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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:36:55 UTC

Update Date

2022-03-07 02:54:13 UTC

HMDB ID

HMDB0034712

Secondary Accession Numbers

HMDB34712

Metabolite Identification

Common Name

Prexanthoperol

Description

Prexanthoperol, also known as hypargenin C, belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Based on a literature review a small amount of articles have been published on Prexanthoperol.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0034712
     RDKit          3D
Prexanthoperol
 49 51  0  0  0  0  0  0  0  0999 V2000
    4.9340    0.6332    1.2078 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5792    0.5160   -0.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3281   -0.6793   -0.8134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1016    0.3108   -0.3567 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3552    0.0869    0.7825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9832   -0.1213    0.7674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3262   -0.1079   -0.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0373    0.1135   -1.5627 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4219    0.3240   -1.5596 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1135    0.5433   -2.7278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1553   -0.2999   -0.6027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2025   -1.4199   -1.6624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6140    0.9456   -1.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8856    1.5459   -0.8190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8373    0.4113   -0.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2673   -0.2045    0.7676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2750   -1.2890    1.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3775    0.8592    1.8377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8914   -0.7359    0.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1710   -0.6068    1.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8499   -0.7064    2.9260 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2403   -0.3790    2.0019 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8781   -0.3856    3.0958 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3554    1.4141    1.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8200   -0.3793    1.6321 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0102    0.9143    1.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8400    1.4480   -0.8176 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5822   -1.4700   -1.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9654   -0.4075   -1.6898 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9680   -1.1051   -0.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8264    0.0655    1.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5709    0.1377   -2.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1063    0.6933   -2.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1454   -0.9933   -2.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1173   -2.0312   -1.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3329   -2.1002   -1.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8452    1.7778   -1.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7466    0.7851   -2.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3140    2.1871   -1.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7277    2.1478    0.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8391    0.7998   -0.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8621   -0.3259   -1.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0399   -1.6977    2.1761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2193   -2.0630    0.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2714   -0.8063    1.1165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0773    1.6781    1.5343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8250    0.4690    2.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4190    1.3736    2.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0345   -1.8662    0.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  7 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  2  0
  9  4  1  0
 19 11  1  0
 22  6  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  5 31  1  0
  8 32  1  0
 10 33  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
M  END


  Mrv0541 02241208552D          

 23 25  0  0  0  0            999 V2000
    1.0739    0.2068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0739    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3593    1.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3552    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3552    0.2068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3593   -0.2054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0698   -0.2054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0698   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3552   -1.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3593   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7857    0.2068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5031   -0.2054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5031   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7857   -1.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1980   -2.1609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3734   -2.1609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3552   -2.2681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0739   -1.4436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0698    0.6190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3593    2.2681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7885    1.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5031    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7885    2.2681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2 21  1  0  0  0  0
  3  4  2  0  0  0  0
  3 20  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  7 19  1  0  0  0  0
  8  9  1  0  0  0  0
  8 14  1  0  0  0  0
  9 10  1  0  0  0  0
  9 17  2  0  0  0  0
 10 18  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034712

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C1=CC2=C(C=C1O)C1(C)CCCC(C)(C)C1C(=O)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O3/c1-11(2)12-9-13-14(10-15(12)21)20(5)8-6-7-19(3,4)18(20)17(23)16(13)22/h9-11,18,21H,6-8H2,1-5H3

> <INCHI_KEY>
KVTOPOITUALWOF-UHFFFAOYSA-N

> <FORMULA>
C20H26O3

> <MOLECULAR_WEIGHT>
314.4186

> <EXACT_MASS>
314.188194698

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
35.92335552449583

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-hydroxy-1,1,4a-trimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-9,10-dione

> <ALOGPS_LOGP>
4.94

> <JCHEM_LOGP>
5.209749638333333

> <ALOGPS_LOGS>
-4.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.81921596605767

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.971581099620339

> <JCHEM_PKA_STRONGEST_BASIC>
-6.7133573020153685

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
91.26509999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.11e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-7-isopropyl-1,1,4a-trimethyl-2,3,4,10a-tetrahydrophenanthrene-9,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034712
     RDKit          3D
Prexanthoperol
 49 51  0  0  0  0  0  0  0  0999 V2000
    4.9340    0.6332    1.2078 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5792    0.5160   -0.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3281   -0.6793   -0.8134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1016    0.3108   -0.3567 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3552    0.0869    0.7825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9832   -0.1213    0.7674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3262   -0.1079   -0.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0373    0.1135   -1.5627 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4219    0.3240   -1.5596 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1135    0.5433   -2.7278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1553   -0.2999   -0.6027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2025   -1.4199   -1.6624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6140    0.9456   -1.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8856    1.5459   -0.8190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8373    0.4113   -0.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2673   -0.2045    0.7676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2750   -1.2890    1.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3775    0.8592    1.8377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8914   -0.7359    0.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1710   -0.6068    1.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8499   -0.7064    2.9260 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2403   -0.3790    2.0019 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8781   -0.3856    3.0958 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3554    1.4141    1.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8200   -0.3793    1.6321 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0102    0.9143    1.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8400    1.4480   -0.8176 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5822   -1.4700   -1.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9654   -0.4075   -1.6898 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9680   -1.1051   -0.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8264    0.0655    1.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5709    0.1377   -2.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1063    0.6933   -2.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1454   -0.9933   -2.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1173   -2.0312   -1.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3329   -2.1002   -1.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8452    1.7778   -1.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7466    0.7851   -2.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3140    2.1871   -1.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7277    2.1478    0.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8391    0.7998   -0.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8621   -0.3259   -1.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0399   -1.6977    2.1761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2193   -2.0630    0.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2714   -0.8063    1.1165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0773    1.6781    1.5343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8250    0.4690    2.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4190    1.3736    2.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0345   -1.8662    0.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  7 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  2  0
  9  4  1  0
 19 11  1  0
 22  6  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  5 31  1  0
  8 32  1  0
 10 33  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       2.005   0.386   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.005   1.925   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.671   2.695   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.663   1.925   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.663   0.386   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.671  -0.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.997  -0.383   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.997  -1.925   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.663  -2.695   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.671  -1.925   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.333   0.386   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.672  -0.383   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.672  -1.925   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.333  -2.695   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.103  -4.034   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.564  -4.034   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.663  -4.234   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.005  -2.695   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.997   1.155   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.671   4.234   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.339   2.695   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.672   1.925   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.339   4.234   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   21                                                  
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    1    5   10                                                  
CONECT    7    5    8   11   19                                             
CONECT    8    7    9   14                                                  
CONECT    9    8   10   17                                                  
CONECT   10    6    9   18                                                  
CONECT   11    7   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14    8   13   15   16                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    9                                                            
CONECT   18   10                                                            
CONECT   19    7                                                            
CONECT   20    3                                                            
CONECT   21    2   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0034712
HETATM    1  C1  UNL     1       4.934   0.633   1.208  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.579   0.516  -0.275  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.328  -0.679  -0.813  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.102   0.311  -0.357  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.355   0.087   0.783  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.983  -0.121   0.767  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.326  -0.108  -0.399  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.037   0.114  -1.563  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.422   0.324  -1.560  1.00  0.00           C  
HETATM   10  O1  UNL     1       3.114   0.543  -2.728  1.00  0.00           O  
HETATM   11  C10 UNL     1      -1.155  -0.300  -0.603  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.203  -1.420  -1.662  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.614   0.946  -1.309  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.886   1.546  -0.819  1.00  0.00           C  
HETATM   15  C14 UNL     1      -3.837   0.411  -0.501  1.00  0.00           C  
HETATM   16  C15 UNL     1      -3.267  -0.205   0.768  1.00  0.00           C  
HETATM   17  C16 UNL     1      -4.275  -1.289   1.177  1.00  0.00           C  
HETATM   18  C17 UNL     1      -3.377   0.859   1.838  1.00  0.00           C  
HETATM   19  C18 UNL     1      -1.891  -0.736   0.581  1.00  0.00           C  
HETATM   20  C19 UNL     1      -1.171  -0.607   1.875  1.00  0.00           C  
HETATM   21  O2  UNL     1      -1.850  -0.706   2.926  1.00  0.00           O  
HETATM   22  C20 UNL     1       0.240  -0.379   2.002  1.00  0.00           C  
HETATM   23  O3  UNL     1       0.878  -0.386   3.096  1.00  0.00           O  
HETATM   24  H1  UNL     1       4.355   1.414   1.707  1.00  0.00           H  
HETATM   25  H2  UNL     1       4.820  -0.379   1.632  1.00  0.00           H  
HETATM   26  H3  UNL     1       6.010   0.914   1.307  1.00  0.00           H  
HETATM   27  H4  UNL     1       4.840   1.448  -0.818  1.00  0.00           H  
HETATM   28  H5  UNL     1       4.582  -1.470  -1.072  1.00  0.00           H  
HETATM   29  H6  UNL     1       5.965  -0.407  -1.690  1.00  0.00           H  
HETATM   30  H7  UNL     1       5.968  -1.105  -0.018  1.00  0.00           H  
HETATM   31  H8  UNL     1       2.826   0.066   1.760  1.00  0.00           H  
HETATM   32  H9  UNL     1       0.571   0.138  -2.545  1.00  0.00           H  
HETATM   33  H10 UNL     1       4.106   0.693  -2.695  1.00  0.00           H  
HETATM   34  H11 UNL     1      -1.145  -0.993  -2.686  1.00  0.00           H  
HETATM   35  H12 UNL     1      -2.117  -2.031  -1.511  1.00  0.00           H  
HETATM   36  H13 UNL     1      -0.333  -2.100  -1.565  1.00  0.00           H  
HETATM   37  H14 UNL     1      -0.845   1.778  -1.281  1.00  0.00           H  
HETATM   38  H15 UNL     1      -1.747   0.785  -2.422  1.00  0.00           H  
HETATM   39  H16 UNL     1      -3.314   2.187  -1.637  1.00  0.00           H  
HETATM   40  H17 UNL     1      -2.728   2.148   0.106  1.00  0.00           H  
HETATM   41  H18 UNL     1      -4.839   0.800  -0.235  1.00  0.00           H  
HETATM   42  H19 UNL     1      -3.862  -0.326  -1.331  1.00  0.00           H  
HETATM   43  H20 UNL     1      -4.040  -1.698   2.176  1.00  0.00           H  
HETATM   44  H21 UNL     1      -4.219  -2.063   0.391  1.00  0.00           H  
HETATM   45  H22 UNL     1      -5.271  -0.806   1.117  1.00  0.00           H  
HETATM   46  H23 UNL     1      -4.077   1.678   1.534  1.00  0.00           H  
HETATM   47  H24 UNL     1      -3.825   0.469   2.786  1.00  0.00           H  
HETATM   48  H25 UNL     1      -2.419   1.374   2.052  1.00  0.00           H  
HETATM   49  H26 UNL     1      -2.035  -1.866   0.505  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    4   27
CONECT    3   28   29   30
CONECT    4    5    5    9
CONECT    5    6   31
CONECT    6    7    7   22
CONECT    7    8   11
CONECT    8    9    9   32
CONECT    9   10
CONECT   10   33
CONECT   11   12   13   19
CONECT   12   34   35   36
CONECT   13   14   37   38
CONECT   14   15   39   40
CONECT   15   16   41   42
CONECT   16   17   18   19
CONECT   17   43   44   45
CONECT   18   46   47   48
CONECT   19   20   49
CONECT   20   21   21   22
CONECT   22   23   23
END

