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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 22:56:17 UTC

Update Date

2021-09-26 23:17:48 UTC

HMDB ID

HMDB0259942

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Xyloketal B

Description

4,7,15,18-tetramethyl-3,5,14,16-tetraoxapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁵,¹⁹]icosa-1(13),2(10),11-trien-11-ol belongs to the class of organic compounds known as pyranochromenes. These are organic heterocyclic compounds containing a pyran ring fused to a chromene (1-benzopyran) moiety. 4,7,15,18-tetramethyl-3,5,14,16-tetraoxapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁵,¹⁹]icosa-1(13),2(10),11-trien-11-ol is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Xyloketal b is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Xyloketal B is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1533004241508162D          

 25 29  0  0  0  0            999 V2000
    5.9039    0.5013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2908    1.0534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3770    1.8738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6233    2.2094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0713    1.5963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7357    2.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2463    1.5963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8338    0.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2463    0.1674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0713    0.1674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4838    0.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8338   -0.5471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2463   -1.2616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0088   -0.5471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5963    0.1674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7713    0.1674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3588    0.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1261    0.2144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4482    1.0534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5344    1.8738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2193    2.2094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3908    3.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7713    1.5963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5963    1.5963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0088    0.8818    0.0000 C   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
  5 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  8 25  1  0  0  0  0
 15 25  2  0  0  0  0
M  END

HMDB0259942
     RDKit          3D
Xyloketal B
 51 55  0  0  0  0  0  0  0  0999 V2000
   -4.5726   -1.4118    1.4210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1838   -0.8227    0.0967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2466    0.1547   -0.4248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5814    1.2615   -0.8975 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2554    0.9575   -1.0420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9954    0.2155   -2.3114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3670    2.0299   -0.9438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0794    1.7629   -0.4992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1348    2.7549   -0.6088 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1956    2.5913   -0.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0976    3.6311   -0.3283 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5859    1.4068    0.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6241    0.3992    0.4595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6845    0.5609    0.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6781   -0.5391    0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0198    0.0884    0.1980 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0780   -0.7983    1.0207 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3344   -1.3413    0.6391 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8165   -2.2034    1.7836 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2401   -2.1203   -0.4869 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1702   -1.7407   -1.4158 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3576   -0.2617   -1.1551 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6905    0.2501   -1.5863 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3581   -0.2797    0.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9493    1.0904    0.8367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2852   -2.4831    1.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6490   -1.3033    1.5678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0497   -0.8777    2.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0477   -1.5886   -0.6754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8127    0.4724    0.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9254   -0.3205   -1.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1017   -0.4066   -2.3177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8649   -0.3853   -2.5926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8447    0.9899   -3.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4112    3.7115   -1.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0344    3.5630   -0.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5314   -1.0491    1.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5419   -1.3220   -0.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0988    0.7618    1.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4340   -1.7632    2.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9361   -2.1704    1.8411 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4811   -3.2495    1.6987 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1398   -2.2353   -1.3434 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7711   -1.8798   -2.4522 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5016    0.3401   -1.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4426    0.2439   -0.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5724    1.3277   -1.8572 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1075   -0.2896   -2.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3700   -0.5461    0.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9554    1.0368    1.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7186    1.7869    0.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 16  2  1  0
 24 18  1  0
 16  5  1  0
 14  8  1  0
 25 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  6 32  1  0
  6 33  1  0
  6 34  1  0
  9 35  1  0
 11 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 21 43  1  0
 21 44  1  0
 22 45  1  0
 23 46  1  0
 23 47  1  0
 23 48  1  0
 24 49  1  0
 25 50  1  0
 25 51  1  0
M  END


  Mrv1533004241508162D          

 25 29  0  0  0  0            999 V2000
    5.9039    0.5013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2908    1.0534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3770    1.8738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6233    2.2094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0713    1.5963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7357    2.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2463    1.5963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8338    0.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2463    0.1674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0713    0.1674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4838    0.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8338   -0.5471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2463   -1.2616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0088   -0.5471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5963    0.1674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7713    0.1674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3588    0.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1261    0.2144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4482    1.0534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5344    1.8738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2193    2.2094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3908    3.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7713    1.5963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5963    1.5963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0088    0.8818    0.0000 C   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
  5 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  8 25  1  0  0  0  0
 15 25  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259942

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1COC2(C)OC3=C(CC12)C(O)=CC1=C3CC2C(C)COC2(C)O1

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O5/c1-10-9-23-20(4)14(10)5-12-16(21)7-17-13(18(12)25-20)6-15-11(2)8-22-19(15,3)24-17/h7,10-11,14-15,21H,5-6,8-9H2,1-4H3

> <INCHI_KEY>
CCNANHBVUNZCKA-UHFFFAOYSA-N

> <FORMULA>
C20H26O5

> <MOLECULAR_WEIGHT>
346.423

> <EXACT_MASS>
346.178023937

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
37.80947811374869

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,7,15,18-tetramethyl-3,5,14,16-tetraoxapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁵,¹⁹]icosa-1(13),2(10),11-trien-11-ol

> <ALOGPS_LOGP>
3.14

> <JCHEM_LOGP>
3.6613069543333325

> <ALOGPS_LOGS>
-4.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.016731243374075

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9557904659769147

> <JCHEM_POLAR_SURFACE_AREA>
57.150000000000006

> <JCHEM_REFRACTIVITY>
92.9259

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.40e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,7,15,18-tetramethyl-3,5,14,16-tetraoxapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁵,¹⁹]icosa-1(13),2(10),11-trien-11-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0259942
     RDKit          3D
Xyloketal B
 51 55  0  0  0  0  0  0  0  0999 V2000
   -4.5726   -1.4118    1.4210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1838   -0.8227    0.0967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2466    0.1547   -0.4248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5814    1.2615   -0.8975 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2554    0.9575   -1.0420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9954    0.2155   -2.3114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3670    2.0299   -0.9438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0794    1.7629   -0.4992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1348    2.7549   -0.6088 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1956    2.5913   -0.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0976    3.6311   -0.3283 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5859    1.4068    0.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6241    0.3992    0.4595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6845    0.5609    0.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6781   -0.5391    0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0198    0.0884    0.1980 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0780   -0.7983    1.0207 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3344   -1.3413    0.6391 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8165   -2.2034    1.7836 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2401   -2.1203   -0.4869 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1702   -1.7407   -1.4158 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3576   -0.2617   -1.1551 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6905    0.2501   -1.5863 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3581   -0.2797    0.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9493    1.0904    0.8367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2852   -2.4831    1.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6490   -1.3033    1.5678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0497   -0.8777    2.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0477   -1.5886   -0.6754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8127    0.4724    0.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9254   -0.3205   -1.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1017   -0.4066   -2.3177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8649   -0.3853   -2.5926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8447    0.9899   -3.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4112    3.7115   -1.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0344    3.5630   -0.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5314   -1.0491    1.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5419   -1.3220   -0.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0988    0.7618    1.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4340   -1.7632    2.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9361   -2.1704    1.8411 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4811   -3.2495    1.6987 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1398   -2.2353   -1.3434 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7711   -1.8798   -2.4522 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5016    0.3401   -1.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4426    0.2439   -0.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5724    1.3277   -1.8572 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1075   -0.2896   -2.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3700   -0.5461    0.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9554    1.0368    1.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7186    1.7869    0.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 16  2  1  0
 24 18  1  0
 16  5  1  0
 14  8  1  0
 25 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  6 32  1  0
  6 33  1  0
  6 34  1  0
  9 35  1  0
 11 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 19 40  1  0
 19 41  1  0
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 21 43  1  0
 21 44  1  0
 22 45  1  0
 23 46  1  0
 23 47  1  0
 23 48  1  0
 24 49  1  0
 25 50  1  0
 25 51  1  0
M  END

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      11.021   0.936   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.876   1.966   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.037   3.498   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.630   4.124   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.600   2.980   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.973   4.387   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.060   2.980   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.290   1.646   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.060   0.312   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.600   0.312   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.370   1.646   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.290  -1.021   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.060  -2.355   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.750  -1.021   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.980   0.312   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.440   0.312   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.670   1.646   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.235   0.400   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.837   1.966   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.998   3.498   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.409   4.124   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.729   5.631   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.440   2.980   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.980   2.980   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.750   1.646   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   11                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   25                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10    2    5                                                  
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   25                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19   23                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   17   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24    8   15                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

COMPND    HMDB0259942
HETATM    1  C1  UNL     1      -4.573  -1.412   1.421  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.184  -0.823   0.097  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.247   0.155  -0.425  1.00  0.00           C  
HETATM    4  O1  UNL     1      -4.581   1.261  -0.897  1.00  0.00           O  
HETATM    5  C4  UNL     1      -3.255   0.957  -1.042  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.995   0.216  -2.311  1.00  0.00           C  
HETATM    7  O2  UNL     1      -2.367   2.030  -0.944  1.00  0.00           O  
HETATM    8  C6  UNL     1      -1.079   1.763  -0.499  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.135   2.755  -0.609  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.196   2.591  -0.191  1.00  0.00           C  
HETATM   11  O3  UNL     1       2.098   3.631  -0.328  1.00  0.00           O  
HETATM   12  C9  UNL     1       1.586   1.407   0.349  1.00  0.00           C  
HETATM   13  C10 UNL     1       0.624   0.399   0.460  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.684   0.561   0.048  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.678  -0.539   0.188  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.020   0.088   0.198  1.00  0.00           C  
HETATM   17  O4  UNL     1       1.078  -0.798   1.021  1.00  0.00           O  
HETATM   18  C14 UNL     1       2.334  -1.341   0.639  1.00  0.00           C  
HETATM   19  C15 UNL     1       2.817  -2.203   1.784  1.00  0.00           C  
HETATM   20  O5  UNL     1       2.240  -2.120  -0.487  1.00  0.00           O  
HETATM   21  C16 UNL     1       3.170  -1.741  -1.416  1.00  0.00           C  
HETATM   22  C17 UNL     1       3.358  -0.262  -1.155  1.00  0.00           C  
HETATM   23  C18 UNL     1       4.691   0.250  -1.586  1.00  0.00           C  
HETATM   24  C19 UNL     1       3.358  -0.280   0.380  1.00  0.00           C  
HETATM   25  C20 UNL     1       2.949   1.090   0.837  1.00  0.00           C  
HETATM   26  H1  UNL     1      -4.285  -2.483   1.406  1.00  0.00           H  
HETATM   27  H2  UNL     1      -5.649  -1.303   1.568  1.00  0.00           H  
HETATM   28  H3  UNL     1      -4.050  -0.878   2.245  1.00  0.00           H  
HETATM   29  H4  UNL     1      -4.048  -1.589  -0.675  1.00  0.00           H  
HETATM   30  H5  UNL     1      -5.813   0.472   0.487  1.00  0.00           H  
HETATM   31  H6  UNL     1      -5.925  -0.321  -1.135  1.00  0.00           H  
HETATM   32  H7  UNL     1      -2.102  -0.407  -2.318  1.00  0.00           H  
HETATM   33  H8  UNL     1      -3.865  -0.385  -2.593  1.00  0.00           H  
HETATM   34  H9  UNL     1      -2.845   0.990  -3.116  1.00  0.00           H  
HETATM   35  H10 UNL     1      -0.411   3.712  -1.034  1.00  0.00           H  
HETATM   36  H11 UNL     1       3.034   3.563  -0.047  1.00  0.00           H  
HETATM   37  H12 UNL     1      -1.531  -1.049   1.167  1.00  0.00           H  
HETATM   38  H13 UNL     1      -1.542  -1.322  -0.583  1.00  0.00           H  
HETATM   39  H14 UNL     1      -3.099   0.762   1.059  1.00  0.00           H  
HETATM   40  H15 UNL     1       2.434  -1.763   2.720  1.00  0.00           H  
HETATM   41  H16 UNL     1       3.936  -2.170   1.841  1.00  0.00           H  
HETATM   42  H17 UNL     1       2.481  -3.250   1.699  1.00  0.00           H  
HETATM   43  H18 UNL     1       4.140  -2.235  -1.343  1.00  0.00           H  
HETATM   44  H19 UNL     1       2.771  -1.880  -2.452  1.00  0.00           H  
HETATM   45  H20 UNL     1       2.502   0.340  -1.531  1.00  0.00           H  
HETATM   46  H21 UNL     1       5.443   0.244  -0.745  1.00  0.00           H  
HETATM   47  H22 UNL     1       4.572   1.328  -1.857  1.00  0.00           H  
HETATM   48  H23 UNL     1       5.108  -0.290  -2.463  1.00  0.00           H  
HETATM   49  H24 UNL     1       4.370  -0.546   0.712  1.00  0.00           H  
HETATM   50  H25 UNL     1       2.955   1.037   1.969  1.00  0.00           H  
HETATM   51  H26 UNL     1       3.719   1.787   0.487  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   16   29
CONECT    3    4   30   31
CONECT    4    5
CONECT    5    6    7   16
CONECT    6   32   33   34
CONECT    7    8
CONECT    8    9    9   14
CONECT    9   10   35
CONECT   10   11   12   12
CONECT   11   36
CONECT   12   13   25
CONECT   13   14   14   17
CONECT   14   15
CONECT   15   16   37   38
CONECT   16   39
CONECT   17   18
CONECT   18   19   20   24
CONECT   19   40   41   42
CONECT   20   21
CONECT   21   22   43   44
CONECT   22   23   24   45
CONECT   23   46   47   48
CONECT   24   25   49
CONECT   25   50   51
END

HMDB0259942
     RDKit          3D
Xyloketal B
 51 55  0  0  0  0  0  0  0  0999 V2000
   -4.5726   -1.4118    1.4210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1838   -0.8227    0.0967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2466    0.1547   -0.4248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5814    1.2615   -0.8975 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2554    0.9575   -1.0420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9954    0.2155   -2.3114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3670    2.0299   -0.9438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0794    1.7629   -0.4992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1348    2.7549   -0.6088 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1956    2.5913   -0.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0976    3.6311   -0.3283 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5859    1.4068    0.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6241    0.3992    0.4595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6845    0.5609    0.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6781   -0.5391    0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0198    0.0884    0.1980 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0780   -0.7983    1.0207 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3344   -1.3413    0.6391 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8165   -2.2034    1.7836 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2401   -2.1203   -0.4869 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1702   -1.7407   -1.4158 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3576   -0.2617   -1.1551 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6905    0.2501   -1.5863 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3581   -0.2797    0.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9493    1.0904    0.8367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2852   -2.4831    1.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6490   -1.3033    1.5678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0497   -0.8777    2.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0477   -1.5886   -0.6754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8127    0.4724    0.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9254   -0.3205   -1.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1017   -0.4066   -2.3177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8649   -0.3853   -2.5926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8447    0.9899   -3.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4112    3.7115   -1.0342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0344    3.5630   -0.0473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5314   -1.0491    1.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5419   -1.3220   -0.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0988    0.7618    1.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4340   -1.7632    2.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9361   -2.1704    1.8411 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4811   -3.2495    1.6987 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1398   -2.2353   -1.3434 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7711   -1.8798   -2.4522 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5016    0.3401   -1.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4426    0.2439   -0.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5724    1.3277   -1.8572 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1075   -0.2896   -2.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3700   -0.5461    0.7121 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9554    1.0368    1.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7186    1.7869    0.4867 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
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  5  6  1  0
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 16  2  1  0
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 19 41  1  0
 19 42  1  0
 21 43  1  0
 21 44  1  0
 22 45  1  0
 23 46  1  0
 23 47  1  0
 23 48  1  0
 24 49  1  0
 25 50  1  0
 25 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₀H₂₆O₅

Average Molecular Weight

346.423

Monoisotopic Molecular Weight

346.178023937

IUPAC Name

4,7,15,18-tetramethyl-3,5,14,16-tetraoxapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁵,¹⁹]icosa-1(13),2(10),11-trien-11-ol

Traditional Name

4,7,15,18-tetramethyl-3,5,14,16-tetraoxapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁵,¹⁹]icosa-1(13),2(10),11-trien-11-ol

CAS Registry Number

Not Available

SMILES

CC1COC2(C)OC3=C(CC12)C(O)=CC1=C3CC2C(C)COC2(C)O1

InChI Identifier

InChI=1S/C20H26O5/c1-10-9-23-20(4)14(10)5-12-16(21)7-17-13(18(12)25-20)6-15-11(2)8-22-19(15,3)24-17/h7,10-11,14-15,21H,5-6,8-9H2,1-4H3

InChI Key

CCNANHBVUNZCKA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranochromenes. These are organic heterocyclic compounds containing a pyran ring fused to a chromene (1-benzopyran) moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Pyranochromenes

Alternative Parents

Substituents

Pyranochromene
Furopyran
1-hydroxy-2-unsubstituted benzenoid
Ketal
Benzenoid
Pyran
Oxolane
Furan
Oxacycle
Acetal
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.14	ALOGPS
logP	3.66	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	10.02	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	57.15 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	92.93 m³·mol⁻¹	ChemAxon
Polarizability	37.81 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	182.766	32859911
AllCCS	[M+H-H2O]+	179.728	32859911
AllCCS	[M+Na]+	186.384	32859911
AllCCS	[M+NH4]+	185.577	32859911
AllCCS	[M-H]-	191.798	32859911
AllCCS	[M+Na-2H]-	191.838	32859911
AllCCS	[M+HCOO]-	192.03	32859911
DeepCCS	[M-2H]-	212.439	30932474
DeepCCS	[M+Na]+	187.666	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Xyloketal B	CC1COC2(C)OC3=C(CC12)C(O)=CC1=C3CC2C(C)COC2(C)O1	3509.3	Standard polar	33892256
Xyloketal B	CC1COC2(C)OC3=C(CC12)C(O)=CC1=C3CC2C(C)COC2(C)O1	2705.1	Standard non polar	33892256
Xyloketal B	CC1COC2(C)OC3=C(CC12)C(O)=CC1=C3CC2C(C)COC2(C)O1	2815.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Xyloketal B GC-MS (Non-derivatized) - 70eV, Positive	splash10-014r-0069000000-5fc648d4834c8a84c1bd	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xyloketal B GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xyloketal B GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xyloketal B GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

21776387

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Xyloketal B (HMDB0259942)

MOL for HMDB0259942 (Xyloketal B)

3D MOL for HMDB0259942 (Xyloketal B)

3D SDF for HMDB0259942 (Xyloketal B)

3D-SDF for HMDB0259942 (Xyloketal B)

PDB for HMDB0259942 (Xyloketal B)

3D PDB for HMDB0259942 (Xyloketal B)

SMILES for HMDB0259942 (Xyloketal B)

INCHI for HMDB0259942 (Xyloketal B)

Structure for HMDB0259942 (Xyloketal B)

3D Structure for HMDB0259942 (Xyloketal B)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra