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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:39:21 UTC

Update Date

2022-03-07 02:52:43 UTC

HMDB ID

HMDB0030841

Secondary Accession Numbers

HMDB30841

Metabolite Identification

Common Name

Sagequinone methide A

Description

Sagequinone methide A belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Sagequinone methide A is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HMDB0030841
     RDKit          3D
Sagequinone methide A
 48 51  0  0  0  0  0  0  0  0999 V2000
    5.0817   -1.0056   -1.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6848   -0.4692    0.3026 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4910    0.7850    0.5420 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2351   -0.2151    0.3710 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4707   -0.4653   -0.6935 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0367   -0.2362   -0.6894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3198   -0.4882   -1.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0372    0.1750   -1.7794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9589    1.5445   -1.5209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2859    1.8428   -0.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6412    2.9220    0.3247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1028    0.5202    0.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7529    0.4507    1.8375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1906   -0.0159    1.8342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8481    0.3652    0.5558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1980   -0.3209   -0.6281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7921   -1.7327   -0.7193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6752    0.4204   -1.8689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7165   -0.3962   -0.5222 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3661    0.2891    0.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1111    0.5456    1.5832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5909    1.0436    2.7713 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5683    0.3041    1.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2565    0.5524    2.5776 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1760   -1.2135   -1.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8487   -0.2460   -1.8437 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5935   -1.9726   -1.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0253   -1.2257    1.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0651    1.6673    0.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6283    0.9994    1.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4933    0.6103    0.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9185   -0.8523   -1.5985 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6886   -1.1055   -2.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5552   -0.1057   -2.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6540    1.3958    2.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2125   -0.3315    2.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3003   -1.0894    1.9969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7122    0.5097    2.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9039   -0.0330    0.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9502    1.4369    0.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9709   -2.4804   -0.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2697   -1.9180   -1.6864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5124   -1.9314    0.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2556    1.4369   -1.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5918   -0.1781   -2.7827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7835    0.5711   -1.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3888   -1.4343   -0.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6106    2.0551    2.8758 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  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 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
 12 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 23  4  1  0
 20  6  1  0
 19  8  1  0
 19 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  5 32  1  0
  7 33  1  0
  8 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 22 48  1  0
M  END


  Mrv0541 02241211282D          

 24 27  0  0  0  0            999 V2000
   -2.4986   -0.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4986   -1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7843   -1.4561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0714   -1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0714   -0.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7843    0.1940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -1.4561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558   -1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558   -0.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.1940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0672    0.1940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0672    1.0158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558    1.4257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    1.0158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7830    1.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558    2.2516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4986    1.0158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7830    2.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0714    1.4286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2847    0.5808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8684    1.1643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3434   -0.5807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1973   -2.1719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5710   -2.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 23  1  0  0  0  0
  3 24  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 20  1  0  0  0  0
  7  8  1  0  0  0  0
  7 22  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 14  2  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 15  1  0  0  0  0
 13 14  1  0  0  0  0
 13 16  2  0  0  0  0
 14 19  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030841

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C1=CC2=CC3OC(=O)C4(CCCC(C)(C)C34)C2=C(O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O4/c1-10(2)12-8-11-9-13-17-19(3,4)6-5-7-20(17,18(23)24-13)14(11)16(22)15(12)21/h8-10,13,17,22H,5-7H2,1-4H3

> <INCHI_KEY>
CYJLXXSGOZGYMC-UHFFFAOYSA-N

> <FORMULA>
C20H24O4

> <MOLECULAR_WEIGHT>
328.4022

> <EXACT_MASS>
328.167459256

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
35.69530798435977

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,5,7-triene-4,15-dione

> <ALOGPS_LOGP>
3.03

> <JCHEM_LOGP>
3.232403470333333

> <ALOGPS_LOGS>
-3.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.389920403335617