HMDB0034712
     RDKit          3D
Prexanthoperol
 49 51  0  0  0  0  0  0  0  0999 V2000
    4.9340    0.6332    1.2078 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5792    0.5160   -0.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3281   -0.6793   -0.8134 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1016    0.3108   -0.3567 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3552    0.0869    0.7825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9832   -0.1213    0.7674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3262   -0.1079   -0.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0373    0.1135   -1.5627 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4219    0.3240   -1.5596 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1135    0.5433   -2.7278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1553   -0.2999   -0.6027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2025   -1.4199   -1.6624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6140    0.9456   -1.3091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8856    1.5459   -0.8190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8373    0.4113   -0.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2673   -0.2045    0.7676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2750   -1.2890    1.1765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3775    0.8592    1.8377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8914   -0.7359    0.5815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1710   -0.6068    1.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8499   -0.7064    2.9260 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2403   -0.3790    2.0019 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8781   -0.3856    3.0958 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3554    1.4141    1.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8200   -0.3793    1.6321 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0102    0.9143    1.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8400    1.4480   -0.8176 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5822   -1.4700   -1.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9654   -0.4075   -1.6898 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9680   -1.1051   -0.0178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8264    0.0655    1.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5709    0.1377   -2.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1063    0.6933   -2.6951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1454   -0.9933   -2.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1173   -2.0312   -1.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3329   -2.1002   -1.5646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8452    1.7778   -1.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7466    0.7851   -2.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3140    2.1871   -1.6367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7277    2.1478    0.1058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8391    0.7998   -0.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8621   -0.3259   -1.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0399   -1.6977    2.1761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2193   -2.0630    0.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2714   -0.8063    1.1165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0773    1.6781    1.5343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8250    0.4690    2.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4190    1.3736    2.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0345   -1.8662    0.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  7 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  2  0
  9  4  1  0
 19 11  1  0
 22  6  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  5 31  1  0
  8 32  1  0
 10 33  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 17 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Hypargenin C	HMDB

Chemical Formula

C₂₀H₂₆O₃

Average Molecular Weight

314.4186

Monoisotopic Molecular Weight

314.188194698

IUPAC Name

6-hydroxy-1,1,4a-trimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-9,10-dione

Traditional Name

6-hydroxy-7-isopropyl-1,1,4a-trimethyl-2,3,4,10a-tetrahydrophenanthrene-9,10-dione

CAS Registry Number

119817-27-5

SMILES

CC(C)C1=CC2=C(C=C1O)C1(C)CCCC(C)(C)C1C(=O)C2=O

InChI Identifier

InChI=1S/C20H26O3/c1-11(2)12-9-13-14(10-15(12)21)20(5)8-6-7-19(3,4)18(20)17(23)16(13)22/h9-11,18,21H,6-8H2,1-5H3

InChI Key

KVTOPOITUALWOF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Abietane diterpenoid
Diterpenoid
Hydrophenanthrene
Phenanthrene
Naphthoquinone
Tetralin
Naphthalene
Aryl ketone
Quinone
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Ketone
Carbonyl group
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Ingestion (HMDB: HMDB34712)

Source

Endogenous

Endogenous (HMDB: HMDB34712)

Plant

Plant (HMDB: HMDB34712)

Animal

Animal (HMDB: HMDB34712)

Exogenous

Food

Food (HMDB: HMDB34712)

Fruit

Fruits (FooDB: FOOD00871)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB34712)

Biochemical process

Fatty acid metabolism (HMDB: HMDB34712)

Cellular process

Cell signaling (HMDB: HMDB34712)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB34712)

Role

Biological role

Membrane stabilizer (HMDB: HMDB34712)

Nutrient

Nutrient (HMDB: HMDB34712)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB34712)

Emulsifier (HMDB: HMDB34712)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	207 - 210 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.37 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0071 g/L	ALOGPS
logP	4.94	ALOGPS
logP	5.21	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	7.97	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	91.27 m³·mol⁻¹	ChemAxon
Polarizability	35.92 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	176.117	31661259
DarkChem	[M-H]-	173.222	31661259
DeepCCS	[M+H]+	184.317	30932474
DeepCCS	[M-H]-	181.959	30932474
DeepCCS	[M-2H]-	215.804	30932474
DeepCCS	[M+Na]+	191.051	30932474
AllCCS	[M+H]+	174.3	32859911
AllCCS	[M+H-H2O]+	171.2	32859911
AllCCS	[M+NH4]+	177.2	32859911
AllCCS	[M+Na]+	178.0	32859911
AllCCS	[M-H]-	185.4	32859911
AllCCS	[M+Na-2H]-	185.6	32859911
AllCCS	[M+HCOO]-	186.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Prexanthoperol	CC(C)C1=CC2=C(C=C1O)C1(C)CCCC(C)(C)C1C(=O)C2=O	3336.8	Standard polar	33892256
Prexanthoperol	CC(C)C1=CC2=C(C=C1O)C1(C)CCCC(C)(C)C1C(=O)C2=O	2243.8	Standard non polar	33892256
Prexanthoperol	CC(C)C1=CC2=C(C=C1O)C1(C)CCCC(C)(C)C1C(=O)C2=O	2677.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Prexanthoperol,1TMS,isomer #1	CC(C)C1=CC2=C(C=C1O[Si](C)(C)C)C1(C)CCCC(C)(C)C1C(=O)C2=O	2761.2	Semi standard non polar	33892256
Prexanthoperol,1TMS,isomer #2	CC(C)C1=CC2=C(C=C1O)C1(C)CCCC(C)(C)C1=C(O[Si](C)(C)C)C2=O	2536.8	Semi standard non polar	33892256
Prexanthoperol,2TMS,isomer #1	CC(C)C1=CC2=C(C=C1O[Si](C)(C)C)C1(C)CCCC(C)(C)C1=C(O[Si](C)(C)C)C2=O	2548.1	Semi standard non polar	33892256
Prexanthoperol,2TMS,isomer #1	CC(C)C1=CC2=C(C=C1O[Si](C)(C)C)C1(C)CCCC(C)(C)C1=C(O[Si](C)(C)C)C2=O	2622.8	Standard non polar	33892256
Prexanthoperol,1TBDMS,isomer #1	CC(C)C1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C1(C)CCCC(C)(C)C1C(=O)C2=O	3006.9	Semi standard non polar	33892256
Prexanthoperol,1TBDMS,isomer #2	CC(C)C1=CC2=C(C=C1O)C1(C)CCCC(C)(C)C1=C(O[Si](C)(C)C(C)(C)C)C2=O	2797.1	Semi standard non polar	33892256
Prexanthoperol,2TBDMS,isomer #1	CC(C)C1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C1(C)CCCC(C)(C)C1=C(O[Si](C)(C)C(C)(C)C)C2=O	3041.5	Semi standard non polar	33892256
Prexanthoperol,2TBDMS,isomer #1	CC(C)C1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C1(C)CCCC(C)(C)C1=C(O[Si](C)(C)C(C)(C)C)C2=O	3067.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Prexanthoperol GC-MS (Non-derivatized) - 70eV, Positive	splash10-007a-0090000000-0b253e86d44ef0ed0927	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prexanthoperol GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-1109000000-76840f44ea0c7a63eeff	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prexanthoperol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prexanthoperol 10V, Positive-QTOF	splash10-014i-0139000000-640d61d83cc6802d7672	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prexanthoperol 20V, Positive-QTOF	splash10-01bj-3693000000-b985e9188166b85692f4	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prexanthoperol 40V, Positive-QTOF	splash10-053r-9430000000-e0135fb1809b28d5ee1d	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prexanthoperol 10V, Negative-QTOF	splash10-03di-0009000000-56338b9e1239fbd4e747	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prexanthoperol 20V, Negative-QTOF	splash10-03di-0019000000-d8c509515cabc261668d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prexanthoperol 40V, Negative-QTOF	splash10-007k-0290000000-51f7c6f24a20330b92be	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prexanthoperol 10V, Positive-QTOF	splash10-014i-0019000000-ba52484b43f69f04c157	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prexanthoperol 20V, Positive-QTOF	splash10-0301-0397000000-76e460d522861191debe	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prexanthoperol 40V, Positive-QTOF	splash10-00l5-5390000000-7d32c559a5b54f2bacca	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prexanthoperol 10V, Negative-QTOF	splash10-03di-0009000000-d8638daf32922c227464	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prexanthoperol 20V, Negative-QTOF	splash10-03di-0029000000-63018d1441af1a82bc6d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prexanthoperol 40V, Negative-QTOF	splash10-0002-0190000000-7a39c02614b86257a6c4	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB014424

KNApSAcK ID

C00056609

Chemspider ID

546062

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

628742

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1845321

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Prexanthoperol (HMDB0034712)

MOL for HMDB0034712 (Prexanthoperol)

3D MOL for HMDB0034712 (Prexanthoperol)

3D SDF for HMDB0034712 (Prexanthoperol)

3D-SDF for HMDB0034712 (Prexanthoperol)

PDB for HMDB0034712 (Prexanthoperol)

3D PDB for HMDB0034712 (Prexanthoperol)

SMILES for HMDB0034712 (Prexanthoperol)

INCHI for HMDB0034712 (Prexanthoperol)

Structure for HMDB0034712 (Prexanthoperol)

3D Structure for HMDB0034712 (Prexanthoperol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra