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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 02:46:52 UTC

Update Date

2021-09-23 02:46:52 UTC

HMDB ID

HMDB0301820

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(3R)-Linalyl diphosphate

Description

(3r)-linalyl diphosphate is a member of the class of compounds known as isoprenoid phosphates. Isoprenoid phosphates are prenol lipids containing a phosphate group linked to an isoprene (2-methylbuta-1,3-diene) unit (3r)-linalyl diphosphate is slightly soluble (in water) and a moderately acidic compound (based on its pKa). (3r)-linalyl diphosphate can be found in common sage, which makes (3r)-linalyl diphosphate a potential biomarker for the consumption of this food product.

Structure

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

HMDB0301820
     RDKit          3D
(3R)-Linalyl diphosphate
 39 38  0  0  0  0  0  0  0  0999 V2000
    0.3938   -0.2118    1.9443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0315   -0.9592    0.9452 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2105   -0.8106   -0.4785 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7558   -2.2047   -0.9232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9166   -0.5677   -1.3915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7740    0.6189   -1.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5191    0.7380    0.0203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8589    0.7613    0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5958    0.6625   -1.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6190    0.8793    1.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2088    0.1341   -0.7414 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7062   -0.2035   -0.1258 P   0  0  0  0  0  5  0  0  0  0  0  0
    2.7195   -1.2510    0.9498 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8214   -0.6263   -1.3585 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3453    1.2346    0.5409 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0199    1.2254    0.5462 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.4840    2.3610   -0.3660 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5795   -0.2515   -0.0452 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5941    1.4860    2.1158 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1123   -0.4757    2.9532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0130    0.6733    1.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6615   -1.8194    1.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2730   -2.7038   -0.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2723   -2.1341   -1.8769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1780   -2.8040   -1.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5207   -0.5436   -2.4568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6279   -1.4571   -1.4509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5653    0.5236   -2.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2759    1.5803   -1.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0238    0.8199    0.9693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3928   -0.3011   -1.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3259    1.5272   -1.8736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7004    0.6893   -1.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9657    1.4030    2.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9215   -0.1017    1.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5736    1.4548    1.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9370   -1.6165   -1.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3835   -0.0461   -0.6158 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2180    2.3170    2.4724 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  3
  8  9  1  0
  8 10  1  0
  3 11  1  1
 11 12  1  0
 12 13  2  0
 12 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 16 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  4 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 10 36  1  0
 14 37  1  0
 18 38  1  0
 19 39  1  0
M  END


  Mrv0541 02241212132D          

 19 18  0  0  0  0            999 V2000
    1.1684    1.2275    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.9934    1.2275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1684    2.0525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1393    0.4030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3434    1.2275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2399    0.6442    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.3434    0.0608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8023    1.2478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2983    1.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4733    1.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0608    0.7753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0608    2.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4733    0.0608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0608   -0.6537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2358   -0.6537    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8233   -1.3681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0017   -1.3681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8233    0.0608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6483    0.0608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  0  0  0  0
  6 18  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  6  5  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 15 18  1  1  0  0  0
 15 19  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0301820

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC[C@@](C)(OP(O)(=O)OP(O)(O)=O)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C10H20O7P2/c1-5-10(4,8-6-7-9(2)3)16-19(14,15)17-18(11,12)13/h5,7H,1,6,8H2,2-4H3,(H,14,15)(H2,11,12,13)/t10-/m0/s1

> <INCHI_KEY>
UOJPTUWXHXNLDB-JTQLQIEISA-N

> <FORMULA>
C10H20O7P2

> <MOLECULAR_WEIGHT>
314.2091

> <EXACT_MASS>
314.068426018

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
27.939765647985503

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[({[(3R)-3,7-dimethylocta-1,6-dien-3-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid

> <ALOGPS_LOGP>
1.48

> <JCHEM_LOGP>
2.1021279423333334

> <ALOGPS_LOGS>
-2.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.1588973842311825

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7474900693418816

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
71.95240000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.41e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{[(3R)-3,7-dimethylocta-1,6-dien-3-yl]oxy(hydroxy)phosphoryl}oxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0301820
     RDKit          3D
(3R)-Linalyl diphosphate
 39 38  0  0  0  0  0  0  0  0999 V2000
    0.3938   -0.2118    1.9443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0315   -0.9592    0.9452 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2105   -0.8106   -0.4785 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7558   -2.2047   -0.9232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9166   -0.5677   -1.3915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7740    0.6189   -1.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5191    0.7380    0.0203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8589    0.7613    0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5958    0.6625   -1.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6190    0.8793    1.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2088    0.1341   -0.7414 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7062   -0.2035   -0.1258 P   0  0  0  0  0  5  0  0  0  0  0  0
    2.7195   -1.2510    0.9498 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8214   -0.6263   -1.3585 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3453    1.2346    0.5409 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0199    1.2254    0.5462 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.4840    2.3610   -0.3660 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5795   -0.2515   -0.0452 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5941    1.4860    2.1158 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1123   -0.4757    2.9532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0130    0.6733    1.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6615   -1.8194    1.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2730   -2.7038   -0.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2723   -2.1341   -1.8769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1780   -2.8040   -1.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5207   -0.5436   -2.4568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6279   -1.4571   -1.4509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5653    0.5236   -2.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2759    1.5803   -1.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0238    0.8199    0.9693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3928   -0.3011   -1.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3259    1.5272   -1.8736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7004    0.6893   -1.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9657    1.4030    2.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9215   -0.1017    1.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5736    1.4548    1.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9370   -1.6165   -1.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3835   -0.0461   -0.6158 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2180    2.3170    2.4724 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  3
  8  9  1  0
  8 10  1  0
  3 11  1  1
 11 12  1  0
 12 13  2  0
 12 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 16 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  4 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 10 36  1  0
 14 37  1  0
 18 38  1  0
 19 39  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  P   UNK     0       2.181   2.291   0.000  0.00  0.00           P+0
HETATM    2  O   UNK     0       3.721   2.291   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       2.181   3.831   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.127   0.752   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       0.641   2.291   0.000  0.00  0.00           O+0
HETATM    6  P   UNK     0      -0.448   1.203   0.000  0.00  0.00           P+0
HETATM    7  O   UNK     0       0.641   0.113   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -1.498   2.329   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -6.157   2.781   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.617   2.781   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.847   1.447   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.847   4.115   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.617   0.113   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.847  -1.220   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.307  -1.220   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.537  -2.554   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.003  -2.554   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.537   0.113   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -3.077   0.113   0.000  0.00  0.00           C+0
CONECT    1    2    3    4    5                                             
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    1    6                                                       
CONECT    6   18    7    8    5                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9   10                                                            
CONECT   10    9   11   12                                                  
CONECT   11   10   13                                                       
CONECT   12   10                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18   19                                             
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18    6   15                                                       
CONECT   19   15                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

