NP-MRD: Showing NP-Card for Oxosorbicillinol (NP0003244)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2020-12-09 00:32:17 UTC

Updated at

2021-07-15 16:45:53 UTC

NP-MRD ID

NP0003244

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Oxosorbicillinol

Provided By

NPAtlas

Description

Oxosorbicillinol is found in Penicillium and Penicillium chrysogenum. It was first documented in 2000 (PMID: 10803967). Based on a literature review very few articles have been published on (2R,6E)-2,5-dihydroxy-6-[(2E,4E)-1-hydroxyhexa-2,4-dien-1-ylidene]-2,4-dimethylcyclohex-4-ene-1,3-dione (PMID: 15974609) (PMID: 32789380) (PMID: 31943627) (PMID: 29790637) (PMID: 29104566) (PMID: 28618182).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117463D          

 35 35  0  0  0  0            999 V2000
    6.3381    0.3043    0.3689 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0987   -0.4858    0.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9334    0.1139    0.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6854   -0.6295    0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5040    0.0039    0.3631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3273   -0.8098    0.2385 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4320   -2.2065   -0.0065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8849   -0.2729    0.3497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1042    1.1349    0.6019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2341    1.7702    1.2044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3925    1.7474    0.1125 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3208    1.7147   -1.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5586    3.0210    0.6064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4520    0.8080    0.5304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4826    1.2432    1.0805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2526   -0.6012    0.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4353   -1.5040    0.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0444   -1.1564    0.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8587   -2.4954   -0.0486 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4379    0.7281    1.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2367   -0.2649    0.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2487    1.1609   -0.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1740   -1.5504    0.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8857    1.1902    0.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7226   -1.6942    0.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5618    1.0433    0.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0478   -2.5768   -0.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1530    2.2809   -1.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3621    0.6274   -1.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3296    2.0785   -1.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7981    3.6095   -0.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3460   -2.3343    0.8427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4462   -1.8626   -0.9354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3731   -0.9204    0.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8051   -3.2150    0.6617 H   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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  1  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18  8  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  2 23  1  0  0  0  0
  3 24  1  0  0  0  0
  4 25  1  0  0  0  0
  5 26  1  0  0  0  0
  7 27  1  0  0  0  0
 12 28  1  0  0  0  0
 12 29  1  0  0  0  0
 12 30  1  0  0  0  0
 13 31  1  0  0  0  0
 17 32  1  0  0  0  0
 17 33  1  0  0  0  0
 17 34  1  0  0  0  0
 19 35  1  0  0  0  0
M  END

     RDKit          3D

 35 35  0  0  0  0  0  0  0  0999 V2000
    6.3381    0.3043    0.3689 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0987   -0.4858    0.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9334    0.1139    0.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6854   -0.6295    0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5040    0.0039    0.3631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3273   -0.8098    0.2385 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4320   -2.2065   -0.0065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8849   -0.2729    0.3497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1042    1.1349    0.6019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2341    1.7702    1.2044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3925    1.7474    0.1125 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3208    1.7147   -1.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5586    3.0210    0.6064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4520    0.8080    0.5304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4826    1.2432    1.0805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2526   -0.6012    0.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4353   -1.5040    0.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0444   -1.1564    0.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8587   -2.4954   -0.0486 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4379    0.7281    1.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2367   -0.2649    0.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2487    1.1609   -0.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1740   -1.5504    0.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8857    1.1902    0.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7226   -1.6942    0.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5618    1.0433    0.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0478   -2.5768   -0.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1530    2.2809   -1.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3621    0.6274   -1.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3296    2.0785   -1.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7981    3.6095   -0.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3460   -2.3343    0.8427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4462   -1.8626   -0.9354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3731   -0.9204    0.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8051   -3.2150    0.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 11 13  1  1
 11 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 18  8  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 17 32  1  0
 17 33  1  0
 17 34  1  0
 19 35  1  0
M  END


