NP-MRD: Showing NP-Card for orirubenone B (NP0027235)

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Record Information

Version

2.0

Created at

2021-06-19 18:55:05 UTC

Updated at

2021-06-29 23:53:14 UTC

NP-MRD ID

NP0027235

Secondary Accession Numbers

None

Natural Product Identification

Common Name

orirubenone B

Provided By

JEOL Database JEOL Logo

Description

orirubenone B is found in Tricholoma orirubens. orirubenone B was first documented in 2004 (Kawagishi, H., et al.). Based on a literature review very few articles have been published on (2E,6E)-2,6-dimethyl-8-oxo-8-(2,4,5-trihydroxyphenyl)octa-2,6-dienoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192120553D          

 40 40  0  0  0  0            999 V2000
    4.1367    0.8476    0.3836 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7796    1.3878    0.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7661    1.5728    0.8862 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8248    1.2292    2.3306 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6875    1.6872    3.0732 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7569    0.3435    2.8703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0388   -0.4273    2.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0222   -1.2556    2.5334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8125   -2.0270    1.7252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2229   -1.3235    3.9092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1950   -2.1392    4.4128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4394   -0.5783    4.7796 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5573    0.2472    4.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3119    0.9413    5.1675 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5812    1.7219   -1.4494 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3602    0.4965   -2.3532 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1363   -0.3052   -1.9852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0724   -0.2711   -2.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4607    0.6155   -3.7257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1241   -1.1593   -2.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1529   -1.6325   -0.8962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0997   -1.3999   -2.9106 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2181    0.5471    1.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3698   -0.0372   -0.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9044    1.6047    0.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8037    1.9440    0.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1110   -0.3996    0.9368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5231   -1.9087    0.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5947   -2.5615    3.6262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5950   -0.6444    5.8518 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0404    1.3903    4.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7322    2.4084   -1.5701 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4586    2.2765   -1.8060 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3081    0.8308   -3.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2311   -0.1687   -2.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2958   -0.9949   -1.1554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5548    0.0316   -4.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2633    1.4147   -3.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4195    1.1059   -3.5244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7272   -1.9963   -2.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
 15  2  1  0  0  0  0
  7  8  2  0  0  0  0
 20 18  1  0  0  0  0
  8 10  1  0  0  0  0
  2  3  2  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 17 16  1  0  0  0  0
 13 14  1  0  0  0  0
  3  4  1  0  0  0  0
  8  9  1  0  0  0  0
  4  6  1  0  0  0  0
 10 11  1  0  0  0  0
  4  5  2  0  0  0  0
 16 15  1  0  0  0  0
  2  1  1  0  0  0  0
 13  6  2  0  0  0  0
 20 21  2  0  0  0  0
 18 17  2  0  0  0  0
 20 22  1  0  0  0  0
  6  7  1  0  0  0  0
 18 19  1  0  0  0  0
 17 36  1  0  0  0  0
 16 34  1  0  0  0  0
 16 35  1  0  0  0  0
 15 32  1  0  0  0  0
 15 33  1  0  0  0  0
  3 26  1  0  0  0  0
  7 27  1  0  0  0  0
 12 30  1  0  0  0  0
 14 31  1  0  0  0  0
  9 28  1  0  0  0  0
 11 29  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
 22 40  1  0  0  0  0
 19 37  1  0  0  0  0
 19 38  1  0  0  0  0
 19 39  1  0  0  0  0
M  END

     RDKit          3D

 40 40  0  0  0  0  0  0  0  0999 V2000
    4.1367    0.8476    0.3836 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7796    1.3878    0.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7661    1.5728    0.8862 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8248    1.2292    2.3306 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6875    1.6872    3.0732 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7569    0.3435    2.8703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0388   -0.4273    2.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0222   -1.2556    2.5334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8125   -2.0270    1.7252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2229   -1.3235    3.9092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1950   -2.1392    4.4128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4394   -0.5783    4.7796 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5573    0.2472    4.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3119    0.9413    5.1675 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5812    1.7219   -1.4494 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3602    0.4965   -2.3532 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1363   -0.3052   -1.9852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0724   -0.2711   -2.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4607    0.6155   -3.7257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1241   -1.1593   -2.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1529   -1.6325   -0.8962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0997   -1.3999   -2.9106 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2181    0.5471    1.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3698   -0.0372   -0.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9044    1.6047    0.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8037    1.9440    0.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1110   -0.3996    0.9368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5231   -1.9087    0.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5947   -2.5615    3.6262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5950   -0.6444    5.8518 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0404    1.3903    4.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7322    2.4084   -1.5701 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4586    2.2765   -1.8060 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3081    0.8308   -3.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2311   -0.1687   -2.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2958   -0.9949   -1.1554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5548    0.0316   -4.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2633    1.4147   -3.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4195    1.1059   -3.5244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7272   -1.9963   -2.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
 15  2  1  0
  7  8  2  0
 20 18  1  0
  8 10  1  0
  2  3  2  0
 10 12  2  0
 12 13  1  0
 17 16  1  0
 13 14  1  0
  3  4  1  0
  8  9  1  0
  4  6  1  0
 10 11  1  0
  4  5  2  0
 16 15  1  0
  2  1  1  0
 13  6  2  0
 20 21  2  0
 18 17  2  0
 20 22  1  0
  6  7  1  0
 18 19  1  0
 17 36  1  0
 16 34  1  0
 16 35  1  0
 15 32  1  0
 15 33  1  0
  3 26  1  0
  7 27  1  0
 12 30  1  0
 14 31  1  0
  9 28  1  0
 11 29  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 22 40  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
M  END


  Mrv1652306192120553D          

 40 40  0  0  0  0            999 V2000
    4.1367    0.8476    0.3836 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7796    1.3878    0.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7661    1.5728    0.8862 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8248    1.2292    2.3306 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6875    1.6872    3.0732 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7569    0.3435    2.8703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0388   -0.4273    2.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0222   -1.2556    2.5334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8125   -2.0270    1.7252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2229   -1.3235    3.9092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1950   -2.1392    4.4128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4394   -0.5783    4.7796 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5573    0.2472    4.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3119    0.9413    5.1675 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5812    1.7219   -1.4494 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3602    0.4965   -2.3532 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1363   -0.3052   -1.9852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0724   -0.2711   -2.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4607    0.6155   -3.7257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1241   -1.1593   -2.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1529   -1.6325   -0.8962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0997   -1.3999   -2.9106 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2181    0.5471    1.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3698   -0.0372   -0.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9044    1.6047    0.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8037    1.9440    0.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1110   -0.3996    0.9368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5231   -1.9087    0.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5947   -2.5615    3.6262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5950   -0.6444    5.8518 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0404    1.3903    4.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7322    2.4084   -1.5701 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4586    2.2765   -1.8060 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3081    0.8308   -3.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2311   -0.1687   -2.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2958   -0.9949   -1.1554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5548    0.0316   -4.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2633    1.4147   -3.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4195    1.1059   -3.5244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7272   -1.9963   -2.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
 15  2  1  0  0  0  0
  7  8  2  0  0  0  0
 20 18  1  0  0  0  0
  8 10  1  0  0  0  0
  2  3  2  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 17 16  1  0  0  0  0
 13 14  1  0  0  0  0
  3  4  1  0  0  0  0
  8  9  1  0  0  0  0
  4  6  1  0  0  0  0
 10 11  1  0  0  0  0
  4  5  2  0  0  0  0
 16 15  1  0  0  0  0
  2  1  1  0  0  0  0
 13  6  2  0  0  0  0
 20 21  2  0  0  0  0
 18 17  2  0  0  0  0
 20 22  1  0  0  0  0
  6  7  1  0  0  0  0
 18 19  1  0  0  0  0
 17 36  1  0  0  0  0
 16 34  1  0  0  0  0
 16 35  1  0  0  0  0
 15 32  1  0  0  0  0
 15 33  1  0  0  0  0
  3 26  1  0  0  0  0
  7 27  1  0  0  0  0
 12 30  1  0  0  0  0
 14 31  1  0  0  0  0
  9 28  1  0  0  0  0
 11 29  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
 22 40  1  0  0  0  0
 19 37  1  0  0  0  0
 19 38  1  0  0  0  0
 19 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0027235

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C(=C(/[H])C([H])([H])C([H])([H])C(=C(/[H])C(=O)C1=C(O[H])C([H])=C(O[H])C(O[H])=C1[H])\C([H])([H])[H])\C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H18O6/c1-9(4-3-5-10(2)16(21)22)6-12(17)11-7-14(19)15(20)8-13(11)18/h5-8,18-20H,3-4H2,1-2H3,(H,21,22)/b9-6+,10-5+

> <INCHI_KEY>
RTSRTVWJAJLQRY-TXFIJWAUSA-N

> <FORMULA>
C16H18O6

> <MOLECULAR_WEIGHT>
306.314

> <EXACT_MASS>
306.1103383

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
31.072210739400212

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,6E)-2,6-dimethyl-8-oxo-8-(2,4,5-trihydroxyphenyl)octa-2,6-dienoic acid

> <ALOGPS_LOGP>
2.77

> <JCHEM_LOGP>
3.5078935169999994

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.532783071485692

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.196218213783415

> <JCHEM_PKA_STRONGEST_BASIC>
-6.255164082646297

> <JCHEM_POLAR_SURFACE_AREA>
115.06000000000002

> <JCHEM_REFRACTIVITY>
82.52649999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.81e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,6E)-2,6-dimethyl-8-oxo-8-(2,4,5-trihydroxyphenyl)octa-2,6-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 40 40  0  0  0  0  0  0  0  0999 V2000
    4.1367    0.8476    0.3836 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7796    1.3878    0.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7661    1.5728    0.8862 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8248    1.2292    2.3306 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6875    1.6872    3.0732 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7569    0.3435    2.8703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0388   -0.4273    2.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0222   -1.2556    2.5334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8125   -2.0270    1.7252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2229   -1.3235    3.9092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1950   -2.1392    4.4128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4394   -0.5783    4.7796 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5573    0.2472    4.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3119    0.9413    5.1675 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5812    1.7219   -1.4494 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3602    0.4965   -2.3532 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1363   -0.3052   -1.9852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0724   -0.2711   -2.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4607    0.6155   -3.7257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1241   -1.1593   -2.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1529   -1.6325   -0.8962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0997   -1.3999   -2.9106 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2181    0.5471    1.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3698   -0.0372   -0.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9044    1.6047    0.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8037    1.9440    0.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1110   -0.3996    0.9368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5231   -1.9087    0.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5947   -2.5615    3.6262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5950   -0.6444    5.8518 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0404    1.3903    4.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7322    2.4084   -1.5701 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4586    2.2765   -1.8060 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3081    0.8308   -3.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2311   -0.1687   -2.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2958   -0.9949   -1.1554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5548    0.0316   -4.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2633    1.4147   -3.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4195    1.1059   -3.5244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7272   -1.9963   -2.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
 15  2  1  0
  7  8  2  0
 20 18  1  0
  8 10  1  0
  2  3  2  0
 10 12  2  0
 12 13  1  0
 17 16  1  0
 13 14  1  0
  3  4  1  0
  8  9  1  0
  4  6  1  0
 10 11  1  0
  4  5  2  0
 16 15  1  0
  2  1  1  0
 13  6  2  0
 20 21  2  0
 18 17  2  0
 20 22  1  0
  6  7  1  0
 18 19  1  0
 17 36  1  0
 16 34  1  0
 16 35  1  0
 15 32  1  0
 15 33  1  0
  3 26  1  0
  7 27  1  0
 12 30  1  0
 14 31  1  0
  9 28  1  0
 11 29  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 22 40  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       4.137   0.848   0.384  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.780   1.388   0.019  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.766   1.573   0.886  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.825   1.229   2.331  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.688   1.687   3.073  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.757   0.344   2.870  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.039  -0.427   2.008  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.022  -1.256   2.533  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.813  -2.027   1.725  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.223  -1.323   3.909  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.195  -2.139   4.413  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.439  -0.578   4.780  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.557   0.247   4.258  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.312   0.941   5.168  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.581   1.722  -1.449  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.360   0.497  -2.353  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.136  -0.305  -1.985  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.072  -0.271  -2.582  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.461   0.616  -3.726  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.124  -1.159  -2.021  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.153  -1.633  -0.896  0.00  0.00           O+0
HETATM   22  O   UNK     0      -2.100  -1.400  -2.911  0.00  0.00           O+0
HETATM   23  H   UNK     0       4.218   0.547   1.431  0.00  0.00           H+0
HETATM   24  H   UNK     0       4.370  -0.037  -0.217  0.00  0.00           H+0
HETATM   25  H   UNK     0       4.904   1.605   0.194  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.804   1.944   0.545  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.111  -0.400   0.937  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.523  -1.909   0.792  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.595  -2.562   3.626  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.595  -0.644   5.852  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.040   1.390   4.682  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.732   2.408  -1.570  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.459   2.276  -1.806  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.308   0.831  -3.395  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.231  -0.169  -2.307  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.296  -0.995  -1.155  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.555   0.032  -4.647  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.263   1.415  -3.906  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.420   1.106  -3.524  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.727  -1.996  -2.453  0.00  0.00           H+0
CONECT    1    2   23   24   25                                             
CONECT    2   15    3    1                                                  
CONECT    3    2    4   26                                                  
CONECT    4    3    6    5                                                  
CONECT    5    4                                                            
CONECT    6    4   13    7                                                  
CONECT    7    8    6   27                                                  
CONECT    8    7   10    9                                                  
CONECT    9    8   28                                                       
CONECT   10    8   12   11                                                  
CONECT   11   10   29                                                       
CONECT   12   10   13   30                                                  
CONECT   13   12   14    6                                                  
CONECT   14   13   31                                                       
CONECT   15    2   16   32   33                                             
CONECT   16   17   15   34   35                                             
CONECT   17   16   18   36                                                  
CONECT   18   20   17   19                                                  
CONECT   19   18   37   38   39                                             
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   40                                                       
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    3                                                            
CONECT   27    7                                                            
CONECT   28    9                                                            
CONECT   29   11                                                            
CONECT   30   12                                                            
CONECT   31   14                                                            
CONECT   32   15                                                            
CONECT   33   15                                                            
CONECT   34   16                                                            
CONECT   35   16                                                            
CONECT   36   17                                                            
CONECT   37   19                                                            
CONECT   38   19                                                            
CONECT   39   19                                                            
CONECT   40   22                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   80    0
END

RDKit          3D

40 40  0  0  0  0  0  0  0  0999 V2000
    4.1367    0.8476    0.3836 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7796    1.3878    0.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7661    1.5728    0.8862 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8248    1.2292    2.3306 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6875    1.6872    3.0732 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7569    0.3435    2.8703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0388   -0.4273    2.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0222   -1.2556    2.5334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8125   -2.0270    1.7252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2229   -1.3235    3.9092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1950   -2.1392    4.4128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4394   -0.5783    4.7796 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5573    0.2472    4.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3119    0.9413    5.1675 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5812    1.7219   -1.4494 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3602    0.4965   -2.3532 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1363   -0.3052   -1.9852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0724   -0.2711   -2.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4607    0.6155   -3.7257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1241   -1.1593   -2.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1529   -1.6325   -0.8962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0997   -1.3999   -2.9106 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2181    0.5471    1.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3698   -0.0372   -0.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9044    1.6047    0.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8037    1.9440    0.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1110   -0.3996    0.9368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5231   -1.9087    0.7918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5947   -2.5615    3.6262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5950   -0.6444    5.8518 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0404    1.3903    4.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7322    2.4084   -1.5701 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4586    2.2765   -1.8060 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3081    0.8308   -3.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2311   -0.1687   -2.3072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2958   -0.9949   -1.1554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5548    0.0316   -4.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2633    1.4147   -3.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4195    1.1059   -3.5244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7272   -1.9963   -2.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
 15  2  1  0
  7  8  2  0
 20 18  1  0
  8 10  1  0
  2  3  2  0
 10 12  2  0
 12 13  1  0
 17 16  1  0
 13 14  1  0
  3  4  1  0
  8  9  1  0
  4  6  1  0
 10 11  1  0
  4  5  2  0
 16 15  1  0
  2  1  1  0
 13  6  2  0
 20 21  2  0
 18 17  2  0
 20 22  1  0
  6  7  1  0
 18 19  1  0
 17 36  1  0
 16 34  1  0
 16 35  1  0
 15 32  1  0
 15 33  1  0
  3 26  1  0
  7 27  1  0
 12 30  1  0
 14 31  1  0
  9 28  1  0
 11 29  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 22 40  1  0
 19 37  1  0
 19 38  1  0
 19 39  1  0
M  END

View in JSmol

Synonyms

Value	Source
(2E,6E)-2,6-Dimethyl-8-oxo-8-(2,4,5-trihydroxyphenyl)octa-2,6-dienoate	Generator

Chemical Formula

C₁₆H₁₈O₆

Average Mass

306.3140 Da

Monoisotopic Mass

306.11034 Da

IUPAC Name

(2E,6E)-2,6-dimethyl-8-oxo-8-(2,4,5-trihydroxyphenyl)octa-2,6-dienoic acid

Traditional Name

(2E,6E)-2,6-dimethyl-8-oxo-8-(2,4,5-trihydroxyphenyl)octa-2,6-dienoic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C(=C(/[H])C([H])([H])C([H])([H])C(=C(/[H])C(=O)C1=C(O[H])C([H])=C(O[H])C(O[H])=C1[H])\C([H])([H])[H])\C([H])([H])[H]

InChI Identifier

InChI=1S/C16H18O6/c1-9(4-3-5-10(2)16(21)22)6-12(17)11-7-14(19)15(20)8-13(11)18/h5-8,18-20H,3-4H2,1-2H3,(H,21,22)/b9-6+,10-5+

InChI Key

RTSRTVWJAJLQRY-TXFIJWAUSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Tricholoma orirubens	JEOL database	Kawagishi, H., et al, Tetrahedron 60, 7049 (2004)

Chemical Taxonomy

Classification

Not classified

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	2.77	ALOGPS
logP	3.51	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	4.2	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.06 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	82.53 m³·mol⁻¹	ChemAxon
Polarizability	31.07 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

8533240

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10357791

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kawagishi, H., et al. (2004). Kawagishi, H., et al, Tetrahedron 60, 7049 (2004). Tetrahedron.

Showing NP-Card for orirubenone B (NP0027235)

MOL for NP0027235 (orirubenone B)

3D MOL for NP0027235 (orirubenone B)

3D SDF for NP0027235 (orirubenone B)

3D-SDF for NP0027235 (orirubenone B)

PDB for NP0027235 (orirubenone B)

3D PDB for NP0027235 (orirubenone B)

SMILES for NP0027235 (orirubenone B)

INCHI for NP0027235 (orirubenone B)

Structure for NP0027235 (orirubenone B)

3D Structure for NP0027235 (orirubenone B)