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6211088155810005

> <JCHEM_POLAR_SURFACE_AREA>
63.599999999999994

> <JCHEM_REFRACTIVITY>
92.64779999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.63e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,5,7-triene-4,15-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030841
     RDKit          3D
Sagequinone methide A
 48 51  0  0  0  0  0  0  0  0999 V2000
    5.0817   -1.0056   -1.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6848   -0.4692    0.3026 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4910    0.7850    0.5420 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2351   -0.2151    0.3710 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4707   -0.4653   -0.6935 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0367   -0.2362   -0.6894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3198   -0.4882   -1.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0372    0.1750   -1.7794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9589    1.5445   -1.5209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2859    1.8428   -0.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6412    2.9220    0.3247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1028    0.5202    0.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7529    0.4507    1.8375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1906   -0.0159    1.8342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8481    0.3652    0.5558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1980   -0.3209   -0.6281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7921   -1.7327   -0.7193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6752    0.4204   -1.8689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7165   -0.3962   -0.5222 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3661    0.2891    0.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1111    0.5456    1.5832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5909    1.0436    2.7713 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5683    0.3041    1.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2565    0.5524    2.5776 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1760   -1.2135   -1.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8487   -0.2460   -1.8437 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5935   -1.9726   -1.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0253   -1.2257    1.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0651    1.6673    0.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6283    0.9994    1.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4933    0.6103    0.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9185   -0.8523   -1.5985 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6886   -1.1055   -2.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5552   -0.1057   -2.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6540    1.3958    2.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2125   -0.3315    2.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3003   -1.0894    1.9969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7122    0.5097    2.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9039   -0.0330    0.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9502    1.4369    0.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9709   -2.4804   -0.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2697   -1.9180   -1.6864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5124   -1.9314    0.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2556    1.4369   -1.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5918   -0.1781   -2.7827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7835    0.5711   -1.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3888   -1.4343   -0.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6106    2.0551    2.8758 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  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 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
 12 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 23  4  1  0
 20  6  1  0
 19  8  1  0
 19 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  5 32  1  0
  7 33  1  0
  8 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 22 48  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      -4.664  -0.406   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.664  -1.947   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.331  -2.718   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.000  -1.947   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.000  -0.406   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.331   0.362   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.667  -2.718   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.664  -1.947   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.664  -0.406   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.667   0.362   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.992   0.362   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.992   1.896   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.664   2.661   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.667   1.896   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.328   2.667   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.664   4.203   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.664   1.896   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.328   4.208   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.000   2.667   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.398   1.084   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.488   2.173   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -0.641  -1.084   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -4.102  -4.054   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.933  -4.208   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   23   24                                             
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   20                                             
CONECT    6    1    5                                                       
CONECT    7    4    8   22                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    5    9   14                                                  
CONECT   11    9   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14   16                                                  
CONECT   14   10   13   19                                                  
CONECT   15   12   17   18                                                  
CONECT   16   13                                                            
CONECT   17   15                                                            
CONECT   18   15                                                            
CONECT   19   14                                                            
CONECT   20    5   21   22                                                  
CONECT   21   20                                                            
CONECT   22    7   20                                                       
CONECT   23    3                                                            
CONECT   24    3                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0030841
HETATM    1  C1  UNL     1       5.082  -1.006  -1.057  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.685  -0.469   0.303  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.491   0.785   0.542  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.235  -0.215   0.371  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.471  -0.465  -0.693  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.037  -0.236  -0.689  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.320  -0.488  -1.771  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.037   0.175  -1.779  1.00  0.00           C  
HETATM    9  O1  UNL     1      -0.959   1.544  -1.521  1.00  0.00           O  
HETATM   10  C9  UNL     1      -1.286   1.843  -0.184  1.00  0.00           C  
HETATM   11  O2  UNL     1      -1.641   2.922   0.325  1.00  0.00           O  
HETATM   12  C10 UNL     1      -1.103   0.520   0.513  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.753   0.451   1.837  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.191  -0.016   1.834  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.848   0.365   0.556  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.198  -0.321  -0.628  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.792  -1.733  -0.719  1.00  0.00           C  
HETATM   18  C16 UNL     1      -3.675   0.420  -1.869  1.00  0.00           C  
HETATM   19  C17 UNL     1      -1.716  -0.396  -0.522  1.00  0.00           C  
HETATM   20  C18 UNL     1       0.366   0.289   0.512  1.00  0.00           C  
HETATM   21  C19 UNL     1       1.111   0.546   1.583  1.00  0.00           C  
HETATM   22  O3  UNL     1       0.591   1.044   2.771  1.00  0.00           O  
HETATM   23  C20 UNL     1       2.568   0.304   1.554  1.00  0.00           C  
HETATM   24  O4  UNL     1       3.256   0.552   2.578  1.00  0.00           O  
HETATM   25  H1  UNL     1       6.176  -1.214  -1.069  1.00  0.00           H  
HETATM   26  H2  UNL     1       4.849  -0.246  -1.844  1.00  0.00           H  
HETATM   27  H3  UNL     1       4.593  -1.973  -1.295  1.00  0.00           H  
HETATM   28  H4  UNL     1       5.025  -1.226   1.065  1.00  0.00           H  
HETATM   29  H5  UNL     1       5.065   1.667   0.056  1.00  0.00           H  
HETATM   30  H6  UNL     1       5.628   0.999   1.613  1.00  0.00           H  
HETATM   31  H7  UNL     1       6.493   0.610   0.086  1.00  0.00           H  
HETATM   32  H8  UNL     1       2.918  -0.852  -1.599  1.00  0.00           H  
HETATM   33  H9  UNL     1       0.689  -1.106  -2.551  1.00  0.00           H  
HETATM   34  H10 UNL     1      -1.555  -0.106  -2.692  1.00  0.00           H  
HETATM   35  H11 UNL     1      -1.654   1.396   2.414  1.00  0.00           H  
HETATM   36  H12 UNL     1      -1.212  -0.331   2.451  1.00  0.00           H  
HETATM   37  H13 UNL     1      -3.300  -1.089   1.997  1.00  0.00           H  
HETATM   38  H14 UNL     1      -3.712   0.510   2.662  1.00  0.00           H  
HETATM   39  H15 UNL     1      -4.904  -0.033   0.601  1.00  0.00           H  
HETATM   40  H16 UNL     1      -3.950   1.437   0.372  1.00  0.00           H  
HETATM   41  H17 UNL     1      -2.971  -2.480  -0.609  1.00  0.00           H  
HETATM   42  H18 UNL     1      -4.270  -1.918  -1.686  1.00  0.00           H  
HETATM   43  H19 UNL     1      -4.512  -1.931   0.075  1.00  0.00           H  
HETATM   44  H20 UNL     1      -3.256   1.437  -1.941  1.00  0.00           H  
HETATM   45  H21 UNL     1      -3.592  -0.178  -2.783  1.00  0.00           H  
HETATM   46  H22 UNL     1      -4.783   0.571  -1.707  1.00  0.00           H  
HETATM   47  H23 UNL     1      -1.389  -1.434  -0.338  1.00  0.00           H  
HETATM   48  H24 UNL     1       0.611   2.055   2.876  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    4   28
CONECT    3   29   30   31
CONECT    4    5    5   23
CONECT    5    6   32
CONECT    6    7    7   20
CONECT    7    8   33
CONECT    8    9   19   34
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   13   19   20
CONECT   13   14   35   36
CONECT   14   15   37   38
CONECT   15   16   39   40
CONECT   16   17   18   19
CONECT   17   41   42   43
CONECT   18   44   45   46
CONECT   19   47
CONECT   20   21   21
CONECT   21   22   23
CONECT   22   48
CONECT   23   24   24
END

HMDB0030841
     RDKit          3D
Sagequinone methide A
 48 51  0  0  0  0  0  0  0  0999 V2000
    5.0817   -1.0056   -1.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6848   -0.4692    0.3026 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4910    0.7850    0.5420 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2351   -0.2151    0.3710 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4707   -0.4653   -0.6935 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0367   -0.2362   -0.6894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3198   -0.4882   -1.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0372    0.1750   -1.7794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9589    1.5445   -1.5209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2859    1.8428   -0.1837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6412    2.9220    0.3247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1028    0.5202    0.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7529    0.4507    1.8375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1906   -0.0159    1.8342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8481    0.3652    0.5558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1980   -0.3209   -0.6281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7921   -1.7327   -0.7193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6752    0.4204   -1.8689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7165   -0.3962   -0.5222 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3661    0.2891    0.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1111    0.5456    1.5832 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5909    1.0436    2.7713 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5683    0.3041    1.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2565    0.5524    2.5776 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1760   -1.2135   -1.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8487   -0.2460   -1.8437 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5935   -1.9726   -1.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0253   -1.2257    1.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0651    1.6673    0.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6283    0.9994    1.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4933    0.6103    0.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9185   -0.8523   -1.5985 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6886   -1.1055   -2.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5552   -0.1057   -2.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6540    1.3958    2.4137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2125   -0.3315    2.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3003   -1.0894    1.9969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7122    0.5097    2.6623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9039   -0.0330    0.6015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9502    1.4369    0.3722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9709   -2.4804   -0.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2697   -1.9180   -1.6864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5124   -1.9314    0.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2556    1.4369   -1.9410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5918   -0.1781   -2.7827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7835    0.5711   -1.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3888   -1.4343   -0.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6106    2.0551    2.8758 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  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 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
 12 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 23  4  1  0
 20  6  1  0
 19  8  1  0
 19 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  5 32  1  0
  7 33  1  0
  8 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 22 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄O₄

Average Molecular Weight

328.4022

Monoisotopic Molecular Weight

328.167459256

IUPAC Name

3-hydroxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,5,7-triene-4,15-dione

Traditional Name

3-hydroxy-5-isopropyl-11,11-dimethyl-16-oxatetracyclo[7.5.2.0¹,¹⁰.0²,⁷]hexadeca-2,5,7-triene-4,15-dione

CAS Registry Number

194472-90-7

SMILES

CC(C)C1=CC2=CC3OC(=O)C4(CCCC(C)(C)C34)C2=C(O)C1=O

InChI Identifier

InChI=1S/C20H24O4/c1-10(2)12-8-11-9-13-17-19(3,4)6-5-7-20(17,18(23)24-13)14(11)16(22)15(12)21/h8-10,13,17,22H,5-7H2,1-4H3

InChI Key

CYJLXXSGOZGYMC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0030841)
Cell membrane (HMDB: HMDB0030841)

Cellular substructure

Extracellular (HMDB: HMDB0030841)
Membrane (HMDB: HMDB0030841)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030841)

Source

Endogenous

Endogenous (HMDB: HMDB0030841)

Plant

Plant (HMDB: HMDB0030841)

Animal

Animal (HMDB: HMDB0030841)

Exogenous

Food

Food (HMDB: HMDB0030841)

Tea

Herb and spice

Herb

Common sage (FooDB: FOOD00165)

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0030841)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0030841)

Cellular process

Cell signaling (HMDB: HMDB0030841)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0030841)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0030841)

Nutrient

Nutrient (HMDB: HMDB0030841)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0030841)

Emulsifier (HMDB: HMDB0030841)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	145 - 147 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.046 g/L	ALOGPS
logP	3.03	ALOGPS
logP	3.23	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	9.39	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	92.65 m³·mol⁻¹	ChemAxon
Polarizability	35.7 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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
DeepCCS	[M-2H]-	219.932	30932474
DeepCCS	[M+Na]+	196.196	30932474
AllCCS	[M+H]+	177.9	32859911
AllCCS	[M+H-H2O]+	174.8	32859911
AllCCS	[M+NH4]+	180.7	32859911
AllCCS	[M+Na]+	181.5	32859911
AllCCS	[M-H]-	186.7	32859911
AllCCS	[M+Na-2H]-	186.7	32859911
AllCCS	[M+HCOO]-	186.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sagequinone methide A	CC(C)C1=CC2=CC3OC(=O)C4(CCCC(C)(C)C34)C2=C(O)C1=O	3859.1	Standard polar	33892256
Sagequinone methide A	CC(C)C1=CC2=CC3OC(=O)C4(CCCC(C)(C)C34)C2=C(O)C1=O	2513.0	Standard non polar	33892256
Sagequinone methide A	CC(C)C1=CC2=CC3OC(=O)C4(CCCC(C)(C)C34)C2=C(O)C1=O	2645.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sagequinone methide A,1TMS,isomer #1	CC(C)C1=CC2=CC3OC(=O)C4(CCCC(C)(C)C34)C2=C(O[Si](C)(C)C)C1=O	2742.3	Semi standard non polar	33892256
Sagequinone methide A,1TBDMS,isomer #1	CC(C)C1=CC2=CC3OC(=O)C4(CCCC(C)(C)C34)C2=C(O[Si](C)(C)C(C)(C)C)C1=O	2998.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Sagequinone methide A GC-MS (Non-derivatized) - 70eV, Positive	splash10-0159-3393000000-e256876a36bb92923ff0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sagequinone methide A GC-MS (1 TMS) - 70eV, Positive	splash10-0076-4029000000-090805ddafa8a3b43830	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sagequinone methide A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sagequinone methide A 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 - Sagequinone methide A 10V, Positive-QTOF	splash10-004i-0049000000-02a5d56a48539ec8a393	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sagequinone methide A 20V, Positive-QTOF	splash10-004r-3293000000-4a9265ace167ed173785	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sagequinone methide A 40V, Positive-QTOF	splash10-0ar3-9660000000-64bcdd77aa01e27843bf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sagequinone methide A 10V, Negative-QTOF	splash10-004i-0029000000-1026a4dc962b7b8a0910	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sagequinone methide A 20V, Negative-QTOF	splash10-004i-0039000000-df1b9176193a8deb9353	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sagequinone methide A 40V, Negative-QTOF	splash10-00lr-1390000000-db447a8beb65d78c0cc4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sagequinone methide A 10V, Negative-QTOF	splash10-004i-0009000000-fd417bc7f7b273e09154	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sagequinone methide A 20V, Negative-QTOF	splash10-004i-0029000000-b8dd09259083e9781ccc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sagequinone methide A 40V, Negative-QTOF	splash10-0032-0092000000-c6f711319afba3c6703f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sagequinone methide A 10V, Positive-QTOF	splash10-004i-0009000000-ff8a01ffca3a9dc33809	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sagequinone methide A 20V, Positive-QTOF	splash10-0059-0198000000-f39b4bfbfeeb62af1ff3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sagequinone methide A 40V, Positive-QTOF	splash10-02t9-2792000000-67d1e514fa8becdcbc94	2021-09-22	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

FDB002799

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

74975865

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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 Sagequinone methide A (HMDB0030841)

MOL for HMDB0030841 (Sagequinone methide A)

3D MOL for HMDB0030841 (Sagequinone methide A)

3D SDF for HMDB0030841 (Sagequinone methide A)

3D-SDF for HMDB0030841 (Sagequinone methide A)

PDB for HMDB0030841 (Sagequinone methide A)

3D PDB for HMDB0030841 (Sagequinone methide A)

SMILES for HMDB0030841 (Sagequinone methide A)

INCHI for HMDB0030841 (Sagequinone methide A)

Structure for HMDB0030841 (Sagequinone methide A)

3D Structure for HMDB0030841 (Sagequinone methide A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra