Natural Product: NPC329550

Natural Product ID:  NPC329550
Common Name:   5-Oxo-Ete
IUPAC Name:   (6E,8Z,11Z,14Z)-5-oxoicosa-6,8,11,14-tetraenoic acid
Synonyms:   5-Oxo-ETE
Molecular Formula:   C20H30O3
Standard InCHIKey:  MEASLHGILYBXFO-XTDASVJISA-N
Standard InCHI:  InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h6-7,9-10,12-14,16H,2-5,8,11,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,13-12-,16-14+
Canonical SMILES:  CCCCC/C=CC/C=CC/C=CC=CC(=O)CCCC(=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 PMID[8906847]
NPO1797 Homo sapiens Species Hominidae Eukaryota blood PMID[21359215]
NPO20338 Mus musculus Species Muridae Eukaryota PMID[25518943]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT183 Individual Protein Arachidonate 5-lipoxygenase Rattus norvegicus IC50 = 18000 nM 3599023
NPT4030 Individual Protein Oxoeicosanoid receptor 1 Homo sapiens EC50 = 7 nM 21316960
NPT4030 Individual Protein Oxoeicosanoid receptor 1 Homo sapiens IC50 = 3 nM 21377873
NPT2 Others Unspecified EC50 = 4 nM 21377873
NPT4030 Individual Protein Oxoeicosanoid receptor 1 Homo sapiens EC50 = 67 nM 10.1039/C1MD00231G
NPT2 Others Unspecified IC50 > 100000 nM 24924423
NPT257 Individual Protein Arachidonate 15-lipoxygenase Oryctolagus cuniculus IC50 > 25000 nM 24924423
NPT1139 Individual Protein Arachidonate 15-lipoxygenase, type II Homo sapiens IC50 > 100000 nM 24924423
NPT792 Individual Protein Arachidonate 15-lipoxygenase Homo sapiens IC50 > 25000 nM 24924423
NPT1119 Individual Protein Arachidonate 12-lipoxygenase Homo sapiens IC50 = 15000 nM 24924423

  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 NPC329550 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
0.9107 High Similarity NPC325977
0.9091 High Similarity NPC322461
0.8814 High Similarity NPC251042
0.8814 High Similarity NPC122521
0.8814 High Similarity NPC174447
0.8667 High Similarity NPC40082
0.8333 Intermediate Similarity NPC274927
0.8333 Intermediate Similarity NPC106851
0.8197 Intermediate Similarity NPC235242
0.8182 Intermediate Similarity NPC149821
0.8182 Intermediate Similarity NPC5413
0.8 Intermediate Similarity NPC207292
0.7937 Intermediate Similarity NPC322457
0.7833 Intermediate Similarity NPC477201
0.7833 Intermediate Similarity NPC18951
0.7761 Intermediate Similarity NPC143396
0.7759 Intermediate Similarity NPC92114
0.7705 Intermediate Similarity NPC225929
0.7679 Intermediate Similarity NPC91495
0.7636 Intermediate Similarity NPC117572
0.7627 Intermediate Similarity NPC321062
0.7627 Intermediate Similarity NPC36061
0.7627 Intermediate Similarity NPC139029
0.7627 Intermediate Similarity NPC1813
0.7627 Intermediate Similarity NPC294548
0.7627 Intermediate Similarity NPC70387
0.7586 Intermediate Similarity NPC28205
0.7586 Intermediate Similarity NPC284212
0.75 Intermediate Similarity NPC281972
0.75 Intermediate Similarity NPC290563
0.75 Intermediate Similarity NPC85813
0.75 Intermediate Similarity NPC424
0.75 Intermediate Similarity NPC6095
0.75 Intermediate Similarity NPC25417
0.75 Intermediate Similarity NPC32467
0.75 Intermediate Similarity NPC154245
0.75 Intermediate Similarity NPC88966
0.75 Intermediate Similarity NPC87564
0.75 Intermediate Similarity NPC261831
0.7458 Intermediate Similarity NPC281245
0.7424 Intermediate Similarity NPC323045
0.7424 Intermediate Similarity NPC317881
0.7424 Intermediate Similarity NPC320642
0.7414 Intermediate Similarity NPC59051
0.7377 Intermediate Similarity NPC274290
0.7377 Intermediate Similarity NPC473863
0.7353 Intermediate Similarity NPC476614
0.7344 Intermediate Similarity NPC229252
0.7344 Intermediate Similarity NPC327112
0.7344 Intermediate Similarity NPC143857
0.7344 Intermediate Similarity NPC328311
0.7324 Intermediate Similarity NPC474321
0.7313 Intermediate Similarity NPC142423
0.7313 Intermediate Similarity NPC308294
0.7302 Intermediate Similarity NPC34416
0.7288 Intermediate Similarity NPC48162
0.7286 Intermediate Similarity NPC288667
0.7258 Intermediate Similarity NPC324224
0.7258 Intermediate Similarity NPC187777
0.7258 Intermediate Similarity NPC472808
0.7258 Intermediate Similarity NPC179764
0.7246 Intermediate Similarity NPC236208
0.7213 Intermediate Similarity NPC300121
0.7206 Intermediate Similarity NPC60120
0.7206 Intermediate Similarity NPC49863
0.7188 Intermediate Similarity NPC329249
0.7164 Intermediate Similarity NPC245947
0.7164 Intermediate Similarity NPC318420
0.7164 Intermediate Similarity NPC326268
0.7164 Intermediate Similarity NPC136164
0.7164 Intermediate Similarity NPC255863
0.7164 Intermediate Similarity NPC323477
0.7121 Intermediate Similarity NPC477707
0.7119 Intermediate Similarity NPC224227
0.7097 Intermediate Similarity NPC54766
0.7097 Intermediate Similarity NPC228473
0.7083 Intermediate Similarity NPC227396
0.7077 Intermediate Similarity NPC243532
0.7059 Intermediate Similarity NPC328653
0.7 Intermediate Similarity NPC262968
0.7 Intermediate Similarity NPC477458
0.6986 Remote Similarity NPC260396
0.6984 Remote Similarity NPC327388
0.697 Remote Similarity NPC201939
0.6964 Remote Similarity NPC270796
0.6944 Remote Similarity NPC215745
0.6944 Remote Similarity NPC12815
0.6944 Remote Similarity NPC238948
0.6935 Remote Similarity NPC137538
0.6923 Remote Similarity NPC102197
0.6923 Remote Similarity NPC322002
0.6901 Remote Similarity NPC318766
0.6897 Remote Similarity NPC42304
0.6885 Remote Similarity NPC129458
0.6875 Remote Similarity NPC283502
0.6875 Remote Similarity NPC323597
0.6875 Remote Similarity NPC323498
0.6875 Remote Similarity NPC211752
0.6875 Remote Similarity NPC323436
0.6875 Remote Similarity NPC281230
0.6875 Remote Similarity NPC192843
0.6866 Remote Similarity NPC477830
0.6825 Remote Similarity NPC52264
0.6812 Remote Similarity NPC83965
0.6806 Remote Similarity NPC319163
0.6806 Remote Similarity NPC67076
0.6795 Remote Similarity NPC238991
0.6795 Remote Similarity NPC302661
0.678 Remote Similarity NPC180534
0.6774 Remote Similarity NPC284224
0.6774 Remote Similarity NPC10081
0.6774 Remote Similarity NPC225066
0.6774 Remote Similarity NPC309606
0.6774 Remote Similarity NPC39633
0.6774 Remote Similarity NPC139545
0.6769 Remote Similarity NPC267817
0.6765 Remote Similarity NPC470320
0.6765 Remote Similarity NPC328089
0.6765 Remote Similarity NPC68343
0.6721 Remote Similarity NPC43053
0.6716 Remote Similarity NPC321838
0.6716 Remote Similarity NPC320305
0.6716 Remote Similarity NPC328776
0.6712 Remote Similarity NPC325627
0.6711 Remote Similarity NPC182292
0.6667 Remote Similarity NPC318306
0.6667 Remote Similarity NPC476654
0.6667 Remote Similarity NPC476655
0.6667 Remote Similarity NPC4492
0.6667 Remote Similarity NPC163345
0.6667 Remote Similarity NPC6247
0.6667 Remote Similarity NPC476657
0.6667 Remote Similarity NPC51391
0.6667 Remote Similarity NPC476660
0.6667 Remote Similarity NPC474127
0.6622 Remote Similarity NPC92558
0.6618 Remote Similarity NPC190049
0.6618 Remote Similarity NPC53109
0.6618 Remote Similarity NPC143168
0.6613 Remote Similarity NPC303765
0.6613 Remote Similarity NPC18357
0.6575 Remote Similarity NPC320119
0.6571 Remote Similarity NPC146811
0.6571 Remote Similarity NPC476659
0.6571 Remote Similarity NPC126899
0.6571 Remote Similarity NPC154728
0.6571 Remote Similarity NPC476656
0.6571 Remote Similarity NPC304665
0.6567 Remote Similarity NPC81896
0.6567 Remote Similarity NPC321919
0.6562 Remote Similarity NPC45626
0.6562 Remote Similarity NPC223677
0.6562 Remote Similarity NPC28779
0.6562 Remote Similarity NPC128061
0.6562 Remote Similarity NPC200845
0.6562 Remote Similarity NPC10316
0.6557 Remote Similarity NPC225974
0.6557 Remote Similarity NPC15325
0.6557 Remote Similarity NPC474391
0.6557 Remote Similarity NPC221467
0.6538 Remote Similarity NPC26139
0.6533 Remote Similarity NPC169056
0.6533 Remote Similarity NPC166018
0.6533 Remote Similarity NPC225665
0.6528 Remote Similarity NPC473603
0.6528 Remote Similarity NPC317583
0.6528 Remote Similarity NPC473772
0.6528 Remote Similarity NPC67608
0.6528 Remote Similarity NPC469914
0.6528 Remote Similarity NPC475982
0.6528 Remote Similarity NPC476059
0.6528 Remote Similarity NPC262673
0.6522 Remote Similarity NPC7029
0.6522 Remote Similarity NPC226592
0.6515 Remote Similarity NPC281195
0.6515 Remote Similarity NPC320421
0.6515 Remote Similarity NPC329819
0.6508 Remote Similarity NPC71761
0.65 Remote Similarity NPC324812
0.6494 Remote Similarity NPC192006
0.6486 Remote Similarity NPC326024
0.6486 Remote Similarity NPC321017
0.6486 Remote Similarity NPC284006
0.6486 Remote Similarity NPC153660
0.6479 Remote Similarity NPC22101
0.6479 Remote Similarity NPC148192
0.6479 Remote Similarity NPC26500
0.6479 Remote Similarity NPC104537
0.6479 Remote Similarity NPC330426
0.6479 Remote Similarity NPC127091
0.6479 Remote Similarity NPC99619
0.6479 Remote Similarity NPC271921
0.6471 Remote Similarity NPC113293
0.6471 Remote Similarity NPC174560
0.6471 Remote Similarity NPC26810
0.6471 Remote Similarity NPC477829
0.6471 Remote Similarity NPC125312
0.6471 Remote Similarity NPC64985
0.6462 Remote Similarity NPC86948
0.6452 Remote Similarity NPC470410

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC329550 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
0.8182 Intermediate Similarity NPD3173 Approved
0.7636 Intermediate Similarity NPD4222 Approved
0.7636 Intermediate Similarity NPD3174 Discontinued
0.7627 Intermediate Similarity NPD3172 Approved
0.75 Intermediate Similarity NPD3196 Approved
0.75 Intermediate Similarity NPD4266 Approved
0.75 Intermediate Similarity NPD3195 Phase 2
0.75 Intermediate Similarity NPD3194 Approved
0.7344 Intermediate Similarity NPD4246 Clinical (unspecified phase)
0.7321 Intermediate Similarity NPD39 Approved
0.7206 Intermediate Similarity NPD4247 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD29 Approved
0.7 Intermediate Similarity NPD28 Approved
0.6964 Remote Similarity NPD5326 Phase 3
0.68 Remote Similarity NPD4756 Discovery
0.678 Remote Similarity NPD622 Approved
0.6765 Remote Similarity NPD3197 Phase 1
0.6667 Remote Similarity NPD4220 Pre-registration
0.6618 Remote Similarity NPD2664 Clinical (unspecified phase)
0.6571 Remote Similarity NPD7331 Phase 2
0.65 Remote Similarity NPD5343 Approved
0.6269 Remote Similarity NPD6109 Phase 1
0.6111 Remote Similarity NPD6108 Clinical (unspecified phase)
0.6 Remote Similarity NPD6096 Approved
0.6 Remote Similarity NPD6097 Approved
0.5972 Remote Similarity NPD7341 Phase 2
0.5952 Remote Similarity NPD5363 Approved
0.5926 Remote Similarity NPD5368 Approved
0.5909 Remote Similarity NPD9298 Approved
0.5875 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5783 Remote Similarity NPD5209 Approved
0.5783 Remote Similarity NPD6435 Approved
0.5775 Remote Similarity NPD4191 Approved
0.5775 Remote Similarity NPD4194 Approved
0.5775 Remote Similarity NPD4193 Approved
0.5775 Remote Similarity NPD4192 Approved
0.5732 Remote Similarity NPD8259 Clinical (unspecified phase)
0.5732 Remote Similarity NPD4252 Approved
0.573 Remote Similarity NPD5281 Approved
0.573 Remote Similarity NPD5284 Approved
0.569 Remote Similarity NPD5783 Phase 3
0.5676 Remote Similarity NPD3704 Approved
0.5663 Remote Similarity NPD5369 Approved
0.5618 Remote Similarity NPD5785 Approved
0.5604 Remote Similarity NPD5122 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   5283159
ChEMBL   CHEMBL18028
ZINC  

Physicochemical Properties

Molecular Weight:  318.22
ALogP:  0.6102
MLogP:  3.33
XLogP:  6.351
# Rotatable Bonds:  16
Polar Surface Area:  54.37
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  0
# Heavy Atoms:  23

Download Data

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Structure MOL file  
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Similar NPs/Drugs