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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:30:35 UTC

Update Date

2022-03-07 02:52:10 UTC

HMDB ID

HMDB0029468

Secondary Accession Numbers

HMDB29468

Metabolite Identification

Common Name

Dolichin B

Description

Dolichin B belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. Dolichin B has been detected, but not quantified in, cowpeas (Vigna unguiculata) and fruits. This could make dolichin b a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Dolichin B.

Structure

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

HMDB0029468
     RDKit          3D
Dolichin B
 45 48  0  0  0  0  0  0  0  0999 V2000
    3.9330    3.0115    0.3743 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1272    1.7230    0.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3309    1.3327   -0.6558 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1867    0.6904    0.6797 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8148   -0.1497    1.5879 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5680   -0.1182   -0.4178 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6320   -1.1537    0.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1114   -2.3369    0.5451 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4701   -2.5519    0.6415 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2404   -3.3089    0.9664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1304   -3.0953    0.8692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5908   -1.9113    0.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2580   -0.9100   -0.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5086    0.1714   -0.5543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6786    0.1106    0.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8598    0.7671   -0.3087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9001    1.7692   -1.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0897    2.3163   -1.6748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2782    1.8084   -1.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4752    2.3610   -1.5868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2741    0.7969   -0.2062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0615    0.2874    0.1993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9984   -0.7523    1.1567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9813   -1.7566    1.1103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9559   -1.3955    0.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0708    3.3413    0.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6227    3.7417   -0.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5274    0.2429   -0.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2194    1.8642   -0.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2404    1.6334   -1.7185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3671    1.2239    1.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5347    0.0537    2.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4279   -0.6049   -0.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0835    0.5149   -1.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7994   -3.4243    1.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5883   -4.2560    1.3816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8207   -3.8380    1.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4451    0.3479    1.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9378    2.1341   -1.6215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1112    3.1172   -2.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3642    2.0311   -1.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2184    0.4156    0.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6376   -1.9409    2.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5194   -2.6897    0.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3172   -1.6139   -0.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 13  7  1  0
 25 15  1  0
 25 12  1  0
 22 16  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 15 38  1  0
 17 39  1  0
 18 40  1  0
 20 41  1  0
 21 42  1  0
 24 43  1  0
 24 44  1  0
 25 45  1  0
M  END

  Mrv0541 05061304472D          

 25 28  0  0  0  0            999 V2000
   -0.3626   -5.2015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0647   -5.2694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3033   -2.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4796   -2.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2608   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5275   -1.5272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -1.2363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1431   -3.6213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1217   -0.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3707   -4.8234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6743   -1.9260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9548   -1.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0270   -2.0203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1823   -2.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7507   -1.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4883   -2.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4099   -3.9994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3980   -1.2834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9156   -2.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2033   -2.0674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4979   -1.8789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2450   -2.7293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2842   -3.5534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9453   -0.5937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6872   -2.7111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  5  2  0  0  0  0
 10  1  2  0  0  0  0
 10  2  1  0  0  0  0
 11  3  1  0  0  0  0
 11  7  2  0  0  0  0
 12  5  1  0  0  0  0
 13  4  1  0  0  0  0
 14  8  1  0  0  0  0
 15  9  1  0  0  0  0
 15 12  1  0  0  0  0
 16  6  1  0  0  0  0
 16 14  2  0  0  0  0
 17  8  1  0  0  0  0
 17 10  1  0  0  0  0
 18  7  1  0  0  0  0
 18 13  2  0  0  0  0
 19 12  2  0  0  0  0
 19 14  1  0  0  0  0
 20 13  1  0  0  0  0
 20 15  1  0  0  0  0
 21 11  1  0  0  0  0
 22 16  1  0  0  0  0
 23 17  1  0  0  0  0
 24  9  1  0  0  0  0
 24 18  1  0  0  0  0
 25 19  1  0  0  0  0
 25 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029468

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=C)C(O)CC1=C(O)C=CC2=C1OC1C2COC2=C1C=CC(O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O5/c1-10(2)17(23)8-14-16(22)6-5-12-15-9-24-18-7-11(21)3-4-13(18)20(15)25-19(12)14/h3-7,15,17,20-23H,1,8-9H2,2H3

> <INCHI_KEY>
LRCYZCCKRIVTHN-UHFFFAOYSA-N

> <FORMULA>
C20H20O5

> <MOLECULAR_WEIGHT>
340.3698

> <EXACT_MASS>
340.13107375

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
35.757688078939466

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
15-(2-hydroxy-3-methylbut-3-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-5,14-diol

> <ALOGPS_LOGP>
2.35

> <JCHEM_LOGP>
2.9190189429999998

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.919685233776612

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.255171791666609

> <JCHEM_PKA_STRONGEST_BASIC>
-3.052774667162698

> <JCHEM_POLAR_SURFACE_AREA>
79.15

> <JCHEM_REFRACTIVITY>
93.26459999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.66e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-(2-hydroxy-3-methylbut-3-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-5,14-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029468
     RDKit          3D
Dolichin B
 45 48  0  0  0  0  0  0  0  0999 V2000
    3.9330    3.0115    0.3743 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1272    1.7230    0.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3309    1.3327   -0.6558 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1867    0.6904    0.6797 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8148   -0.1497    1.5879 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5680   -0.1182   -0.4178 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6320   -1.1537    0.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1114   -2.3369    0.5451 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4701   -2.5519    0.6415 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2404   -3.3089    0.9664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1304   -3.0953    0.8692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5908   -1.9113    0.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2580   -0.9100   -0.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5086    0.1714   -0.5543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6786    0.1106    0.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8598    0.7671   -0.3087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9001    1.7692   -1.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0897    2.3163   -1.6748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2782    1.8084   -1.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4752    2.3610   -1.5868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2741    0.7969   -0.2062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0615    0.2874    0.1993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9984   -0.7523    1.1567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9813   -1.7566    1.1103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9559   -1.3955    0.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0708    3.3413    0.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6227    3.7417   -0.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5274    0.2429   -0.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2194    1.8642   -0.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2404    1.6334   -1.7185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3671    1.2239    1.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5347    0.0537    2.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4279   -0.6049   -0.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0835    0.5149   -1.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7994   -3.4243    1.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5883   -4.2560    1.3816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8207   -3.8380    1.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4451    0.3479    1.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9378    2.1341   -1.6215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1112    3.1172   -2.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3642    2.0311   -1.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2184    0.4156    0.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6376   -1.9409    2.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5194   -2.6897    0.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3172   -1.6139   -0.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 13  7  1  0
 25 15  1  0
 25 12  1  0
 22 16  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 15 38  1  0
 17 39  1  0
 18 40  1  0
 20 41  1  0
 21 42  1  0
 24 43  1  0
 24 44  1  0
 25 45  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      -0.677  -9.709   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.987  -9.836   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.899  -4.971   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.362  -5.059   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.353  -2.145   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.985  -2.851   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.747  -2.308   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.134  -6.760   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.827  -1.196   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.692  -9.004   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.592  -3.595   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.649  -2.978   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.517  -3.771   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.207  -5.221   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.135  -2.572   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.911  -4.389   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.765  -7.466   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.210  -2.396   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.576  -4.516   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.979  -3.859   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.129  -3.507   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -0.457  -5.095   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -0.531  -6.633   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       7.365  -1.108   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       5.016  -5.061   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3    4   11                                                       
CONECT    4    3   13                                                       
CONECT    5    6   12                                                       
CONECT    6    5   16                                                       
CONECT    7   11   18                                                       
CONECT    8   14   17                                                       
CONECT    9   15   24                                                       
CONECT   10    1    2   17                                                  
CONECT   11    3    7   21                                                  
CONECT   12    5   15   19                                                  
CONECT   13    4   18   20                                                  
CONECT   14    8   16   19                                                  
CONECT   15    9   12   20                                                  
CONECT   16    6   14   22                                                  
CONECT   17    8   10   23                                                  
CONECT   18    7   13   24                                                  
CONECT   19   12   14   25                                                  
CONECT   20   13   15   25                                                  
CONECT   21   11                                                            
CONECT   22   16                                                            
CONECT   23   17                                                            
CONECT   24    9   18                                                       
CONECT   25   19   20                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0029468
HETATM    1  C1  UNL     1       3.933   3.011   0.374  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.127   1.723   0.151  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.331   1.333  -0.656  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.187   0.690   0.680  1.00  0.00           C  
HETATM    5  O1  UNL     1       3.815  -0.150   1.588  1.00  0.00           O  
HETATM    6  C5  UNL     1       2.568  -0.118  -0.418  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.632  -1.154   0.028  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.111  -2.337   0.545  1.00  0.00           C  
HETATM    9  O2  UNL     1       3.470  -2.552   0.642  1.00  0.00           O  
HETATM   10  C8  UNL     1       1.240  -3.309   0.966  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.130  -3.095   0.869  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.591  -1.911   0.352  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.258  -0.910  -0.082  1.00  0.00           C  
HETATM   14  O3  UNL     1      -0.509   0.171  -0.554  1.00  0.00           O  
HETATM   15  C12 UNL     1      -1.679   0.111   0.235  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.860   0.767  -0.309  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.900   1.769  -1.233  1.00  0.00           C  
HETATM   18  C15 UNL     1      -4.090   2.316  -1.675  1.00  0.00           C  
HETATM   19  C16 UNL     1      -5.278   1.808  -1.141  1.00  0.00           C  
HETATM   20  O4  UNL     1      -6.475   2.361  -1.587  1.00  0.00           O  
HETATM   21  C17 UNL     1      -5.274   0.797  -0.206  1.00  0.00           C  
HETATM   22  C18 UNL     1      -4.062   0.287   0.199  1.00  0.00           C  
HETATM   23  O5  UNL     1      -3.998  -0.752   1.157  1.00  0.00           O  
HETATM   24  C19 UNL     1      -2.981  -1.757   1.110  1.00  0.00           C  
HETATM   25  C20 UNL     1      -1.956  -1.395   0.116  1.00  0.00           C  
HETATM   26  H1  UNL     1       3.071   3.341   0.955  1.00  0.00           H  
HETATM   27  H2  UNL     1       4.623   3.742  -0.014  1.00  0.00           H  
HETATM   28  H3  UNL     1       5.527   0.243  -0.580  1.00  0.00           H  
HETATM   29  H4  UNL     1       6.219   1.864  -0.258  1.00  0.00           H  
HETATM   30  H5  UNL     1       5.240   1.633  -1.719  1.00  0.00           H  
HETATM   31  H6  UNL     1       2.367   1.224   1.204  1.00  0.00           H  
HETATM   32  H7  UNL     1       3.535   0.054   2.505  1.00  0.00           H  
HETATM   33  H8  UNL     1       3.428  -0.605  -0.969  1.00  0.00           H  
HETATM   34  H9  UNL     1       2.084   0.515  -1.198  1.00  0.00           H  
HETATM   35  H10 UNL     1       3.799  -3.424   1.023  1.00  0.00           H  
HETATM   36  H11 UNL     1       1.588  -4.256   1.382  1.00  0.00           H  
HETATM   37  H12 UNL     1      -0.821  -3.838   1.191  1.00  0.00           H  
HETATM   38  H13 UNL     1      -1.445   0.348   1.285  1.00  0.00           H  
HETATM   39  H14 UNL     1      -1.938   2.134  -1.621  1.00  0.00           H  
HETATM   40  H15 UNL     1      -4.111   3.117  -2.414  1.00  0.00           H  
HETATM   41  H16 UNL     1      -7.364   2.031  -1.234  1.00  0.00           H  
HETATM   42  H17 UNL     1      -6.218   0.416   0.198  1.00  0.00           H  
HETATM   43  H18 UNL     1      -2.638  -1.941   2.135  1.00  0.00           H  
HETATM   44  H19 UNL     1      -3.519  -2.690   0.766  1.00  0.00           H  
HETATM   45  H20 UNL     1      -2.317  -1.614  -0.909  1.00  0.00           H  
CONECT    1    2    2   26   27
CONECT    2    3    4
CONECT    3   28   29   30
CONECT    4    5    6   31
CONECT    5   32
CONECT    6    7   33   34
CONECT    7    8    8   13
CONECT    8    9   10
CONECT    9   35
CONECT   10   11   11   36
CONECT   11   12   37
CONECT   12   13   13   25
CONECT   13   14
CONECT   14   15
CONECT   15   16   25   38
CONECT   16   17   17   22
CONECT   17   18   39
CONECT   18   19   19   40
CONECT   19   20   21
CONECT   20   41
CONECT   21   22   22   42
CONECT   22   23
CONECT   23   24
CONECT   24   25   43   44
CONECT   25   45
END

HMDB0029468
     RDKit          3D
Dolichin B
 45 48  0  0  0  0  0  0  0  0999 V2000
    3.9330    3.0115    0.3743 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1272    1.7230    0.1510 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3309    1.3327   -0.6558 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1867    0.6904    0.6797 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8148   -0.1497    1.5879 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5680   -0.1182   -0.4178 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6320   -1.1537    0.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1114   -2.3369    0.5451 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4701   -2.5519    0.6415 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2404   -3.3089    0.9664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1304   -3.0953    0.8692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5908   -1.9113    0.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2580   -0.9100   -0.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5086    0.1714   -0.5543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6786    0.1106    0.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8598    0.7671   -0.3087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9001    1.7692   -1.2332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0897    2.3163   -1.6748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2782    1.8084   -1.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4752    2.3610   -1.5868 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2741    0.7969   -0.2062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0615    0.2874    0.1993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9984   -0.7523    1.1567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9813   -1.7566    1.1103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9559   -1.3955    0.1163 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0708    3.3413    0.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6227    3.7417   -0.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5274    0.2429   -0.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2194    1.8642   -0.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2404    1.6334   -1.7185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3671    1.2239    1.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5347    0.0537    2.5046 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4279   -0.6049   -0.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0835    0.5149   -1.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7994   -3.4243    1.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5883   -4.2560    1.3816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8207   -3.8380    1.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4451    0.3479    1.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9378    2.1341   -1.6215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1112    3.1172   -2.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3642    2.0311   -1.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2184    0.4156    0.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6376   -1.9409    2.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5194   -2.6897    0.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3172   -1.6139   -0.9093 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 13  7  1  0
 25 15  1  0
 25 12  1  0
 22 16  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 15 38  1  0
 17 39  1  0
 18 40  1  0
 20 41  1  0
 21 42  1  0
 24 43  1  0
 24 44  1  0
 25 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₀H₂₀O₅

Average Molecular Weight

340.3698

Monoisotopic Molecular Weight

340.13107375

IUPAC Name

15-(2-hydroxy-3-methylbut-3-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-5,14-diol

Traditional Name

15-(2-hydroxy-3-methylbut-3-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-5,14-diol

CAS Registry Number

78859-49-1

SMILES

CC(=C)C(O)CC1=C(O)C=CC2=C1OC1C2COC2=C1C=CC(O)=C2

InChI Identifier

InChI=1S/C20H20O5/c1-10(2)17(23)8-14-16(22)6-5-12-15-9-24-18-7-11(21)3-4-13(18)20(15)25-19(12)14/h3-7,15,17,20-23H,1,8-9H2,2H3

InChI Key

LRCYZCCKRIVTHN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Furanoisoflavonoids

Direct Parent

Pterocarpans

Alternative Parents

Substituents

Pterocarpan
Isoflavanol
Neolignan skeleton
Isoflavan
Chromane
Benzopyran
1-benzopyran
Coumaran
Benzofuran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Ether
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0029468)
Cytoplasm (HMDB: HMDB0029468)

Source

Endogenous

Endogenous (HMDB: HMDB0029468)

Exogenous

Exogenous (HMDB: HMDB0029468)

Food

Pulse

Pea

Cowpea (FooDB: FOOD00202)

Fruit

Fruits (FooDB: FOOD00871)

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
Water Solubility	0.17 g/L	ALOGPS
logP	2.35	ALOGPS
logP	2.92	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	9.26	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	79.15 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	93.26 m³·mol⁻¹	ChemAxon
Polarizability	35.76 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	179.646	31661259
DarkChem	[M-H]-	177.477	31661259
DeepCCS	[M+H]+	175.186	30932474
DeepCCS	[M-H]-	172.828	30932474
DeepCCS	[M-2H]-	206.587	30932474
DeepCCS	[M+Na]+	181.815	30932474
AllCCS	[M+H]+	183.4	32859911
AllCCS	[M+H-H2O]+	180.2	32859911
AllCCS	[M+NH4]+	186.4	32859911
AllCCS	[M+Na]+	187.2	32859911
AllCCS	[M-H]-	186.1	32859911
AllCCS	[M+Na-2H]-	185.8	32859911
AllCCS	[M+HCOO]-	185.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dolichin B	CC(=C)C(O)CC1=C(O)C=CC2=C1OC1C2COC2=C1C=CC(O)=C2	4028.7	Standard polar	33892256
Dolichin B	CC(=C)C(O)CC1=C(O)C=CC2=C1OC1C2COC2=C1C=CC(O)=C2	2939.3	Standard non polar	33892256
Dolichin B	CC(=C)C(O)CC1=C(O)C=CC2=C1OC1C2COC2=C1C=CC(O)=C2	3305.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dolichin B,1TMS,isomer #1	C=C(C)C(CC1=C(O)C=CC2=C1OC1C3=CC=C(O)C=C3OCC21)O[Si](C)(C)C	2996.1	Semi standard non polar	33892256
Dolichin B,1TMS,isomer #2	C=C(C)C(O)CC1=C(O[Si](C)(C)C)C=CC2=C1OC1C3=CC=C(O)C=C3OCC21	2971.4	Semi standard non polar	33892256
Dolichin B,1TMS,isomer #3	C=C(C)C(O)CC1=C(O)C=CC2=C1OC1C3=CC=C(O[Si](C)(C)C)C=C3OCC21	3021.1	Semi standard non polar	33892256
Dolichin B,2TMS,isomer #1	C=C(C)C(CC1=C(O[Si](C)(C)C)C=CC2=C1OC1C3=CC=C(O)C=C3OCC21)O[Si](C)(C)C	2949.8	Semi standard non polar	33892256
Dolichin B,2TMS,isomer #2	C=C(C)C(CC1=C(O)C=CC2=C1OC1C3=CC=C(O[Si](C)(C)C)C=C3OCC21)O[Si](C)(C)C	2995.5	Semi standard non polar	33892256
Dolichin B,2TMS,isomer #3	C=C(C)C(O)CC1=C(O[Si](C)(C)C)C=CC2=C1OC1C3=CC=C(O[Si](C)(C)C)C=C3OCC21	2995.7	Semi standard non polar	33892256
Dolichin B,3TMS,isomer #1	C=C(C)C(CC1=C(O[Si](C)(C)C)C=CC2=C1OC1C3=CC=C(O[Si](C)(C)C)C=C3OCC21)O[Si](C)(C)C	2980.9	Semi standard non polar	33892256
Dolichin B,1TBDMS,isomer #1	C=C(C)C(CC1=C(O)C=CC2=C1OC1C3=CC=C(O)C=C3OCC21)O[Si](C)(C)C(C)(C)C	3249.7	Semi standard non polar	33892256
Dolichin B,1TBDMS,isomer #2	C=C(C)C(O)CC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1OC1C3=CC=C(O)C=C3OCC21	3203.5	Semi standard non polar	33892256
Dolichin B,1TBDMS,isomer #3	C=C(C)C(O)CC1=C(O)C=CC2=C1OC1C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3OCC21	3254.5	Semi standard non polar	33892256
Dolichin B,2TBDMS,isomer #1	C=C(C)C(CC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1OC1C3=CC=C(O)C=C3OCC21)O[Si](C)(C)C(C)(C)C	3409.1	Semi standard non polar	33892256
Dolichin B,2TBDMS,isomer #2	C=C(C)C(CC1=C(O)C=CC2=C1OC1C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3OCC21)O[Si](C)(C)C(C)(C)C	3446.6	Semi standard non polar	33892256
Dolichin B,2TBDMS,isomer #3	C=C(C)C(O)CC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1OC1C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3OCC21	3432.4	Semi standard non polar	33892256
Dolichin B,3TBDMS,isomer #1	C=C(C)C(CC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1OC1C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3OCC21)O[Si](C)(C)C(C)(C)C	3622.5	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 - Dolichin B GC-MS (Non-derivatized) - 70eV, Positive	splash10-01b9-6191000000-a016024461a9e2795c93	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dolichin B GC-MS (3 TMS) - 70eV, Positive	splash10-0006-5200690000-7d7a454208ce65f5847a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dolichin B 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 - Dolichin B 10V, Positive-QTOF	splash10-00dl-1029000000-23fd4d423c777d232389	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolichin B 20V, Positive-QTOF	splash10-00xr-9133000000-50b99461ff9cbb159265	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolichin B 40V, Positive-QTOF	splash10-006w-9220000000-0cf61dce5f51499a6715	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolichin B 10V, Negative-QTOF	splash10-000i-0019000000-5cce1e65c3e385aac1eb	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolichin B 20V, Negative-QTOF	splash10-0a4r-2095000000-c0915fd11ddf625d7dcd	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolichin B 40V, Negative-QTOF	splash10-014r-9230000000-5caf140dbd60d2255722	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolichin B 10V, Positive-QTOF	splash10-01b9-0095000000-1d35ebf20afce02ab1ce	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolichin B 20V, Positive-QTOF	splash10-014i-0091000000-e4bafbb5cc12f9ff1ad0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolichin B 40V, Positive-QTOF	splash10-014j-1591000000-4f4c147607544650d0bf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolichin B 10V, Negative-QTOF	splash10-000i-0009000000-f6924abc9aa909ea7db0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolichin B 20V, Negative-QTOF	splash10-00di-1079000000-70e67706e4d6617fd9a2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolichin B 40V, Negative-QTOF	splash10-0a4i-3290000000-f4c7b9067d5da92c91cf	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB000590

KNApSAcK ID

C00009647

Chemspider ID

35013059

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

74977387

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1809691

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 Dolichin B (HMDB0029468)

MOL for HMDB0029468 (Dolichin B)

3D MOL for HMDB0029468 (Dolichin B)

3D SDF for HMDB0029468 (Dolichin B)

3D-SDF for HMDB0029468 (Dolichin B)

PDB for HMDB0029468 (Dolichin B)

3D PDB for HMDB0029468 (Dolichin B)

SMILES for HMDB0029468 (Dolichin B)

INCHI for HMDB0029468 (Dolichin B)

Structure for HMDB0029468 (Dolichin B)

3D Structure for HMDB0029468 (Dolichin B)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra