NP-MRD: Showing NP-Card for xylariacyclone B (NP0042774)

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Record Information

Version

1.0

Created at

2021-06-21 00:21:02 UTC

Updated at

2021-06-30 00:18:03 UTC

NP-MRD ID

NP0042774

Secondary Accession Numbers

None

Natural Product Identification

Common Name

xylariacyclone B

Provided By

JEOL Database JEOL Logo

Description

(1R,5R,6S)-5,6-dihydroxy-4-methoxy-6-methyl-2-oxocyclohex-3-en-1-yl acetate belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. xylariacyclone B is found in Xylaria feejeensis and Xylaria plebeja PSU-G30. It was first documented in 2013 (Rukachaisirikul, V., et al.). Based on a literature review very few articles have been published on (1R,5R,6S)-5,6-dihydroxy-4-methoxy-6-methyl-2-oxocyclohex-3-en-1-yl acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102213D          

 30 30  0  0  0  0            999 V2000
   -4.1681    2.7558   -1.8628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2103    3.0321   -0.8403 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4563    1.9192   -0.4983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3996    1.5528    0.7859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653    0.4096    1.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5762    0.1024    2.4069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7428   -0.3510    0.1707 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4235   -0.8296    0.8860 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0673   -1.9010    0.3681 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1525   -2.3624    1.2892 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8182   -2.3930   -0.7238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3718    0.5360   -1.0450 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7474    1.5328   -0.7216 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0928   -0.2632   -2.1646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6389    1.2569   -1.5735 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4780    0.2845   -2.2136 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7625    1.8678   -1.6217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8468    3.6118   -1.9242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6799    2.6451   -2.8358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9617    2.0650    1.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3467   -1.2135   -0.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9341   -1.6013    1.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5872   -3.2880    0.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7373   -2.5670    2.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6830    1.0123   -0.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4955    2.1850    0.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9646    2.1642   -1.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4709   -1.1039   -1.8256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3533    1.9850   -2.3425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8678   -0.2093   -2.8010 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  7  5  1  0  0  0  0
  2  1  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15  3  1  0  0  0  0
 12 14  1  6  0  0  0
  3  4  2  0  0  0  0
 12 13  1  0  0  0  0
  4  5  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5  6  2  0  0  0  0
  9 10  1  0  0  0  0
  7 12  1  0  0  0  0
  9 11  2  0  0  0  0
  7 21  1  6  0  0  0
 15 29  1  6  0  0  0
  4 20  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
 16 30  1  0  0  0  0
 14 28  1  0  0  0  0
 13 25  1  0  0  0  0
 13 26  1  0  0  0  0
 13 27  1  0  0  0  0
 10 22  1  0  0  0  0
 10 23  1  0  0  0  0
 10 24  1  0  0  0  0
M  END

     RDKit          3D

 30 30  0  0  0  0  0  0  0  0999 V2000
   -4.1681    2.7558   -1.8628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2103    3.0321   -0.8403 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4563    1.9192   -0.4983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3996    1.5528    0.7859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653    0.4096    1.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5762    0.1024    2.4069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7428   -0.3510    0.1707 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4235   -0.8296    0.8860 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0673   -1.9010    0.3681 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1525   -2.3624    1.2892 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8182   -2.3930   -0.7238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3718    0.5360   -1.0450 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7474    1.5328   -0.7216 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0928   -0.2632   -2.1646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6389    1.2569   -1.5735 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4780    0.2845   -2.2136 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7625    1.8678   -1.6217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8468    3.6118   -1.9242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6799    2.6451   -2.8358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9617    2.0650    1.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3467   -1.2135   -0.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9341   -1.6013    1.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5872   -3.2880    0.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7373   -2.5670    2.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6830    1.0123   -0.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4955    2.1850    0.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9646    2.1642   -1.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4709   -1.1039   -1.8256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3533    1.9850   -2.3425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8678   -0.2093   -2.8010 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  7  5  1  0
  2  1  1  0
 12 15  1  0
 15 16  1  0
 15  3  1  0
 12 14  1  6
  3  4  2  0
 12 13  1  0
  4  5  1  0
  7  8  1  0
  8  9  1  0
  5  6  2  0
  9 10  1  0
  7 12  1  0
  9 11  2  0
  7 21  1  6
 15 29  1  6
  4 20  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
 16 30  1  0
 14 28  1  0
 13 25  1  0
 13 26  1  0
 13 27  1  0
 10 22  1  0
 10 23  1  0
 10 24  1  0
M  END


  Mrv1652306212102213D          

 30 30  0  0  0  0            999 V2000
   -4.1681    2.7558   -1.8628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2103    3.0321   -0.8403 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4563    1.9192   -0.4983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3996    1.5528    0.7859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653    0.4096    1.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5762    0.1024    2.4069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7428   -0.3510    0.1707 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4235   -0.8296    0.8860 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0673   -1.9010    0.3681 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1525   -2.3624    1.2892 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8182   -2.3930   -0.7238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3718    0.5360   -1.0450 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7474    1.5328   -0.7216 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0928   -0.2632   -2.1646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6389    1.2569   -1.5735 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4780    0.2845   -2.2136 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7625    1.8678   -1.6217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8468    3.6118   -1.9242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6799    2.6451   -2.8358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9617    2.0650    1.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3467   -1.2135   -0.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9341   -1.6013    1.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5872   -3.2880    0.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7373   -2.5670    2.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6830    1.0123   -0.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4955    2.1850    0.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9646    2.1642   -1.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4709   -1.1039   -1.8256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3533    1.9850   -2.3425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8678   -0.2093   -2.8010 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  7  5  1  0  0  0  0
  2  1  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15  3  1  0  0  0  0
 12 14  1  6  0  0  0
  3  4  2  0  0  0  0
 12 13  1  0  0  0  0
  4  5  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5  6  2  0  0  0  0
  9 10  1  0  0  0  0
  7 12  1  0  0  0  0
  9 11  2  0  0  0  0
  7 21  1  6  0  0  0
 15 29  1  6  0  0  0
  4 20  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
 16 30  1  0  0  0  0
 14 28  1  0  0  0  0
 13 25  1  0  0  0  0
 13 26  1  0  0  0  0
 13 27  1  0  0  0  0
 10 22  1  0  0  0  0
 10 23  1  0  0  0  0
 10 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042774

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C(OC([H])([H])[H])=C([H])C(=O)[C@]([H])(OC(=O)C([H])([H])[H])[C@]1(O[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C10H14O6/c1-5(11)16-9-6(12)4-7(15-3)8(13)10(9,2)14/h4,8-9,13-14H,1-3H3/t8-,9-,10-/m0/s1

> <INCHI_KEY>
ODYIVPXZDYKWBQ-GUBZILKMSA-N

> <FORMULA>
C10H14O6

> <MOLECULAR_WEIGHT>
230.216

> <EXACT_MASS>
230.079038171

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
21.711029834360623

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,5R,6S)-5,6-dihydroxy-4-methoxy-6-methyl-2-oxocyclohex-3-en-1-yl acetate

> <ALOGPS_LOGP>
-0.50

> <JCHEM_LOGP>
-1.2152653513333331

> <ALOGPS_LOGS>
-0.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.382849762764884

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.234271275248979

> <JCHEM_PKA_STRONGEST_BASIC>
-3.785038024806064

> <JCHEM_POLAR_SURFACE_AREA>
93.06000000000002

> <JCHEM_REFRACTIVITY>
53.8351

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.46e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5R,6S)-5,6-dihydroxy-4-methoxy-6-methyl-2-oxocyclohex-3-en-1-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 30 30  0  0  0  0  0  0  0  0999 V2000
   -4.1681    2.7558   -1.8628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2103    3.0321   -0.8403 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4563    1.9192   -0.4983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3996    1.5528    0.7859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653    0.4096    1.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5762    0.1024    2.4069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7428   -0.3510    0.1707 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4235   -0.8296    0.8860 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0673   -1.9010    0.3681 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1525   -2.3624    1.2892 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8182   -2.3930   -0.7238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3718    0.5360   -1.0450 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7474    1.5328   -0.7216 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0928   -0.2632   -2.1646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6389    1.2569   -1.5735 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4780    0.2845   -2.2136 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7625    1.8678   -1.6217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8468    3.6118   -1.9242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6799    2.6451   -2.8358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9617    2.0650    1.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3467   -1.2135   -0.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9341   -1.6013    1.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5872   -3.2880    0.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7373   -2.5670    2.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6830    1.0123   -0.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4955    2.1850    0.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9646    2.1642   -1.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4709   -1.1039   -1.8256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3533    1.9850   -2.3425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8678   -0.2093   -2.8010 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  7  5  1  0
  2  1  1  0
 12 15  1  0
 15 16  1  0
 15  3  1  0
 12 14  1  6
  3  4  2  0
 12 13  1  0
  4  5  1  0
  7  8  1  0
  8  9  1  0
  5  6  2  0
  9 10  1  0
  7 12  1  0
  9 11  2  0
  7 21  1  6
 15 29  1  6
  4 20  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
 16 30  1  0
 14 28  1  0
 13 25  1  0
 13 26  1  0
 13 27  1  0
 10 22  1  0
 10 23  1  0
 10 24  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.168   2.756  -1.863  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.210   3.032  -0.840  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.456   1.919  -0.498  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.400   1.553   0.786  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.565   0.410   1.214  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.576   0.102   2.407  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.743  -0.351   0.171  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.424  -0.830   0.886  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.067  -1.901   0.368  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.152  -2.362   1.289  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.818  -2.393  -0.724  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.372   0.536  -1.045  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.747   1.533  -0.722  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.093  -0.263  -2.165  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.639   1.257  -1.573  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.478   0.285  -2.214  0.00  0.00           O+0
HETATM   17  H   UNK     0      -4.763   1.868  -1.622  0.00  0.00           H+0
HETATM   18  H   UNK     0      -4.847   3.612  -1.924  0.00  0.00           H+0
HETATM   19  H   UNK     0      -3.680   2.645  -2.836  0.00  0.00           H+0
HETATM   20  H   UNK     0      -2.962   2.065   1.558  0.00  0.00           H+0
HETATM   21  H   UNK     0      -1.347  -1.214  -0.142  0.00  0.00           H+0
HETATM   22  H   UNK     0       2.934  -1.601   1.350  0.00  0.00           H+0
HETATM   23  H   UNK     0       2.587  -3.288   0.901  0.00  0.00           H+0
HETATM   24  H   UNK     0       1.737  -2.567   2.279  0.00  0.00           H+0
HETATM   25  H   UNK     0       1.683   1.012  -0.489  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.496   2.185   0.120  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.965   2.164  -1.591  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.471  -1.104  -1.826  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.353   1.985  -2.342  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.868  -0.209  -2.801  0.00  0.00           H+0
CONECT    1    2   17   18   19                                             
CONECT    2    3    1                                                       
CONECT    3    2   15    4                                                  
CONECT    4    3    5   20                                                  
CONECT    5    7    4    6                                                  
CONECT    6    5                                                            
CONECT    7    5    8   12   21                                             
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9   22   23   24                                             
CONECT   11    9                                                            
CONECT   12   15   14   13    7                                             
CONECT   13   12   25   26   27                                             
CONECT   14   12   28                                                       
CONECT   15   12   16    3   29                                             
CONECT   16   15   30                                                       
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19    1                                                            
CONECT   20    4                                                            
CONECT   21    7                                                            
CONECT   22   10                                                            
CONECT   23   10                                                            
CONECT   24   10                                                            
CONECT   25   13                                                            
CONECT   26   13                                                            
CONECT   27   13                                                            
CONECT   28   14                                                            
CONECT   29   15                                                            
CONECT   30   16                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   60    0
END

RDKit          3D

30 30  0  0  0  0  0  0  0  0999 V2000
   -4.1681    2.7558   -1.8628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2103    3.0321   -0.8403 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4563    1.9192   -0.4983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3996    1.5528    0.7859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5653    0.4096    1.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5762    0.1024    2.4069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7428   -0.3510    0.1707 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4235   -0.8296    0.8860 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0673   -1.9010    0.3681 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1525   -2.3624    1.2892 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8182   -2.3930   -0.7238 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3718    0.5360   -1.0450 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7474    1.5328   -0.7216 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0928   -0.2632   -2.1646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6389    1.2569   -1.5735 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4780    0.2845   -2.2136 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7625    1.8678   -1.6217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8468    3.6118   -1.9242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6799    2.6451   -2.8358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9617    2.0650    1.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3467   -1.2135   -0.1418 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9341   -1.6013    1.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5872   -3.2880    0.9014 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7373   -2.5670    2.2794 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6830    1.0123   -0.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4955    2.1850    0.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9646    2.1642   -1.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4709   -1.1039   -1.8256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3533    1.9850   -2.3425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8678   -0.2093   -2.8010 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  7  5  1  0
  2  1  1  0
 12 15  1  0
 15 16  1  0
 15  3  1  0
 12 14  1  6
  3  4  2  0
 12 13  1  0
  4  5  1  0
  7  8  1  0
  8  9  1  0
  5  6  2  0
  9 10  1  0
  7 12  1  0
  9 11  2  0
  7 21  1  6
 15 29  1  6
  4 20  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
 16 30  1  0
 14 28  1  0
 13 25  1  0
 13 26  1  0
 13 27  1  0
 10 22  1  0
 10 23  1  0
 10 24  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
(1R,5R,6S)-5,6-Dihydroxy-4-methoxy-6-methyl-2-oxocyclohex-3-en-1-yl acetic acid	Generator

Chemical Formula

C₁₀H₁₄O₆

Average Mass

230.2160 Da

Monoisotopic Mass

230.07904 Da

IUPAC Name

(1R,5R,6S)-5,6-dihydroxy-4-methoxy-6-methyl-2-oxocyclohex-3-en-1-yl acetate

Traditional Name

(1R,5R,6S)-5,6-dihydroxy-4-methoxy-6-methyl-2-oxocyclohex-3-en-1-yl acetate

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])C(OC([H])([H])[H])=C([H])C(=O)[C@]([H])(OC(=O)C([H])([H])[H])[C@]1(O[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C10H14O6/c1-5(11)16-9-6(12)4-7(15-3)8(13)10(9,2)14/h4,8-9,13-14H,1-3H3/t8-,9-,10-/m0/s1

InChI Key

ODYIVPXZDYKWBQ-GUBZILKMSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Xylaria feejeensis	LOTUS Database	35616633
Xylaria plebeja PSU-G30	JEOL database	Rukachaisirikul, V., et. al, Tetrahedron 69, 10711 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Alpha-acyloxy ketone
Cyclitol or derivatives
Vinylogous ester
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
1,2-diol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	-0.5	ALOGPS
logP	-1.2	ChemAxon
logS	-0.2	ALOGPS
pKa (Strongest Acidic)	11.23	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	53.84 m³·mol⁻¹	ChemAxon
Polarizability	21.71 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

78437910

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102222775

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rukachaisirikul, V., et al. (2013). Rukachaisirikul, V., et. al, Tetrahedron 69, 10711 (2013). Tetrahedron.

Showing NP-Card for xylariacyclone B (NP0042774)

MOL for NP0042774 (xylariacyclone B)

3D MOL for NP0042774 (xylariacyclone B)

3D SDF for NP0042774 (xylariacyclone B)

3D-SDF for NP0042774 (xylariacyclone B)

PDB for NP0042774 (xylariacyclone B)

3D PDB for NP0042774 (xylariacyclone B)

SMILES for NP0042774 (xylariacyclone B)

INCHI for NP0042774 (xylariacyclone B)

Structure for NP0042774 (xylariacyclone B)

3D Structure for NP0042774 (xylariacyclone B)