Natural Product: NPC322461

Natural Product ID:  NPC322461
Common Name:   12-Oxo-5,8,10,14-(Z,Z,E,Z)-Eicosatetraenoic Acid
IUPAC Name:   (5Z,8Z,10E,14Z)-12-oxoicosa-5,8,10,14-tetraenoic acid
Synonyms:  
Molecular Formula:   C20H30O3
Standard InCHIKey:  GURBRQGDZZKITB-VXBMJZGYSA-N
Standard InCHI:  InChI=1S/C20H30O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h7-11,13-14,17H,2-6,12,15-16,18H2,1H3,(H,22,23)/b9-7-,11-8-,13-10-,17-14+
Canonical SMILES:  CCCCC/C=CCC(=O)/C=C/C=CC/C=CCCCC(=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[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
NPT792 Individual Protein Arachidonate 15-lipoxygenase Homo sapiens Ki = 36800 nM 24924423
NPT2 Others Unspecified IC50 > 100000 nM 24924423
NPT257 Individual Protein Arachidonate 15-lipoxygenase Oryctolagus cuniculus IC50 > 50000 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 = 3000 nM 24924423
NPT1119 Individual Protein Arachidonate 12-lipoxygenase Homo sapiens IC50 = 8000 nM 24924423
NPT570 Individual Protein Arachidonate 5-lipoxygenase Homo sapiens IC50 > 50000 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 NPC322461 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
0.9615 High Similarity NPC325977
0.9091 High Similarity NPC329550
0.8929 High Similarity NPC251042
0.8929 High Similarity NPC122521
0.8929 High Similarity NPC174447
0.8772 High Similarity NPC40082
0.8621 High Similarity NPC322457
0.8431 Intermediate Similarity NPC91495
0.8421 Intermediate Similarity NPC106851
0.8421 Intermediate Similarity NPC274927
0.84 Intermediate Similarity NPC117572
0.8276 Intermediate Similarity NPC235242
0.8269 Intermediate Similarity NPC5413
0.8269 Intermediate Similarity NPC149821
0.8113 Intermediate Similarity NPC59051
0.8077 Intermediate Similarity NPC207292
0.7963 Intermediate Similarity NPC48162
0.7895 Intermediate Similarity NPC18951
0.7895 Intermediate Similarity NPC324224
0.7895 Intermediate Similarity NPC477201
0.7895 Intermediate Similarity NPC472808
0.7857 Intermediate Similarity NPC300121
0.7818 Intermediate Similarity NPC92114
0.7812 Intermediate Similarity NPC143396
0.7797 Intermediate Similarity NPC329249
0.7759 Intermediate Similarity NPC225929
0.7679 Intermediate Similarity NPC294548
0.7679 Intermediate Similarity NPC321062
0.7679 Intermediate Similarity NPC36061
0.7679 Intermediate Similarity NPC1813
0.7679 Intermediate Similarity NPC70387
0.7679 Intermediate Similarity NPC139029
0.7667 Intermediate Similarity NPC328311
0.7667 Intermediate Similarity NPC327112
0.7647 Intermediate Similarity NPC270796
0.7636 Intermediate Similarity NPC28205
0.7636 Intermediate Similarity NPC284212
0.7586 Intermediate Similarity NPC327388
0.7547 Intermediate Similarity NPC42304
0.7544 Intermediate Similarity NPC88966
0.7544 Intermediate Similarity NPC424
0.7544 Intermediate Similarity NPC281972
0.7544 Intermediate Similarity NPC25417
0.7544 Intermediate Similarity NPC154245
0.7544 Intermediate Similarity NPC85813
0.7544 Intermediate Similarity NPC87564
0.7544 Intermediate Similarity NPC261831
0.7544 Intermediate Similarity NPC32467
0.7544 Intermediate Similarity NPC6095
0.7544 Intermediate Similarity NPC290563
0.7538 Intermediate Similarity NPC236208
0.75 Intermediate Similarity NPC129458
0.75 Intermediate Similarity NPC322002
0.75 Intermediate Similarity NPC281245
0.7463 Intermediate Similarity NPC12815
0.7463 Intermediate Similarity NPC215745
0.7463 Intermediate Similarity NPC238948
0.7458 Intermediate Similarity NPC323498
0.7458 Intermediate Similarity NPC323597
0.7458 Intermediate Similarity NPC323436
0.7458 Intermediate Similarity NPC211752
0.7458 Intermediate Similarity NPC283502
0.7414 Intermediate Similarity NPC473863
0.7414 Intermediate Similarity NPC274290
0.7385 Intermediate Similarity NPC476614
0.7377 Intermediate Similarity NPC229252
0.7377 Intermediate Similarity NPC143857
0.7368 Intermediate Similarity NPC10081
0.7368 Intermediate Similarity NPC225066
0.7368 Intermediate Similarity NPC284224
0.7353 Intermediate Similarity NPC474321
0.7344 Intermediate Similarity NPC142423
0.7344 Intermediate Similarity NPC308294
0.7333 Intermediate Similarity NPC34416
0.7321 Intermediate Similarity NPC477458
0.7321 Intermediate Similarity NPC43053
0.7313 Intermediate Similarity NPC288667
0.7288 Intermediate Similarity NPC179764
0.7288 Intermediate Similarity NPC187777
0.7246 Intermediate Similarity NPC260396
0.7241 Intermediate Similarity NPC137538
0.7241 Intermediate Similarity NPC474127
0.7213 Intermediate Similarity NPC318306
0.7193 Intermediate Similarity NPC303765
0.7188 Intermediate Similarity NPC476657
0.7188 Intermediate Similarity NPC326268
0.7188 Intermediate Similarity NPC245947
0.7188 Intermediate Similarity NPC476655
0.7188 Intermediate Similarity NPC476654
0.7188 Intermediate Similarity NPC255863
0.7188 Intermediate Similarity NPC317881
0.7188 Intermediate Similarity NPC318420
0.7188 Intermediate Similarity NPC136164
0.7188 Intermediate Similarity NPC320642
0.7188 Intermediate Similarity NPC323045
0.7167 Intermediate Similarity NPC192843
0.7167 Intermediate Similarity NPC281230
0.7164 Intermediate Similarity NPC318766
0.7143 Intermediate Similarity NPC224227
0.7143 Intermediate Similarity NPC51391
0.7143 Intermediate Similarity NPC221467
0.7143 Intermediate Similarity NPC4492
0.7143 Intermediate Similarity NPC15325
0.7143 Intermediate Similarity NPC225974
0.7119 Intermediate Similarity NPC45626
0.7119 Intermediate Similarity NPC228473
0.7119 Intermediate Similarity NPC52264
0.7119 Intermediate Similarity NPC54766
0.7101 Intermediate Similarity NPC227396
0.7097 Intermediate Similarity NPC321919
0.7097 Intermediate Similarity NPC81896
0.7097 Intermediate Similarity NPC243532
0.7077 Intermediate Similarity NPC476659
0.7077 Intermediate Similarity NPC476656
0.7077 Intermediate Similarity NPC146811
0.7059 Intermediate Similarity NPC319163
0.7059 Intermediate Similarity NPC67076
0.7049 Intermediate Similarity NPC281195
0.7049 Intermediate Similarity NPC329819
0.7037 Intermediate Similarity NPC191337
0.7018 Intermediate Similarity NPC178586
0.7018 Intermediate Similarity NPC262968
0.7015 Intermediate Similarity NPC473603
0.7015 Intermediate Similarity NPC476059
0.7015 Intermediate Similarity NPC475982
0.7 Intermediate Similarity NPC155880
0.7 Intermediate Similarity NPC92863
0.6984 Remote Similarity NPC320305
0.6984 Remote Similarity NPC321838
0.6984 Remote Similarity NPC328776
0.6984 Remote Similarity NPC201939
0.6984 Remote Similarity NPC64985
0.6984 Remote Similarity NPC26810
0.697 Remote Similarity NPC49863
0.6957 Remote Similarity NPC284006
0.6944 Remote Similarity NPC182292
0.6935 Remote Similarity NPC322186
0.6923 Remote Similarity NPC471566
0.6923 Remote Similarity NPC471556
0.6923 Remote Similarity NPC323477
0.6923 Remote Similarity NPC471565
0.6885 Remote Similarity NPC268185
0.6875 Remote Similarity NPC155849
0.6875 Remote Similarity NPC68110
0.6875 Remote Similarity NPC190049
0.6875 Remote Similarity NPC477707
0.6875 Remote Similarity NPC477830
0.6863 Remote Similarity NPC217923
0.6852 Remote Similarity NPC477686
0.6849 Remote Similarity NPC265980
0.6849 Remote Similarity NPC63326
0.6842 Remote Similarity NPC288381
0.6842 Remote Similarity NPC474391
0.6842 Remote Similarity NPC20934
0.6818 Remote Similarity NPC328653
0.6818 Remote Similarity NPC83965
0.6812 Remote Similarity NPC293114
0.6786 Remote Similarity NPC180534
0.6786 Remote Similarity NPC324812
0.678 Remote Similarity NPC309606
0.678 Remote Similarity NPC39633
0.678 Remote Similarity NPC61177
0.678 Remote Similarity NPC139545
0.678 Remote Similarity NPC37644
0.678 Remote Similarity NPC217188
0.6774 Remote Similarity NPC474084
0.6774 Remote Similarity NPC471619
0.6774 Remote Similarity NPC267817
0.6769 Remote Similarity NPC68343
0.6769 Remote Similarity NPC470320
0.6769 Remote Similarity NPC328089
0.6769 Remote Similarity NPC476658
0.6761 Remote Similarity NPC169056
0.6761 Remote Similarity NPC166018
0.6761 Remote Similarity NPC225665
0.6761 Remote Similarity NPC68624
0.6731 Remote Similarity NPC113082
0.6727 Remote Similarity NPC474362
0.6727 Remote Similarity NPC474202
0.6721 Remote Similarity NPC86948
0.6719 Remote Similarity NPC113293
0.6719 Remote Similarity NPC151648
0.6716 Remote Similarity NPC122627
0.6716 Remote Similarity NPC106613
0.6716 Remote Similarity NPC21998
0.6714 Remote Similarity NPC287878
0.6714 Remote Similarity NPC153660
0.6667 Remote Similarity NPC296436
0.6667 Remote Similarity NPC222852
0.6667 Remote Similarity NPC476037
0.6667 Remote Similarity NPC176215
0.6667 Remote Similarity NPC470688
0.6667 Remote Similarity NPC163345
0.6667 Remote Similarity NPC476012
0.6667 Remote Similarity NPC476660
0.6618 Remote Similarity NPC474823
0.6618 Remote Similarity NPC287705
0.6615 Remote Similarity NPC143168
0.6615 Remote Similarity NPC53109
0.6615 Remote Similarity NPC474774

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC322461 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
0.84 Intermediate Similarity NPD4222 Approved
0.8269 Intermediate Similarity NPD3173 Approved
0.8039 Intermediate Similarity NPD39 Approved
0.7692 Intermediate Similarity NPD3174 Discontinued
0.7679 Intermediate Similarity NPD3172 Approved
0.7667 Intermediate Similarity NPD4246 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD5326 Phase 3
0.7544 Intermediate Similarity NPD3194 Approved
0.7544 Intermediate Similarity NPD3196 Approved
0.7544 Intermediate Similarity NPD4266 Approved
0.7544 Intermediate Similarity NPD3195 Phase 2
0.7273 Intermediate Similarity NPD4220 Pre-registration
0.7091 Intermediate Similarity NPD5343 Approved
0.7018 Intermediate Similarity NPD29 Approved
0.7018 Intermediate Similarity NPD28 Approved
0.697 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6806 Remote Similarity NPD4756 Discovery
0.6786 Remote Similarity NPD622 Approved
0.6774 Remote Similarity NPD6109 Phase 1
0.6769 Remote Similarity NPD3197 Phase 1
0.6615 Remote Similarity NPD2664 Clinical (unspecified phase)
0.6545 Remote Similarity NPD6097 Approved
0.6545 Remote Similarity NPD6096 Approved
0.6324 Remote Similarity NPD7331 Phase 2
0.6226 Remote Similarity NPD5783 Phase 3
0.6212 Remote Similarity NPD4193 Approved
0.6212 Remote Similarity NPD4192 Approved
0.6212 Remote Similarity NPD4194 Approved
0.6212 Remote Similarity NPD4191 Approved
0.6087 Remote Similarity NPD6108 Clinical (unspecified phase)
0.6071 Remote Similarity NPD9411 Phase 1
0.5949 Remote Similarity NPD5209 Approved
0.5926 Remote Similarity NPD5363 Approved
0.5902 Remote Similarity NPD6927 Phase 3
0.5897 Remote Similarity NPD8259 Clinical (unspecified phase)
0.5873 Remote Similarity NPD539 Approved
0.5846 Remote Similarity NPD8779 Phase 3
0.5844 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5781 Remote Similarity NPD4627 Clinical (unspecified phase)
0.5775 Remote Similarity NPD3709 Clinical (unspecified phase)
0.5714 Remote Similarity NPD7341 Phase 2
0.5698 Remote Similarity NPD5284 Approved
0.5698 Remote Similarity NPD5281 Approved
0.5696 Remote Similarity NPD5368 Approved
0.5696 Remote Similarity NPD4252 Approved
0.5641 Remote Similarity NPD4268 Approved
0.5641 Remote Similarity NPD4271 Approved
0.5634 Remote Similarity NPD3704 Approved
0.5625 Remote Similarity NPD5369 Approved

Structure

External Identifiers

PubChem CID   5283162
ChEMBL   CHEMBL3310737
ZINC  

Physicochemical Properties

Molecular Weight:  318.22
ALogP:  0.8034
MLogP:  3.33
XLogP:  6.14
# Rotatable Bonds:  16
Polar Surface Area:  54.37
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  0
# Heavy Atoms:  23

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