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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:57:53 UTC

Update Date

2022-03-07 02:56:35 UTC

HMDB ID

HMDB0040421

Secondary Accession Numbers

HMDB40421

Metabolite Identification

Common Name

Safficinolide

Description

Safficinolide belongs to the class of organic compounds known as 3,4-dihydrocoumarins. These are 3,4-dihydrogenated coumarins. Coumarin is a bicyclic compound that are 1-benzopyran carrying an oxo group at the 2-position. Safficinolide has been detected, but not quantified in, several different foods, such as green tea, black tea, common sages (Salvia officinalis), herbs and spices, and red tea. This could make safficinolide a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Safficinolide.

Structure

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

HMDB0040421
     RDKit          3D
Safficinolide
 49 51  0  0  0  0  0  0  0  0999 V2000
    5.4448    0.9894   -0.7539 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5208    0.2214    0.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8775    0.0869    1.5798 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0981    0.2468   -0.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6123   -0.6043   -1.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2251   -0.7601   -1.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8428   -1.6404   -2.4621 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7343   -2.4136   -2.9627 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3646    0.0116   -0.6006 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8508    0.8669    0.3437 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1891    0.9856    0.5612 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6440    1.8379    1.5252 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0001    1.6926    1.1171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3321    1.6205    0.8725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0946    2.5847    1.0355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8536    0.3407    0.4035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3469    0.2993    0.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8898    0.6189    1.7140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9494    1.2664   -0.6675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7416   -1.1053   -0.0140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6027   -2.0241    0.2713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3499   -1.7822   -0.5581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1296   -0.2917   -0.7621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5601    0.1790   -2.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7993    0.7332   -2.8177 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3559    0.4055   -0.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8254    1.9204   -0.2423 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9625    1.2280   -1.7128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8084   -0.9025   -0.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3845    0.7379    2.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0028    0.0649    1.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5628   -0.9649    1.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2732   -1.1879   -1.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1083   -1.7133   -2.8842 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0587    2.4061    2.1297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6116   -0.3760    1.2817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2053    0.3004    2.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9061    0.1275    1.7915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1005    1.7162    1.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7243    1.8625   -0.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5746    0.7218   -1.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2602    2.0064   -1.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1410   -1.2181   -1.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5863   -1.4154    0.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3930   -2.0385    1.3425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9044   -3.1101    0.0562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5115   -2.1559    0.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3853   -2.4200   -1.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5764    0.0447   -2.4413 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  1  0
  7  8  2  0
  6  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 11  4  1  0
 23 16  1  0
 23  9  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  5 33  1  0
  7 34  1  0
 12 35  1  0
 16 36  1  0
 18 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
 21 45  1  0
 21 46  1  0
 22 47  1  0
 22 48  1  0
 24 49  1  0
M  END

  Mrv0541 05061311502D          

 25 27  0  0  0  0            999 V2000
    4.5375    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1877    2.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2692    3.1769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.4934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.2211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    3.0789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    3.7934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    3.0789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 12  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13  8  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  2  0  0  0  0
 16 14  2  0  0  0  0
 16 15  1  0  0  0  0
 18 17  1  0  0  0  0
 19  3  1  0  0  0  0
 19  4  1  0  0  0  0
 19  6  1  0  0  0  0
 19 17  1  0  0  0  0
 20  7  1  0  0  0  0
 20 10  1  0  0  0  0
 20 14  1  0  0  0  0
 20 17  1  0  0  0  0
 21  9  2  0  0  0  0
 22 10  2  0  0  0  0
 23 15  1  0  0  0  0
 24 18  2  0  0  0  0
 25 16  1  0  0  0  0
 25 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040421

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C1=C(O)C2=C(C(C=O)=C1)C1(CCCC(C)(C)C1C(=O)O2)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O5/c1-11(2)13-8-12(9-21)14-16(15(13)23)25-18(24)17-19(3,4)6-5-7-20(14,17)10-22/h8-11,17,23H,5-7H2,1-4H3

> <INCHI_KEY>
VBEKTSBYXBBXEO-UHFFFAOYSA-N

> <FORMULA>
C20H24O5

> <MOLECULAR_WEIGHT>
344.4016

> <EXACT_MASS>
344.162373878

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
36.73926389958122

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-7,7-dimethyl-6-oxo-3-(propan-2-yl)-6H,6aH,7H,8H,9H,10H,10aH-benzo[c]isochromene-1,10a-dicarbaldehyde

> <ALOGPS_LOGP>
3.75

> <JCHEM_LOGP>
4.365722117666666

> <ALOGPS_LOGS>
-4.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.511672391726224

> <JCHEM_PKA_STRONGEST_BASIC>
-5.570783740759709

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
94.02449999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.67e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-3-isopropyl-7,7-dimethyl-6-oxo-6aH,8H,9H,10H-benzo[c]isochromene-1,10a-dicarbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040421
     RDKit          3D
Safficinolide
 49 51  0  0  0  0  0  0  0  0999 V2000
    5.4448    0.9894   -0.7539 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5208    0.2214    0.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8775    0.0869    1.5798 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0981    0.2468   -0.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6123   -0.6043   -1.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2251   -0.7601   -1.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8428   -1.6404   -2.4621 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7343   -2.4136   -2.9627 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3646    0.0116   -0.6006 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8508    0.8669    0.3437 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1891    0.9856    0.5612 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6440    1.8379    1.5252 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0001    1.6926    1.1171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3321    1.6205    0.8725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0946    2.5847    1.0355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8536    0.3407    0.4035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3469    0.2993    0.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8898    0.6189    1.7140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9494    1.2664   -0.6675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7416   -1.1053   -0.0140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6027   -2.0241    0.2713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3499   -1.7822   -0.5581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1296   -0.2917   -0.7621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5601    0.1790   -2.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7993    0.7332   -2.8177 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3559    0.4055   -0.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8254    1.9204   -0.2423 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9625    1.2280   -1.7128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8084   -0.9025   -0.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3845    0.7379    2.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0028    0.0649    1.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5628   -0.9649    1.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2732   -1.1879   -1.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1083   -1.7133   -2.8842 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0587    2.4061    2.1297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6116   -0.3760    1.2817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2053    0.3004    2.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9061    0.1275    1.7915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1005    1.7162    1.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7243    1.8625   -0.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5746    0.7218   -1.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2602    2.0064   -1.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1410   -1.2181   -1.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5863   -1.4154    0.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3930   -2.0385    1.3425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9044   -3.1101    0.0562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5115   -2.1559    0.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3853   -2.4200   -1.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5764    0.0447   -2.4413 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  1  0
  7  8  2  0
  6  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 11  4  1  0
 23 16  1  0
 23  9  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  5 33  1  0
  7 34  1  0
 12 35  1  0
 16 36  1  0
 18 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
 21 45  1  0
 21 46  1  0
 22 47  1  0
 22 48  1  0
 24 49  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       8.470   4.414   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.470   1.746   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.217   4.940   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.503   5.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.770   1.746   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.540   3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.770   1.746   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.390   1.746   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.080   0.413   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.310   1.746   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.700   3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.850   1.746   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.160   3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080   3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.390   4.414   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.850   4.414   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.770   4.414   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.540   5.747   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.770   4.414   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.540   3.080   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.850  -0.921   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.540   0.413   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       6.160   5.747   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.770   7.081   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       3.080   5.747   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   19                                                            
CONECT    4   19                                                            
CONECT    5    6    7                                                       
CONECT    6    5   19                                                       
CONECT    7    5   20                                                       
CONECT    8   12   13                                                       
CONECT    9   12   21                                                       
CONECT   10   20   22                                                       
CONECT   11    1    2   13                                                  
CONECT   12    8    9   14                                                  
CONECT   13    8   11   15                                                  
CONECT   14   12   16   20                                                  
CONECT   15   13   16   23                                                  
CONECT   16   14   15   25                                                  
CONECT   17   18   19   20                                                  
CONECT   18   17   24   25                                                  
CONECT   19    3    4    6   17                                             
CONECT   20    7   10   14   17                                             
CONECT   21    9                                                            
CONECT   22   10                                                            
CONECT   23   15                                                            
CONECT   24   18                                                            
CONECT   25   16   18                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0040421
HETATM    1  C1  UNL     1       5.445   0.989  -0.754  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.521   0.221   0.156  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.878   0.087   1.580  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.098   0.247  -0.188  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.612  -0.604  -1.152  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.225  -0.760  -1.395  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.843  -1.640  -2.462  1.00  0.00           C  
HETATM    8  O1  UNL     1       1.734  -2.414  -2.963  1.00  0.00           O  
HETATM    9  C8  UNL     1       0.365   0.012  -0.601  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.851   0.867   0.344  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.189   0.986   0.561  1.00  0.00           C  
HETATM   12  O2  UNL     1       2.644   1.838   1.525  1.00  0.00           O  
HETATM   13  O3  UNL     1       0.000   1.693   1.117  1.00  0.00           O  
HETATM   14  C11 UNL     1      -1.332   1.620   0.872  1.00  0.00           C  
HETATM   15  O4  UNL     1      -2.095   2.585   1.035  1.00  0.00           O  
HETATM   16  C12 UNL     1      -1.854   0.341   0.403  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.347   0.299   0.308  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.890   0.619   1.714  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.949   1.266  -0.667  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.742  -1.105  -0.014  1.00  0.00           C  
HETATM   21  C17 UNL     1      -2.603  -2.024   0.271  1.00  0.00           C  
HETATM   22  C18 UNL     1      -1.350  -1.782  -0.558  1.00  0.00           C  
HETATM   23  C19 UNL     1      -1.130  -0.292  -0.762  1.00  0.00           C  
HETATM   24  C20 UNL     1      -1.560   0.179  -2.082  1.00  0.00           C  
HETATM   25  O5  UNL     1      -0.799   0.733  -2.818  1.00  0.00           O  
HETATM   26  H1  UNL     1       6.356   0.405  -0.963  1.00  0.00           H  
HETATM   27  H2  UNL     1       5.825   1.920  -0.242  1.00  0.00           H  
HETATM   28  H3  UNL     1       4.963   1.228  -1.713  1.00  0.00           H  
HETATM   29  H4  UNL     1       4.808  -0.902  -0.254  1.00  0.00           H  
HETATM   30  H5  UNL     1       4.385   0.738   2.317  1.00  0.00           H  
HETATM   31  H6  UNL     1       6.003   0.065   1.684  1.00  0.00           H  
HETATM   32  H7  UNL     1       4.563  -0.965   1.911  1.00  0.00           H  
HETATM   33  H8  UNL     1       3.273  -1.188  -1.762  1.00  0.00           H  
HETATM   34  H9  UNL     1      -0.108  -1.713  -2.884  1.00  0.00           H  
HETATM   35  H10 UNL     1       2.059   2.406   2.130  1.00  0.00           H  
HETATM   36  H11 UNL     1      -1.612  -0.376   1.282  1.00  0.00           H  
HETATM   37  H12 UNL     1      -3.205   0.300   2.495  1.00  0.00           H  
HETATM   38  H13 UNL     1      -4.906   0.127   1.791  1.00  0.00           H  
HETATM   39  H14 UNL     1      -4.100   1.716   1.779  1.00  0.00           H  
HETATM   40  H15 UNL     1      -4.724   1.862  -0.092  1.00  0.00           H  
HETATM   41  H16 UNL     1      -4.575   0.722  -1.433  1.00  0.00           H  
HETATM   42  H17 UNL     1      -3.260   2.006  -1.100  1.00  0.00           H  
HETATM   43  H18 UNL     1      -4.141  -1.218  -1.044  1.00  0.00           H  
HETATM   44  H19 UNL     1      -4.586  -1.415   0.663  1.00  0.00           H  
HETATM   45  H20 UNL     1      -2.393  -2.038   1.342  1.00  0.00           H  
HETATM   46  H21 UNL     1      -2.904  -3.110   0.056  1.00  0.00           H  
HETATM   47  H22 UNL     1      -0.512  -2.156   0.119  1.00  0.00           H  
HETATM   48  H23 UNL     1      -1.385  -2.420  -1.430  1.00  0.00           H  
HETATM   49  H24 UNL     1      -2.576   0.045  -2.441  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3    4   29
CONECT    3   30   31   32
CONECT    4    5    5   11
CONECT    5    6   33
CONECT    6    7    9    9
CONECT    7    8    8   34
CONECT    9   10   23
CONECT   10   11   11   13
CONECT   11   12
CONECT   12   35
CONECT   13   14
CONECT   14   15   15   16
CONECT   16   17   23   36
CONECT   17   18   19   20
CONECT   18   37   38   39
CONECT   19   40   41   42
CONECT   20   21   43   44
CONECT   21   22   45   46
CONECT   22   23   47   48
CONECT   23   24
CONECT   24   25   25   49
END

HMDB0040421
     RDKit          3D
Safficinolide
 49 51  0  0  0  0  0  0  0  0999 V2000
    5.4448    0.9894   -0.7539 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5208    0.2214    0.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8775    0.0869    1.5798 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0981    0.2468   -0.1880 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6123   -0.6043   -1.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2251   -0.7601   -1.3946 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8428   -1.6404   -2.4621 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7343   -2.4136   -2.9627 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3646    0.0116   -0.6006 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8508    0.8669    0.3437 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1891    0.9856    0.5612 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6440    1.8379    1.5252 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0001    1.6926    1.1171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3321    1.6205    0.8725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0946    2.5847    1.0355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8536    0.3407    0.4035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3469    0.2993    0.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8898    0.6189    1.7140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9494    1.2664   -0.6675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7416   -1.1053   -0.0140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6027   -2.0241    0.2713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3499   -1.7822   -0.5581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1296   -0.2917   -0.7621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5601    0.1790   -2.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7993    0.7332   -2.8177 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3559    0.4055   -0.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8254    1.9204   -0.2423 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9625    1.2280   -1.7128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8084   -0.9025   -0.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3845    0.7379    2.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0028    0.0649    1.6839 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5628   -0.9649    1.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2732   -1.1879   -1.7622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1083   -1.7133   -2.8842 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0587    2.4061    2.1297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6116   -0.3760    1.2817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2053    0.3004    2.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9061    0.1275    1.7915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1005    1.7162    1.7785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7243    1.8625   -0.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5746    0.7218   -1.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2602    2.0064   -1.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1410   -1.2181   -1.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5863   -1.4154    0.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3930   -2.0385    1.3425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9044   -3.1101    0.0562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5115   -2.1559    0.1194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3853   -2.4200   -1.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5764    0.0447   -2.4413 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  1  0
  7  8  2  0
  6  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 11  4  1  0
 23 16  1  0
 23  9  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  3 32  1  0
  5 33  1  0
  7 34  1  0
 12 35  1  0
 16 36  1  0
 18 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
 21 45  1  0
 21 46  1  0
 22 47  1  0
 22 48  1  0
 24 49  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄O₅

Average Molecular Weight

344.4016

Monoisotopic Molecular Weight

344.162373878

IUPAC Name

4-hydroxy-7,7-dimethyl-6-oxo-3-(propan-2-yl)-6H,6aH,7H,8H,9H,10H,10aH-benzo[c]isochromene-1,10a-dicarbaldehyde

Traditional Name

4-hydroxy-3-isopropyl-7,7-dimethyl-6-oxo-6aH,8H,9H,10H-benzo[c]isochromene-1,10a-dicarbaldehyde

CAS Registry Number

153660-18-5

SMILES

CC(C)C1=C(O)C2=C(C(C=O)=C1)C1(CCCC(C)(C)C1C(=O)O2)C=O

InChI Identifier

InChI=1S/C20H24O5/c1-11(2)13-8-12(9-21)14-16(15(13)23)25-18(24)17-19(3,4)6-5-7-20(14,17)10-22/h8-11,17,23H,5-7H2,1-4H3

InChI Key

VBEKTSBYXBBXEO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3,4-dihydrocoumarins. These are 3,4-dihydrogenated coumarins. Coumarin is a bicyclic compound that are 1-benzopyran carrying an oxo group at the 2-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

3,4-dihydrocoumarins

Sub Class

Not Available

Direct Parent

3,4-dihydrocoumarins

Alternative Parents

Substituents

3,4-dihydrocoumarin
Chromane
Benzopyran
1-benzopyran
Aryl-aldehyde
Benzenoid
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aldehyde
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040421)

Source

Endogenous

Endogenous (HMDB: HMDB0040421)

Plant

Plant (HMDB: HMDB0040421)

Exogenous

Food

Food (HMDB: HMDB0040421)

Tea

Herb and spice

Herb

Common sage (FooDB: FOOD00165)

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0040421)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0040421)

Role

Biological role

Energy source (HMDB: HMDB0040421)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0040421)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	223 - 224 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	92.26 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.017 g/L	ALOGPS
logP	3.75	ALOGPS
logP	4.37	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	8.51	ChemAxon
pKa (Strongest Basic)	-5.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	94.02 m³·mol⁻¹	ChemAxon
Polarizability	36.74 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
DarkChem	[M+H]+	177.793	31661259
DarkChem	[M-H]-	174.941	31661259
DeepCCS	[M+H]+	188.405	30932474
DeepCCS	[M-H]-	186.047	30932474
DeepCCS	[M-2H]-	220.219	30932474
DeepCCS	[M+Na]+	195.447	30932474
AllCCS	[M+H]+	180.1	32859911
AllCCS	[M+H-H2O]+	177.1	32859911
AllCCS	[M+NH4]+	182.8	32859911
AllCCS	[M+Na]+	183.6	32859911
AllCCS	[M-H]-	188.5	32859911
AllCCS	[M+Na-2H]-	188.6	32859911
AllCCS	[M+HCOO]-	189.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Safficinolide	CC(C)C1=C(O)C2=C(C(C=O)=C1)C1(CCCC(C)(C)C1C(=O)O2)C=O	3528.9	Standard polar	33892256
Safficinolide	CC(C)C1=C(O)C2=C(C(C=O)=C1)C1(CCCC(C)(C)C1C(=O)O2)C=O	2426.0	Standard non polar	33892256
Safficinolide	CC(C)C1=C(O)C2=C(C(C=O)=C1)C1(CCCC(C)(C)C1C(=O)O2)C=O	2628.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Safficinolide,1TMS,isomer #1	CC(C)C1=CC(C=O)=C2C(=C1O[Si](C)(C)C)OC(=O)C1C(C)(C)CCCC21C=O	2668.8	Semi standard non polar	33892256
Safficinolide,1TBDMS,isomer #1	CC(C)C1=CC(C=O)=C2C(=C1O[Si](C)(C)C(C)(C)C)OC(=O)C1C(C)(C)CCCC21C=O	2912.7	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 - Safficinolide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0i29-0109000000-5f918d326227e91979bf	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Safficinolide GC-MS (1 TMS) - 70eV, Positive	splash10-0udr-2319400000-0a394bc1c22dce5ce54c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Safficinolide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Safficinolide 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 - Safficinolide 10V, Positive-QTOF	splash10-0002-0009000000-3be2be958f42a15e2e67	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Safficinolide 20V, Positive-QTOF	splash10-0gdj-1229000000-a6ae87096da9d6a002c1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Safficinolide 40V, Positive-QTOF	splash10-0aor-7914000000-bee307344ff2c123b232	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Safficinolide 10V, Negative-QTOF	splash10-0006-0029000000-b0dc6fa102bbb2edb6e5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Safficinolide 20V, Negative-QTOF	splash10-00kg-0249000000-54f7c264a9c1d9d22ec4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Safficinolide 40V, Negative-QTOF	splash10-045i-0921000000-0aa554a4dd86592ce5a8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Safficinolide 10V, Negative-QTOF	splash10-0006-0009000000-17d008ed064cb6dd1d3e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Safficinolide 20V, Negative-QTOF	splash10-000i-0092000000-a6ef07519828ff749960	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Safficinolide 40V, Negative-QTOF	splash10-000i-0971000000-4f7c981b65102eb55dc5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Safficinolide 10V, Positive-QTOF	splash10-0002-0009000000-e4d2bba94b960fbf21ce	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Safficinolide 20V, Positive-QTOF	splash10-014i-0029000000-740d9722751498e7626e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Safficinolide 40V, Positive-QTOF	splash10-0553-5961000000-bf8019c6536d52d072e6	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

FDB020154

KNApSAcK ID

C00057108

Chemspider ID

35014944

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85152699

PDB ID

Not Available

ChEBI ID

174648

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1883321

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Safficinolide (HMDB0040421)

MOL for HMDB0040421 (Safficinolide)

3D MOL for HMDB0040421 (Safficinolide)

3D SDF for HMDB0040421 (Safficinolide)

3D-SDF for HMDB0040421 (Safficinolide)

PDB for HMDB0040421 (Safficinolide)

3D PDB for HMDB0040421 (Safficinolide)

SMILES for HMDB0040421 (Safficinolide)

INCHI for HMDB0040421 (Safficinolide)

Structure for HMDB0040421 (Safficinolide)

3D Structure for HMDB0040421 (Safficinolide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra