Natural Product: NPC328776

Natural Product ID:  NPC328776
Common Name:   Cis-14,15-Epoxyeicosa-5(Z),8(Z),11(Z)-Trienoic Acid
IUPAC Name:   (5Z,8Z,11Z)-13-[(2R,3S)-3-pentyloxiran-2-yl]trideca-5,8,11-trienoic acid
Synonyms:  
Molecular Formula:   C20H32O3
Standard InCHIKey:  JBSCUHKPLGKXKH-LLZJRKGESA-N
Standard InCHI:  InChI=1S/C20H32O3/c1-2-3-12-15-18-19(23-18)16-13-10-8-6-4-5-7-9-11-14-17-20(21)22/h4,6-7,9-10,13,18-19H,2-3,5,8,11-12,14-17H2,1H3,(H,21,22)/b6-4-,9-7-,13-10-/t18-,19+/m0/s1
Canonical SMILES:  CCCCC[C@@H]1O[C@@H]1C/C=CC/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 cerebrospinal fluid John W. Newman, USDA ARS Western Human Nutrition Research Center, Davis CA (personal communication - March 2, 2009)
NPO1797 Homo sapiens Species Hominidae Eukaryota blood PMID[21359215]
NPO31575 Cavia porcellus Species Caviidae Eukaryota PMID[11060896]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified Activity = 85 % 19653681
NPT2 Others Unspecified ED50 = 2.2 nM 19653681

  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 NPC328776 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 NPC320305
0.9661 High Similarity NPC68343
0.9661 High Similarity NPC328089
0.9298 High Similarity NPC211752
0.9298 High Similarity NPC323498
0.9298 High Similarity NPC323597
0.9123 High Similarity NPC327388
0.9 High Similarity NPC201939
0.8947 High Similarity NPC52264
0.8906 High Similarity NPC317583
0.8833 High Similarity NPC243532
0.8772 High Similarity NPC137538
0.8689 High Similarity NPC321838
0.8308 Intermediate Similarity NPC148192
0.8308 Intermediate Similarity NPC271921
0.8308 Intermediate Similarity NPC22101
0.8308 Intermediate Similarity NPC104537
0.8308 Intermediate Similarity NPC127091
0.8308 Intermediate Similarity NPC330426
0.8305 Intermediate Similarity NPC223677
0.8305 Intermediate Similarity NPC200845
0.8305 Intermediate Similarity NPC28779
0.8305 Intermediate Similarity NPC10316
0.8305 Intermediate Similarity NPC128061
0.8182 Intermediate Similarity NPC473559
0.8182 Intermediate Similarity NPC324981
0.8182 Intermediate Similarity NPC141481
0.8182 Intermediate Similarity NPC48218
0.8167 Intermediate Similarity NPC477201
0.8136 Intermediate Similarity NPC261831
0.8136 Intermediate Similarity NPC88966
0.8136 Intermediate Similarity NPC290563
0.8136 Intermediate Similarity NPC154245
0.8136 Intermediate Similarity NPC32467
0.8136 Intermediate Similarity NPC424
0.8136 Intermediate Similarity NPC25417
0.8136 Intermediate Similarity NPC6095
0.8136 Intermediate Similarity NPC85813
0.8136 Intermediate Similarity NPC281972
0.8136 Intermediate Similarity NPC87564
0.8103 Intermediate Similarity NPC92114
0.807 Intermediate Similarity NPC59051
0.8033 Intermediate Similarity NPC323436
0.803 Intermediate Similarity NPC475443
0.803 Intermediate Similarity NPC26500
0.803 Intermediate Similarity NPC99619
0.803 Intermediate Similarity NPC473829
0.8 Intermediate Similarity NPC136164
0.8 Intermediate Similarity NPC318420
0.8 Intermediate Similarity NPC245947
0.8 Intermediate Similarity NPC476654
0.8 Intermediate Similarity NPC326268
0.8 Intermediate Similarity NPC476657
0.8 Intermediate Similarity NPC255863
0.8 Intermediate Similarity NPC476655
0.7969 Intermediate Similarity NPC54925
0.7966 Intermediate Similarity NPC36061
0.7966 Intermediate Similarity NPC294548
0.7966 Intermediate Similarity NPC139545
0.7966 Intermediate Similarity NPC321062
0.7966 Intermediate Similarity NPC70387
0.7966 Intermediate Similarity NPC39633
0.7966 Intermediate Similarity NPC1813
0.7966 Intermediate Similarity NPC71761
0.7966 Intermediate Similarity NPC309606
0.7966 Intermediate Similarity NPC139029
0.7941 Intermediate Similarity NPC476660
0.7941 Intermediate Similarity NPC42526
0.7937 Intermediate Similarity NPC321919
0.7937 Intermediate Similarity NPC328311
0.7937 Intermediate Similarity NPC81896
0.7937 Intermediate Similarity NPC327112
0.7937 Intermediate Similarity NPC229252
0.7937 Intermediate Similarity NPC143857
0.7895 Intermediate Similarity NPC207815
0.7879 Intermediate Similarity NPC476659
0.7879 Intermediate Similarity NPC476656
0.7869 Intermediate Similarity NPC18951
0.7857 Intermediate Similarity NPC92558
0.7846 Intermediate Similarity NPC470320
0.7812 Intermediate Similarity NPC113293
0.7797 Intermediate Similarity NPC281245
0.7794 Intermediate Similarity NPC470436
0.7794 Intermediate Similarity NPC473772
0.7778 Intermediate Similarity NPC274927
0.7778 Intermediate Similarity NPC329249
0.7778 Intermediate Similarity NPC106851
0.7778 Intermediate Similarity NPC478095
0.7719 Intermediate Similarity NPC91495
0.7714 Intermediate Similarity NPC470435
0.7705 Intermediate Similarity NPC228473
0.7692 Intermediate Similarity NPC29697
0.7681 Intermediate Similarity NPC475310
0.7647 Intermediate Similarity NPC273508
0.7647 Intermediate Similarity NPC209327
0.7627 Intermediate Similarity NPC262968
0.7619 Intermediate Similarity NPC478096
0.7606 Intermediate Similarity NPC474321
0.7586 Intermediate Similarity NPC5413
0.7586 Intermediate Similarity NPC149821
0.7586 Intermediate Similarity NPC163345
0.7581 Intermediate Similarity NPC187777
0.7581 Intermediate Similarity NPC179764
0.7576 Intermediate Similarity NPC476658
0.7576 Intermediate Similarity NPC226592
0.7538 Intermediate Similarity NPC66460
0.7538 Intermediate Similarity NPC325929
0.7538 Intermediate Similarity NPC271282
0.75 Intermediate Similarity NPC260396
0.75 Intermediate Similarity NPC478097
0.75 Intermediate Similarity NPC478100
0.75 Intermediate Similarity NPC25298
0.746 Intermediate Similarity NPC225929
0.7458 Intermediate Similarity NPC224227
0.7419 Intermediate Similarity NPC54766
0.7419 Intermediate Similarity NPC274290
0.7419 Intermediate Similarity NPC473863
0.7414 Intermediate Similarity NPC207292
0.7397 Intermediate Similarity NPC188860
0.7385 Intermediate Similarity NPC251042
0.7385 Intermediate Similarity NPC122521
0.7385 Intermediate Similarity NPC235242
0.7385 Intermediate Similarity NPC174447
0.7368 Intermediate Similarity NPC117572
0.7353 Intermediate Similarity NPC478101
0.7353 Intermediate Similarity NPC83965
0.7344 Intermediate Similarity NPC469373
0.7324 Intermediate Similarity NPC320119
0.7297 Intermediate Similarity NPC233071
0.7286 Intermediate Similarity NPC143396
0.7286 Intermediate Similarity NPC475004
0.7286 Intermediate Similarity NPC130618
0.7286 Intermediate Similarity NPC101622
0.7273 Intermediate Similarity NPC475984
0.7273 Intermediate Similarity NPC40082
0.7273 Intermediate Similarity NPC477829
0.7258 Intermediate Similarity NPC87394
0.7246 Intermediate Similarity NPC49863
0.7231 Intermediate Similarity NPC322002
0.7231 Intermediate Similarity NPC474267
0.7222 Intermediate Similarity NPC327383
0.7222 Intermediate Similarity NPC325627
0.7222 Intermediate Similarity NPC185186
0.7222 Intermediate Similarity NPC329914
0.7222 Intermediate Similarity NPC329890
0.7206 Intermediate Similarity NPC317881
0.7206 Intermediate Similarity NPC320642
0.7206 Intermediate Similarity NPC478099
0.7206 Intermediate Similarity NPC478098
0.7206 Intermediate Similarity NPC323045
0.72 Intermediate Similarity NPC218817
0.72 Intermediate Similarity NPC11796
0.72 Intermediate Similarity NPC182292
0.7183 Intermediate Similarity NPC4299
0.7183 Intermediate Similarity NPC318766
0.7164 Intermediate Similarity NPC470965
0.7162 Intermediate Similarity NPC271070
0.7143 Intermediate Similarity NPC474823
0.7143 Intermediate Similarity NPC218477
0.7123 Intermediate Similarity NPC227396
0.7119 Intermediate Similarity NPC216130
0.7119 Intermediate Similarity NPC180534
0.7105 Intermediate Similarity NPC471537
0.7105 Intermediate Similarity NPC263574
0.7105 Intermediate Similarity NPC469747
0.7101 Intermediate Similarity NPC328653
0.7101 Intermediate Similarity NPC284447
0.7083 Intermediate Similarity NPC477983
0.7083 Intermediate Similarity NPC477981
0.7069 Intermediate Similarity NPC76976
0.7067 Intermediate Similarity NPC84360
0.7059 Intermediate Similarity NPC475221
0.7049 Intermediate Similarity NPC48162
0.7049 Intermediate Similarity NPC28205
0.7049 Intermediate Similarity NPC284212
0.7042 Intermediate Similarity NPC236208
0.7042 Intermediate Similarity NPC329656
0.7042 Intermediate Similarity NPC199557
0.7031 Intermediate Similarity NPC325977
0.7027 Intermediate Similarity NPC113639
0.7027 Intermediate Similarity NPC285840
0.7027 Intermediate Similarity NPC327041
0.7027 Intermediate Similarity NPC475861
0.7018 Intermediate Similarity NPC270796
0.7015 Intermediate Similarity NPC174560
0.7015 Intermediate Similarity NPC125312
0.7013 Intermediate Similarity NPC200446
0.7 Intermediate Similarity NPC473357
0.7 Intermediate Similarity NPC193029
0.6986 Remote Similarity NPC326024
0.6986 Remote Similarity NPC477085
0.6986 Remote Similarity NPC474705
0.6984 Remote Similarity NPC322461
0.6974 Remote Similarity NPC260814
0.6974 Remote Similarity NPC39547
0.6974 Remote Similarity NPC267231
0.6974 Remote Similarity NPC323249
0.6974 Remote Similarity NPC27949
0.697 Remote Similarity NPC159650
0.697 Remote Similarity NPC322186

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC328776 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
0.8136 Intermediate Similarity NPD3194 Approved
0.8136 Intermediate Similarity NPD3196 Approved
0.8136 Intermediate Similarity NPD3195 Phase 2
0.8136 Intermediate Similarity NPD4266 Approved
0.8125 Intermediate Similarity NPD3197 Phase 1
0.7966 Intermediate Similarity NPD3172 Approved
0.7937 Intermediate Similarity NPD4246 Clinical (unspecified phase)
0.7719 Intermediate Similarity NPD5343 Approved
0.7627 Intermediate Similarity NPD29 Approved
0.7627 Intermediate Similarity NPD28 Approved
0.7619 Intermediate Similarity NPD6109 Phase 1
0.7586 Intermediate Similarity NPD3173 Approved
0.7368 Intermediate Similarity NPD4222 Approved
0.7368 Intermediate Similarity NPD39 Approved
0.7246 Intermediate Similarity NPD4247 Clinical (unspecified phase)
0.7237 Intermediate Similarity NPD5790 Clinical (unspecified phase)
0.7193 Intermediate Similarity NPD6097 Approved
0.7193 Intermediate Similarity NPD6096 Approved
0.7119 Intermediate Similarity NPD622 Approved
0.7069 Intermediate Similarity NPD3174 Discontinued
0.7018 Intermediate Similarity NPD5326 Phase 3
0.6974 Remote Similarity NPD4268 Approved
0.6974 Remote Similarity NPD4271 Approved
0.6962 Remote Similarity NPD7154 Phase 3
0.6923 Remote Similarity NPD5369 Approved
0.6835 Remote Similarity NPD6435 Approved
0.6795 Remote Similarity NPD4820 Approved
0.6795 Remote Similarity NPD4819 Approved
0.6795 Remote Similarity NPD4822 Approved
0.6795 Remote Similarity NPD4821 Approved
0.675 Remote Similarity NPD5362 Discontinued
0.6714 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6627 Remote Similarity NPD4251 Approved
0.6627 Remote Similarity NPD4250 Approved
0.6625 Remote Similarity NPD4270 Approved
0.6625 Remote Similarity NPD4269 Approved
0.661 Remote Similarity NPD2699 Approved
0.6588 Remote Similarity NPD46 Approved
0.6588 Remote Similarity NPD6698 Approved
0.6582 Remote Similarity NPD4252 Approved
0.6582 Remote Similarity NPD5368 Approved
0.6543 Remote Similarity NPD5331 Approved
0.6543 Remote Similarity NPD5332 Approved
0.6538 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6508 Remote Similarity NPD6927 Phase 3
0.6506 Remote Similarity NPD4249 Approved
0.6506 Remote Similarity NPD5786 Approved
0.65 Remote Similarity NPD4790 Discontinued
0.6471 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6471 Remote Similarity NPD6101 Approved
0.6462 Remote Similarity NPD3730 Approved
0.6462 Remote Similarity NPD3728 Approved
0.641 Remote Similarity NPD4756 Discovery
0.6395 Remote Similarity NPD7838 Discovery
0.6389 Remote Similarity NPD6108 Clinical (unspecified phase)
0.6386 Remote Similarity NPD5363 Approved
0.6364 Remote Similarity NPD8039 Approved
0.6329 Remote Similarity NPD3732 Approved
0.6322 Remote Similarity NPD7983 Approved
0.6322 Remote Similarity NPD6411 Approved
0.631 Remote Similarity NPD6422 Discontinued
0.6282 Remote Similarity NPD819 Approved
0.6282 Remote Similarity NPD818 Approved
0.6279 Remote Similarity NPD5370 Suspended
0.625 Remote Similarity NPD5778 Approved
0.625 Remote Similarity NPD5779 Approved
0.6207 Remote Similarity NPD5785 Approved
0.6197 Remote Similarity NPD2664 Clinical (unspecified phase)
0.619 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6164 Remote Similarity NPD7331 Phase 2
0.6164 Remote Similarity NPD3704 Approved
0.6136 Remote Similarity NPD4810 Clinical (unspecified phase)
0.6102 Remote Similarity NPD2270 Approved
0.6071 Remote Similarity NPD5766 Clinical (unspecified phase)
0.6067 Remote Similarity NPD5781 Clinical (unspecified phase)
0.6067 Remote Similarity NPD6399 Phase 3
0.6044 Remote Similarity NPD7839 Suspended
0.6032 Remote Similarity NPD6125 Clinical (unspecified phase)
0.6024 Remote Similarity NPD5209 Approved
0.6 Remote Similarity NPD1733 Clinical (unspecified phase)
0.597 Remote Similarity NPD3729 Clinical (unspecified phase)
0.5955 Remote Similarity NPD7637 Suspended
0.5857 Remote Similarity NPD585 Clinical (unspecified phase)
0.5824 Remote Similarity NPD7748 Approved
0.5806 Remote Similarity NPD3199 Clinical (unspecified phase)
0.5783 Remote Similarity NPD8259 Clinical (unspecified phase)
0.5763 Remote Similarity NPD9448 Phase 2
0.5763 Remote Similarity NPD633 Phase 3
0.5761 Remote Similarity NPD1698 Clinical (unspecified phase)
0.5747 Remote Similarity NPD5330 Approved
0.5747 Remote Similarity NPD7521 Approved
0.5747 Remote Similarity NPD7334 Approved
0.5747 Remote Similarity NPD6409 Approved
0.5747 Remote Similarity NPD7146 Approved
0.5747 Remote Similarity NPD6684 Approved
0.5745 Remote Similarity NPD8029 Clinical (unspecified phase)
0.573 Remote Similarity NPD1695 Approved
0.5714 Remote Similarity NPD4265 Approved
0.5698 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5698 Remote Similarity NPD4786 Approved
0.5676 Remote Similarity NPD5325 Clinical (unspecified phase)
0.5647 Remote Similarity NPD3667 Approved
0.5638 Remote Similarity NPD7902 Approved
0.5625 Remote Similarity NPD5344 Discontinued
0.5618 Remote Similarity NPD6903 Approved
0.5618 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5604 Remote Similarity NPD7515 Phase 2
0.56 Remote Similarity NPD7341 Phase 2

Structure

External Identifiers

PubChem CID   5283201
ChEMBL   CHEMBL564452
ZINC  

Physicochemical Properties

Molecular Weight:  320.24
ALogP:  0.1908
MLogP:  3.33
XLogP:  6.368
# Rotatable Bonds:  16
Polar Surface Area:  49.83
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  1
# Heavy Atoms:  23

Download Data

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