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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 04:47:28 UTC

Update Date

2021-09-24 04:47:28 UTC

HMDB ID

HMDB0303808

Secondary Accession Numbers

None

Metabolite Identification

Common Name

11b,13-Dihydrolactucin

Description

(3R,3aR,4R,9aS,9bS)-4-hydroxy-9-(hydroxymethyl)-3,6,9a-trimethyl-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione belongs to the class of organic compounds known as ambrosanolides and secoambrosanolides. These are sesquiterpene lactones from the Ambrosia family, with a backbone derivative of azuleno[6,5-b]furan-2-one (ambrosanolides) or azuleno[4,5-b]furan-2-one (secoambrosanolides). Based on a literature review very few articles have been published on (3R,3aR,4R,9aS,9bS)-4-hydroxy-9-(hydroxymethyl)-3,6,9a-trimethyl-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione.

Structure

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

HMDB0303808
     RDKit          3D
11b,13-Dihydrolactucin
 41 43  0  0  0  0  0  0  0  0999 V2000
   -1.5974    3.2197    0.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7718    2.0495    0.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4745    0.9203    0.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8956    0.7913    0.3065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6795    1.7451    0.5440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1625   -0.6289    0.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0806   -1.3261   -0.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0009   -2.8167   -0.1978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5572   -3.1965   -1.4563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9656   -0.4180   -0.2750 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7279   -0.4003   -1.8073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3111   -0.7612    0.3715 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6326   -2.1265    0.1750 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0055   -2.2217    0.3171 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6851   -3.1816    0.7360 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5783   -0.9322   -0.1314 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6035   -0.4601    0.8595 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4252    0.0033   -0.3042 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5843    1.3029    0.4163 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2881    1.0987    1.7632 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6361    2.3379   -0.1111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0641    3.1248    1.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9941    4.1539    0.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3179    3.4015   -0.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1447   -1.0717    0.3790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9942   -3.2838    0.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3186   -3.2138    0.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2920   -3.3937   -2.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0182   -1.1334   -2.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6820   -0.6681   -2.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4775    0.6077   -2.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2991   -0.5901    1.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0989   -1.1141   -1.0867 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3193   -1.3209    1.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2145   -0.2222    1.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2058    0.3373    0.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2999    0.1993   -1.3597 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6332    1.6488    0.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6631    1.7908    2.3505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8125    2.4035   -1.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8843    3.3453    0.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  6
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21  2  1  0
 10  3  1  0
 18 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  6 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
 11 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  1
 16 33  1  6
 17 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  6
 19 38  1  1
 20 39  1  0
 21 40  1  0
 21 41  1  0
M  END

  Mrv0541 02241221532D          

 23 25  0  0  1  0            999 V2000
    1.9908    2.1417    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4139    2.8499    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2356    2.9239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711    3.4712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0547    4.2755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1125    3.1470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1865    2.3253    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5415    1.8109    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3942    2.6226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2432    2.0658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4981    2.8505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0539    3.4636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7281    1.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2432    0.7310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4981   -0.0537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5415    0.9859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1865    0.4715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0029   -0.3328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9908    0.6551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3487    1.3984    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1737    1.3984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3094    1.5095    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5783    2.8562    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  6  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
  1 20  1  0  0  0  0
 20 21  1  6  0  0  0
  7 22  1  6  0  0  0
  1 23  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0303808

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12OC(=O)[C@H](C)[C@]1([H])[C@H](O)CC(C)=C1C(=O)C=C(CO)[C@]21C

> <INCHI_IDENTIFIER>
InChI=1S/C16H20O5/c1-7-4-10(18)12-8(2)15(20)21-14(12)16(3)9(6-17)5-11(19)13(7)16/h5,8,10,12,14,17-18H,4,6H2,1-3H3/t8-,10-,12-,14+,16+/m1/s1

> <INCHI_KEY>
AVVAXORRBBPMQM-YRRGMINMSA-N

> <FORMULA>
C16H20O5

> <MOLECULAR_WEIGHT>
292.327

> <EXACT_MASS>
292.13107375

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
30.092423421867682

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,3aR,4R,9aS,9bS)-4-hydroxy-9-(hydroxymethyl)-3,6,9a-trimethyl-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione

> <ALOGPS_LOGP>
0.38

> <JCHEM_LOGP>
0.2186050260000003

> <ALOGPS_LOGS>
-2.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.252313435551947

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.59532430011151

> <JCHEM_PKA_STRONGEST_BASIC>
-2.76385307698707

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
76.45979999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.69e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,3aR,4R,9aS,9bS)-4-hydroxy-9-(hydroxymethyl)-3,6,9a-trimethyl-3H,3aH,4H,5H,9bH-azuleno[4,5-b]furan-2,7-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0303808
     RDKit          3D
11b,13-Dihydrolactucin
 41 43  0  0  0  0  0  0  0  0999 V2000
   -1.5974    3.2197    0.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7718    2.0495    0.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4745    0.9203    0.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8956    0.7913    0.3065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6795    1.7451    0.5440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1625   -0.6289    0.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0806   -1.3261   -0.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0009   -2.8167   -0.1978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5572   -3.1965   -1.4563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9656   -0.4180   -0.2750 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7279   -0.4003   -1.8073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3111   -0.7612    0.3715 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6326   -2.1265    0.1750 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0055   -2.2217    0.3171 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6851   -3.1816    0.7360 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5783   -0.9322   -0.1314 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6035   -0.4601    0.8595 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4252    0.0033   -0.3042 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5843    1.3029    0.4163 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2881    1.0987    1.7632 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6361    2.3379   -0.1111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0641    3.1248    1.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9941    4.1539    0.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3179    3.4015   -0.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1447   -1.0717    0.3790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9942   -3.2838    0.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3186   -3.2138    0.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2920   -3.3937   -2.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0182   -1.1334   -2.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6820   -0.6681   -2.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4775    0.6077   -2.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2991   -0.5901    1.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0989   -1.1141   -1.0867 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3193   -1.3209    1.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2145   -0.2222    1.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2058    0.3373    0.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2999    0.1993   -1.3597 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6332    1.6488    0.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6631    1.7908    2.3505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8125    2.4035   -1.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8843    3.3453    0.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  6
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21  2  1  0
 10  3  1  0
 18 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  6 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
 11 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  1
 16 33  1  6
 17 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  6
 19 38  1  1
 20 39  1  0
 21 40  1  0
 21 41  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       3.716   3.998   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.506   5.320   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.040   5.458   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.493   6.480   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.835   7.981   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       2.077   5.874   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.215   4.341   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.011   3.380   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.736   4.896   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.454   3.856   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.930   5.321   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.101   6.465   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.359   2.610   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.454   1.365   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.930  -0.100   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.011   1.840   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.215   0.880   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.872  -0.621   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.716   1.223   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.384   2.610   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.924   2.610   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0       2.444   2.818   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       2.946   5.332   0.000  0.00  0.00           H+0
CONECT    1    2    7   20   23                                             
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    1    8   22                                             
CONECT    8    7    9   10   16                                             
CONECT    9    8                                                            
CONECT   10    8   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    8   17                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19    1   21                                                  
CONECT   21   20                                                            
CONECT   22    7                                                            
CONECT   23    1                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0303808
HETATM    1  C1  UNL     1      -1.597   3.220   0.462  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.772   2.050   0.100  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.474   0.920   0.047  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.896   0.791   0.307  1.00  0.00           C  
HETATM    5  O1  UNL     1      -3.679   1.745   0.544  1.00  0.00           O  
HETATM    6  C5  UNL     1      -3.162  -0.629   0.227  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.081  -1.326  -0.051  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.001  -2.817  -0.198  1.00  0.00           C  
HETATM    9  O2  UNL     1      -1.557  -3.196  -1.456  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.966  -0.418  -0.275  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.728  -0.400  -1.807  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.311  -0.761   0.371  1.00  0.00           C  
HETATM   13  O3  UNL     1       0.633  -2.127   0.175  1.00  0.00           O  
HETATM   14  C11 UNL     1       2.006  -2.222   0.317  1.00  0.00           C  
HETATM   15  O4  UNL     1       2.685  -3.182   0.736  1.00  0.00           O  
HETATM   16  C12 UNL     1       2.578  -0.932  -0.131  1.00  0.00           C  
HETATM   17  C13 UNL     1       3.604  -0.460   0.860  1.00  0.00           C  
HETATM   18  C14 UNL     1       1.425   0.003  -0.304  1.00  0.00           C  
HETATM   19  C15 UNL     1       1.584   1.303   0.416  1.00  0.00           C  
HETATM   20  O5  UNL     1       1.288   1.099   1.763  1.00  0.00           O  
HETATM   21  C16 UNL     1       0.636   2.338  -0.111  1.00  0.00           C  
HETATM   22  H1  UNL     1      -2.064   3.125   1.478  1.00  0.00           H  
HETATM   23  H2  UNL     1      -0.994   4.154   0.537  1.00  0.00           H  
HETATM   24  H3  UNL     1      -2.318   3.401  -0.345  1.00  0.00           H  
HETATM   25  H4  UNL     1      -4.145  -1.072   0.379  1.00  0.00           H  
HETATM   26  H5  UNL     1      -2.994  -3.284   0.007  1.00  0.00           H  
HETATM   27  H6  UNL     1      -1.319  -3.214   0.564  1.00  0.00           H  
HETATM   28  H7  UNL     1      -2.292  -3.394  -2.070  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.018  -1.133  -2.097  1.00  0.00           H  
HETATM   30  H9  UNL     1      -1.682  -0.668  -2.316  1.00  0.00           H  
HETATM   31  H10 UNL     1      -0.477   0.608  -2.150  1.00  0.00           H  
HETATM   32  H11 UNL     1       0.299  -0.590   1.467  1.00  0.00           H  
HETATM   33  H12 UNL     1       3.099  -1.114  -1.087  1.00  0.00           H  
HETATM   34  H13 UNL     1       4.319  -1.321   1.002  1.00  0.00           H  
HETATM   35  H14 UNL     1       3.214  -0.222   1.846  1.00  0.00           H  
HETATM   36  H15 UNL     1       4.206   0.337   0.388  1.00  0.00           H  
HETATM   37  H16 UNL     1       1.300   0.199  -1.360  1.00  0.00           H  
HETATM   38  H17 UNL     1       2.633   1.649   0.352  1.00  0.00           H  
HETATM   39  H18 UNL     1       1.663   1.791   2.350  1.00  0.00           H  
HETATM   40  H19 UNL     1       0.813   2.403  -1.219  1.00  0.00           H  
HETATM   41  H20 UNL     1       0.884   3.345   0.280  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    3   21
CONECT    3    4   10
CONECT    4    5    5    6
CONECT    6    7    7   25
CONECT    7    8   10
CONECT    8    9   26   27
CONECT    9   28
CONECT   10   11   12
CONECT   11   29   30   31
CONECT   12   13   18   32
CONECT   13   14
CONECT   14   15   15   16
CONECT   16   17   18   33
CONECT   17   34   35   36
CONECT   18   19   37
CONECT   19   20   21   38
CONECT   20   39
CONECT   21   40   41
END

HMDB0303808
     RDKit          3D
11b,13-Dihydrolactucin
 41 43  0  0  0  0  0  0  0  0999 V2000
   -1.5974    3.2197    0.4619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7718    2.0495    0.1003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4745    0.9203    0.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8956    0.7913    0.3065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6795    1.7451    0.5440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1625   -0.6289    0.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0806   -1.3261   -0.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0009   -2.8167   -0.1978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5572   -3.1965   -1.4563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9656   -0.4180   -0.2750 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7279   -0.4003   -1.8073 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3111   -0.7612    0.3715 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6326   -2.1265    0.1750 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0055   -2.2217    0.3171 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6851   -3.1816    0.7360 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5783   -0.9322   -0.1314 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6035   -0.4601    0.8595 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4252    0.0033   -0.3042 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5843    1.3029    0.4163 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2881    1.0987    1.7632 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6361    2.3379   -0.1111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0641    3.1248    1.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9941    4.1539    0.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3179    3.4015   -0.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1447   -1.0717    0.3790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9942   -3.2838    0.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3186   -3.2138    0.5644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2920   -3.3937   -2.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0182   -1.1334   -2.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6820   -0.6681   -2.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4775    0.6077   -2.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2991   -0.5901    1.4666 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0989   -1.1141   -1.0867 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3193   -1.3209    1.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2145   -0.2222    1.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2058    0.3373    0.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2999    0.1993   -1.3597 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6332    1.6488    0.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6631    1.7908    2.3505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8125    2.4035   -1.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8843    3.3453    0.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  6
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21  2  1  0
 10  3  1  0
 18 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  6 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
 11 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  1
 16 33  1  6
 17 34  1  0
 17 35  1  0
 17 36  1  0
 18 37  1  6
 19 38  1  1
 20 39  1  0
 21 40  1  0
 21 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₂₀O₅

Average Molecular Weight

292.327

Monoisotopic Molecular Weight

292.13107375

IUPAC Name

(3R,3aR,4R,9aS,9bS)-4-hydroxy-9-(hydroxymethyl)-3,6,9a-trimethyl-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione

Traditional Name

(3R,3aR,4R,9aS,9bS)-4-hydroxy-9-(hydroxymethyl)-3,6,9a-trimethyl-3H,3aH,4H,5H,9bH-azuleno[4,5-b]furan-2,7-dione

CAS Registry Number

Not Available

SMILES

[H][C@]12OC(=O)[C@H](C)[C@]1([H])[C@H](O)CC(C)=C1C(=O)C=C(CO)[C@]21C

InChI Identifier

InChI=1S/C16H20O5/c1-7-4-10(18)12-8(2)15(20)21-14(12)16(3)9(6-17)5-11(19)13(7)16/h5,8,10,12,14,17-18H,4,6H2,1-3H3/t8-,10-,12-,14+,16+/m1/s1

InChI Key

AVVAXORRBBPMQM-YRRGMINMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ambrosanolides and secoambrosanolides. These are sesquiterpene lactones from the Ambrosia family, with a backbone derivative of azuleno[6,5-b]furan-2-one (ambrosanolides) or azuleno[4,5-b]furan-2-one (secoambrosanolides).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Ambrosanolides and secoambrosanolides

Alternative Parents

Substituents

Ambrosanolide
Pseudoguaiane sesquiterpenoid
Sesquiterpenoid
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Primary alcohol
Organooxygen compound
Organic oxygen compound
Organic oxide
Alcohol
Hydrocarbon derivative
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0303808)

Chicory (FooDB: FOOD00049)

Herb and spice

Herb

Dandelion (FooDB: FOOD00181)

Process

Not Available

Role

Biological role

Bitter (HMDB: HMDB0303808)

Physical Properties

State

Solid

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	0.38	ALOGPS
logP	0.22	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	14.6	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	76.46 m³·mol⁻¹	ChemAxon
Polarizability	30.09 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]+	166.841	32859911
AllCCS	[M+H-H2O]+	163.559	32859911
AllCCS	[M+Na]+	170.754	32859911
AllCCS	[M+NH4]+	169.88	32859911
AllCCS	[M-H]-	171.448	32859911
AllCCS	[M+Na-2H]-	171.331	32859911
AllCCS	[M+HCOO]-	171.324	32859911
DeepCCS	[M-2H]-	204.984	30932474
DeepCCS	[M+Na]+	179.861	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 - 11b,13-Dihydrolactucin 10V, Positive-QTOF	splash10-004l-0090000000-fb87a1fbe8eacf8a1550	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11b,13-Dihydrolactucin 20V, Positive-QTOF	splash10-0pdi-0190000000-1b9cc06e97b6ba5451f8	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11b,13-Dihydrolactucin 40V, Positive-QTOF	splash10-0ziu-6590000000-1f24f15ddca0bb603877	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11b,13-Dihydrolactucin 10V, Negative-QTOF	splash10-0006-0090000000-bfcab6041a24ed0cbfcf	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11b,13-Dihydrolactucin 20V, Negative-QTOF	splash10-01vp-0090000000-a65b899ee89830e0f4ce	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11b,13-Dihydrolactucin 40V, Negative-QTOF	splash10-0pdl-3950000000-1973c2bc8b8ec5e3eaac	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11b,13-Dihydrolactucin 10V, Positive-QTOF	splash10-004i-0090000000-a24e40f173f1cf50e12f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11b,13-Dihydrolactucin 20V, Positive-QTOF	splash10-056r-0490000000-38cec6861363a519750f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11b,13-Dihydrolactucin 40V, Positive-QTOF	splash10-014i-0290000000-99468b12b98cf12f7f39	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11b,13-Dihydrolactucin 10V, Negative-QTOF	splash10-0006-0090000000-98ee3cd4933435e64319	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11b,13-Dihydrolactucin 20V, Negative-QTOF	splash10-0006-0090000000-6b37cba5b9c7045cbb27	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 11b,13-Dihydrolactucin 40V, Negative-QTOF	splash10-052f-0490000000-ae384c78950e6299a3d9	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

FDB021725

KNApSAcK ID

Not Available

Chemspider ID

59696905

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 11b,13-Dihydrolactucin (HMDB0303808)

MOL for HMDB0303808 (11b,13-Dihydrolactucin)

3D MOL for HMDB0303808 (11b,13-Dihydrolactucin)

3D SDF for HMDB0303808 (11b,13-Dihydrolactucin)

3D-SDF for HMDB0303808 (11b,13-Dihydrolactucin)

PDB for HMDB0303808 (11b,13-Dihydrolactucin)

3D PDB for HMDB0303808 (11b,13-Dihydrolactucin)

SMILES for HMDB0303808 (11b,13-Dihydrolactucin)

INCHI for HMDB0303808 (11b,13-Dihydrolactucin)

Structure for HMDB0303808 (11b,13-Dihydrolactucin)

3D Structure for HMDB0303808 (11b,13-Dihydrolactucin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra