NP-MRD: Showing NP-Card for (2r,3s)-6-({2,6-dihydroxy-4-[(2s,3r)-3-hydroxybutan-2-yl]-3-methylphenyl}methyl)-2,3,4-trimethyl-2,3-dihydro-1-benzofuran-5,7-diol (NP0320442)

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Record Information

Version

2.0

Created at

2022-09-11 22:05:39 UTC

Updated at

2022-09-11 22:05:39 UTC

NP-MRD ID

NP0320442

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3s)-6-({2,6-dihydroxy-4-[(2s,3r)-3-hydroxybutan-2-yl]-3-methylphenyl}methyl)-2,3,4-trimethyl-2,3-dihydro-1-benzofuran-5,7-diol

Description

Dicitrinone E belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. (2r,3s)-6-({2,6-dihydroxy-4-[(2s,3r)-3-hydroxybutan-2-yl]-3-methylphenyl}methyl)-2,3,4-trimethyl-2,3-dihydro-1-benzofuran-5,7-diol is found in Penicillium citrinum. Based on a literature review very few articles have been published on Dicitrinone E.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122200052D          

 29 31  0  0  1  0            999 V2000
    5.4957   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    0.6979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6391    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246   -0.1271    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6391   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -0.5396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4457    0.3568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  1  0  0  0
  3  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 14 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 19 26  1  0  0  0  0
 26 27  1  6  0  0  0
 12 28  2  0  0  0  0
  2 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END

     RDKit          3D

 59 61  0  0  0  0  0  0  0  0999 V2000
   -2.9761   -0.9843    2.5068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7011   -0.1904    1.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5811   -0.1418    0.2387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8535   -0.9246    0.3103 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5500   -2.4164    0.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8221   -0.6130   -0.7962 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1491    0.8540   -0.7823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3800   -0.9673   -2.0594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2118    0.6300   -0.8288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0241    1.3451   -0.8891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7281    2.1139   -2.0124 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1222    1.2992    0.1844 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0822    2.1037    0.0615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3820    1.4125   -0.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6447    0.5904   -1.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6533    0.4147   -2.0409 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8802   -0.0016   -1.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2176   -0.8800   -2.4050 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8927    0.1885   -0.3050 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6195    0.9920    0.7614 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3780    1.6194    0.9300 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1950    2.4212    2.0425 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7576    1.0601    1.6018 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4844   -0.1520    1.3365 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9383    0.0296    1.6995 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2633   -0.2745   -0.1442 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5892   -1.6120   -0.6993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4820    0.5326    1.2546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6659    0.4320    2.3459 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9773   -1.4198    2.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2533   -1.8178    2.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8866   -0.3611    3.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3810   -0.6911    1.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4905   -2.6043    0.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9056   -2.8459   -0.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1358   -2.9598    1.0494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7398   -1.2302   -0.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4651    1.4105   -0.1027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1560    1.2672   -1.7966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2079    0.9502   -0.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0990   -1.1363   -2.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8707    0.6889   -1.6865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3693    2.1429   -2.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1691    2.8789    0.8717 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0421    2.7637   -0.8725 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5726   -0.0890   -2.8709 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3517   -0.9090   -3.0891 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0441   -0.4508   -3.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3923   -1.9337   -2.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4255    2.9349    2.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0256   -1.0163    1.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4934   -0.8165    1.2513 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0028   -0.0102    2.8008 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2987    0.9703    1.2695 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9334    0.4734   -0.6371 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5968   -1.8963   -0.2642 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9193   -2.4228   -0.3347 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7438   -1.5796   -1.7750 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1960    0.8288    2.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  8  1  0
  6  4  1  0
  4  5  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 28  1  0
 28 29  1  0
 28 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 19 26  1  0
 26 27  1  0
 26 24  1  0
 24 25  1  0
 24 23  1  0
 23 20  1  0
 20 21  2  0
 21 22  1  0
 12 10  1  0
 10 11  1  0
 10  9  2  0
  9  3  1  0
 21 14  1  0
 20 19  1  0
  7 38  1  0
  7 39  1  0
  7 40  1  0
  6 37  1  1
  8 41  1  0
  4 33  1  1
  5 34  1  0
  5 35  1  0
  5 36  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 29 59  1  0
 13 44  1  0
 13 45  1  0
 16 46  1  0
 18 47  1  0
 18 48  1  0
 18 49  1  0
 26 55  1  6
 27 56  1  0
 27 57  1  0
 27 58  1  0
 24 51  1  1
 25 52  1  0
 25 53  1  0
 25 54  1  0
 22 50  1  0
 11 43  1  0
  9 42  1  0
M  END


  Mrv1652309122200052D          

 29 31  0  0  1  0            999 V2000
    5.4957   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    0.6979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6391    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246   -0.1271    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6391   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -0.5396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4457    0.3568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  1  0  0  0
  3  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 14 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 19 26  1  0  0  0  0
 26 27  1  6  0  0  0
 12 28  2  0  0  0  0
  2 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0320442

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](O)[C@@H](C)C1=C(C)C(O)=C(CC2=C(O)C(C)=C3[C@H](C)[C@@H](C)OC3=C2O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H30O6/c1-9(13(5)24)15-8-18(25)16(20(26)11(15)3)7-17-21(27)12(4)19-10(2)14(6)29-23(19)22(17)28/h8-10,13-14,24-28H,7H2,1-6H3/t9-,10-,13-,14-/m1/s1

> <INCHI_KEY>
VVYMCJNWXOSIMS-DMTCVQMQSA-N

> <FORMULA>
C23H30O6

> <MOLECULAR_WEIGHT>
402.487

> <EXACT_MASS>
402.204238686

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
43.93623357641408

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S)-6-({2,6-dihydroxy-4-[(2S,3R)-3-hydroxybutan-2-yl]-3-methylphenyl}methyl)-2,3,4-trimethyl-2,3-dihydro-1-benzofuran-5,7-diol

> <JCHEM_LOGP>
4.844245715333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.888980722510308

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.128775107034457

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7279279542302826

> <JCHEM_POLAR_SURFACE_AREA>
110.38000000000001

> <JCHEM_REFRACTIVITY>
112.92569999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S)-6-({2,6-dihydroxy-4-[(2S,3R)-3-hydroxybutan-2-yl]-3-methylphenyl}methyl)-2,3,4-trimethyl-2,3-dihydro-1-benzofuran-5,7-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      10.259  -0.237   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.259   1.303   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.592   2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.926   1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.260   2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.926  -0.237   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.260  -1.007   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      11.592  -1.007   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      11.592   3.613   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.259   4.383   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.259   5.923   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.591   1.303   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.924  -0.237   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.924   5.923   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.320   2.843   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.925   2.073   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.299   0.666   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   28                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    3   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   28                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   26                                                  
CONECT   20   19   21   23                                                  
CONECT   21   20   14   22                                                  
CONECT   22   21                                                            
CONECT   23   20   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   19   27                                                  
CONECT   27   26                                                            
CONECT   28   12    2   29                                                  
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₀O₆

Average Mass

402.4870 Da

Monoisotopic Mass

402.20424 Da

IUPAC Name

(2R,3S)-6-({2,6-dihydroxy-4-[(2S,3R)-3-hydroxybutan-2-yl]-3-methylphenyl}methyl)-2,3,4-trimethyl-2,3-dihydro-1-benzofuran-5,7-diol

Traditional Name

(2R,3S)-6-({2,6-dihydroxy-4-[(2S,3R)-3-hydroxybutan-2-yl]-3-methylphenyl}methyl)-2,3,4-trimethyl-2,3-dihydro-1-benzofuran-5,7-diol

CAS Registry Number

Not Available

SMILES

C[C@@H](O)[C@@H](C)C1=C(C)C(O)=C(CC2=C(O)C(C)=C3[C@H](C)[C@@H](C)OC3=C2O)C(O)=C1

InChI Identifier

InChI=1S/C23H30O6/c1-9(13(5)24)15-8-18(25)16(20(26)11(15)3)7-17-21(27)12(4)19-10(2)14(6)29-23(19)22(17)28/h8-10,13-14,24-28H,7H2,1-6H3/t9-,10-,13-,14-/m1/s1

InChI Key

VVYMCJNWXOSIMS-DMTCVQMQSA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Penicillium citrinum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Bicyclic monoterpenoid
Aromatic monoterpenoid
P-cymene
Coumaran
Phenylpropane
Resorcinol
P-cresol
O-cresol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Toluene
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	4.84	ChemAxon
pKa (Strongest Acidic)	8.13	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	110.38 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	112.93 m³·mol⁻¹	ChemAxon
Polarizability	43.94 Å³	ChemAxon
Number of Rings	3	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

78315768

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

146682130

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3s)-6-({2,6-dihydroxy-4-[(2s,3r)-3-hydroxybutan-2-yl]-3-methylphenyl}methyl)-2,3,4-trimethyl-2,3-dihydro-1-benzofuran-5,7-diol (NP0320442)

MOL for NP0320442 ((2r,3s)-6-({2,6-dihydroxy-4-[(2s,3r)-3-hydroxybutan-2-yl]-3-methylphenyl}methyl)-2,3,4-trimethyl-2,3-dihydro-1-benzofuran-5,7-diol)

3D MOL for NP0320442 ((2r,3s)-6-({2,6-dihydroxy-4-[(2s,3r)-3-hydroxybutan-2-yl]-3-methylphenyl}methyl)-2,3,4-trimethyl-2,3-dihydro-1-benzofuran-5,7-diol)

3D SDF for NP0320442 ((2r,3s)-6-({2,6-dihydroxy-4-[(2s,3r)-3-hydroxybutan-2-yl]-3-methylphenyl}methyl)-2,3,4-trimethyl-2,3-dihydro-1-benzofuran-5,7-diol)

3D-SDF for NP0320442 ((2r,3s)-6-({2,6-dihydroxy-4-[(2s,3r)-3-hydroxybutan-2-yl]-3-methylphenyl}methyl)-2,3,4-trimethyl-2,3-dihydro-1-benzofuran-5,7-diol)

PDB for NP0320442 ((2r,3s)-6-({2,6-dihydroxy-4-[(2s,3r)-3-hydroxybutan-2-yl]-3-methylphenyl}methyl)-2,3,4-trimethyl-2,3-dihydro-1-benzofuran-5,7-diol)

3D PDB for NP0320442 ((2r,3s)-6-({2,6-dihydroxy-4-[(2s,3r)-3-hydroxybutan-2-yl]-3-methylphenyl}methyl)-2,3,4-trimethyl-2,3-dihydro-1-benzofuran-5,7-diol)

SMILES for NP0320442 ((2r,3s)-6-({2,6-dihydroxy-4-[(2s,3r)-3-hydroxybutan-2-yl]-3-methylphenyl}methyl)-2,3,4-trimethyl-2,3-dihydro-1-benzofuran-5,7-diol)

INCHI for NP0320442 ((2r,3s)-6-({2,6-dihydroxy-4-[(2s,3r)-3-hydroxybutan-2-yl]-3-methylphenyl}methyl)-2,3,4-trimethyl-2,3-dihydro-1-benzofuran-5,7-diol)

Structure for NP0320442 ((2r,3s)-6-({2,6-dihydroxy-4-[(2s,3r)-3-hydroxybutan-2-yl]-3-methylphenyl}methyl)-2,3,4-trimethyl-2,3-dihydro-1-benzofuran-5,7-diol)

3D Structure for NP0320442 ((2r,3s)-6-({2,6-dihydroxy-4-[(2s,3r)-3-hydroxybutan-2-yl]-3-methylphenyl}methyl)-2,3,4-trimethyl-2,3-dihydro-1-benzofuran-5,7-diol)