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Showing metabocard for (4Z)-6-[(1R,4S,5S,6R)-6-[(1E,3S,5Z,8Z)-3-hydroperoxyundeca-1,5,8-trien-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoyl-CoA (HMDB0301565)

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Record Information
Version5.0
StatusPredicted
Creation Date2021-09-22 01:03:40 UTC
Update Date2021-10-01 16:55:00 UTC
HMDB IDHMDB0301565
Secondary Accession NumbersNone
Metabolite Identification
Common Name(4Z)-6-[(1R,4S,5S,6R)-6-[(1E,3S,5Z,8Z)-3-hydroperoxyundeca-1,5,8-trien-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoyl-CoA
Description(4z)-6-[(1r,4s,5s,6r)-6-[(1e,3s,5z,8z)-3-hydroperoxyundeca-1,5,8-trien-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoyl-coa is an acyl-CoA or acyl-coenzyme A. More specifically, it is a (4Z)-6-[(1R_4S_5S_6R)-6-[(1E_3S_5Z_8Z)-3-hydroperoxyundeca-1_5_8-trien-1-yl]-2_3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoic acid thioester of coenzyme A. (4z)-6-[(1r,4s,5s,6r)-6-[(1e,3s,5z,8z)-3-hydroperoxyundeca-1,5,8-trien-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoyl-coa is an acyl-CoA with 22 fatty acid group as the acyl moiety attached to coenzyme A. Coenzyme A was discovered in 1946 by Fritz Lipmann (Journal of Biological Chemistry (1946) 162 (3): 743–744) and its structure was determined in the early 1950s at the Lister Institute in London. Coenzyme A is a complex, thiol-containing molecule that is naturally synthesized from pantothenate (vitamin B5), which is found in various foods such as meat, vegetables, cereal grains, legumes, eggs, and milk. More specifically, coenzyme A (CoASH or CoA) consists of a beta-mercaptoethylamine group linked to the vitamin pantothenic acid (B5) through an amide linkage and 3'-phosphorylated ADP. Coenzyme A is synthesized in a five-step process that requires four molecules of ATP, pantothenate and cysteine. It is believed that there are more than 1100 types of acyl-CoA’s in the human body, which also corresponds to the number of acylcarnitines in the human body. Acyl-CoAs exists in all living species, ranging from bacteria to plants to humans. The general role of acyl-CoA’s is to assist in transferring fatty acids from the cytoplasm to mitochondria. This process facilitates the production of fatty acids in cells, which are essential in cell membrane structure. Acyl-CoA's are also susceptible to beta oxidation, forming, ultimately, acetyl-CoA. Acetyl-CoA can enter the citric acid cycle, eventually forming several equivalents of ATP. In this way, fats are converted to ATP -- or biochemical energy. Acyl-CoAs can be classified into 9 different categories depending on the size of their acyl-group: 1) short-chain acyl-CoAs; 2) medium-chain acyl-CoAs; 3) long-chain acyl-CoAs; and 4) very long-chain acyl-CoAs; 5) hydroxy acyl-CoAs; 6) branched chain acyl-CoAs; 7) unsaturated acyl-CoAs; 8) dicarboxylic acyl-CoAs and 9) miscellaneous acyl-CoAs. Short-chain acyl-CoAs have acyl-groups with two to four carbons (C2-C4), medium-chain acyl-CoAs have acyl-groups with five to eleven carbons (C5-C11), long-chain acyl-CoAs have acyl-groups with twelve to twenty carbons (C12-C20) while very long-chain acyl-CoAs have acyl groups with more than 20 carbons. (4z)-6-[(1r,4s,5s,6r)-6-[(1e,3s,5z,8z)-3-hydroperoxyundeca-1,5,8-trien-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoyl-coa is therefore classified as a very long chain acyl-CoA. The oxidative degradation of fatty acids is a two-step process, catalyzed by acyl-CoA synthetase/synthase. Fatty acids are first converted to their acyl phosphate, the precursor to acyl-CoA. The latter conversion is mediated by acyl-CoA synthase. Three types of acyl-CoA synthases are employed, depending on the chain length of the fatty acid. (4z)-6-[(1r,4s,5s,6r)-6-[(1e,3s,5z,8z)-3-hydroperoxyundeca-1,5,8-trien-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoyl-coa, being a very long chain acyl-CoA is a substrate for very long chain acyl-CoA synthase. The second step of fatty acid degradation is beta oxidation. Beta oxidation occurs in mitochondria and, in the case of very long chain acyl-CoAs, the peroxisome. After its formation in the cytosol, (4Z)-6-[(1R,4S,5S,6R)-6-[(1E,3S,5Z,8Z)-3-hydroperoxyundeca-1,5,8-trien-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoyl-CoA is transported into the mitochondria, the locus of beta oxidation. Transport of (4Z)-6-[(1R,4S,5S,6R)-6-[(1E,3S,5Z,8Z)-3-hydroperoxyundeca-1,5,8-trien-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoyl-CoA into the mitochondria requires carnitine palmitoyltransferase 1 (CPT1), which converts (4Z)-6-[(1R,4S,5S,6R)-6-[(1E,3S,5Z,8Z)-3-hydroperoxyundeca-1,5,8-trien-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoyl-CoA into (4Z)-6-[(1R_4S_5S_6R)-6-[(1E_3S_5Z_8Z)-3-hydroperoxyundeca-1_5_8-trien-1-yl]-2_3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoylcarnitine, which gets transported into the mitochondrial matrix. Once in the matrix, (4Z)-6-[(1R_4S_5S_6R)-6-[(1E_3S_5Z_8Z)-3-hydroperoxyundeca-1_5_8-trien-1-yl]-2_3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoylcarnitine is converted back to (4Z)-6-[(1R,4S,5S,6R)-6-[(1E,3S,5Z,8Z)-3-hydroperoxyundeca-1,5,8-trien-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoyl-CoA by CPT2, whereupon beta-oxidation can begin. Beta oxidation of (4Z)-6-[(1R,4S,5S,6R)-6-[(1E,3S,5Z,8Z)-3-hydroperoxyundeca-1,5,8-trien-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoyl-CoA occurs in four steps. First, since (4Z)-6-[(1R,4S,5S,6R)-6-[(1E,3S,5Z,8Z)-3-hydroperoxyundeca-1,5,8-trien-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoyl-CoA is a very long chain acyl-CoA it is the substrate for a very long chain acyl-CoA dehydrogenase, which catalyzes dehydrogenation of (4Z)-6-[(1R,4S,5S,6R)-6-[(1E,3S,5Z,8Z)-3-hydroperoxyundeca-1,5,8-trien-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoyl-CoA, creating a double bond between the alpha and beta carbons. FAD is the hydrogen acceptor, yielding FADH2. Second, Enoyl-CoA hydrase catalyzes the addition of water across the newly formed double bond to make an alcohol. Third, 3-hydroxyacyl-CoA dehydrogenase oxidizes the alcohol group to a ketone and NADH is produced from NAD+. Finally, Thiolase cleaves between the alpha carbon and ketone to release one molecule of acetyl-CoA and a new acyl-CoA which is now 2 carbons shorter. This four-step process repeats until (4Z)-6-[(1R,4S,5S,6R)-6-[(1E,3S,5Z,8Z)-3-hydroperoxyundeca-1,5,8-trien-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoyl-CoA has had all its carbons removed from the chain, leaving only acetyl-CoA. Beta oxidation, as well as alpha-oxidation, also occurs in the peroxisome. The peroxisome handles beta oxidation of fatty acids that have more than 20 carbons in their chain because the peroxisome contains very-long-chain Acyl-CoA synthetases and dehydrogenases. The heart primarily metabolizes fat for energy and Acyl-CoA metabolism has been identified as a critical molecule in early-stage heart muscle pump failure. Cellular acyl-CoA content also correlates with insulin resistance, suggesting that it can mediate lipotoxicity in non-adipose tissues. Acyl-CoA: diacylglycerol acyltransferase (DGAT) plays an important role in energy metabolism on account of key enzyme in triglyceride biosynthesis. The study of acyl-CoAs is an active area of research and it is likely that many novel acyl-CoAs will be discovered in the coming years. It is also likely that many novel roles in health and disease will be uncovered for these molecules.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0301565 ((4Z)-6-[(1R,4S,5S,6R)-6-[(1E,3S,5Z,8Z)-3-hydroperoxyundeca-1,5,8-trien-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoyl-CoA)


  Mrv1652304102105382D          

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M  END
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3D MOL for HMDB0301565 ((4Z)-6-[(1R,4S,5S,6R)-6-[(1E,3S,5Z,8Z)-3-hydroperoxyundeca-1,5,8-trien-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoyl-CoA)

HMDB0301565
     RDKit          3D
(4Z)-6-[(1R,4S,5S,6R)-6-[(1E,3S,5Z,8Z)-3-hydroperoxyundeca-1,5,8-trien-1-yl]-...
141145  0  0  0  0  0  0  0  0999 V2000
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  -17.0181   -1.6685    1.7632 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.9502   -2.4176    1.8928 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
Download

3D SDF for HMDB0301565 ((4Z)-6-[(1R,4S,5S,6R)-6-[(1E,3S,5Z,8Z)-3-hydroperoxyundeca-1,5,8-trien-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoyl-CoA)


  Mrv1652304102105382D          

 75 79  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
HMDB0301565

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC=CCC=CCC(OO)C=CC1C2CC(OO2)C1CC=CCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N

> <INCHI_IDENTIFIER>
InChI=1S/C43H66N7O21P3S/c1-4-5-6-7-8-10-13-27(67-56)16-17-29-28(30-22-31(29)69-68-30)14-11-9-12-15-34(52)75-21-20-45-33(51)18-19-46-41(55)38(54)43(2,3)24-65-74(62,63)71-73(60,61)64-23-32-37(70-72(57,58)59)36(53)42(66-32)50-26-49-35-39(44)47-25-48-40(35)50/h5-6,8-11,16-17,25-32,36-38,42,53-54,56H,4,7,12-15,18-24H2,1-3H3,(H,45,51)(H,46,55)(H,60,61)(H,62,63)(H2,44,47,48)(H2,57,58,59)

> <INCHI_KEY>
RHAAWTZEYOCREL-UHFFFAOYSA-N

> <FORMULA>
C43H66N7O21P3S

> <MOLECULAR_WEIGHT>
1142.01

> <EXACT_MASS>
1141.324534341

> <JCHEM_ACCEPTOR_COUNT>
21

> <JCHEM_ATOM_COUNT>
141

> <JCHEM_AVERAGE_POLARIZABILITY>
110.7884170104789

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[5-(6-amino-9H-purin-9-yl)-2-[({[({3-[(2-{[2-({6-[6-(3-hydroperoxyundeca-1,5,8-trien-1-yl)-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
2.16