COMPND    HMDB0301820
HETATM    1  C1  UNL     1       0.394  -0.212   1.944  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.031  -0.959   0.945  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.211  -0.811  -0.478  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.756  -2.205  -0.923  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.917  -0.568  -1.391  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.774   0.619  -1.247  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.519   0.738   0.020  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.859   0.761   0.071  1.00  0.00           C  
HETATM    9  C9  UNL     1      -4.596   0.662  -1.205  1.00  0.00           C  
HETATM   10  C10 UNL     1      -4.619   0.879   1.325  1.00  0.00           C  
HETATM   11  O1  UNL     1       1.209   0.134  -0.741  1.00  0.00           O  
HETATM   12  P1  UNL     1       2.706  -0.203  -0.126  1.00  0.00           P  
HETATM   13  O2  UNL     1       2.719  -1.251   0.950  1.00  0.00           O  
HETATM   14  O3  UNL     1       3.821  -0.626  -1.359  1.00  0.00           O  
HETATM   15  O4  UNL     1       3.345   1.235   0.541  1.00  0.00           O  
HETATM   16  P2  UNL     1       5.020   1.225   0.546  1.00  0.00           P  
HETATM   17  O5  UNL     1       5.484   2.361  -0.366  1.00  0.00           O  
HETATM   18  O6  UNL     1       5.580  -0.252  -0.045  1.00  0.00           O  
HETATM   19  O7  UNL     1       5.594   1.486   2.116  1.00  0.00           O  
HETATM   20  H1  UNL     1       0.112  -0.476   2.953  1.00  0.00           H  
HETATM   21  H2  UNL     1       1.013   0.673   1.848  1.00  0.00           H  
HETATM   22  H3  UNL     1      -0.662  -1.819   1.245  1.00  0.00           H  
HETATM   23  H4  UNL     1       1.273  -2.704  -0.109  1.00  0.00           H  
HETATM   24  H5  UNL     1       1.272  -2.134  -1.877  1.00  0.00           H  
HETATM   25  H6  UNL     1      -0.178  -2.804  -1.097  1.00  0.00           H  
HETATM   26  H7  UNL     1      -0.521  -0.544  -2.457  1.00  0.00           H  
HETATM   27  H8  UNL     1      -1.628  -1.457  -1.451  1.00  0.00           H  
HETATM   28  H9  UNL     1      -2.565   0.524  -2.060  1.00  0.00           H  
HETATM   29  H10 UNL     1      -1.276   1.580  -1.534  1.00  0.00           H  
HETATM   30  H11 UNL     1      -2.024   0.820   0.969  1.00  0.00           H  
HETATM   31  H12 UNL     1      -4.393  -0.301  -1.712  1.00  0.00           H  
HETATM   32  H13 UNL     1      -4.326   1.527  -1.874  1.00  0.00           H  
HETATM   33  H14 UNL     1      -5.700   0.689  -1.042  1.00  0.00           H  
HETATM   34  H15 UNL     1      -3.966   1.403   2.067  1.00  0.00           H  
HETATM   35  H16 UNL     1      -4.922  -0.102   1.740  1.00  0.00           H  
HETATM   36  H17 UNL     1      -5.574   1.455   1.183  1.00  0.00           H  
HETATM   37  H18 UNL     1       3.937  -1.616  -1.396  1.00  0.00           H  
HETATM   38  H19 UNL     1       6.384  -0.046  -0.616  1.00  0.00           H  
HETATM   39  H20 UNL     1       5.218   2.317   2.472  1.00  0.00           H  
CONECT    1    2    2   20   21
CONECT    2    3   22
CONECT    3    4    5   11
CONECT    4   23   24   25
CONECT    5    6   26   27
CONECT    6    7   28   29
CONECT    7    8    8   30
CONECT    8    9   10
CONECT    9   31   32   33
CONECT   10   34   35   36
CONECT   11   12
CONECT   12   13   13   14   15
CONECT   14   37
CONECT   15   16
CONECT   16   17   17   18   19
CONECT   18   38
CONECT   19   39
END

HMDB0301820
     RDKit          3D
(3R)-Linalyl diphosphate
 39 38  0  0  0  0  0  0  0  0999 V2000
    0.3938   -0.2118    1.9443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0315   -0.9592    0.9452 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2105   -0.8106   -0.4785 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7558   -2.2047   -0.9232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9166   -0.5677   -1.3915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7740    0.6189   -1.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5191    0.7380    0.0203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8589    0.7613    0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5958    0.6625   -1.2050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6190    0.8793    1.3247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2088    0.1341   -0.7414 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7062   -0.2035   -0.1258 P   0  0  0  0  0  5  0  0  0  0  0  0
    2.7195   -1.2510    0.9498 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8214   -0.6263   -1.3585 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3453    1.2346    0.5409 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0199    1.2254    0.5462 P   0  0  0  0  0  5  0  0  0  0  0  0
    5.4840    2.3610   -0.3660 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5795   -0.2515   -0.0452 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5941    1.4860    2.1158 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1123   -0.4757    2.9532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0130    0.6733    1.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6615   -1.8194    1.2452 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2730   -2.7038   -0.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2723   -2.1341   -1.8769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1780   -2.8040   -1.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5207   -0.5436   -2.4568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6279   -1.4571   -1.4509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5653    0.5236   -2.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2759    1.5803   -1.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0238    0.8199    0.9693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3928   -0.3011   -1.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3259    1.5272   -1.8736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7004    0.6893   -1.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9657    1.4030    2.0665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9215   -0.1017    1.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5736    1.4548    1.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9370   -1.6165   -1.3964 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3835   -0.0461   -0.6158 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2180    2.3170    2.4724 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  3
  8  9  1  0
  8 10  1  0
  3 11  1  1
 11 12  1  0
 12 13  2  0
 12 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 16 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  4 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 10 36  1  0
 14 37  1  0
 18 38  1  0
 19 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
[({[(3R)-3,7-dimethylocta-1,6-dien-3-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonate	Generator
(3R)-Linalyl diphosphoric acid	Generator

Chemical Formula

C₁₀H₂₀O₇P₂

Average Molecular Weight

314.2091

Monoisotopic Molecular Weight

314.068426018

IUPAC Name

[({[(3R)-3,7-dimethylocta-1,6-dien-3-yl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid

Traditional Name

{[(3R)-3,7-dimethylocta-1,6-dien-3-yl]oxy(hydroxy)phosphoryl}oxyphosphonic acid

CAS Registry Number

Not Available

SMILES

CC(C)=CCC[C@@](C)(OP(O)(=O)OP(O)(O)=O)C=C

InChI Identifier

InChI=1S/C10H20O7P2/c1-5-10(4,8-6-7-9(2)3)16-19(14,15)17-18(11,12)13/h5,7H,1,6,8H2,2-4H3,(H,14,15)(H2,11,12,13)/t10-/m0/s1

InChI Key

UOJPTUWXHXNLDB-JTQLQIEISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoprenoid phosphates. These are prenol lipids containing a phosphate group linked to an isoprene (2-methylbuta-1,3-diene) unit.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Isoprenoid phosphates

Direct Parent

Isoprenoid phosphates

Alternative Parents

Substituents

Organic pyrophosphate
Monoterpenoid
Isoprenoid phosphate
Acyclic monoterpenoid
Monoalkyl phosphate
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Common sage (FooDB: FOOD00165)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.48	ALOGPS
logP	2.1	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	1.75	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	71.95 m³·mol⁻¹	ChemAxon
Polarizability	27.94 Å³	ChemAxon
Number of Rings	0	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
AllCCS	[M+H]+	173.722	32859911
AllCCS	[M+H-H2O]+	170.673	32859911
AllCCS	[M+Na]+	177.354	32859911
AllCCS	[M+NH4]+	176.544	32859911
AllCCS	[M-H]-	166.109	32859911
AllCCS	[M+Na-2H]-	166.94	32859911
AllCCS	[M+HCOO]-	167.969	32859911
DeepCCS	[M+H]+	148.901	30932474
DeepCCS	[M-H]-	146.543	30932474
DeepCCS	[M-2H]-	179.474	30932474
DeepCCS	[M+Na]+	154.994	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(3R)-Linalyl diphosphate,1TMS,isomer #1	C=C[C@@](C)(CCC=C(C)C)OP(=O)(O[Si](C)(C)C)OP(=O)(O)O	2170.1	Semi standard non polar	33892256
(3R)-Linalyl diphosphate,1TMS,isomer #1	C=C[C@@](C)(CCC=C(C)C)OP(=O)(O[Si](C)(C)C)OP(=O)(O)O	1960.0	Standard non polar	33892256
(3R)-Linalyl diphosphate,1TMS,isomer #1	C=C[C@@](C)(CCC=C(C)C)OP(=O)(O[Si](C)(C)C)OP(=O)(O)O	2931.6	Standard polar	33892256
(3R)-Linalyl diphosphate,1TMS,isomer #2	C=C[C@@](C)(CCC=C(C)C)OP(=O)(O)OP(=O)(O)O[Si](C)(C)C	2148.2	Semi standard non polar	33892256
(3R)-Linalyl diphosphate,1TMS,isomer #2	C=C[C@@](C)(CCC=C(C)C)OP(=O)(O)OP(=O)(O)O[Si](C)(C)C	1970.0	Standard non polar	33892256
(3R)-Linalyl diphosphate,1TMS,isomer #2	C=C[C@@](C)(CCC=C(C)C)OP(=O)(O)OP(=O)(O)O[Si](C)(C)C	2941.5	Standard polar	33892256
(3R)-Linalyl diphosphate,2TMS,isomer #1	C=C[C@@](C)(CCC=C(C)C)OP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C	2186.0	Semi standard non polar	33892256
(3R)-Linalyl diphosphate,2TMS,isomer #1	C=C[C@@](C)(CCC=C(C)C)OP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C	2036.2	Standard non polar	33892256
(3R)-Linalyl diphosphate,2TMS,isomer #1	C=C[C@@](C)(CCC=C(C)C)OP(=O)(O[Si](C)(C)C)OP(=O)(O)O[Si](C)(C)C	2660.3	Standard polar	33892256
(3R)-Linalyl diphosphate,2TMS,isomer #2	C=C[C@@](C)(CCC=C(C)C)OP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2190.4	Semi standard non polar	33892256
(3R)-Linalyl diphosphate,2TMS,isomer #2	C=C[C@@](C)(CCC=C(C)C)OP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2037.8	Standard non polar	33892256
(3R)-Linalyl diphosphate,2TMS,isomer #2	C=C[C@@](C)(CCC=C(C)C)OP(=O)(O)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2645.7	Standard polar	33892256
(3R)-Linalyl diphosphate,3TMS,isomer #1	C=C[C@@](C)(CCC=C(C)C)OP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2222.9	Semi standard non polar	33892256
(3R)-Linalyl diphosphate,3TMS,isomer #1	C=C[C@@](C)(CCC=C(C)C)OP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2111.7	Standard non polar	33892256
(3R)-Linalyl diphosphate,3TMS,isomer #1	C=C[C@@](C)(CCC=C(C)C)OP(=O)(O[Si](C)(C)C)OP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	2374.0	Standard polar	33892256
(3R)-Linalyl diphosphate,1TBDMS,isomer #1	C=C[C@@](C)(CCC=C(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O	2403.3	Semi standard non polar	33892256
(3R)-Linalyl diphosphate,1TBDMS,isomer #1	C=C[C@@](C)(CCC=C(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O	2140.4	Standard non polar	33892256
(3R)-Linalyl diphosphate,1TBDMS,isomer #1	C=C[C@@](C)(CCC=C(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O	3072.0	Standard polar	33892256
(3R)-Linalyl diphosphate,1TBDMS,isomer #2	C=C[C@@](C)(CCC=C(C)C)OP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C	2381.6	Semi standard non polar	33892256
(3R)-Linalyl diphosphate,1TBDMS,isomer #2	C=C[C@@](C)(CCC=C(C)C)OP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C	2170.0	Standard non polar	33892256
(3R)-Linalyl diphosphate,1TBDMS,isomer #2	C=C[C@@](C)(CCC=C(C)C)OP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C	3079.2	Standard polar	33892256
(3R)-Linalyl diphosphate,2TBDMS,isomer #1	C=C[C@@](C)(CCC=C(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C	2598.6	Semi standard non polar	33892256
(3R)-Linalyl diphosphate,2TBDMS,isomer #1	C=C[C@@](C)(CCC=C(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C	2372.3	Standard non polar	33892256
(3R)-Linalyl diphosphate,2TBDMS,isomer #1	C=C[C@@](C)(CCC=C(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O[Si](C)(C)C(C)(C)C	2824.8	Standard polar	33892256
(3R)-Linalyl diphosphate,2TBDMS,isomer #2	C=C[C@@](C)(CCC=C(C)C)OP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2602.2	Semi standard non polar	33892256
(3R)-Linalyl diphosphate,2TBDMS,isomer #2	C=C[C@@](C)(CCC=C(C)C)OP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2361.1	Standard non polar	33892256
(3R)-Linalyl diphosphate,2TBDMS,isomer #2	C=C[C@@](C)(CCC=C(C)C)OP(=O)(O)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2833.8	Standard polar	33892256
(3R)-Linalyl diphosphate,3TBDMS,isomer #1	C=C[C@@](C)(CCC=C(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2782.5	Semi standard non polar	33892256
(3R)-Linalyl diphosphate,3TBDMS,isomer #1	C=C[C@@](C)(CCC=C(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2563.5	Standard non polar	33892256
(3R)-Linalyl diphosphate,3TBDMS,isomer #1	C=C[C@@](C)(CCC=C(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2645.1	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R)-Linalyl diphosphate 10V, Positive-QTOF	splash10-000i-1952000000-d1479d2db19f5d726d3a	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R)-Linalyl diphosphate 20V, Positive-QTOF	splash10-000i-8910000000-d4d8e523fe2de1259535	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R)-Linalyl diphosphate 40V, Positive-QTOF	splash10-0gc9-9300000000-146292342e71615f3929	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R)-Linalyl diphosphate 10V, Negative-QTOF	splash10-03di-0419000000-e79e354003619a40fea3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R)-Linalyl diphosphate 20V, Negative-QTOF	splash10-0059-9520000000-c7355131ed3151aa01c9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R)-Linalyl diphosphate 40V, Negative-QTOF	splash10-004i-9000000000-949a64f900829e97aae3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R)-Linalyl diphosphate 10V, Positive-QTOF	splash10-01qi-6900000000-48badea602c95234af49	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R)-Linalyl diphosphate 20V, Positive-QTOF	splash10-000i-5920000000-497234a233e0c4587ba4	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R)-Linalyl diphosphate 40V, Positive-QTOF	splash10-001i-9300000000-871787638ee1fe8b293f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R)-Linalyl diphosphate 10V, Negative-QTOF	splash10-03di-0209000000-a1d9f0598deb46539b9c	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R)-Linalyl diphosphate 20V, Negative-QTOF	splash10-0a6r-1912000000-00ef41c36bed66619e63	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R)-Linalyl diphosphate 40V, Negative-QTOF	splash10-0a4i-2900000000-bb27d3a4c5704e42d43b	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB001458

KNApSAcK ID

Not Available

Chemspider ID

59696189

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13856096

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

Not Available

Showing metabocard for (3R)-Linalyl diphosphate (HMDB0301820)

MOL for HMDB0301820 ((3R)-Linalyl diphosphate)

3D MOL for HMDB0301820 ((3R)-Linalyl diphosphate)

3D SDF for HMDB0301820 ((3R)-Linalyl diphosphate)

3D-SDF for HMDB0301820 ((3R)-Linalyl diphosphate)

PDB for HMDB0301820 ((3R)-Linalyl diphosphate)

3D PDB for HMDB0301820 ((3R)-Linalyl diphosphate)

SMILES for HMDB0301820 ((3R)-Linalyl diphosphate)

INCHI for HMDB0301820 ((3R)-Linalyl diphosphate)

Structure for HMDB0301820 ((3R)-Linalyl diphosphate)

3D Structure for HMDB0301820 ((3R)-Linalyl diphosphate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra