NP-MRD: Showing NP-Card for (3s)-3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-3-methoxyphenoxy)oxan-2-yl]methoxy}pentanoic acid (NP0223347)

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Record Information

Version

2.0

Created at

2022-09-06 01:24:59 UTC

Updated at

2022-09-06 01:24:59 UTC

NP-MRD ID

NP0223347

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s)-3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-3-methoxyphenoxy)oxan-2-yl]methoxy}pentanoic acid

Description

(3S)-3-hydroxy-3-methyl-5-oxo-5-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-hydroxy-3-methoxyphenoxy)oxan-2-yl]methoxy}pentanoic acid belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety. (3s)-3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-3-methoxyphenoxy)oxan-2-yl]methoxy}pentanoic acid is found in Eurycorymbus cavaleriei. Based on a literature review very few articles have been published on (3S)-3-hydroxy-3-methyl-5-oxo-5-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-hydroxy-3-methoxyphenoxy)oxan-2-yl]methoxy}pentanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062203252D          

 31 32  0  0  1  0            999 V2000
    1.4289    0.0000    0.0000 C   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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0177   -8.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8427   -7.1230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -9.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -9.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    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
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  6  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  9 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
  7 26  1  0  0  0  0
 26 27  1  1  0  0  0
  5 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
  3 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

     RDKit          3D

 57 58  0  0  0  0  0  0  0  0999 V2000
   -2.8936    4.0733    0.3401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2052    3.8994   -0.1623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7164    2.6126   -0.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9656    1.4924   -0.0444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4243    0.2095   -0.2081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7210   -0.9359    0.0751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4386   -0.9412    0.5954 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5656   -1.3400   -0.4536 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2511   -1.0060   -0.0988 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7289   -1.3979   -1.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0526   -1.0604   -0.8528 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4604    0.2454   -0.6455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6263    1.1507   -0.7273 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8701    0.5993   -0.3282 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7649   -0.5866   -0.2700 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3551   -1.5906    0.7778 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7343   -1.2609   -1.4995 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1807   -0.1472   -0.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7452    0.7238   -1.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8587    1.2613   -0.8259 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1055    0.9598   -2.2357 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1332   -1.7018    1.2003 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2642   -0.7836    2.2381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9404   -2.7179    1.5059 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1092   -3.5309    0.3911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2533   -1.9656    1.6990 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2356   -1.3997    2.9489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7359    0.1233   -0.7132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4974    1.2246   -1.0189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0041    2.4948   -0.8418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7370    3.6334   -1.1370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1902    3.5005   -0.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8153    3.6258    1.3593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6469    5.1515    0.3700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9517    1.6826    0.3423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1266    0.0579    0.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2575    0.0782    0.1105 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7137   -2.4865   -1.3727 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3812   -0.9209   -2.1118 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8491    1.1315    0.6610 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2037    1.3184   -1.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2276   -1.7844    1.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5549   -1.2031    1.4401 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0703   -2.5827    0.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6019   -1.7433   -1.6551 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2145    0.3516    0.9979 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7816   -1.0762    0.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0015    1.9429   -2.5316 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1057   -2.1943    1.0762 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1206   -0.2818    2.1497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6898   -3.3158    2.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0469   -3.6304    0.1110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1033   -2.6793    1.6189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1833   -2.0736    3.6487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1210   -0.8799   -0.8523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5076    1.1163   -1.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3719    4.5573   -1.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  6
 15 18  1  0
 18 19  1  0
 19 21  1  0
 19 20  2  0
  9 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
  5 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 30  3  1  0
 26  7  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  7 36  1  1
  9 37  1  1
 10 38  1  0
 10 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 21 48  1  0
 22 49  1  6
 23 50  1  0
 24 51  1  1
 25 52  1  0
 26 53  1  1
 27 54  1  0
 28 55  1  0
 29 56  1  0
 31 57  1  0
M  END


  Mrv1652309062203252D          

 31 32  0  0  1  0            999 V2000
    1.4289    0.0000    0.0000 C   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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -7.8375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0177   -8.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8427   -7.1230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -9.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -9.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    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
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  6  0  0  0
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  9 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
  7 26  1  0  0  0  0
 26 27  1  1  0  0  0
  5 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
  3 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0223347

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O[C@@H]2O[C@H](COC(=O)C[C@@](C)(O)CC(O)=O)[C@@H](O)[C@H](O)[C@H]2O)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O12/c1-19(27,6-13(21)22)7-14(23)29-8-12-15(24)16(25)17(26)18(31-12)30-9-3-4-10(20)11(5-9)28-2/h3-5,12,15-18,20,24-27H,6-8H2,1-2H3,(H,21,22)/t12-,15-,16+,17-,18-,19+/m1/s1

> <INCHI_KEY>
WBYNLMZRMZGSGJ-LPSXLJMFSA-N

> <FORMULA>
C19H26O12

> <MOLECULAR_WEIGHT>
446.405

> <EXACT_MASS>
446.142426277

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
42.460968901422746

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-3-hydroxy-3-methyl-5-oxo-5-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-hydroxy-3-methoxyphenoxy)oxan-2-yl]methoxy}pentanoic acid

> <JCHEM_LOGP>
-1.143394302666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.26404731184696

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7531630186229283

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0083920901482806

> <JCHEM_POLAR_SURFACE_AREA>
192.43999999999997

> <JCHEM_REFRACTIVITY>
99.27290000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-3-hydroxy-3-methyl-5-oxo-5-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-hydroxy-3-methoxyphenoxy)oxan-2-yl]methoxy}pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.336 -11.550   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      12.003 -11.550   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.003 -14.630   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.233 -15.964   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.773 -13.296   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      13.337 -15.400   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.337 -16.940   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      14.670 -17.710   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      12.003 -17.710   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   30                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   28                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   26                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   22                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22    9   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24    7   27                                                  
CONECT   27   26                                                            
CONECT   28    5   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29    3   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

View in JSmol

Synonyms

Value	Source
(3S)-3-Hydroxy-3-methyl-5-oxo-5-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-hydroxy-3-methoxyphenoxy)oxan-2-yl]methoxy}pentanoate	Generator

Chemical Formula

C₁₉H₂₆O₁₂

Average Mass

446.4050 Da

Monoisotopic Mass

446.14243 Da

IUPAC Name

(3S)-3-hydroxy-3-methyl-5-oxo-5-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-hydroxy-3-methoxyphenoxy)oxan-2-yl]methoxy}pentanoic acid

Traditional Name

(3S)-3-hydroxy-3-methyl-5-oxo-5-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-hydroxy-3-methoxyphenoxy)oxan-2-yl]methoxy}pentanoic acid

CAS Registry Number

Not Available

SMILES

COC1=CC(O[C@@H]2O[C@H](COC(=O)C[C@@](C)(O)CC(O)=O)[C@@H](O)[C@H](O)[C@H]2O)=CC=C1O

InChI Identifier

InChI=1S/C19H26O12/c1-19(27,6-13(21)22)7-14(23)29-8-12-15(24)16(25)17(26)18(31-12)30-9-3-4-10(20)11(5-9)28-2/h3-5,12,15-18,20,24-27H,6-8H2,1-2H3,(H,21,22)/t12-,15-,16+,17-,18-,19+/m1/s1

InChI Key

WBYNLMZRMZGSGJ-LPSXLJMFSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Eurycorymbus cavaleriei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Saccharolipids

Sub Class

Not Available

Direct Parent

Saccharolipids

Alternative Parents

Substituents

Saccharolipid
Phenolic glycoside
Glycosyl compound
O-glycosyl compound
Methoxyphenol
4-alkoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Fatty acid ester
Phenol
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Fatty acyl
Monosaccharide
Oxane
Benzenoid
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Polyol
Oxacycle
Ether
Acetal
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Carbonyl group
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

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	-1.1	ChemAxon
pKa (Strongest Acidic)	3.75	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	192.44 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	99.27 m³·mol⁻¹	ChemAxon
Polarizability	42.46 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

Not Available

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

163002544

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s)-3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-3-methoxyphenoxy)oxan-2-yl]methoxy}pentanoic acid (NP0223347)

MOL for NP0223347 ((3s)-3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-3-methoxyphenoxy)oxan-2-yl]methoxy}pentanoic acid)

3D MOL for NP0223347 ((3s)-3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-3-methoxyphenoxy)oxan-2-yl]methoxy}pentanoic acid)

3D SDF for NP0223347 ((3s)-3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-3-methoxyphenoxy)oxan-2-yl]methoxy}pentanoic acid)

3D-SDF for NP0223347 ((3s)-3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-3-methoxyphenoxy)oxan-2-yl]methoxy}pentanoic acid)

PDB for NP0223347 ((3s)-3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-3-methoxyphenoxy)oxan-2-yl]methoxy}pentanoic acid)

3D PDB for NP0223347 ((3s)-3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-3-methoxyphenoxy)oxan-2-yl]methoxy}pentanoic acid)

SMILES for NP0223347 ((3s)-3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-3-methoxyphenoxy)oxan-2-yl]methoxy}pentanoic acid)

INCHI for NP0223347 ((3s)-3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-3-methoxyphenoxy)oxan-2-yl]methoxy}pentanoic acid)

Structure for NP0223347 ((3s)-3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-3-methoxyphenoxy)oxan-2-yl]methoxy}pentanoic acid)

3D Structure for NP0223347 ((3s)-3-hydroxy-3-methyl-5-oxo-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-hydroxy-3-methoxyphenoxy)oxan-2-yl]methoxy}pentanoic acid)