> <JCHEM_LOGP>
-1.0867164188234544

> <ALOGPS_LOGS>
-3.54

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.900120734722976

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8209787813350444

> <JCHEM_PKA_STRONGEST_BASIC>
4.006053262292161

> <JCHEM_POLAR_SURFACE_AREA>
411.55000000000007

> <JCHEM_REFRACTIVITY>
270.3916

> <JCHEM_ROTATABLE_BOND_COUNT>
33

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.29e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[5-(6-aminopurin-9-yl)-2-{[({3-[(2-{[2-({6-[6-(3-hydroperoxyundeca-1,5,8-trien-1-yl)-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0301565 ((4Z)-6-[(1R,4S,5S,6R)-6-[(1E,3S,5Z,8Z)-3-hydroperoxyundeca-1,5,8-trien-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoyl-CoA)

HMDB0301565
     RDKit          3D
(4Z)-6-[(1R,4S,5S,6R)-6-[(1E,3S,5Z,8Z)-3-hydroperoxyundeca-1,5,8-trien-1-yl]-...
141145  0  0  0  0  0  0  0  0999 V2000
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  -15.1902   -4.2262    1.0050 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.2789   -3.0204   -0.1620 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.1542   -1.2529    2.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6416   -1.2166    2.3681 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2100    0.0693    1.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9932   -2.5935    0.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0122   -1.3254    0.7018 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8724    1.0810    0.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8898    0.7534    0.8115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8291    2.1340    2.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0318    3.3000    1.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2716    4.5030    1.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4597    4.4095   -0.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2485    1.9016   -1.4370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3606    2.5847   -0.6688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1489    2.6406   -2.2348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5543    0.1873   -2.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7992   -1.0908   -1.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9142   -0.1617    0.7998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1262    1.5145    0.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3790   -0.6396   -1.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6308    1.0453   -1.6968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9651    3.3361   -1.3634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8849    4.7311   -0.9391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3617    4.2890   -2.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9740    4.1543   -3.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4814    2.0472   -4.0506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7497    0.3371   -4.5996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2953   -0.5667   -3.1756 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8909   -1.1869   -3.8685 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5469    0.4415   -3.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5100   -0.3197   -1.1409 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5059   -1.9827    0.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5318   -2.1001   -1.5139 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6407    1.3750    0.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1552   -0.1343    1.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1565    1.1458    1.8822 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8925    0.5807   -0.7396 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3162    1.4866   -0.9879 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3640    1.8182    0.4954 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3050    0.4502    2.3718 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6642   -1.2834    2.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1381    0.1921    2.7667 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8968    0.1089   -0.8038 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8710   -0.3118   -1.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4212   -2.0008   -1.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3189   -0.4699   -1.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.5839    1.2311    2.0340 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4839    1.8336   -1.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.0934    1.5507   -1.1002 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.6743    3.1219   -0.3772 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.4091    0.0664    3.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.8365   -1.1445    2.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5217   -0.2466    2.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1920   -2.5538    0.4584 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.2787   -4.8929    0.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.1661   -3.6954   -2.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6769   -1.7745   -2.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  2  3
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  3
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  3
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  2  0
 35 37  1  0
 37 38  1  0
 37 39  1  0
 39 40  1  0
 39 41  1  0
 39 42  1  0
 42 43  1  0
 43 44  1  0
 44 45  2  0
 44 46  1  0
 44 47  1  0
 47 48  1  0
 48 49  2  0
 48 50  1  0
 48 51  1  0
 51 52  1  0
 52 53  1  0
 53 54  1  0
 54 55  1  0
 55 56  1  0
 56 57  1  0
 57 58  2  0
 58 59  1  0
 59 60  2  0
 60 61  1  0
 60 62  1  0
 62 63  2  0
 63 64  1  0
 64 65  2  0
 55 66  1  0
 66 67  1  0
 66 68  1  0
 68 69  1  0
 69 70  1  0
 70 71  2  0
 70 72  1  0
 70 73  1  0
  9 74  1  0
 74 75  1  0
 18 12  1  0
 68 53  1  0
 17 13  1  0
 65 56  1  0
 65 59  1  0
  1 76  1  0
  1 77  1  0
  1 78  1  0
  2 79  1  0
  2 80  1  0
  3 81  1  0
  4 82  1  0
  5 83  1  0
  5 84  1  0
  6 85  1  0
  7 86  1  0
  8 87  1  0
  8 88  1  0
  9 89  1  0
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 21101  1  0
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 40118  1  0
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 61133  1  0
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 63135  1  0
 66136  1  0
 67137  1  0
 68138  1  0
 72139  1  0
 73140  1  0
 75141  1  0
M  END
Download

PDB for HMDB0301565 ((4Z)-6-[(1R,4S,5S,6R)-6-[(1E,3S,5Z,8Z)-3-hydroperoxyundeca-1,5,8-trien-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoyl-CoA)

HEADER    PROTEIN                                 10-APR-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-APR-21         0                                  
HETATM    1  O   UNK     0      25.692 -15.308   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      25.400 -13.796   0.000  0.00  0.00           C+0
HETATM    3  S   UNK     0      23.945 -13.292   0.000  0.00  0.00           S+0
HETATM    4  C   UNK     0      22.781 -14.300   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.326 -13.796   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      20.162 -14.804   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      18.707 -14.300   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      18.416 -12.788   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      17.543 -15.308   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.087 -14.804   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      15.796 -13.292   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      14.341 -12.788   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      14.050 -11.276   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      13.177 -13.796   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      13.468 -15.308   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      11.722 -13.292   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.218 -14.747   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.226 -11.837   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.267 -12.788   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.103 -13.796   0.000  0.00  0.00           O+0
HETATM   21  P   UNK     0       7.647 -13.292   0.000  0.00  0.00           P+0
HETATM   22  O   UNK     0       7.143 -14.747   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       8.152 -11.837   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.192 -12.788   0.000  0.00  0.00           O+0
HETATM   25  P   UNK     0       5.028 -13.796   0.000  0.00  0.00           P+0
HETATM   26  O   UNK     0       6.036 -14.960   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       4.020 -12.632   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       3.864 -14.804   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.409 -14.300   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.245 -15.308   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.376 -16.843   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -0.043 -17.442   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0      -0.392 -18.942   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0       0.616 -20.106   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0      -0.179 -21.424   0.000  0.00  0.00           N+0
HETATM   36  C   UNK     0      -1.679 -21.075   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.942 -21.956   0.000  0.00  0.00           C+0
HETATM   38  N   UNK     0      -4.337 -21.303   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0      -4.468 -19.768   0.000  0.00  0.00           C+0
HETATM   40  N   UNK     0      -3.205 -18.887   0.000  0.00  0.00           N+0
HETATM   41  C   UNK     0      -1.810 -19.541   0.000  0.00  0.00           C+0
HETATM   42  N   UNK     0      -2.811 -23.491   0.000  0.00  0.00           N+0
HETATM   43  C   UNK     0      -1.051 -16.278   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -2.585 -16.409   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -0.255 -14.959   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -0.854 -13.540   0.000  0.00  0.00           O+0
HETATM   47  P   UNK     0       0.075 -12.312   0.000  0.00  0.00           P+0
HETATM   48  O   UNK     0       1.303 -13.241   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      -1.153 -11.383   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0       1.004 -11.084   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      26.565 -12.788   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      28.020 -13.292   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      28.311 -14.804   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      27.147 -15.812   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      27.438 -17.325   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      26.274 -18.333   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      24.818 -17.829   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      23.654 -18.837   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0      23.945 -20.349   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      25.400 -20.853   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      25.488 -19.268   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      26.565 -19.845   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      28.020 -20.349   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      28.311 -21.861   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      29.766 -22.365   0.000  0.00  0.00           C+0
HETATM   66  O   UNK     0      30.930 -21.357   0.000  0.00  0.00           O+0
HETATM   67  O   UNK     0      32.385 -21.861   0.000  0.00  0.00           O+0
HETATM   68  C   UNK     0      30.057 -23.878   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      31.512 -24.382   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      31.803 -25.894   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      33.258 -26.398   0.000  0.00  0.00           C+0
HETATM   72  C   UNK     0      34.423 -25.390   0.000  0.00  0.00           C+0
HETATM   73  C   UNK     0      35.878 -25.894   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0      37.042 -24.886   0.000  0.00  0.00           C+0
HETATM   75  C   UNK     0      38.497 -25.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   51                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21   25                                                       
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   45                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   43                                                  
CONECT   33   32   34   41                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   41                                                  
CONECT   37   36   38   42                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   36   33                                                  
CONECT   42   37                                                            
CONECT   43   32   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   30   46                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48   49   50                                             
CONECT   48   47                                                            
CONECT   49   47                                                            
CONECT   50   47                                                            
CONECT   51    2   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57   62                                                  
CONECT   57   56   58   61                                                  
CONECT   58   57   59                                                       
CONECT   59   58   60                                                       
CONECT   60   59   61   62                                                  
CONECT   61   60   57                                                       
CONECT   62   60   56   63                                                  
CONECT   63   62   64                                                       
CONECT   64   63   65                                                       
CONECT   65   64   66   68                                                  
CONECT   66   65   67                                                       
CONECT   67   66                                                            
CONECT   68   65   69                                                       
CONECT   69   68   70                                                       
CONECT   70   69   71                                                       
CONECT   71   70   72                                                       
CONECT   72   71   73                                                       
CONECT   73   72   74                                                       
CONECT   74   73   75                                                       
CONECT   75   74                                                            
MASTER        0    0    0    0    0    0    0    0   75    0  158    0
END
Download

3D PDB for HMDB0301565 ((4Z)-6-[(1R,4S,5S,6R)-6-[(1E,3S,5Z,8Z)-3-hydroperoxyundeca-1,5,8-trien-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoyl-CoA)

COMPND    HMDB0301565
HETATM    1  C1  UNL     1     -19.192  -1.901   0.685  1.00  0.00           C  
HETATM    2  C2  UNL     1     -17.756  -1.405   0.515  1.00  0.00           C  
HETATM    3  C3  UNL     1     -17.018  -1.669   1.763  1.00  0.00           C  
HETATM    4  C4  UNL     1     -15.950  -2.418   1.893  1.00  0.00           C  
HETATM    5  C5  UNL     1     -15.319  -3.125   0.771  1.00  0.00           C  
HETATM    6  C6  UNL     1     -13.900  -2.591   0.614  1.00  0.00           C  
HETATM    7  C7  UNL     1     -13.465  -1.648   1.412  1.00  0.00           C  
HETATM    8  C8  UNL     1     -12.144  -1.048   1.376  1.00  0.00           C  
HETATM    9  C9  UNL     1     -11.199  -1.525   0.326  1.00  0.00           C  
HETATM   10  C10 UNL     1      -9.893  -0.751   0.507  1.00  0.00           C  
HETATM   11  C11 UNL     1      -9.969   0.550   0.405  1.00  0.00           C  
HETATM   12  C12 UNL     1      -8.742   1.393   0.568  1.00  0.00           C  
HETATM   13  C13 UNL     1      -8.974   2.444   1.634  1.00  0.00           C  
HETATM   14  C14 UNL     1      -8.080   3.563   1.137  1.00  0.00           C  
HETATM   15  C15 UNL     1      -8.798   3.620  -0.227  1.00  0.00           C  
HETATM   16  O1  UNL     1     -10.104   3.638   0.212  1.00  0.00           O  
HETATM   17  O2  UNL     1     -10.213   3.010   1.330  1.00  0.00           O  
HETATM   18  C16 UNL     1      -8.494   2.205  -0.683  1.00  0.00           C  
HETATM   19  C17 UNL     1      -7.119   2.078  -1.250  1.00  0.00           C  
HETATM   20  C18 UNL     1      -6.859   0.654  -1.578  1.00  0.00           C  
HETATM   21  C19 UNL     1      -5.876  -0.037  -1.063  1.00  0.00           C  
HETATM   22  C20 UNL     1      -4.924   0.527  -0.103  1.00  0.00           C  
HETATM   23  C21 UNL     1      -3.540   0.431  -0.788  1.00  0.00           C  
HETATM   24  C22 UNL     1      -2.524   1.001   0.098  1.00  0.00           C  
HETATM   25  O3  UNL     1      -1.914   0.319   0.907  1.00  0.00           O  
HETATM   26  S1  UNL     1      -2.087   2.749   0.075  1.00  0.00           S  
HETATM   27  C23 UNL     1      -2.872   3.625  -1.241  1.00  0.00           C  
HETATM   28  C24 UNL     1      -2.265   3.571  -2.573  1.00  0.00           C  
HETATM   29  N1  UNL     1      -1.922   2.360  -3.203  1.00  0.00           N  
HETATM   30  C25 UNL     1      -0.869   1.501  -2.789  1.00  0.00           C  
HETATM   31  O4  UNL     1      -0.168   1.823  -1.814  1.00  0.00           O  
HETATM   32  C26 UNL     1      -0.596   0.252  -3.493  1.00  0.00           C  
HETATM   33  C27 UNL     1       0.789  -0.217  -3.282  1.00  0.00           C  
HETATM   34  N2  UNL     1       1.189  -0.466  -1.915  1.00  0.00           N  
HETATM   35  C28 UNL     1       2.519  -0.910  -1.712  1.00  0.00           C  
HETATM   36  O5  UNL     1       3.248  -1.059  -2.751  1.00  0.00           O  
HETATM   37  C29 UNL     1       3.131  -1.211  -0.424  1.00  0.00           C  
HETATM   38  O6  UNL     1       4.444  -1.695  -0.619  1.00  0.00           O  
HETATM   39  C30 UNL     1       3.254  -0.034   0.519  1.00  0.00           C  
HETATM   40  C31 UNL     1       1.962   0.583   0.920  1.00  0.00           C  
HETATM   41  C32 UNL     1       4.040   1.067  -0.231  1.00  0.00           C  
HETATM   42  C33 UNL     1       4.106  -0.403   1.691  1.00  0.00           C  
HETATM   43  O7  UNL     1       5.380  -0.764   1.188  1.00  0.00           O  
HETATM   44  P1  UNL     1       6.444  -1.203   2.409  1.00  0.00           P  
HETATM   45  O8  UNL     1       5.636  -1.867   3.522  1.00  0.00           O  
HETATM   46  O9  UNL     1       7.172   0.204   3.044  1.00  0.00           O  
HETATM   47  O10 UNL     1       7.644  -2.270   1.890  1.00  0.00           O  
HETATM   48  P2  UNL     1       8.259  -1.758   0.405  1.00  0.00           P  
HETATM   49  O11 UNL     1       8.192  -2.943  -0.544  1.00  0.00           O  
HETATM   50  O12 UNL     1       7.345  -0.516  -0.270  1.00  0.00           O  
HETATM   51  O13 UNL     1       9.860  -1.256   0.629  1.00  0.00           O  
HETATM   52  C34 UNL     1      10.494  -1.068  -0.601  1.00  0.00           C  
HETATM   53  C35 UNL     1      11.922  -0.603  -0.472  1.00  0.00           C  
HETATM   54  O14 UNL     1      11.905   0.604   0.202  1.00  0.00           O  
HETATM   55  C36 UNL     1      12.881   0.572   1.168  1.00  0.00           C  
HETATM   56  N3  UNL     1      14.133   1.007   0.603  1.00  0.00           N  
HETATM   57  C37 UNL     1      14.258   1.596  -0.614  1.00  0.00           C  
HETATM   58  N4  UNL     1      15.545   1.873  -0.826  1.00  0.00           N  
HETATM   59  C38 UNL     1      16.277   1.478   0.227  1.00  0.00           C  
HETATM   60  C39 UNL     1      17.631   1.520   0.530  1.00  0.00           C  
HETATM   61  N5  UNL     1      18.543   2.088  -0.397  1.00  0.00           N  
HETATM   62  N6  UNL     1      17.999   1.006   1.724  1.00  0.00           N  
HETATM   63  C40 UNL     1      17.115   0.483   2.578  1.00  0.00           C  
HETATM   64  N7  UNL     1      15.819   0.453   2.265  1.00  0.00           N  
HETATM   65  C41 UNL     1      15.365   0.937   1.110  1.00  0.00           C  
HETATM   66  C42 UNL     1      12.889  -0.852   1.649  1.00  0.00           C  
HETATM   67  O15 UNL     1      11.832  -1.061   2.499  1.00  0.00           O  
HETATM   68  C43 UNL     1      12.699  -1.597   0.324  1.00  0.00           C  
HETATM   69  O16 UNL     1      13.978  -1.771  -0.266  1.00  0.00           O  
HETATM   70  P3  UNL     1      14.199  -3.413  -0.520  1.00  0.00           P  
HETATM   71  O17 UNL     1      12.988  -4.048  -1.144  1.00  0.00           O  
HETATM   72  O18 UNL     1      14.574  -4.231   0.932  1.00  0.00           O  
HETATM   73  O19 UNL     1      15.499  -3.693  -1.596  1.00  0.00           O  
HETATM   74  O20 UNL     1     -11.672  -1.095  -0.931  1.00  0.00           O  
HETATM   75  O21 UNL     1     -11.425  -2.058  -1.789  1.00  0.00           O  
HETATM   76  H1  UNL     1     -19.847  -1.143   0.236  1.00  0.00           H  
HETATM   77  H2  UNL     1     -19.413  -1.907   1.780  1.00  0.00           H  
HETATM   78  H3  UNL     1     -19.276  -2.912   0.260  1.00  0.00           H  
HETATM   79  H4  UNL     1     -17.774  -0.282   0.349  1.00  0.00           H  
HETATM   80  H5  UNL     1     -17.264  -1.864  -0.341  1.00  0.00           H  
HETATM   81  H6  UNL     1     -17.422  -1.173   2.685  1.00  0.00           H  
HETATM   82  H7  UNL     1     -15.499  -2.535   2.916  1.00  0.00           H  
HETATM   83  H8  UNL     1     -15.799  -3.021  -0.204  1.00  0.00           H  
HETATM   84  H9  UNL     1     -15.190  -4.226   1.005  1.00  0.00           H  
HETATM   85  H10 UNL     1     -13.279  -3.020  -0.162  1.00  0.00           H  
HETATM   86  H11 UNL     1     -14.154  -1.253   2.190  1.00  0.00           H  
HETATM   87  H12 UNL     1     -11.642  -1.217   2.368  1.00  0.00           H  
HETATM   88  H13 UNL     1     -12.210   0.069   1.258  1.00  0.00           H  
HETATM   89  H14 UNL     1     -10.993  -2.593   0.298  1.00  0.00           H  
HETATM   90  H15 UNL     1      -9.012  -1.325   0.702  1.00  0.00           H  
HETATM   91  H16 UNL     1     -10.872   1.081   0.200  1.00  0.00           H  
HETATM   92  H17 UNL     1      -7.890   0.753   0.812  1.00  0.00           H  
HETATM   93  H18 UNL     1      -8.829   2.134   2.643  1.00  0.00           H  
HETATM   94  H19 UNL     1      -7.032   3.300   1.061  1.00  0.00           H  
HETATM   95  H20 UNL     1      -8.272   4.503   1.699  1.00  0.00           H  
HETATM   96  H21 UNL     1      -8.460   4.410  -0.853  1.00  0.00           H  
HETATM   97  H22 UNL     1      -9.249   1.902  -1.437  1.00  0.00           H  
HETATM   98  H23 UNL     1      -6.361   2.585  -0.669  1.00  0.00           H  
HETATM   99  H24 UNL     1      -7.149   2.641  -2.235  1.00  0.00           H  
HETATM  100  H25 UNL     1      -7.554   0.187  -2.300  1.00  0.00           H  
HETATM  101  H26 UNL     1      -5.799  -1.091  -1.396  1.00  0.00           H  
HETATM  102  H27 UNL     1      -4.914  -0.162   0.800  1.00  0.00           H  
HETATM  103  H28 UNL     1      -5.126   1.515   0.296  1.00  0.00           H  
HETATM  104  H29 UNL     1      -3.379  -0.640  -1.022  1.00  0.00           H  
HETATM  105  H30 UNL     1      -3.631   1.045  -1.697  1.00  0.00           H  
HETATM  106  H31 UNL     1      -3.965   3.336  -1.363  1.00  0.00           H  
HETATM  107  H32 UNL     1      -2.885   4.731  -0.939  1.00  0.00           H  
HETATM  108  H33 UNL     1      -1.362   4.289  -2.587  1.00  0.00           H  
HETATM  109  H34 UNL     1      -2.974   4.154  -3.264  1.00  0.00           H  
HETATM  110  H35 UNL     1      -2.481   2.047  -4.051  1.00  0.00           H  
HETATM  111  H36 UNL     1      -0.750   0.337  -4.600  1.00  0.00           H  
HETATM  112  H37 UNL     1      -1.295  -0.567  -3.176  1.00  0.00           H  
HETATM  113  H38 UNL     1       0.891  -1.187  -3.868  1.00  0.00           H  
HETATM  114  H39 UNL     1       1.547   0.442  -3.787  1.00  0.00           H  
HETATM  115  H40 UNL     1       0.510  -0.320  -1.141  1.00  0.00           H  
HETATM  116  H41 UNL     1       2.506  -1.983   0.081  1.00  0.00           H  
HETATM  117  H42 UNL     1       4.532  -2.100  -1.514  1.00  0.00           H  
HETATM  118  H43 UNL     1       1.641   1.375   0.197  1.00  0.00           H  
HETATM  119  H44 UNL     1       1.155  -0.134   1.153  1.00  0.00           H  
HETATM  120  H45 UNL     1       2.156   1.146   1.882  1.00  0.00           H  
HETATM  121  H46 UNL     1       4.892   0.581  -0.740  1.00  0.00           H  
HETATM  122  H47 UNL     1       3.316   1.487  -0.988  1.00  0.00           H  
HETATM  123  H48 UNL     1       4.364   1.818   0.495  1.00  0.00           H  
HETATM  124  H49 UNL     1       4.305   0.450   2.372  1.00  0.00           H  
HETATM  125  H50 UNL     1       3.664  -1.283   2.199  1.00  0.00           H  
HETATM  126  H51 UNL     1       8.138   0.192   2.767  1.00  0.00           H  
HETATM  127  H52 UNL     1       7.897   0.109  -0.804  1.00  0.00           H  
HETATM  128  H53 UNL     1       9.871  -0.312  -1.165  1.00  0.00           H  
HETATM  129  H54 UNL     1      10.421  -2.001  -1.224  1.00  0.00           H  
HETATM  130  H55 UNL     1      12.319  -0.470  -1.507  1.00  0.00           H  
HETATM  131  H56 UNL     1      12.584   1.231   2.034  1.00  0.00           H  
HETATM  132  H57 UNL     1      13.484   1.834  -1.338  1.00  0.00           H  
HETATM  133  H58 UNL     1      19.093   1.551  -1.100  1.00  0.00           H  
HETATM  134  H59 UNL     1      18.674   3.122  -0.377  1.00  0.00           H  
HETATM  135  H60 UNL     1      17.409   0.066   3.547  1.00  0.00           H  
HETATM  136  H61 UNL     1      13.836  -1.145   2.136  1.00  0.00           H  
HETATM  137  H62 UNL     1      11.522  -0.247   2.958  1.00  0.00           H  
HETATM  138  H63 UNL     1      12.192  -2.554   0.458  1.00  0.00           H  
HETATM  139  H64 UNL     1      15.279  -4.893   0.794  1.00  0.00           H  
HETATM  140  H65 UNL     1      15.166  -3.695  -2.532  1.00  0.00           H  
HETATM  141  H66 UNL     1     -11.677  -1.774  -2.697  1.00  0.00           H  
CONECT    1    2   76   77   78
CONECT    2    3   79   80
CONECT    3    4    4   81
CONECT    4    5   82
CONECT    5    6   83   84
CONECT    6    7    7   85
CONECT    7    8   86
CONECT    8    9   87   88
CONECT    9   10   74   89
CONECT   10   11   11   90
CONECT   11   12   91
CONECT   12   13   18   92
CONECT   13   14   17   93
CONECT   14   15   94   95
CONECT   15   16   18   96
CONECT   16   17
CONECT   18   19   97
CONECT   19   20   98   99
CONECT   20   21   21  100
CONECT   21   22  101
CONECT   22   23  102  103
CONECT   23   24  104  105
CONECT   24   25   25   26
CONECT   26   27
CONECT   27   28  106  107
CONECT   28   29  108  109
CONECT   29   30  110
CONECT   30   31   31   32
CONECT   32   33  111  112
CONECT   33   34  113  114
CONECT   34   35  115
CONECT   35   36   36   37
CONECT   37   38   39  116
CONECT   38  117
CONECT   39   40   41   42
CONECT   40  118  119  120
CONECT   41  121  122  123
CONECT   42   43  124  125
CONECT   43   44
CONECT   44   45   45   46   47
CONECT   46  126
CONECT   47   48
CONECT   48   49   49   50   51
CONECT   50  127
CONECT   51   52
CONECT   52   53  128  129
CONECT   53   54   68  130
CONECT   54   55
CONECT   55   56   66  131
CONECT   56   57   65
CONECT   57   58   58  132
CONECT   58   59
CONECT   59   60   60   65
CONECT   60   61   62
CONECT   61  133  134
CONECT   62   63   63
CONECT   63   64  135
CONECT   64   65   65
CONECT   66   67   68  136
CONECT   67  137
CONECT   68   69  138
CONECT   69   70
CONECT   70   71   71   72   73
CONECT   72  139
CONECT   73  140
CONECT   74   75
CONECT   75  141
END
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SMILES for HMDB0301565 ((4Z)-6-[(1R,4S,5S,6R)-6-[(1E,3S,5Z,8Z)-3-hydroperoxyundeca-1,5,8-trien-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoyl-CoA)

CCC=CCC=CCC(OO)C=CC1C2CC(OO2)C1CC=CCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
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INCHI for HMDB0301565 ((4Z)-6-[(1R,4S,5S,6R)-6-[(1E,3S,5Z,8Z)-3-hydroperoxyundeca-1,5,8-trien-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoyl-CoA)

InChI=1S/C43H66N7O21P3S/c1-4-5-6-7-8-10-13-27(67-56)16-17-29-28(30-22-31(29)69-68-30)14-11-9-12-15-34(52)75-21-20-45-33(51)18-19-46-41(55)38(54)43(2,3)24-65-74(62,63)71-73(60,61)64-23-32-37(70-72(57,58)59)36(53)42(66-32)50-26-49-35-39(44)47-25-48-40(35)50/h5-6,8-11,16-17,25-32,36-38,42,53-54,56H,4,7,12-15,18-24H2,1-3H3,(H,45,51)(H,46,55)(H,60,61)(H,62,63)(H2,44,47,48)(H2,57,58,59)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-N-(2-{[2-({6-[6-(3-hydroperoxyundeca-1,5,8-trien-1-yl)-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoyl}sulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidateGenerator
4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-N-(2-{[2-({6-[6-(3-hydroperoxyundeca-1,5,8-trien-1-yl)-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoyl}sulphanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidateGenerator
4-({[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-N-(2-{[2-({6-[6-(3-hydroperoxyundeca-1,5,8-trien-1-yl)-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoyl}sulphanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acidGenerator
Chemical FormulaC43H66N7O21P3S
Average Molecular Weight1142.01
Monoisotopic Molecular Weight1141.324534341
IUPAC Name{[5-(6-amino-9H-purin-9-yl)-2-[({[({3-[(2-{[2-({6-[6-(3-hydroperoxyundeca-1,5,8-trien-1-yl)-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
Traditional Name[5-(6-aminopurin-9-yl)-2-{[({3-[(2-{[2-({6-[6-(3-hydroperoxyundeca-1,5,8-trien-1-yl)-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid
CAS Registry NumberNot Available
SMILES
CCC=CCC=CCC(OO)C=CC1C2CC(OO2)C1CC=CCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
InChI Identifier
InChI=1S/C43H66N7O21P3S/c1-4-5-6-7-8-10-13-27(67-56)16-17-29-28(30-22-31(29)69-68-30)14-11-9-12-15-34(52)75-21-20-45-33(51)18-19-46-41(55)38(54)43(2,3)24-65-74(62,63)71-73(60,61)64-23-32-37(70-72(57,58)59)36(53)42(66-32)50-26-49-35-39(44)47-25-48-40(35)50/h5-6,8-11,16-17,25-32,36-38,42,53-54,56H,4,7,12-15,18-24H2,1-3H3,(H,45,51)(H,46,55)(H,60,61)(H,62,63)(H2,44,47,48)(H2,57,58,59)
InChI KeyRHAAWTZEYOCREL-UHFFFAOYSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP2.16ALOGPS
logP-1.1ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count21ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area411.55 ŲChemAxon
Rotatable Bond Count33ChemAxon
Refractivity270.39 m³·mol⁻¹ChemAxon
Polarizability110.79 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+303.75432859911
AllCCS[M+H-H2O]+304.42232859911
AllCCS[M+Na]+302.90232859911
AllCCS[M+NH4]+303.09732859911
AllCCS[M-H]-306.42632859911
AllCCS[M+Na-2H]-312.20932859911
AllCCS[M+HCOO]-318.44232859911
DeepCCS[M+H]+262.61430932474
DeepCCS[M-H]-260.62530932474
DeepCCS[M-2H]-294.3730932474
DeepCCS[M+Na]+269.57230932474

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
MSMass Spectrum (Electron Ionization)Not Available2022-08-06Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (4Z)-6-[(1R,4S,5S,6R)-6-[(1E,3S,5Z,8Z)-3-hydroperoxyundeca-1,5,8-trien-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoyl-CoA 10V, Negative-QTOFsplash10-0a4i-2900000000-7453780f297d20b0f9d92021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (4Z)-6-[(1R,4S,5S,6R)-6-[(1E,3S,5Z,8Z)-3-hydroperoxyundeca-1,5,8-trien-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoyl-CoA 20V, Negative-QTOFsplash10-0a70-9701100002-e9c26412ab278197cc212021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (4Z)-6-[(1R,4S,5S,6R)-6-[(1E,3S,5Z,8Z)-3-hydroperoxyundeca-1,5,8-trien-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoyl-CoA 40V, Negative-QTOFsplash10-000i-9001400204-5da752bed14f8c8e60542021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (4Z)-6-[(1R,4S,5S,6R)-6-[(1E,3S,5Z,8Z)-3-hydroperoxyundeca-1,5,8-trien-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoyl-CoA 10V, Positive-QTOFsplash10-0006-0900000000-b25b931b0823f9ffb2c42021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (4Z)-6-[(1R,4S,5S,6R)-6-[(1E,3S,5Z,8Z)-3-hydroperoxyundeca-1,5,8-trien-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoyl-CoA 20V, Positive-QTOFsplash10-06yc-3900000012-b7931d3bc36a4861d4d02021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (4Z)-6-[(1R,4S,5S,6R)-6-[(1E,3S,5Z,8Z)-3-hydroperoxyundeca-1,5,8-trien-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hex-4-enoyl-CoA 40V, Positive-QTOFsplash10-000i-0000009000-5f8905d66fa4285a211a2021-10-21Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Abe T, Fujino T, Fukuyama R, Minoshima S, Shimizu N, Toh H, Suzuki H, Yamamoto T: Human long-chain acyl-CoA synthetase: structure and chromosomal location. J Biochem. 1992 Jan;111(1):123-8. [PubMed:1607358 ]
  2. Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]