  Mrv1652306242117463D          

 35 35  0  0  0  0            999 V2000
    6.3381    0.3043    0.3689 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0987   -0.4858    0.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9334    0.1139    0.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6854   -0.6295    0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5040    0.0039    0.3631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3273   -0.8098    0.2385 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4320   -2.2065   -0.0065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8849   -0.2729    0.3497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1042    1.1349    0.6019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2341    1.7702    1.2044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3925    1.7474    0.1125 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3208    1.7147   -1.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5586    3.0210    0.6064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4520    0.8080    0.5304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4826    1.2432    1.0805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2526   -0.6012    0.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4353   -1.5040    0.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0444   -1.1564    0.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8587   -2.4954   -0.0486 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4379    0.7281    1.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2367   -0.2649    0.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2487    1.1609   -0.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1740   -1.5504    0.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8857    1.1902    0.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7226   -1.6942    0.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5618    1.0433    0.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0478   -2.5768   -0.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1530    2.2809   -1.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3621    0.6274   -1.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3296    2.0785   -1.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7981    3.6095   -0.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3460   -2.3343    0.8427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4462   -1.8626   -0.9354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3731   -0.9204    0.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8051   -3.2150    0.6617 H   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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  1  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18  8  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  2 23  1  0  0  0  0
  3 24  1  0  0  0  0
  4 25  1  0  0  0  0
  5 26  1  0  0  0  0
  7 27  1  0  0  0  0
 12 28  1  0  0  0  0
 12 29  1  0  0  0  0
 12 30  1  0  0  0  0
 13 31  1  0  0  0  0
 17 32  1  0  0  0  0
 17 33  1  0  0  0  0
 17 34  1  0  0  0  0
 19 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003244

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H16O5/c1-4-5-6-7-9(15)10-11(16)8(2)12(17)14(3,19)13(10)18/h4-7,15-16,19H,1-3H3/b5-4+,7-6+,10-9+/t14-/m1/s1

> <INCHI_KEY>
JSSFRHLBNRCOAQ-KGAWMYLDSA-N

> <FORMULA>
C14H16O5

> <MOLECULAR_WEIGHT>
264.277

> <EXACT_MASS>
264.099773615

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
27.771739001912394

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,6E)-2,5-dihydroxy-6-[(2E,4E)-1-hydroxyhexa-2,4-dien-1-ylidene]-2,4-dimethylcyclohex-4-ene-1,3-dione

> <ALOGPS_LOGP>
0.86

> <JCHEM_LOGP>
1.4825725003333332

> <ALOGPS_LOGS>
-2.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.56825382715303

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7475284509970934

> <JCHEM_PKA_STRONGEST_BASIC>
-4.343054231107362

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
74.9157

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.58e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,6E)-2,5-dihydroxy-6-[(2E,4E)-1-hydroxyhexa-2,4-dien-1-ylidene]-2,4-dimethylcyclohex-4-ene-1,3-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 35 35  0  0  0  0  0  0  0  0999 V2000
    6.3381    0.3043    0.3689 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0987   -0.4858    0.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9334    0.1139    0.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6854   -0.6295    0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5040    0.0039    0.3631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3273   -0.8098    0.2385 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4320   -2.2065   -0.0065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8849   -0.2729    0.3497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1042    1.1349    0.6019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2341    1.7702    1.2044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3925    1.7474    0.1125 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3208    1.7147   -1.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5586    3.0210    0.6064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4520    0.8080    0.5304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4826    1.2432    1.0805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2526   -0.6012    0.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4353   -1.5040    0.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0444   -1.1564    0.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8587   -2.4954   -0.0486 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4379    0.7281    1.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2367   -0.2649    0.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2487    1.1609   -0.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1740   -1.5504    0.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8857    1.1902    0.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7226   -1.6942    0.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5618    1.0433    0.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0478   -2.5768   -0.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1530    2.2809   -1.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3621    0.6274   -1.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3296    2.0785   -1.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7981    3.6095   -0.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3460   -2.3343    0.8427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4462   -1.8626   -0.9354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3731   -0.9204    0.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8051   -3.2150    0.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 11 13  1  1
 11 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 18  8  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 17 32  1  0
 17 33  1  0
 17 34  1  0
 19 35  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       6.338   0.304   0.369  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.099  -0.486   0.249  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.933   0.114   0.359  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.685  -0.630   0.247  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.504   0.004   0.363  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.327  -0.810   0.239  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.432  -2.207  -0.007  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.885  -0.273   0.350  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.104   1.135   0.602  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.234   1.770   1.204  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.393   1.747   0.113  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.321   1.715  -1.406  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.559   3.021   0.606  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.452   0.808   0.530  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.483   1.243   1.081  0.00  0.00           O+0
HETATM   16  C   UNK     0      -3.253  -0.601   0.283  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.435  -1.504   0.122  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.044  -1.156   0.189  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.859  -2.495  -0.049  0.00  0.00           O+0
HETATM   20  H   UNK     0       6.438   0.728   1.395  0.00  0.00           H+0
HETATM   21  H   UNK     0       7.237  -0.265   0.055  0.00  0.00           H+0
HETATM   22  H   UNK     0       6.249   1.161  -0.342  0.00  0.00           H+0
HETATM   23  H   UNK     0       5.174  -1.550   0.072  0.00  0.00           H+0
HETATM   24  H   UNK     0       3.886   1.190   0.538  0.00  0.00           H+0
HETATM   25  H   UNK     0       2.723  -1.694   0.072  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.562   1.043   0.522  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.048  -2.577  -0.688  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.153   2.281  -1.868  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.362   0.627  -1.691  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.330   2.079  -1.752  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.798   3.610  -0.160  0.00  0.00           H+0
HETATM   32  H   UNK     0      -4.346  -2.334   0.843  0.00  0.00           H+0
HETATM   33  H   UNK     0      -4.446  -1.863  -0.935  0.00  0.00           H+0
HETATM   34  H   UNK     0      -5.373  -0.920   0.278  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.805  -3.215   0.662  0.00  0.00           H+0
CONECT    1    2   20   21   22                                             
CONECT    2    1    3   23                                                  
CONECT    3    2    4   24                                                  
CONECT    4    3    5   25                                                  
CONECT    5    4    6   26                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6   27                                                       
CONECT    8    6    9   18                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13   14                                             
CONECT   12   11   28   29   30                                             
CONECT   13   11   31                                                       
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16   32   33   34                                             
CONECT   18   16   19    8                                                  
CONECT   19   18   35                                                       
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    2                                                            
CONECT   24    3                                                            
CONECT   25    4                                                            
CONECT   26    5                                                            
CONECT   27    7                                                            
CONECT   28   12                                                            
CONECT   29   12                                                            
CONECT   30   12                                                            
CONECT   31   13                                                            
CONECT   32   17                                                            
CONECT   33   17                                                            
CONECT   34   17                                                            
CONECT   35   19                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   70    0
END

RDKit          3D

35 35  0  0  0  0  0  0  0  0999 V2000
    6.3381    0.3043    0.3689 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0987   -0.4858    0.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9334    0.1139    0.3592 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6854   -0.6295    0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5040    0.0039    0.3631 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3273   -0.8098    0.2385 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4320   -2.2065   -0.0065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8849   -0.2729    0.3497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1042    1.1349    0.6019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2341    1.7702    1.2044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3925    1.7474    0.1125 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3208    1.7147   -1.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5586    3.0210    0.6064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4520    0.8080    0.5304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4826    1.2432    1.0805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2526   -0.6012    0.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4353   -1.5040    0.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0444   -1.1564    0.1885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8587   -2.4954   -0.0486 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4379    0.7281    1.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2367   -0.2649    0.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2487    1.1609   -0.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1740   -1.5504    0.0715 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8857    1.1902    0.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7226   -1.6942    0.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5618    1.0433    0.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0478   -2.5768   -0.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1530    2.2809   -1.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3621    0.6274   -1.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3296    2.0785   -1.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7981    3.6095   -0.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3460   -2.3343    0.8427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4462   -1.8626   -0.9354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3731   -0.9204    0.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8051   -3.2150    0.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 11 13  1  1
 11 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 18  8  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  7 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 17 32  1  0
 17 33  1  0
 17 34  1  0
 19 35  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₄H₁₆O₅

Average Mass

264.2770 Da

Monoisotopic Mass

264.09977 Da

IUPAC Name

(2R,6E)-2,5-dihydroxy-6-[(2E,4E)-1-hydroxyhexa-2,4-dien-1-ylidene]-2,4-dimethylcyclohex-4-ene-1,3-dione

Traditional Name

(2R,6E)-2,5-dihydroxy-6-[(2E,4E)-1-hydroxyhexa-2,4-dien-1-ylidene]-2,4-dimethylcyclohex-4-ene-1,3-dione

CAS Registry Number

Not Available

SMILES

C\C=C\C=C\C(\O)=C1\C(O)=C(C)C(=O)[C@@](C)(O)C1=O

InChI Identifier

InChI=1S/C14H16O5/c1-4-5-6-7-9(15)10-11(16)8(2)12(17)14(3,19)13(10)18/h4-7,15-16,19H,1-3H3/b5-4+,7-6+,10-9+/t14-/m1/s1

InChI Key

JSSFRHLBNRCOAQ-KGAWMYLDSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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	NPAtlas	10803967
Penicillium chrysogenum	LOTUS Database	35616633

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	0.86	ALOGPS
logP	1.48	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	3.75	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	74.92 m³·mol⁻¹	ChemAxon
Polarizability	27.77 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

NPAtlas ID

NPA001693

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8191223

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10015650

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Abe N, Yamamoto K, Hirota A: Novel fungal metabolites, demethylsorbicillin and oxosorbicillinol, isolated from Trichoderma sp. USF-2690. Biosci Biotechnol Biochem. 2000 Mar;64(3):620-2. doi: 10.1271/bbb.64.620. [PubMed:10803967 ]
Maskey RP, Grun-Wollny I, Laatsch H: Sorbicillin analogues and related dimeric compounds from Penicillium notatum. J Nat Prod. 2005 Jun;68(6):865-70. doi: 10.1021/np040137t. [PubMed:15974609 ]
Kahlert L, Cox RJ, Skellam E: The same but different: multiple functions of the fungal flavin dependent monooxygenase SorD from Penicillium chrysogenum. Chem Commun (Camb). 2020 Sep 21;56(74):10934-10937. doi: 10.1039/d0cc03203d. Epub 2020 Aug 13. [PubMed:32789380 ]
Kahlert L, Bassiony EF, Cox RJ, Skellam EJ: Diels-Alder Reactions During the Biosynthesis of Sorbicillinoids. Angew Chem Int Ed Engl. 2020 Mar 27;59(14):5816-5822. doi: 10.1002/anie.201915486. Epub 2020 Feb 4. [PubMed:31943627 ]
Sib A, Gulder TAM: Chemo-enzymatic Total Synthesis of Oxosorbicillinol, Sorrentanone, Rezishanones B and C, Sorbicatechol A, Bisvertinolone, and (+)-Epoxysorbicillinol. Angew Chem Int Ed Engl. 2018 Oct 26;57(44):14650-14653. doi: 10.1002/anie.201802176. Epub 2018 Jun 25. [PubMed:29790637 ]
Derntl C, Guzman-Chavez F, Mello-de-Sousa TM, Busse HJ, Driessen AJM, Mach RL, Mach-Aigner AR: In Vivo Study of the Sorbicillinoid Gene Cluster in Trichoderma reesei. Front Microbiol. 2017 Oct 20;8:2037. doi: 10.3389/fmicb.2017.02037. eCollection 2017. [PubMed:29104566 ]
Guzman-Chavez F, Salo O, Nygard Y, Lankhorst PP, Bovenberg RAL, Driessen AJM: Mechanism and regulation of sorbicillin biosynthesis by Penicillium chrysogenum. Microb Biotechnol. 2017 Jul;10(4):958-968. doi: 10.1111/1751-7915.12736. Epub 2017 Jun 15. [PubMed:28618182 ]
Komoda T, Nishikawa M: 6'-Hydroxyoxosorbicillinol, a new lipoxygenase inhibitor and PGD2/LTB4 release suppressor from Penicillium sp. Biosci Biotechnol Biochem. 2012;76(7):1404-6. doi: 10.1271/bbb.120115. Epub 2012 Jul 7. [PubMed:22785490 ]
Abe N, Arakawa T, Hirota A: The biosynthesis of bisvertinolone: evidence for oxosorbicillinol as a direct precursor. Chem Commun (Camb). 2002 Feb 7;(3):204-5. doi: 10.1039/b109505f. [PubMed:12120368 ]

Showing NP-Card for Oxosorbicillinol (NP0003244)

MOL for NP0003244 (Oxosorbicillinol)

3D MOL for NP0003244 (Oxosorbicillinol)

3D SDF for NP0003244 (Oxosorbicillinol)

3D-SDF for NP0003244 (Oxosorbicillinol)

PDB for NP0003244 (Oxosorbicillinol)

3D PDB for NP0003244 (Oxosorbicillinol)

SMILES for NP0003244 (Oxosorbicillinol)

INCHI for NP0003244 (Oxosorbicillinol)

Structure for NP0003244 (Oxosorbicillinol)

3D Structure for NP0003244 (Oxosorbicillinol)