Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 19:58:29 UTC

Update Date

2021-09-23 19:58:35 UTC

HMDB ID

HMDB0302709

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Santamarin

Description

Santamarin, also known as (+)-santamarine or balchanin, belongs to eudesmanolides, secoeudesmanolides, and derivatives class of compounds. Those are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. Santamarin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Santamarin can be found in sweet bay, which makes santamarin a potential biomarker for the consumption of this food product.

Structure

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

HMDB0302709
     RDKit          3D
Santamarin
 38 40  0  0  0  0  0  0  0  0999 V2000
    4.2070    1.1010   -0.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1974    0.2828   -0.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2251   -1.1612   -0.0660 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2388   -1.8661    0.2057 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9123   -1.6253   -0.0970 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1030   -0.5114    0.0860 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8029    0.4986   -0.8414 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2407    1.8307   -0.5546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2430    1.8056   -0.8451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9591    0.7186   -0.0953 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9125    1.0310    1.3828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2907   -0.6101   -0.4043 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0566   -1.7628    0.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4004   -3.0900    0.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3359   -1.6698    0.3891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0930   -0.3894    0.3371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3840    0.6346   -0.5279 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0626    1.8313   -0.4697 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1631    0.7573    0.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0672    2.1368   -0.5903 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1944   -0.1830    1.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6801    0.1418   -1.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4948    2.1543    0.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6805    2.5605   -1.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3403    1.5663   -1.9346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7048    2.7940   -0.6947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0201    1.5098    1.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1513    0.1198    1.9845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7398    1.7507    1.5917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2481   -0.6586   -1.5320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3414   -3.2555   -0.6787 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1481   -3.2426    1.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1429   -3.9270    0.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8910   -2.5457    0.7260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0747   -0.5855   -0.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2396   -0.0272    1.3698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4331    0.2577   -1.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0136    1.6281   -0.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  1
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  7  2  1  0
 17 10  1  0
 12  6  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  1
  7 22  1  6
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  6
 14 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  6
 18 38  1  0
M  END


  Mrv0541 02241220542D          

 18 20  0  0  1  0            999 V2000
    1.6425    0.0689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0325    0.7959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8571    0.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2470    1.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8124    2.2499    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9878    2.2242    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5978    1.4972    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7732    1.4714    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3386    2.1727    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7286    2.8997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5532    2.9254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4626    1.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0926    2.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5232    1.1532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2244    0.7186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2406    0.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3778    2.9512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2024    2.9770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  2  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
  9 12  1  6  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  8 16  1  1  0  0  0
  6 17  1  6  0  0  0
  5 18  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0302709

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC[C@@H](O)[C@]2(C)CC[C@@H]3[C@H](OC(=O)C3=C)[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-8-4-5-11(16)15(3)7-6-10-9(2)14(17)18-13(10)12(8)15/h4,10-13,16H,2,5-7H2,1,3H3/t10-,11+,12+,13-,15-/m0/s1

> <INCHI_KEY>
PLSSEPIRACGCBO-PFFFPCNUSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.3175

> <EXACT_MASS>
248.141244506

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.414728372980612

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,5aR,6R,9aS,9bS)-6-hydroxy-5a,9-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,5aH,6H,7H,9aH,9bH-naphtho[1,2-b]furan-2-one

> <ALOGPS_LOGP>
2.44

> <JCHEM_LOGP>
2.1471843146666667

> <ALOGPS_LOGS>
-2.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.625811789902102

> <JCHEM_PKA_STRONGEST_BASIC>
-2.962469923096821

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
68.7084

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.67e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-santamarine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302709
     RDKit          3D
Santamarin
 38 40  0  0  0  0  0  0  0  0999 V2000
    4.2070    1.1010   -0.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1974    0.2828   -0.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2251   -1.1612   -0.0660 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2388   -1.8661    0.2057 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9123   -1.6253   -0.0970 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1030   -0.5114    0.0860 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8029    0.4986   -0.8414 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2407    1.8307   -0.5546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2430    1.8056   -0.8451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9591    0.7186   -0.0953 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9125    1.0310    1.3828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2907   -0.6101   -0.4043 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0566   -1.7628    0.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4004   -3.0900    0.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3359   -1.6698    0.3891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0930   -0.3894    0.3371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3840    0.6346   -0.5279 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0626    1.8313   -0.4697 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1631    0.7573    0.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0672    2.1368   -0.5903 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1944   -0.1830    1.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6801    0.1418   -1.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4948    2.1543    0.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6805    2.5605   -1.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3403    1.5663   -1.9346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7048    2.7940   -0.6947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0201    1.5098    1.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1513    0.1198    1.9845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7398    1.7507    1.5917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2481   -0.6586   -1.5320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3414   -3.2555   -0.6787 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1481   -3.2426    1.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1429   -3.9270    0.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8910   -2.5457    0.7260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0747   -0.5855   -0.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2396   -0.0272    1.3698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4331    0.2577   -1.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0136    1.6281   -0.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  1
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  7  2  1  0
 17 10  1  0
 12  6  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  1
  7 22  1  6
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  6
 14 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  6
 18 38  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       3.066   0.129   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.794   1.486   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.333   1.534   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.061   2.891   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.250   4.200   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.711   4.152   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.983   2.795   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.443   2.747   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.632   4.056   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.360   5.413   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.899   5.461   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.864   3.689   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.040   4.683   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.977   2.153   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.286   1.341   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.449   1.571   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.439   5.509   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.978   5.557   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7   11   17                                             
CONECT    7    6    2    8                                                  
CONECT    8    7    9   16                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10    6                                                       
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    8                                                       
CONECT   17    6                                                            
CONECT   18    5                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0302709
HETATM    1  C1  UNL     1       4.207   1.101  -0.314  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.197   0.283  -0.405  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.225  -1.161  -0.066  1.00  0.00           C  
HETATM    4  O1  UNL     1       4.239  -1.866   0.206  1.00  0.00           O  
HETATM    5  O2  UNL     1       1.912  -1.625  -0.097  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.103  -0.511   0.086  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.803   0.499  -0.841  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.241   1.831  -0.555  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.243   1.806  -0.845  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.959   0.719  -0.095  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.912   1.031   1.383  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.291  -0.610  -0.404  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.057  -1.763   0.049  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.400  -3.090   0.139  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.336  -1.670   0.389  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.093  -0.389   0.337  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.384   0.635  -0.528  1.00  0.00           C  
HETATM   18  O3  UNL     1      -3.063   1.831  -0.470  1.00  0.00           O  
HETATM   19  H1  UNL     1       5.163   0.757   0.030  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.067   2.137  -0.590  1.00  0.00           H  
HETATM   21  H3  UNL     1       1.194  -0.183   1.142  1.00  0.00           H  
HETATM   22  H4  UNL     1       1.680   0.142  -1.862  1.00  0.00           H  
HETATM   23  H5  UNL     1       1.495   2.154   0.450  1.00  0.00           H  
HETATM   24  H6  UNL     1       1.681   2.561  -1.296  1.00  0.00           H  
HETATM   25  H7  UNL     1      -0.340   1.566  -1.935  1.00  0.00           H  
HETATM   26  H8  UNL     1      -0.705   2.794  -0.695  1.00  0.00           H  
HETATM   27  H9  UNL     1       0.020   1.510   1.703  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.151   0.120   1.985  1.00  0.00           H  
HETATM   29  H11 UNL     1      -1.740   1.751   1.592  1.00  0.00           H  
HETATM   30  H12 UNL     1      -0.248  -0.659  -1.532  1.00  0.00           H  
HETATM   31  H13 UNL     1       0.341  -3.255  -0.679  1.00  0.00           H  
HETATM   32  H14 UNL     1       0.148  -3.243   1.089  1.00  0.00           H  
HETATM   33  H15 UNL     1      -1.143  -3.927   0.018  1.00  0.00           H  
HETATM   34  H16 UNL     1      -2.891  -2.546   0.726  1.00  0.00           H  
HETATM   35  H17 UNL     1      -4.075  -0.586  -0.141  1.00  0.00           H  
HETATM   36  H18 UNL     1      -3.240  -0.027   1.370  1.00  0.00           H  
HETATM   37  H19 UNL     1      -2.433   0.258  -1.572  1.00  0.00           H  
HETATM   38  H20 UNL     1      -4.014   1.628  -0.234  1.00  0.00           H  
CONECT    1    2    2   19   20
CONECT    2    3    7
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   12   21
CONECT    7    8   22
CONECT    8    9   23   24
CONECT    9   10   25   26
CONECT   10   11   12   17
CONECT   11   27   28   29
CONECT   12   13   30
CONECT   13   14   15   15
CONECT   14   31   32   33
CONECT   15   16   34
CONECT   16   17   35   36
CONECT   17   18   37
CONECT   18   38
END

HMDB0302709
     RDKit          3D
Santamarin
 38 40  0  0  0  0  0  0  0  0999 V2000
    4.2070    1.1010   -0.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1974    0.2828   -0.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2251   -1.1612   -0.0660 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2388   -1.8661    0.2057 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9123   -1.6253   -0.0970 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1030   -0.5114    0.0860 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8029    0.4986   -0.8414 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2407    1.8307   -0.5546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2430    1.8056   -0.8451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9591    0.7186   -0.0953 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9125    1.0310    1.3828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2907   -0.6101   -0.4043 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0566   -1.7628    0.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4004   -3.0900    0.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3359   -1.6698    0.3891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0930   -0.3894    0.3371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3840    0.6346   -0.5279 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0626    1.8313   -0.4697 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1631    0.7573    0.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0672    2.1368   -0.5903 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1944   -0.1830    1.1416 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6801    0.1418   -1.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4948    2.1543    0.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6805    2.5605   -1.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3403    1.5663   -1.9346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7048    2.7940   -0.6947 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0201    1.5098    1.7033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1513    0.1198    1.9845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7398    1.7507    1.5917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2481   -0.6586   -1.5320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3414   -3.2555   -0.6787 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1481   -3.2426    1.0892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1429   -3.9270    0.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8910   -2.5457    0.7260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0747   -0.5855   -0.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2396   -0.0272    1.3698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4331    0.2577   -1.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0136    1.6281   -0.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  1
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  7  2  1  0
 17 10  1  0
 12  6  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  1
  7 22  1  6
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  6
 14 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  6
 18 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Santamarine	ChEBI
(3AS)-2,3,3abeta,4,5,5a,6,7,9abeta,9balpha-decahydro-6alpha-hydroxy-5aalpha,9-dimethyl-3-methylenenaphtho[1,2-b]furan-2-one	ChEBI
(3AS,5ar,6R,9as,9BS)-6-hydroxy-5a,9-dimethyl-3-methylene-3a,4,5,5a,6,7,9a,9b-octahydro-3H-naphtho[1,2-b]furan-2-one	ChEBI
(3AS,5ar,6R,9as,9BS)-6-hydroxy-5a,9-dimethyl-3-methylidene-4,5,6,7,9a,9b-hexahydro-3ah-benzo[g][1]benzofuran-2-one	ChEBI
Balchanin	ChEBI
Santamarine	ChEBI
(3AS)-2,3,3abeta,4,5,5a,6,7,9abeta,9balpha-decahydro-6a-hydroxy-5aalpha,9-dimethyl-3-methylenenaphtho[1,2-b]furan-2-one	Generator
(3AS)-2,3,3abeta,4,5,5a,6,7,9abeta,9balpha-decahydro-6α-hydroxy-5aalpha,9-dimethyl-3-methylenenaphtho[1,2-b]furan-2-one	Generator

Chemical Formula

C₁₅H₂₀O₃

Average Molecular Weight

248.3175

Monoisotopic Molecular Weight

248.141244506

IUPAC Name

(3aS,5aR,6R,9aS,9bS)-6-hydroxy-5a,9-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,5aH,6H,7H,9aH,9bH-naphtho[1,2-b]furan-2-one

Traditional Name

(+)-santamarine

CAS Registry Number

Not Available

SMILES

CC1=CC[C@@H](O)[C@]2(C)CC[C@@H]3[C@H](OC(=O)C3=C)[C@@H]12

InChI Identifier

InChI=1S/C15H20O3/c1-8-4-5-11(16)15(3)7-6-10-9(2)14(17)18-13(10)12(8)15/h4,10-13,16H,2,5-7H2,1,3H3/t10-,11+,12+,13-,15-/m0/s1

InChI Key

PLSSEPIRACGCBO-PFFFPCNUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Eudesmanolides, secoeudesmanolides, and derivatives

Alternative Parents

Substituents

Eudesmanolide
Sesquiterpenoid
Naphthofuran
Gamma butyrolactone
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

sesquiterpene lactone (CHEBI:9023 )
Eudesmanes (C09544 )

Ontology

Not Available

Sweet bay (FooDB: FOOD00097)

Process

Not Available

Role

Biological role

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	2.44	ALOGPS
logP	2.15	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	14.63	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.71 m³·mol⁻¹	ChemAxon
Polarizability	27.41 Å³	ChemAxon
Number of Rings	3	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]+	158.93	32859911
AllCCS	[M+H-H2O]+	155.206	32859911
AllCCS	[M+Na]+	163.386	32859911
AllCCS	[M+NH4]+	162.391	32859911
AllCCS	[M-H]-	163.996	32859911
AllCCS	[M+Na-2H]-	163.943	32859911
AllCCS	[M+HCOO]-	164.001	32859911
DeepCCS	[M-2H]-	199.043	30932474
DeepCCS	[M+Na]+	173.73	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Santamarin 10V, Positive-QTOF	splash10-001j-0290000000-789eefe074e1b12c084d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Santamarin 20V, Positive-QTOF	splash10-0f8a-1940000000-dc7583a16431bb675821	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Santamarin 40V, Positive-QTOF	splash10-1003-9310000000-6677ba80414870d17185	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Santamarin 10V, Negative-QTOF	splash10-0002-0090000000-d29ad4e4535fa5263291	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Santamarin 20V, Negative-QTOF	splash10-0f6t-0190000000-997de3e007cc13186660	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Santamarin 40V, Negative-QTOF	splash10-0udi-3920000000-2246bdfb040620ee52eb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Santamarin 10V, Positive-QTOF	splash10-0002-0090000000-b55c1d7eb34f2d130aca	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Santamarin 20V, Positive-QTOF	splash10-0002-0390000000-aa9891c63c3267405779	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Santamarin 40V, Positive-QTOF	splash10-0a6r-1910000000-296693f45a2dbc58341a	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Santamarin 10V, Negative-QTOF	splash10-0002-0090000000-7b3a58b796a0e4263959	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Santamarin 20V, Negative-QTOF	splash10-0002-0090000000-7e0e38a32353911a24e1	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Santamarin 40V, Negative-QTOF	splash10-016u-3390000000-b3cad309313dc9047892	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

188297

PDB ID

Not Available

ChEBI ID

9023

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 Santamarin (HMDB0302709)

MOL for HMDB0302709 (Santamarin)

3D MOL for HMDB0302709 (Santamarin)

3D SDF for HMDB0302709 (Santamarin)

3D-SDF for HMDB0302709 (Santamarin)

PDB for HMDB0302709 (Santamarin)

3D PDB for HMDB0302709 (Santamarin)

SMILES for HMDB0302709 (Santamarin)

INCHI for HMDB0302709 (Santamarin)

Structure for HMDB0302709 (Santamarin)

3D Structure for HMDB0302709 (Santamarin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra