NP-MRD: Showing NP-Card for phorbasin C (NP0038600)

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Record Information

Version

2.0

Created at

2021-06-20 21:14:52 UTC

Updated at

2021-06-30 00:11:28 UTC

NP-MRD ID

NP0038600

Secondary Accession Numbers

None

Natural Product Identification

Common Name

phorbasin C

Provided By

JEOL Database JEOL Logo

Description

phorbasin C is found in Phorbas sp. phorbasin C was first documented in 2008 (Zhang, H., et al.). Based on a literature review very few articles have been published on (4S)-2-(Hydroxymethyl)-4alpha-acetoxy-5alpha-[(1E,3E,5S,6E)-1,5,9-trimethyl-1,3,6-decatrienyl]-6beta-hydroxy-2-cyclohexene-1-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123143D          

 59 59  0  0  0  0            999 V2000
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    0.2238    0.2745   -2.6628 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6511    0.2407   -2.5208 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6549    0.4948   -1.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9173    1.2433   -1.9691 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9377    1.6766   -3.3254 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5187    0.0217   -0.2580 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4405    0.1856    0.5446 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1977   -0.6179    0.1813 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.5865   -1.4533   -0.9610 C   0  0  1  0  0  0  0  0  0  0  0  0
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 10  7  1  0  0  0  0
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  6  5  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306202123143D          

 59 59  0  0  0  0            999 V2000
   -0.7692    1.3084   -2.2283 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2238    0.2745   -2.6628 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0138    1.1654   -1.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6843    1.2017   -2.8178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1950   -1.1734   -3.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7195    0.6150   -3.5414 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7889    0.6005   -1.8072 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9998    2.1290   -1.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7839    2.1386   -3.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5371    0.1944    0.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1602   -0.9917    1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3363   -2.2237   -1.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9288   -4.0657   -1.5322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1975   -4.0250   -1.2701 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8928   -3.0803   -2.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7024   -0.9935    0.9660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1706   -3.3121    0.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2345   -1.1838    2.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0596   -3.5517    1.5336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7477   -3.5854    3.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9938   -3.7645    3.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6919   -2.2121    4.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0408   -2.1949    2.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1778   -0.0263    1.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2282    1.2571    1.7264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2083   -0.1938    1.6850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6569    1.1843   -0.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0249    1.7149   -1.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4483    2.3384   -0.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7393    0.8648   -1.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1325   -1.3119   -1.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7932   -1.2886   -0.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3998   -0.4546   -2.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 22  1  0  0  0  0
  5  4  1  0  0  0  0
 22 23  2  0  0  0  0
 10  7  1  0  0  0  0
 23 24  1  0  0  0  0
 14 15  1  0  0  0  0
 24 25  1  0  0  0  0
 10 12  1  0  0  0  0
 25 26  1  0  0  0  0
 12 13  1  0  0  0  0
 10 11  2  0  0  0  0
  7  6  2  0  0  0  0
  7  8  1  0  0  0  0
 15 17  2  0  0  0  0
  8  9  1  0  0  0  0
  6  5  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 20 21  1  0  0  0  0
  5 14  1  0  0  0  0
 25 27  1  0  0  0  0
 18 19  2  0  0  0  0
  4  2  1  0  0  0  0
 14 12  1  0  0  0  0
  2  1  1  0  0  0  0
 19 20  1  0  0  0  0
  2  3  2  0  0  0  0
  6 32  1  0  0  0  0
  5 31  1  6  0  0  0
 14 38  1  6  0  0  0
 12 36  1  1  0  0  0
 13 37  1  0  0  0  0
 17 42  1  0  0  0  0
 18 43  1  0  0  0  0
 19 44  1  0  0  0  0
 20 45  1  6  0  0  0
 22 49  1  0  0  0  0
 23 50  1  0  0  0  0
 24 51  1  0  0  0  0
 24 52  1  0  0  0  0
 25 53  1  1  0  0  0
 26 54  1  0  0  0  0
 26 55  1  0  0  0  0
 26 56  1  0  0  0  0
  8 33  1  0  0  0  0
  8 34  1  0  0  0  0
  9 35  1  0  0  0  0
 16 39  1  0  0  0  0
 16 40  1  0  0  0  0
 16 41  1  0  0  0  0
 21 46  1  0  0  0  0
 21 47  1  0  0  0  0
 21 48  1  0  0  0  0
 27 57  1  0  0  0  0
 27 58  1  0  0  0  0
 27 59  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0038600

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O5/c1-14(2)8-6-9-15(3)10-7-11-16(4)20-19(27-17(5)24)12-18(13-23)21(25)22(20)26/h6-7,9-12,14-15,19-20,22-23,26H,8,13H2,1-5H3/b9-6+,10-7+,16-11+/t15-,19-,20-,22+/m0/s1

> <INCHI_KEY>
DPOPAXHJZJBKAU-TYWKLVCPSA-N

> <FORMULA>
C22H32O5

> <MOLECULAR_WEIGHT>
376.493

> <EXACT_MASS>
376.22497413

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
42.91006795028922

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,5R,6R)-6-[(2E,4E,6S,7E)-6,10-dimethylundeca-2,4,7-trien-2-yl]-5-hydroxy-3-(hydroxymethyl)-4-oxocyclohex-2-en-1-yl acetate

> <ALOGPS_LOGP>
3.55

> <JCHEM_LOGP>
3.079327542333333

> <ALOGPS_LOGS>
-4.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.965964010124345

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.9806730717678

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8215121466053628

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
110.14249999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.36e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5R,6R)-6-[(2E,4E,6S,7E)-6,10-dimethylundeca-2,4,7-trien-2-yl]-5-hydroxy-3-(hydroxymethyl)-4-oxocyclohex-2-en-1-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 59 59  0  0  0  0  0  0  0  0999 V2000
   -0.7692    1.3084   -2.2283 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2238    0.2745   -2.6628 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0065   -0.5725   -3.5165 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3831    0.4297   -1.9673 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4115   -0.5483   -2.2089 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6511    0.2407   -2.5208 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6549    0.4948   -1.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9173    1.2433   -1.9691 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9377    1.6766   -3.3254 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5187    0.0217   -0.2580 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4405    0.1856    0.5446 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1977   -0.6179    0.1813 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4664   -1.4490    1.3168 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5865   -1.4533   -0.9610 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2796   -2.2191   -0.6441 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0527   -3.4082   -1.5514 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4433   -1.8526    0.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8154   -2.4694    0.7105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5694   -2.0290    1.7314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8891   -2.6463    2.1316 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8264   -3.0729    3.6011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0879   -1.7462    1.9064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1054   -0.5057    1.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3599    0.3043    1.1979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7331    0.5907   -0.2705 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6718    1.4224   -0.9928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0275   -0.6919   -1.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3627    2.3086   -2.3978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0138    1.1654   -1.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6843    1.2017   -2.8178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1950   -1.1734   -3.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7195    0.6150   -3.5414 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7889    0.6005   -1.8072 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9998    2.1290   -1.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7839    2.1386   -3.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5371    0.1944    0.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1602   -0.9917    1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3363   -2.2237   -1.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9288   -4.0657   -1.5322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1975   -4.0250   -1.2701 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8928   -3.0803   -2.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7024   -0.9935    0.9660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1706   -3.3121    0.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2345   -1.1838    2.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0596   -3.5517    1.5336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7477   -3.5854    3.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9938   -3.7645    3.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6919   -2.2121    4.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0408   -2.1949    2.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1778   -0.0263    1.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2282    1.2571    1.7264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2083   -0.1938    1.6850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6569    1.1843   -0.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0249    1.7149   -1.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4483    2.3384   -0.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7393    0.8648   -1.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1325   -1.3119   -1.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7932   -1.2886   -0.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3998   -0.4546   -2.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 22  1  0
  5  4  1  0
 22 23  2  0
 10  7  1  0
 23 24  1  0
 14 15  1  0
 24 25  1  0
 10 12  1  0
 25 26  1  0
 12 13  1  0
 10 11  2  0
  7  6  2  0
  7  8  1  0
 15 17  2  0
  8  9  1  0
  6  5  1  0
 15 16  1  0
 17 18  1  0
 20 21  1  0
  5 14  1  0
 25 27  1  0
 18 19  2  0
  4  2  1  0
 14 12  1  0
  2  1  1  0
 19 20  1  0
  2  3  2  0
  6 32  1  0
  5 31  1  6
 14 38  1  6
 12 36  1  1
 13 37  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  6
 22 49  1  0
 23 50  1  0
 24 51  1  0
 24 52  1  0
 25 53  1  1
 26 54  1  0
 26 55  1  0
 26 56  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 21 46  1  0
 21 47  1  0
 21 48  1  0
 27 57  1  0
 27 58  1  0
 27 59  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.769   1.308  -2.228  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.224   0.275  -2.663  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.007  -0.573  -3.517  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.383   0.430  -1.967  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.412  -0.548  -2.209  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.651   0.241  -2.521  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.655   0.495  -1.664  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.917   1.243  -1.969  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.938   1.677  -3.325  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.519   0.022  -0.258  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.441   0.186   0.545  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.198  -0.618   0.181  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.466  -1.449   1.317  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.587  -1.453  -0.961  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.280  -2.219  -0.644  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.053  -3.408  -1.551  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.443  -1.853   0.350  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.815  -2.469   0.711  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.569  -2.029   1.731  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.889  -2.646   2.132  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.826  -3.073   3.601  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.088  -1.746   1.906  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.105  -0.506   1.388  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.360   0.304   1.198  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.733   0.591  -0.271  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.672   1.422  -0.993  0.00  0.00           C+0
HETATM   27  C   UNK     0      -6.027  -0.692  -1.051  0.00  0.00           C+0
HETATM   28  H   UNK     0      -0.363   2.309  -2.398  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.014   1.165  -1.173  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.684   1.202  -2.818  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.195  -1.173  -3.083  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.720   0.615  -3.541  0.00  0.00           H+0
HETATM   33  H   UNK     0       6.789   0.601  -1.807  0.00  0.00           H+0
HETATM   34  H   UNK     0       6.000   2.129  -1.331  0.00  0.00           H+0
HETATM   35  H   UNK     0       6.784   2.139  -3.454  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.537   0.194   0.505  0.00  0.00           H+0
HETATM   37  H   UNK     0       4.160  -0.992   1.833  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.336  -2.224  -1.201  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.929  -4.066  -1.532  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.198  -4.025  -1.270  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.893  -3.080  -2.583  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.702  -0.994   0.966  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.171  -3.312   0.126  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.234  -1.184   2.330  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.060  -3.552   1.534  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.748  -3.585   3.901  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.994  -3.765   3.774  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.692  -2.212   4.267  0.00  0.00           H+0
HETATM   49  H   UNK     0      -5.041  -2.195   2.188  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.178  -0.026   1.086  0.00  0.00           H+0
HETATM   51  H   UNK     0      -5.228   1.257   1.726  0.00  0.00           H+0
HETATM   52  H   UNK     0      -6.208  -0.194   1.685  0.00  0.00           H+0
HETATM   53  H   UNK     0      -6.657   1.184  -0.254  0.00  0.00           H+0
HETATM   54  H   UNK     0      -5.025   1.715  -1.988  0.00  0.00           H+0
HETATM   55  H   UNK     0      -4.448   2.338  -0.436  0.00  0.00           H+0
HETATM   56  H   UNK     0      -3.739   0.865  -1.124  0.00  0.00           H+0
HETATM   57  H   UNK     0      -5.133  -1.312  -1.168  0.00  0.00           H+0
HETATM   58  H   UNK     0      -6.793  -1.289  -0.544  0.00  0.00           H+0
HETATM   59  H   UNK     0      -6.400  -0.455  -2.053  0.00  0.00           H+0
CONECT    1    2   28   29   30                                             
CONECT    2    4    1    3                                                  
CONECT    3    2                                                            
CONECT    4    5    2                                                       
CONECT    5    4    6   14   31                                             
CONECT    6    7    5   32                                                  
CONECT    7   10    6    8                                                  
CONECT    8    7    9   33   34                                             
CONECT    9    8   35                                                       
CONECT   10    7   12   11                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14   36                                             
CONECT   13   12   37                                                       
CONECT   14   15    5   12   38                                             
CONECT   15   14   17   16                                                  
CONECT   16   15   39   40   41                                             
CONECT   17   15   18   42                                                  
CONECT   18   17   19   43                                                  
CONECT   19   18   20   44                                                  
CONECT   20   22   21   19   45                                             
CONECT   21   20   46   47   48                                             
CONECT   22   20   23   49                                                  
CONECT   23   22   24   50                                                  
CONECT   24   23   25   51   52                                             
CONECT   25   24   26   27   53                                             
CONECT   26   25   54   55   56                                             
CONECT   27   25   57   58   59                                             
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    5                                                            
CONECT   32    6                                                            
CONECT   33    8                                                            
CONECT   34    8                                                            
CONECT   35    9                                                            
CONECT   36   12                                                            
CONECT   37   13                                                            
CONECT   38   14                                                            
CONECT   39   16                                                            
CONECT   40   16                                                            
CONECT   41   16                                                            
CONECT   42   17                                                            
CONECT   43   18                                                            
CONECT   44   19                                                            
CONECT   45   20                                                            
CONECT   46   21                                                            
CONECT   47   21                                                            
CONECT   48   21                                                            
CONECT   49   22                                                            
CONECT   50   23                                                            
CONECT   51   24                                                            
CONECT   52   24                                                            
CONECT   53   25                                                            
CONECT   54   26                                                            
CONECT   55   26                                                            
CONECT   56   26                                                            
CONECT   57   27                                                            
CONECT   58   27                                                            
CONECT   59   27                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  118    0
END

RDKit          3D

59 59  0  0  0  0  0  0  0  0999 V2000
   -0.7692    1.3084   -2.2283 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2238    0.2745   -2.6628 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0065   -0.5725   -3.5165 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3831    0.4297   -1.9673 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4115   -0.5483   -2.2089 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6511    0.2407   -2.5208 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6549    0.4948   -1.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9173    1.2433   -1.9691 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9377    1.6766   -3.3254 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5187    0.0217   -0.2580 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4405    0.1856    0.5446 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1977   -0.6179    0.1813 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4664   -1.4490    1.3168 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5865   -1.4533   -0.9610 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2796   -2.2191   -0.6441 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0527   -3.4082   -1.5514 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4433   -1.8526    0.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8154   -2.4694    0.7105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5694   -2.0290    1.7314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8891   -2.6463    2.1316 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8264   -3.0729    3.6011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0879   -1.7462    1.9064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1054   -0.5057    1.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3599    0.3043    1.1979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7331    0.5907   -0.2705 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6718    1.4224   -0.9928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0275   -0.6919   -1.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3627    2.3086   -2.3978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0138    1.1654   -1.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6843    1.2017   -2.8178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1950   -1.1734   -3.0835 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7195    0.6150   -3.5414 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7889    0.6005   -1.8072 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9998    2.1290   -1.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7839    2.1386   -3.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5371    0.1944    0.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1602   -0.9917    1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3363   -2.2237   -1.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9288   -4.0657   -1.5322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1975   -4.0250   -1.2701 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8928   -3.0803   -2.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7024   -0.9935    0.9660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1706   -3.3121    0.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2345   -1.1838    2.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0596   -3.5517    1.5336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7477   -3.5854    3.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9938   -3.7645    3.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6919   -2.2121    4.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0408   -2.1949    2.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1778   -0.0263    1.0861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2282    1.2571    1.7264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2083   -0.1938    1.6850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6569    1.1843   -0.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0249    1.7149   -1.9877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4483    2.3384   -0.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7393    0.8648   -1.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1325   -1.3119   -1.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7932   -1.2886   -0.5442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3998   -0.4546   -2.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 22  1  0
  5  4  1  0
 22 23  2  0
 10  7  1  0
 23 24  1  0
 14 15  1  0
 24 25  1  0
 10 12  1  0
 25 26  1  0
 12 13  1  0
 10 11  2  0
  7  6  2  0
  7  8  1  0
 15 17  2  0
  8  9  1  0
  6  5  1  0
 15 16  1  0
 17 18  1  0
 20 21  1  0
  5 14  1  0
 25 27  1  0
 18 19  2  0
  4  2  1  0
 14 12  1  0
  2  1  1  0
 19 20  1  0
  2  3  2  0
  6 32  1  0
  5 31  1  6
 14 38  1  6
 12 36  1  1
 13 37  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  6
 22 49  1  0
 23 50  1  0
 24 51  1  0
 24 52  1  0
 25 53  1  1
 26 54  1  0
 26 55  1  0
 26 56  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 21 46  1  0
 21 47  1  0
 21 48  1  0
 27 57  1  0
 27 58  1  0
 27 59  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
M  END

View in JSmol

Synonyms

Value	Source
(4S)-2-(Hydroxymethyl)-4a-acetoxy-5a-[(1E,3E,5S,6E)-1,5,9-trimethyl-1,3,6-decatrienyl]-6b-hydroxy-2-cyclohexene-1-one	Generator
(4S)-2-(Hydroxymethyl)-4α-acetoxy-5α-[(1E,3E,5S,6E)-1,5,9-trimethyl-1,3,6-decatrienyl]-6β-hydroxy-2-cyclohexene-1-one	Generator

Chemical Formula

C₂₂H₃₂O₅

Average Mass

376.4930 Da

Monoisotopic Mass

376.22497 Da

IUPAC Name

(1S,5R,6R)-6-[(2E,4E,6S,7E)-6,10-dimethylundeca-2,4,7-trien-2-yl]-5-hydroxy-3-(hydroxymethyl)-4-oxocyclohex-2-en-1-yl acetate

Traditional Name

(1S,5R,6R)-6-[(2E,4E,6S,7E)-6,10-dimethylundeca-2,4,7-trien-2-yl]-5-hydroxy-3-(hydroxymethyl)-4-oxocyclohex-2-en-1-yl acetate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C22H32O5/c1-14(2)8-6-9-15(3)10-7-11-16(4)20-19(27-17(5)24)12-18(13-23)21(25)22(20)26/h6-7,9-12,14-15,19-20,22-23,26H,8,13H2,1-5H3/b9-6+,10-7+,16-11+/t15-,19-,20-,22+/m0/s1

InChI Key

DPOPAXHJZJBKAU-TYWKLVCPSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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
Phorbas sp.	JEOL database	Zhang, H., et al, Org. Lett. 10, 1959 (2008)

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	3.55	ALOGPS
logP	3.08	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	12.98	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	110.14 m³·mol⁻¹	ChemAxon
Polarizability	42.91 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

26000838

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102036848

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang, H., et al. (2008). Zhang, H., et al, Org. Lett. 10, 1959 (2008). Org. Lett..

Showing NP-Card for phorbasin C (NP0038600)

MOL for NP0038600 (phorbasin C)

3D MOL for NP0038600 (phorbasin C)

3D SDF for NP0038600 (phorbasin C)

3D-SDF for NP0038600 (phorbasin C)

PDB for NP0038600 (phorbasin C)

3D PDB for NP0038600 (phorbasin C)

SMILES for NP0038600 (phorbasin C)

INCHI for NP0038600 (phorbasin C)

Structure for NP0038600 (phorbasin C)

3D Structure for NP0038600 (phorbasin C)