NP-MRD: Showing NP-Card for lipid IVA (NP0334366)

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Record Information

Version

2.0

Created at

2024-09-09 23:21:24 UTC

Updated at

2024-09-09 23:21:24 UTC

NP-MRD ID

NP0334366

Secondary Accession Numbers

None

Natural Product Identification

Common Name

lipid IVA

Description

(2-N,3-o-bis(3-hydroxytetradecanoyl)-4-o-phosphono-beta-d-glucosaminyl)-(1->6)-(2-n,3-o-bis(3-hydroxytetradecanoyl)-beta-d-glucosaminyl phosphate), also known as lipid iva (e. Coli), is a member of the class of compounds known as acylaminosugars. Acylaminosugars are organic compounds containing a sugar linked to a chain through N-acyl group (2-n,3-o-bis(3-hydroxytetradecanoyl)-4-o-phosphono-beta-d-glucosaminyl)-(1->6)-(2-n,3-o-bis(3-hydroxytetradecanoyl)-beta-d-glucosaminyl phosphate) is practically insoluble (in water) and an extremely strong acidic compound (based on its pKa). (2-N,3-o-bis(3-hydroxytetradecanoyl)-4-o-phosphono-beta-d-glucosaminyl)-(1->6)-(2-n,3-o-bis(3-hydroxytetradecanoyl)-beta-d-glucosaminyl phosphate) can be found in a number of food items such as kohlrabi, sugar apple, common chokecherry, and lovage, which makes (2-n,3-o-bis(3-hydroxytetradecanoyl)-4-o-phosphono-beta-d-glucosaminyl)-(1->6)-(2-n,3-o-bis(3-hydroxytetradecanoyl)-beta-d-glucosaminyl phosphate) a potential biomarker for the consumption of these food products (2-n,3-o-bis(3-hydroxytetradecanoyl)-4-o-phosphono-beta-d-glucosaminyl)-(1->6)-(2-n,3-o-bis(3-hydroxytetradecanoyl)-beta-d-glucosaminyl phosphate) may be a unique E.Coli metabolite.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 10101211152D          

109110  0  0  0  0            999 V2000
    7.1447    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -13.5749   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4289    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.8579    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4125    1.7605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2868   -2.4750    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.4750    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2822   -0.7752    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414    0.6817    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6704    0.1433    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842   -1.0445    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8545   -2.0127    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414    0.1433    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8545    0.3627    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16 12  1  0  0  0  0
 17 13  1  0  0  0  0
 18 14  1  0  0  0  0
 19 15  1  0  0  0  0
 20 16  1  0  0  0  0
 21 17  1  0  0  0  0
 22 18  1  0  0  0  0
 23 19  1  0  0  0  0
 24 20  1  0  0  0  0
 25 21  1  0  0  0  0
 26 22  1  0  0  0  0
 27 23  1  0  0  0  0
 28 24  1  0  0  0  0
 29 25  1  0  0  0  0
 30 26  1  0  0  0  0
 31 27  1  0  0  0  0
 32 28  1  0  0  0  0
 33 29  1  0  0  0  0
 34 30  1  0  0  0  0
 35 31  1  0  0  0  0
 36 32  1  0  0  0  0
 37 33  1  0  0  0  0
 38 34  1  0  0  0  0
 39 35  1  0  0  0  0
 40 36  1  0  0  0  0
 41 37  1  0  0  0  0
 42 38  1  0  0  0  0
 43 39  1  0  0  0  0
 44 40  1  0  0  0  0
 51 41  1  0  0  0  0
 51 45  1  0  0  0  0
 52 42  1  0  0  0  0
 52 46  1  0  0  0  0
 53 43  1  0  0  0  0
 53 47  1  0  0  0  0
 54 44  1  0  0  0  0
 54 48  1  0  0  0  0
 55 49  1  6  0  0  0
 56 50  1  1  0  0  0
 57 45  1  0  0  0  0
 58 46  1  0  0  0  0
 59 47  1  0  0  0  0
 60 48  1  0  0  0  0
 63 56  1  0  0  0  0
 64 55  1  0  0  0  0
 65 61  1  0  0  0  0
 65 63  1  0  0  0  0
 66 62  1  0  0  0  0
 66 64  1  0  0  0  0
 67 62  1  0  0  0  0
 68 61  1  0  0  0  0
 69 57  2  0  0  0  0
 61 69  1  6  0  0  0
 70 58  2  0  0  0  0
 62 70  1  1  0  0  0
 71 49  1  0  0  0  0
 51 72  1  1  0  0  0
 52 73  1  6  0  0  0
 53 74  1  1  0  0  0
 54 75  1  1  0  0  0
 57 76  1  4  0  0  0
 58 77  1  4  0  0  0
 78 59  2  0  0  0  0
 79 60  2  0  0  0  0
 63 80  1  6  0  0  0
 87 50  1  0  0  0  0
 67 87  1  6  0  0  0
 88 55  1  0  0  0  0
 88 67  1  0  0  0  0
 89 56  1  0  0  0  0
 89 68  1  0  0  0  0
 90 59  1  0  0  0  0
 65 90  1  1  0  0  0
 91 60  1  0  0  0  0
 66 91  1  6  0  0  0
 64 92  1  1  0  0  0
 68 93  1  6  0  0  0
 94 81  1  0  0  0  0
 94 82  1  0  0  0  0
 94 83  2  0  0  0  0
 94 92  1  0  0  0  0
 95 84  1  0  0  0  0
 95 85  1  0  0  0  0
 95 86  2  0  0  0  0
 95 93  1  0  0  0  0
 51 96  1  1  0  0  0
 52 97  1  6  0  0  0
 53 98  1  1  0  0  0
 54 99  1  1  0  0  0
 55100  1  1  0  0  0
 56101  1  6  0  0  0
 61102  1  1  0  0  0
 62103  1  6  0  0  0
 63104  1  1  0  0  0
 64105  1  6  0  0  0
 65106  1  6  0  0  0
 66107  1  1  0  0  0
 67108  1  1  0  0  0
 68109  1  1  0  0  0
M  CHG  4  76  -1  77  -1  81  -1  82  -1
M  END


  Mrv0541 10101211152D          

109110  0  0  0  0            999 V2000
    7.1447    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4302    9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5749   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -11.4315    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.7171   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 66 62  1  0  0  0  0
 66 64  1  0  0  0  0
 67 62  1  0  0  0  0
 68 61  1  0  0  0  0
 69 57  2  0  0  0  0
 61 69  1  6  0  0  0
 70 58  2  0  0  0  0
 62 70  1  1  0  0  0
 71 49  1  0  0  0  0
 51 72  1  1  0  0  0
 52 73  1  6  0  0  0
 53 74  1  1  0  0  0
 54 75  1  1  0  0  0
 57 76  1  4  0  0  0
 58 77  1  4  0  0  0
 78 59  2  0  0  0  0
 79 60  2  0  0  0  0
 63 80  1  6  0  0  0
 87 50  1  0  0  0  0
 67 87  1  6  0  0  0
 88 55  1  0  0  0  0
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 89 56  1  0  0  0  0
 89 68  1  0  0  0  0
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 91 60  1  0  0  0  0
 66 91  1  6  0  0  0
 64 92  1  1  0  0  0
 68 93  1  6  0  0  0
 94 81  1  0  0  0  0
 94 82  1  0  0  0  0
 94 83  2  0  0  0  0
 94 92  1  0  0  0  0
 95 84  1  0  0  0  0
 95 85  1  0  0  0  0
 95 86  2  0  0  0  0
 95 93  1  0  0  0  0
 51 96  1  1  0  0  0
 52 97  1  6  0  0  0
 53 98  1  1  0  0  0
 54 99  1  1  0  0  0
 55100  1  1  0  0  0
 56101  1  6  0  0  0
 61102  1  1  0  0  0
 62103  1  6  0  0  0
 63104  1  1  0  0  0
 64105  1  6  0  0  0
 65106  1  6  0  0  0
 66107  1  1  0  0  0
 67108  1  1  0  0  0
 68109  1  1  0  0  0
M  CHG  4  76  -1  77  -1  81  -1  82  -1
M  END
> <DATABASE_ID>
NP0334366

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@](O)(CCCCCCCCCCC)CC(=O)O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO[C@]2([H])O[C@]([H])(CO)[C@@]([H])(OP([O-])([O-])=O)[C@]([H])(OC(=O)C[C@]([H])(O)CCCCCCCCCCC)[C@@]2([H])N=C([O-])C[C@]([H])(O)CCCCCCCCCCC)O[C@]([H])(OP(O)(O)=O)[C@]1([H])N=C([O-])C[C@]([H])(O)CCCCCCCCCCC

> <INCHI_IDENTIFIER>
InChI=1S/C68H130N2O23P2/c1-5-9-13-17-21-25-29-33-37-41-51(72)45-57(76)69-61-65(90-59(78)47-53(74)43-39-35-31-27-23-19-15-11-7-3)63(80)56(89-68(61)93-95(84,85)86)50-87-67-62(70-58(77)46-52(73)42-38-34-30-26-22-18-14-10-6-2)66(64(55(49-71)88-67)92-94(81,82)83)91-60(79)48-54(75)44-40-36-32-28-24-20-16-12-8-4/h51-56,61-68,71-75,80H,5-50H2,1-4H3,(H,69,76)(H,70,77)(H2,81,82,83)(H2,84,85,86)/p-4/t51-,52-,53-,54-,55-,56-,61-,62-,63-,64-,65-,66-,67-,68-/m1/s1

> <INCHI_KEY>
KVJWZTLXIROHIL-QDORLFPLSA-J

> <FORMULA>
C68H126N2O23P2

> <MOLECULAR_WEIGHT>
1401.6752

> <EXACT_MASS>
1400.822661372

> <JCHEM_ACCEPTOR_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
158.79510194630961

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
-4

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3-hydroxy-N-[(2R,3R,4R,5S,6R)-5-hydroxy-6-({[(2R,3R,4R,5S,6R)-3-{[(3R)-3-hydroxy-1-oxidotetradecylidene]amino}-6-(hydroxymethyl)-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-5-(phosphonatooxy)oxan-2-yl]oxy}methyl)-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-2-(phosphonooxy)oxan-3-yl]tetradecanecarboximidate

> <ALOGPS_LOGP>
5.44

> <JCHEM_LOGP>
14.434802140999997

> <ALOGPS_LOGS>
-4.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.2074309347487864

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.5522234059867817

> <JCHEM_PKA_STRONGEST_BASIC>
-3.657648083909957

> <JCHEM_POLAR_SURFACE_AREA>
411.6900000000001

> <JCHEM_REFRACTIVITY>
377.5022999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
62

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.04e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-3-hydroxy-N-[(2R,3R,4R,5S,6R)-5-hydroxy-6-({[(2R,3R,4R,5S,6R)-3-{[(3R)-3-hydroxy-1-oxidotetradecylidene]amino}-6-(hydroxymethyl)-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-5-(phosphonatooxy)oxan-2-yl]oxy}methyl)-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-2-(phosphonooxy)oxan-3-yl]tetradecanecarboximidate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-OCT-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-OCT-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   69  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   70  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   71  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   72  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   73  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   74  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   75  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   76  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O-1
HETATM   77  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O-1
HETATM   78  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   79  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   80  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   81  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O-1
HETATM   82  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O-1
HETATM   83  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   84  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   85  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   86  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   87  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   88  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   89  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   90  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   91  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   92  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   93  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   94  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   95  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   96  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   97  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   98  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   99  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM  100  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM  101  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM  102  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM  103  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM  104  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM  105  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM  106  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM  107  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM  108  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM  109  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    5                                                            
CONECT    2    6                                                            
CONECT    3    7                                                            
CONECT    4    8                                                            
CONECT    5    1    9                                                       
CONECT    6    2   10                                                       
CONECT    7    3   11                                                       
CONECT    8    4   12                                                       
CONECT    9    5   13                                                       
CONECT   10    6   14                                                       
CONECT   11    7   15                                                       
CONECT   12    8   16                                                       
CONECT   13    9   17                                                       
CONECT   14   10   18                                                       
CONECT   15   11   19                                                       
CONECT   16   12   20                                                       
CONECT   17   13   21                                                       
CONECT   18   14   22                                                       
CONECT   19   15   23                                                       
CONECT   20   16   24                                                       
CONECT   21   17   25                                                       
CONECT   22   18   26                                                       
CONECT   23   19   27                                                       
CONECT   24   20   28                                                       
CONECT   25   21   29                                                       
CONECT   26   22   30                                                       
CONECT   27   23   31                                                       
CONECT   28   24   32                                                       
CONECT   29   25   33                                                       
CONECT   30   26   34                                                       
CONECT   31   27   35                                                       
CONECT   32   28   36                                                       
CONECT   33   29   37                                                       
CONECT   34   30   38                                                       
CONECT   35   31   39                                                       
CONECT   36   32   40                                                       
CONECT   37   33   41                                                       
CONECT   38   34   42                                                       
CONECT   39   35   43                                                       
CONECT   40   36   44                                                       
CONECT   41   37   51                                                       
CONECT   42   38   52                                                       
CONECT   43   39   53                                                       
CONECT   44   40   54                                                       
CONECT   45   51   57                                                       
CONECT   46   52   58                                                       
CONECT   47   53   59                                                       
CONECT   48   54   60                                                       
CONECT   49   55   71                                                       
CONECT   50   56   87                                                       
CONECT   51   41   45   72   96                                             
CONECT   52   42   46   73   97                                             
CONECT   53   43   47   74   98                                             
CONECT   54   44   48   75   99                                             
CONECT   55   49   64   88  100                                             
CONECT   56   50   63   89  101                                             
CONECT   57   45   69   76                                                  
CONECT   58   46   70   77                                                  
CONECT   59   47   78   90                                                  
CONECT   60   48   79   91                                                  
CONECT   61   65   68   69  102                                             
CONECT   62   66   67   70  103                                             
CONECT   63   56   65   80  104                                             
CONECT   64   55   66   92  105                                             
CONECT   65   61   63   90  106                                             
CONECT   66   62   64   91  107                                             
CONECT   67   62   87   88  108                                             
CONECT   68   61   89   93  109                                             
CONECT   69   57   61                                                       
CONECT   70   58   62                                                       
CONECT   71   49                                                            
CONECT   72   51                                                            
CONECT   73   52                                                            
CONECT   74   53                                                            
CONECT   75   54                                                            
CONECT   76   57                                                            
CONECT   77   58                                                            
CONECT   78   59                                                            
CONECT   79   60                                                            
CONECT   80   63                                                            
CONECT   81   94                                                            
CONECT   82   94                                                            
CONECT   83   94                                                            
CONECT   84   95                                                            
CONECT   85   95                                                            
CONECT   86   95                                                            
CONECT   87   50   67                                                       
CONECT   88   55   67                                                       
CONECT   89   56   68                                                       
CONECT   90   59   65                                                       
CONECT   91   60   66                                                       
CONECT   92   64   94                                                       
CONECT   93   68   95                                                       
CONECT   94   81   82   83   92                                             
CONECT   95   84   85   86   93                                             
CONECT   96   51                                                            
CONECT   97   52                                                            
CONECT   98   53                                                            
CONECT   99   54                                                            
CONECT  100   55                                                            
CONECT  101   56                                                            
CONECT  102   61                                                            
CONECT  103   62                                                            
CONECT  104   63                                                            
CONECT  105   64                                                            
CONECT  106   65                                                            
CONECT  107   66                                                            
CONECT  108   67                                                            
CONECT  109   68                                                            
MASTER        0    0    0    0    0    0    0    0  109    0  220    0
END

View in JSmol

Synonyms

Value	Source
Lipid iva (e. coli)	ChEBI
Compound 406	MeSH
Lipid a precursor ia	MeSH
Lipid a precursors, bacterial	MeSH
Tetraacyl disaccharide 1,4'-bisphosphate	MeSH
Lipid a precursor, salmonella typhimurium	MeSH
Lipid a precursors, pseudomonas	MeSH
Lipid a precursors, salmonella	MeSH

Chemical Formula

C₆₈H₁₂₆N₂O₂₃P₂

Average Mass

1401.6752 Da

Monoisotopic Mass

1400.82266 Da

IUPAC Name

(3R)-3-hydroxy-N-[(2R,3R,4R,5S,6R)-5-hydroxy-6-({[(2R,3R,4R,5S,6R)-3-{[(3R)-3-hydroxy-1-oxidotetradecylidene]amino}-6-(hydroxymethyl)-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-5-(phosphonatooxy)oxan-2-yl]oxy}methyl)-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-2-(phosphonooxy)oxan-3-yl]tetradecanecarboximidate

Traditional Name

CAS Registry Number

Not Available

SMILES

[H][C@@](O)(CCCCCCCCCCC)CC(=O)O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO[C@]2([H])O[C@]([H])(CO)[C@@]([H])(OP([O-])([O-])=O)[C@]([H])(OC(=O)C[C@]([H])(O)CCCCCCCCCCC)[C@@]2([H])N=C([O-])C[C@]([H])(O)CCCCCCCCCCC)O[C@]([H])(OP(O)(O)=O)[C@]1([H])N=C([O-])C[C@]([H])(O)CCCCCCCCCCC

InChI Identifier

InChI=1S/C68H130N2O23P2/c1-5-9-13-17-21-25-29-33-37-41-51(72)45-57(76)69-61-65(90-59(78)47-53(74)43-39-35-31-27-23-19-15-11-7-3)63(80)56(89-68(61)93-95(84,85)86)50-87-67-62(70-58(77)46-52(73)42-38-34-30-26-22-18-14-10-6-2)66(64(55(49-71)88-67)92-94(81,82)83)91-60(79)48-54(75)44-40-36-32-28-24-20-16-12-8-4/h51-56,61-68,71-75,80H,5-50H2,1-4H3,(H,69,76)(H,70,77)(H2,81,82,83)(H2,84,85,86)/p-4/t51-,52-,53-,54-,55-,56-,61-,62-,63-,64-,65-,66-,67-,68-/m1/s1

InChI Key

KVJWZTLXIROHIL-QDORLFPLSA-J

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Acylaminosugars

Alternative Parents

Substituents

Acylaminosugar
Saccharolipid
Hexose phosphate
Disaccharide phosphate
N-acyl-alpha-hexosamine
Disaccharide
Glycosyl compound
O-glycosyl compound
Beta-hydroxy acid
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty amide
Fatty acyl
Hydroxy acid
N-acyl-amine
Alkyl phosphate
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Secondary carboxylic acid amide
Secondary alcohol
Carboxylic acid ester
Carboxamide group
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Oxacycle
Primary alcohol
Carbonyl group
Alcohol
Organonitrogen compound
Organic oxide
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Organic anion
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

lipid IVA oxoanion (CHEBI:58603 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.44	ALOGPS
logP	14.43	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	0.55	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	411.69 Å²	ChemAxon
Rotatable Bond Count	62	ChemAxon
Refractivity	377.5 m³·mol⁻¹	ChemAxon
Polarizability	158.8 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB030982

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10329123

PDB ID

Not Available

ChEBI ID

58603

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for lipid IVA (NP0334366)

MOL for NP0334366 (lipid IVA)

3D MOL for NP0334366 (lipid IVA)

3D SDF for NP0334366 (lipid IVA)

3D-SDF for NP0334366 (lipid IVA)

PDB for NP0334366 (lipid IVA)

3D PDB for NP0334366 (lipid IVA)

SMILES for NP0334366 (lipid IVA)

INCHI for NP0334366 (lipid IVA)

Structure for NP0334366 (lipid IVA)

3D Structure for NP0334366 (lipid IVA)