMID[9106023]
NPO1797 Homo sapiens Species Hominidae Eukaryota urine PMID[9869358]
NPO6956 Citrus limonia Species Rutaceae Eukaryota TCM_Taiwan*
NPO19398.1 Streptomyces roseochromogenes var. oscitans Varieties Streptomycetaceae Bacteria StreptomeDB*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT661 Individual Protein Solute carrier family 22 member 6 Mus musculus Ki = 72443.6 nM 17553798
NPT661 Individual Protein Solute carrier family 22 member 6 Mus musculus Ki = 73000 nM 17553798
NPT662 Individual Protein Solute carrier family 22 member 20 Mus musculus Ki = 66069.34 nM 17553798
NPT662 Individual Protein Solute carrier family 22 member 20 Mus musculus Ki = 66000 nM 17553798
NPT661 Individual Protein Solute carrier family 22 member 6 Mus musculus Ki = 73000 nM 21571536
NPT2 Others Unspecified IC50 = 103000 nM 10.1039/C1MD00188D

  Similar Natural Products 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 NPC13495 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
0.9588 High Similarity NPC52472
0.9485 High Similarity NPC245561
0.9286 High Similarity NPC280869
0.9223 High Similarity NPC326187
0.9184 High Similarity NPC260000
0.901 High Similarity NPC13426
0.8962 High Similarity NPC48525
0.8952 High Similarity NPC21162
0.8796 High Similarity NPC221870
0.8785 High Similarity NPC17693
0.8774 High Similarity NPC222084
0.8762 High Similarity NPC31274
0.875 High Similarity NPC188677
0.875 High Similarity NPC317592
0.875 High Similarity NPC70843
0.8738 High Similarity NPC120693
0.8738 High Similarity NPC261573
0.8738 High Similarity NPC8931
0.8692 High Similarity NPC212718
0.8667 High Similarity NPC226699
0.8571 High Similarity NPC6984
0.8571 High Similarity NPC29989
0.8571 High Similarity NPC95178
0.8571 High Similarity NPC69332
0.8545 High Similarity NPC4665
0.8532 High Similarity NPC309808
0.8532 High Similarity NPC11824
0.8532 High Similarity NPC148969
0.8505 High Similarity NPC95172
0.8505 High Similarity NPC88141
0.8505 High Similarity NPC234639
0.85 High Similarity NPC32977
0.85 High Similarity NPC81010
0.8491 Intermediate Similarity NPC29883
0.8491 Intermediate Similarity NPC228737
0.8482 Intermediate Similarity NPC63126
0.8482 Intermediate Similarity NPC104514
0.8468 Intermediate Similarity NPC128249
0.8411 Intermediate Similarity NPC17525
0.8411 Intermediate Similarity NPC317305
0.8396 Intermediate Similarity NPC184658
0.8349 Intermediate Similarity NPC114682
0.8349 Intermediate Similarity NPC177576
0.8319 Intermediate Similarity NPC311091
0.8319 Intermediate Similarity NPC471033
0.8318 Intermediate Similarity NPC34715
0.8318 Intermediate Similarity NPC141523
0.8304 Intermediate Similarity NPC325646
0.8304 Intermediate Similarity NPC28951
0.8286 Intermediate Similarity NPC470202
0.8265 Intermediate Similarity NPC23167
0.8257 Intermediate Similarity NPC116842
0.8257 Intermediate Similarity NPC252544
0.8257 Intermediate Similarity NPC321252
0.8252 Intermediate Similarity NPC175852
0.8252 Intermediate Similarity NPC160548
0.8252 Intermediate Similarity NPC210529
0.8247 Intermediate Similarity NPC175313
0.8241 Intermediate Similarity NPC224584
0.8235 Intermediate Similarity NPC246679
0.8224 Intermediate Similarity NPC187913
0.8224 Intermediate Similarity NPC1065
0.8218 Intermediate Similarity NPC181709
0.82 Intermediate Similarity NPC300017
0.8198 Intermediate Similarity NPC109241
0.8198 Intermediate Similarity NPC242136
0.819 Intermediate Similarity NPC472585
0.8182 Intermediate Similarity NPC268388
0.8182 Intermediate Similarity NPC25493
0.8182 Intermediate Similarity NPC113460
0.8173 Intermediate Similarity NPC171843
0.8163 Intermediate Similarity NPC197783
0.8158 Intermediate Similarity NPC328694
0.8158 Intermediate Similarity NPC474890
0.8158 Intermediate Similarity NPC161943
0.8158 Intermediate Similarity NPC273282
0.8144 Intermediate Similarity NPC265146
0.8144 Intermediate Similarity NPC95965
0.8142 Intermediate Similarity NPC188867
0.8142 Intermediate Similarity NPC106551
0.8142 Intermediate Similarity NPC471924
0.8142 Intermediate Similarity NPC471928
0.8142 Intermediate Similarity NPC131192
0.8142 Intermediate Similarity NPC471925
0.8142 Intermediate Similarity NPC281686
0.8131 Intermediate Similarity NPC303141
0.8125 Intermediate Similarity NPC285350
0.812 Intermediate Similarity NPC68167
0.8119 Intermediate Similarity NPC45040
0.8113 Intermediate Similarity NPC68269
0.8108 Intermediate Similarity NPC231717
0.8108 Intermediate Similarity NPC286222
0.8103 Intermediate Similarity NPC294361
0.8103 Intermediate Similarity NPC236520
0.81 Intermediate Similarity NPC123273
0.81 Intermediate Similarity NPC280347
0.81 Intermediate Similarity NPC177420
0.81 Intermediate Similarity NPC258219
0.81 Intermediate Similarity NPC242240
0.81 Intermediate Similarity NPC318325
0.8095 Intermediate Similarity NPC253746
0.8091 Intermediate Similarity NPC222905
0.8087 Intermediate Similarity NPC319950
0.8077 Intermediate Similarity NPC140619
0.8073 Intermediate Similarity NPC100551
0.807 Intermediate Similarity NPC471926
0.8061 Intermediate Similarity NPC248817
0.8058 Intermediate Similarity NPC257182
0.8053 Intermediate Similarity NPC23402
0.8053 Intermediate Similarity NPC322197
0.8053 Intermediate Similarity NPC51345
0.8051 Intermediate Similarity NPC14141
0.8039 Intermediate Similarity NPC138117
0.8039 Intermediate Similarity NPC325292
0.8037 Intermediate Similarity NPC38209
0.8034 Intermediate Similarity NPC198336
0.802 Intermediate Similarity NPC55561
0.8018 Intermediate Similarity NPC228609
0.8017 Intermediate Similarity NPC473136
0.8 Intermediate Similarity NPC79543
0.8 Intermediate Similarity NPC104216
0.8 Intermediate Similarity NPC27633
0.8 Intermediate Similarity NPC94298
0.8 Intermediate Similarity NPC130193
0.8 Intermediate Similarity NPC259554
0.7982 Intermediate Similarity NPC83718
0.7982 Intermediate Similarity NPC277394
0.7982 Intermediate Similarity NPC61062
0.7982 Intermediate Similarity NPC299252
0.798 Intermediate Similarity NPC155393
0.7966 Intermediate Similarity NPC164947
0.7966 Intermediate Similarity NPC283514
0.7965 Intermediate Similarity NPC81808
0.7963 Intermediate Similarity NPC243677
0.7963 Intermediate Similarity NPC219913
0.7963 Intermediate Similarity NPC127676
0.7961 Intermediate Similarity NPC151715
0.7961 Intermediate Similarity NPC128062
0.7959 Intermediate Similarity NPC124436
0.7949 Intermediate Similarity NPC164852
0.7944 Intermediate Similarity NPC304638
0.7944 Intermediate Similarity NPC298224
0.7944 Intermediate Similarity NPC135784
0.7944 Intermediate Similarity NPC160382
0.7941 Intermediate Similarity NPC304541
0.7938 Intermediate Similarity NPC285773
0.7931 Intermediate Similarity NPC239697
0.7931 Intermediate Similarity NPC158222
0.7931 Intermediate Similarity NPC42657
0.7928 Intermediate Similarity NPC63345
0.7928 Intermediate Similarity NPC183700
0.7917 Intermediate Similarity NPC287473
0.7913 Intermediate Similarity NPC325295
0.7913 Intermediate Similarity NPC160199
0.7913 Intermediate Similarity NPC76308
0.7913 Intermediate Similarity NPC125252
0.7913 Intermediate Similarity NPC150919
0.7905 Intermediate Similarity NPC201967
0.79 Intermediate Similarity NPC184169
0.79 Intermediate Similarity NPC407
0.79 Intermediate Similarity NPC307235
0.7899 Intermediate Similarity NPC473942
0.789 Intermediate Similarity NPC1075
0.789 Intermediate Similarity NPC294902
0.789 Intermediate Similarity NPC1786
0.7885 Intermediate Similarity NPC274678
0.7885 Intermediate Similarity NPC26244
0.7885 Intermediate Similarity NPC313650
0.7885 Intermediate Similarity NPC286006
0.7881 Intermediate Similarity NPC31936
0.7881 Intermediate Similarity NPC177291
0.7881 Intermediate Similarity NPC194416
0.7881 Intermediate Similarity NPC322332
0.7881 Intermediate Similarity NPC27581
0.7881 Intermediate Similarity NPC472271
0.7881 Intermediate Similarity NPC142577
0.7876 Intermediate Similarity NPC211421
0.7876 Intermediate Similarity NPC223004
0.787 Intermediate Similarity NPC93831
0.7863 Intermediate Similarity NPC159525
0.7851 Intermediate Similarity NPC473751
0.785 Intermediate Similarity NPC25458
0.7845 Intermediate Similarity NPC241089
0.7845 Intermediate Similarity NPC40649
0.7845 Intermediate Similarity NPC209486
0.7845 Intermediate Similarity NPC249435
0.7845 Intermediate Similarity NPC205502
0.7843 Intermediate Similarity NPC300478
0.7843 Intermediate Similarity NPC110704
0.7838 Intermediate Similarity NPC471954
0.7838 Intermediate Similarity NPC75272
0.7833 Intermediate Similarity NPC288945
0.7833 Intermediate Similarity NPC474766
0.7833 Intermediate Similarity NPC474803
0.7833 Intermediate Similarity NPC85565
0.7826 Intermediate Similarity NPC128825
0.7826 Intermediate Similarity NPC19290
0.7823 Intermediate Similarity NPC198249
0.7822 Intermediate Similarity NPC27974
0.7815 Intermediate Similarity NPC67300

  Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC13495 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
0.8491 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.8252 Intermediate Similarity NPD9495 Approved
0.8214 Intermediate Similarity NPD255 Approved
0.8214 Intermediate Similarity NPD256 Approved
0.8142 Intermediate Similarity NPD9568 Approved
0.8073 Intermediate Similarity NPD74 Approved
0.8073 Intermediate Similarity NPD9266 Approved
0.8 Intermediate Similarity NPD9545 Approved
0.7982 Intermediate Similarity NPD9264 Approved
0.7982 Intermediate Similarity NPD9263 Approved
0.7982 Intermediate Similarity NPD9267 Approved
0.7966 Intermediate Similarity NPD1481 Phase 2
0.7961 Intermediate Similarity NPD2933 Approved
0.7961 Intermediate Similarity NPD2934 Approved
0.7959 Intermediate Similarity NPD111 Approved
0.7938 Intermediate Similarity NPD9491 Approved
0.7885 Intermediate Similarity NPD2860 Approved
0.7885 Intermediate Similarity NPD2859 Approved
0.7881 Intermediate Similarity NPD1535 Discovery
0.7845 Intermediate Similarity NPD1759 Phase 1
0.7826 Intermediate Similarity NPD9493 Approved
0.7788 Intermediate Similarity NPD1432 Clinical (unspecified phase)
0.7759 Intermediate Similarity NPD1758 Phase 1
0.7745 Intermediate Similarity NPD9256 Approved
0.7745 Intermediate Similarity NPD9258 Approved
0.7664 Intermediate Similarity NPD3020 Approved
0.7652 Intermediate Similarity NPD9281 Approved
0.7623 Intermediate Similarity NPD1164 Approved
0.7615 Intermediate Similarity NPD9261 Approved
0.7563 Intermediate Similarity NPD3019 Approved
0.7563 Intermediate Similarity NPD2932 Approved
0.7561 Intermediate Similarity NPD258 Approved
0.7561 Intermediate Similarity NPD257 Approved
0.7551 Intermediate Similarity NPD226 Approved
0.7545 Intermediate Similarity NPD1237 Approved
0.7542 Intermediate Similarity NPD1894 Discontinued
0.7526 Intermediate Similarity NPD9490 Approved
0.7523 Intermediate Similarity NPD940 Approved
0.7523 Intermediate Similarity NPD846 Approved
0.7521 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD690 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD9569 Approved
0.7479 Intermediate Similarity NPD4196 Clinical (unspecified phase)
0.7476 Intermediate Similarity NPD800 Approved
0.746 Intermediate Similarity NPD3764 Approved
0.7453 Intermediate Similarity NPD1693 Approved
0.7414 Intermediate Similarity NPD1241 Discontinued
0.7404 Intermediate Similarity NPD1086 Approved
0.7404 Intermediate Similarity NPD1090 Approved
0.7404 Intermediate Similarity NPD1089 Approved
0.7398 Intermediate Similarity NPD1283 Approved
0.7383 Intermediate Similarity NPD1809 Phase 2
0.7383 Intermediate Similarity NPD844 Approved
0.7377 Intermediate Similarity NPD9717 Approved
0.7377 Intermediate Similarity NPD9269 Phase 2
0.7358 Intermediate Similarity NPD845 Approved
0.7358 Intermediate Similarity NPD1202 Approved
0.7355 Intermediate Similarity NPD3847 Discontinued
0.7353 Intermediate Similarity NPD9257 Approved
0.7353 Intermediate Similarity NPD9259 Approved
0.7339 Intermediate Similarity NPD1203 Approved
0.7333 Intermediate Similarity NPD1239 Approved
0.7333 Intermediate Similarity NPD9268 Approved
0.7323 Intermediate Similarity NPD6798 Discontinued
0.7315 Intermediate Similarity NPD288 Approved
0.7295 Intermediate Similarity NPD1201 Approved
0.7281 Intermediate Similarity NPD6831 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD289 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD1242 Phase 1
0.7266 Intermediate Similarity NPD4062 Phase 3
0.7266 Intermediate Similarity NPD6233 Phase 2
0.7266 Intermediate Similarity NPD259 Phase 1
0.7264 Intermediate Similarity NPD1088 Approved
0.7258 Intermediate Similarity NPD196 Phase 1
0.7245 Intermediate Similarity NPD227 Approved
0.7245 Intermediate Similarity NPD225 Approved
0.7244 Intermediate Similarity NPD9536 Phase 1
0.7244 Intermediate Similarity NPD9537 Phase 1
0.7236 Intermediate Similarity NPD1608 Approved
0.7232 Intermediate Similarity NPD9610 Approved
0.7232 Intermediate Similarity NPD9608 Approved
0.7222 Intermediate Similarity NPD454 Approved
0.7217 Intermediate Similarity NPD3021 Approved
0.7217 Intermediate Similarity NPD3022 Approved
0.7209 Intermediate Similarity NPD826 Approved
0.7209 Intermediate Similarity NPD825 Approved
0.7203 Intermediate Similarity NPD2629 Approved
0.72 Intermediate Similarity NPD1470 Approved
0.7196 Intermediate Similarity NPD5122 Clinical (unspecified phase)
0.7182 Intermediate Similarity NPD2066 Phase 3
0.7177 Intermediate Similarity NPD1755 Approved
0.7165 Intermediate Similarity NPD2614 Approved
0.7154 Intermediate Similarity NPD1281 Approved
0.7154 Intermediate Similarity NPD6355 Discontinued
0.7154 Intermediate Similarity NPD555 Phase 2
0.7154 Intermediate Similarity NPD274 Approved
0.7154 Intermediate Similarity NPD275 Approved
0.7132 Intermediate Similarity NPD6663 Approved
0.713 Intermediate Similarity NPD688 Clinical (unspecified phase)
0.7121 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD3028 Approved
0.7115 Intermediate Similarity NPD1087 Approved
0.7115 Intermediate Similarity NPD4793 Discontinued
0.7109 Intermediate Similarity NPD3136 Phase 2
0.7087 Intermediate Similarity NPD5736 Approved
0.7077 Intermediate Similarity NPD943 Approved
0.7073 Intermediate Similarity NPD3026 Approved
0.7073 Intermediate Similarity NPD3023 Approved
0.7069 Intermediate Similarity NPD9380 Clinical (unspecified phase)
0.7068 Intermediate Similarity NPD2935 Discontinued
0.7063 Intermediate Similarity NPD2797 Approved
0.7054 Intermediate Similarity NPD3268 Approved
0.7054 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7049 Intermediate Similarity NPD3024 Approved
0.7049 Intermediate Similarity NPD3025 Approved
0.7043 Intermediate Similarity NPD1358 Approved
0.7034 Intermediate Similarity NPD5535 Approved
0.7023 Intermediate Similarity NPD230 Phase 1
0.7016 Intermediate Similarity NPD422 Phase 1
0.701 Intermediate Similarity NPD9087 Approved
0.7 Intermediate Similarity NPD1564 Approved
0.7 Intermediate Similarity NPD520 Approved
0.7 Intermediate Similarity NPD1566 Phase 3
0.7 Intermediate Similarity NPD1565 Approved
0.6992 Remote Similarity NPD2799 Discontinued
0.6992 Remote Similarity NPD17 Approved
0.6991 Remote Similarity NPD1931 Clinical (unspecified phase)
0.6991 Remote Similarity NPD1930 Approved
0.6991 Remote Similarity NPD1929 Approved
0.6985 Remote Similarity NPD3750 Approved
0.6981 Remote Similarity NPD5347 Phase 2
0.6981 Remote Similarity NPD5346 Phase 2
0.6977 Remote Similarity NPD7095 Approved
0.6977 Remote Similarity NPD9718 Approved
0.6957 Remote Similarity NPD3134 Approved
0.6949 Remote Similarity NPD228 Approved
0.6947 Remote Similarity NPD1240 Approved
0.694 Remote Similarity NPD5404 Approved
0.694 Remote Similarity NPD5406 Approved
0.694 Remote Similarity NPD5408 Approved
0.694 Remote Similarity NPD1537 Approved
0.694 Remote Similarity NPD5405 Approved
0.694 Remote Similarity NPD9570 Approved
0.694 Remote Similarity NPD1519 Approved
0.694 Remote Similarity NPD1538 Phase 1
0.6937 Remote Similarity NPD9273 Approved
0.6934 Remote Similarity NPD2354 Approved
0.693 Remote Similarity NPD164 Approved
0.6929 Remote Similarity NPD987 Approved
0.6923 Remote Similarity NPD2313 Discontinued
0.6912 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6911 Remote Similarity NPD4102 Approved
0.6911 Remote Similarity NPD1651 Approved
0.6911 Remote Similarity NPD4105 Approved
0.69 Remote Similarity NPD9088 Approved
0.6891 Remote Similarity NPD9379 Approved
0.6891 Remote Similarity NPD9377 Approved
0.6875 Remote Similarity NPD1238 Approved
0.6875 Remote Similarity NPD5647 Approved
0.687 Remote Similarity NPD5729 Clinical (unspecified phase)
0.6866 Remote Similarity NPD1510 Phase 2
0.6866 Remote Similarity NPD3299 Clinical (unspecified phase)
0.6861 Remote Similarity NPD8166 Discontinued
0.6855 Remote Similarity NPD4626 Approved
0.6855 Remote Similarity NPD5306 Approved
0.6855 Remote Similarity NPD5305 Approved
0.6855 Remote Similarity NPD1778 Approved
0.685 Remote Similarity NPD3225 Approved
0.6842 Remote Similarity NPD1607 Approved
0.6842 Remote Similarity NPD5738 Clinical (unspecified phase)
0.6842 Remote Similarity NPD6647 Phase 2
0.6838 Remote Similarity NPD970 Clinical (unspecified phase)
0.6833 Remote Similarity NPD2228 Approved
0.6833 Remote Similarity NPD2234 Approved
0.6833 Remote Similarity NPD2229 Approved
0.6825 Remote Similarity NPD3972 Approved
0.6822 Remote Similarity NPD9494 Approved
0.6818 Remote Similarity NPD9260 Approved
0.6818 Remote Similarity NPD4060 Phase 1
0.6815 Remote Similarity NPD1522 Approved
0.6815 Remote Similarity NPD1523 Approved
0.6812 Remote Similarity NPD6190 Approved
0.681 Remote Similarity NPD1445 Approved
0.681 Remote Similarity NPD1444 Approved
0.681 Remote Similarity NPD968 Approved
0.6807 Remote Similarity NPD9508 Approved
0.6807 Remote Similarity NPD6124 Clinical (unspecified phase)
0.68 Remote Similarity NPD4136 Approved
0.68 Remote Similarity NPD4135 Approved
0.68 Remote Similarity NPD9294 Approved
0.68 Remote Similarity NPD4106 Approved
0.6797 Remote Similarity NPD3267 Approved
0.6797 Remote Similarity NPD3266 Approved
0.6794 Remote Similarity NPD411 Approved
0.6791 Remote Similarity NPD1536 Approved
0.6788 Remote Similarity NPD2976 Clinical (unspecified phase)
0.6783 Remote Similarity NPD5909 Discontinued
0.678 Remote Similarity NPD2067 Discontinued
0.6777 Remote Similarity NPD5951 Approved
0.6772 Remote Similarity NPD4379 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   979
ChEMBL   CHEMBL607712
ZINC  

Physicochemical Properties

Molecular Weight:  180.04
ALogP:  -0.9291
MLogP:  2.01
XLogP:  0.716
# Rotatable Bonds:  5
Polar Surface Area:  74.6
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  1
# Heavy Atoms:  13

Download Data

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Structure MOL file  
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Biological Activities  
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