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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:51:06 UTC

Update Date

2022-03-07 02:54:39 UTC

HMDB ID

HMDB0035828

Secondary Accession Numbers

HMDB35828

Metabolite Identification

Common Name

Lactupicrin

Description

Lactupicrin belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. Lactupicrin has been detected, but not quantified in, several different foods, such as lettuces (Lactuca sativa), endives (Cichorium endivia), robusta coffees (Coffea canephora), chicories (Cichorium intybus), and romaine lettuces (Lactuca sativa L. var. longifolia). This could make lactupicrin a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Lactupicrin.

Structure

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


  Mrv0541 05061308442D          

 30 33  0  0  0  0            999 V2000
    3.6754   -0.1941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1007    0.9600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1453   -2.8544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2677   -2.6414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0224   -3.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3906   -3.4572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871   -0.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3767   -1.5242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9493    2.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642    3.2305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304    0.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5878    1.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4997   -2.3400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1541    2.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7456   -3.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864    1.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5438    0.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0217   -1.0099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140    1.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3602    1.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6996    1.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8746    1.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248    2.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    3.8678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8686   -4.7874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6749    0.9600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7897   -1.3113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0202    2.7530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8988   -0.1941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201    2.4581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
 11  1  1  0  0  0  0
 11  7  1  0  0  0  0
 12  2  2  0  0  0  0
 13  3  2  0  0  0  0
 13  4  1  0  0  0  0
 13  8  1  0  0  0  0
 14  9  2  0  0  0  0
 14 10  1  0  0  0  0
 15  5  2  0  0  0  0
 15  6  1  0  0  0  0
 16  9  1  0  0  0  0
 17  7  1  0  0  0  0
 18  8  1  0  0  0  0
 19 11  2  0  0  0  0
 19 16  1  0  0  0  0
 20 12  1  0  0  0  0
 20 17  1  0  0  0  0
 21 14  1  0  0  0  0
 21 19  1  0  0  0  0
 22 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 12  1  0  0  0  0
 24 10  1  0  0  0  0
 25 15  1  0  0  0  0
 26 16  2  0  0  0  0
 27 18  2  0  0  0  0
 28 23  2  0  0  0  0
 29 17  1  0  0  0  0
 29 18  1  0  0  0  0
 30 22  1  0  0  0  0
 30 23  1  0  0  0  0
M  END

HMDB0035828
     RDKit          3D
Lactupicrin
 52 55  0  0  0  0  0  0  0  0999 V2000
   -1.4233   -2.7140   -1.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9251   -1.4964   -1.2604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3638   -1.2501   -1.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3276   -2.0667   -1.1616 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5174    0.1483   -1.3384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4083    0.6952   -0.6489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6215    0.6092    0.8475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0739    0.9242    1.0996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7829    2.1838    0.7649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7090    2.3689   -0.6092 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6629   -0.1014    1.6881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7241   -1.1744    1.8939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9850   -2.2978    2.4365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4414   -0.7392    1.3722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3410   -1.4707    1.3891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4303   -2.8298    1.9912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0146   -1.1094    0.8817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0907   -0.1219   -0.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0555   -0.1393   -1.0599 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9258    0.9417   -1.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6462    1.9249   -0.4408 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1044    0.8384   -2.0537 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3559    1.0225   -1.2883 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8583    2.2895   -1.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0375    2.4242   -0.3622 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6689    1.3029    0.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8444    1.4535    0.8407 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1418    0.0396   -0.0971 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9705   -0.1281   -0.8100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2841   -0.1973   -1.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1056   -3.5434   -1.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3533   -2.9040   -1.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2606    1.7663   -0.9069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0497    1.4018    1.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3814    3.0491    1.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8559    2.0600    1.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5670    2.2021   -1.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7271   -0.1634    1.9946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4116   -3.2520    2.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7912   -2.7549    3.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0727   -3.5066    1.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5266   -2.0409    0.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5506   -0.6673    1.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0864    0.8850    0.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0985   -0.1432   -2.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0077    1.6948   -2.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3910    3.1893   -1.4483 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4750    3.3884   -0.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9336    1.5753    1.8251 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6621   -0.8327    0.2991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5495   -1.1073   -0.9890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0144    0.1894   -2.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 18 30  1  0
 30  2  1  0
 30  6  1  0
 14  7  1  0
 29 23  1  0
  1 31  1  0
  1 32  1  0
  6 33  1  0
  7 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 22 45  1  0
 22 46  1  0
 24 47  1  0
 25 48  1  0
 27 49  1  0
 28 50  1  0
 29 51  1  0
 30 52  1  0
M  END


  Mrv0541 05061308442D          

 30 33  0  0  0  0            999 V2000
    3.6754   -0.1941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1007    0.9600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1453   -2.8544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2677   -2.6414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0224   -3.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3906   -3.4572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871   -0.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3767   -1.5242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9493    2.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8642    3.2305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304    0.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5878    1.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4997   -2.3400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1541    2.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7456   -3.9716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864    1.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5438    0.3203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0217   -1.0099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140    1.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3602    1.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6996    1.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8746    1.7696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248    2.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    3.8678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8686   -4.7874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6749    0.9600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7897   -1.3113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0202    2.7530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8988   -0.1941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201    2.4581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
 11  1  1  0  0  0  0
 11  7  1  0  0  0  0
 12  2  2  0  0  0  0
 13  3  2  0  0  0  0
 13  4  1  0  0  0  0
 13  8  1  0  0  0  0
 14  9  2  0  0  0  0
 14 10  1  0  0  0  0
 15  5  2  0  0  0  0
 15  6  1  0  0  0  0
 16  9  1  0  0  0  0
 17  7  1  0  0  0  0
 18  8  1  0  0  0  0
 19 11  2  0  0  0  0
 19 16  1  0  0  0  0
 20 12  1  0  0  0  0
 20 17  1  0  0  0  0
 21 14  1  0  0  0  0
 21 19  1  0  0  0  0
 22 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 12  1  0  0  0  0
 24 10  1  0  0  0  0
 25 15  1  0  0  0  0
 26 16  2  0  0  0  0
 27 18  2  0  0  0  0
 28 23  2  0  0  0  0
 29 17  1  0  0  0  0
 29 18  1  0  0  0  0
 30 22  1  0  0  0  0
 30 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035828

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C2C(C3OC(=O)C(=C)C3C(C1)OC(=O)CC1=CC=C(O)C=C1)C(CO)=CC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H22O7/c1-11-7-17(29-18(27)8-13-3-5-15(25)6-4-13)20-12(2)23(28)30-22(20)21-14(10-24)9-16(26)19(11)21/h3-6,9,17,20-22,24-25H,2,7-8,10H2,1H3

> <INCHI_KEY>
UMVSOHBRAQTGQI-UHFFFAOYSA-N

> <FORMULA>
C23H22O7

> <MOLECULAR_WEIGHT>
410.4166

> <EXACT_MASS>
410.136553058

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
41.17921259620253

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate

> <ALOGPS_LOGP>
1.99

> <JCHEM_LOGP>
1.954158788666667

> <ALOGPS_LOGS>
-3.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.496684158744628

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.517997262325441

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7605641572173

> <JCHEM_POLAR_SURFACE_AREA>
110.13

> <JCHEM_REFRACTIVITY>
107.71939999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.77e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035828
     RDKit          3D
Lactupicrin
 52 55  0  0  0  0  0  0  0  0999 V2000
   -1.4233   -2.7140   -1.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9251   -1.4964   -1.2604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3638   -1.2501   -1.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3276   -2.0667   -1.1616 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5174    0.1483   -1.3384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4083    0.6952   -0.6489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6215    0.6092    0.8475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0739    0.9242    1.0996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7829    2.1838    0.7649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7090    2.3689   -0.6092 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6629   -0.1014    1.6881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7241   -1.1744    1.8939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9850   -2.2978    2.4365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4414   -0.7392    1.3722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3410   -1.4707    1.3891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4303   -2.8298    1.9912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0146   -1.1094    0.8817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0907   -0.1219   -0.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0555   -0.1393   -1.0599 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9258    0.9417   -1.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6462    1.9249   -0.4408 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1044    0.8384   -2.0537 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3559    1.0225   -1.2883 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8583    2.2895   -1.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0375    2.4242   -0.3622 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6689    1.3029    0.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8444    1.4535    0.8407 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1418    0.0396   -0.0971 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9705   -0.1281   -0.8100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2841   -0.1973   -1.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1056   -3.5434   -1.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3533   -2.9040   -1.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2606    1.7663   -0.9069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0497    1.4018    1.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3814    3.0491    1.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8559    2.0600    1.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5670    2.2021   -1.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7271   -0.1634    1.9946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4116   -3.2520    2.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7912   -2.7549    3.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0727   -3.5066    1.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5266   -2.0409    0.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5506   -0.6673    1.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0864    0.8850    0.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0985   -0.1432   -2.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0077    1.6948   -2.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3910    3.1893   -1.4483 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4750    3.3884   -0.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9336    1.5753    1.8251 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6621   -0.8327    0.2991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5495   -1.1073   -0.9890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0144    0.1894   -2.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 18 30  1  0
 30  2  1  0
 30  6  1  0
 14  7  1  0
 29 23  1  0
  1 31  1  0
  1 32  1  0
  6 33  1  0
  7 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 22 45  1  0
 22 46  1  0
 24 47  1  0
 25 48  1  0
 27 49  1  0
 28 50  1  0
 29 51  1  0
 30 52  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       6.861  -0.362   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.188   1.792   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.271  -5.328   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.366  -4.931   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.042  -6.851   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.596  -6.453   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.269  -0.070   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.703  -2.845   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.372   4.179   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.347   6.030   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.657   0.598   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.097   2.640   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.933  -4.368   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.888   4.588   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.392  -7.414   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.441   2.640   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.882   0.598   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.907  -1.885   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.999   2.099   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.539   2.099   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.039   3.303   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.499   3.303   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.166   4.179   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.325   7.220   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       1.621  -8.936   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       8.726   1.792   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       3.341  -2.448   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -0.038   5.139   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       1.678  -0.362   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.651   4.588   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   12                                                            
CONECT    3    5   13                                                       
CONECT    4    6   13                                                       
CONECT    5    3   15                                                       
CONECT    6    4   15                                                       
CONECT    7   11   17                                                       
CONECT    8   13   18                                                       
CONECT    9   14   16                                                       
CONECT   10   14   24                                                       
CONECT   11    1    7   19                                                  
CONECT   12    2   20   23                                                  
CONECT   13    3    4    8                                                  
CONECT   14    9   10   21                                                  
CONECT   15    5    6   25                                                  
CONECT   16    9   19   26                                                  
CONECT   17    7   20   29                                                  
CONECT   18    8   27   29                                                  
CONECT   19   11   16   21                                                  
CONECT   20   12   17   22                                                  
CONECT   21   14   19   22                                                  
CONECT   22   20   21   30                                                  
CONECT   23   12   28   30                                                  
CONECT   24   10                                                            
CONECT   25   15                                                            
CONECT   26   16                                                            
CONECT   27   18                                                            
CONECT   28   23                                                            
CONECT   29   17   18                                                       
CONECT   30   22   23                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

COMPND    HMDB0035828
HETATM    1  C1  UNL     1      -1.423  -2.714  -1.394  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.925  -1.496  -1.260  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.364  -1.250  -1.243  1.00  0.00           C  
HETATM    4  O1  UNL     1      -4.328  -2.067  -1.162  1.00  0.00           O  
HETATM    5  O2  UNL     1      -3.517   0.148  -1.338  1.00  0.00           O  
HETATM    6  C4  UNL     1      -2.408   0.695  -0.649  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.622   0.609   0.847  1.00  0.00           C  
HETATM    8  C6  UNL     1      -4.074   0.924   1.100  1.00  0.00           C  
HETATM    9  C7  UNL     1      -4.783   2.184   0.765  1.00  0.00           C  
HETATM   10  O3  UNL     1      -4.709   2.369  -0.609  1.00  0.00           O  
HETATM   11  C8  UNL     1      -4.663  -0.101   1.688  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.724  -1.174   1.894  1.00  0.00           C  
HETATM   13  O4  UNL     1      -3.985  -2.298   2.437  1.00  0.00           O  
HETATM   14  C10 UNL     1      -2.441  -0.739   1.372  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.341  -1.471   1.389  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.430  -2.830   1.991  1.00  0.00           C  
HETATM   17  C13 UNL     1      -0.015  -1.109   0.882  1.00  0.00           C  
HETATM   18  C14 UNL     1      -0.091  -0.122  -0.223  1.00  0.00           C  
HETATM   19  O5  UNL     1       1.055  -0.139  -1.060  1.00  0.00           O  
HETATM   20  C15 UNL     1       1.926   0.942  -1.144  1.00  0.00           C  
HETATM   21  O6  UNL     1       1.646   1.925  -0.441  1.00  0.00           O  
HETATM   22  C16 UNL     1       3.104   0.838  -2.054  1.00  0.00           C  
HETATM   23  C17 UNL     1       4.356   1.022  -1.288  1.00  0.00           C  
HETATM   24  C18 UNL     1       4.858   2.290  -1.083  1.00  0.00           C  
HETATM   25  C19 UNL     1       6.038   2.424  -0.362  1.00  0.00           C  
HETATM   26  C20 UNL     1       6.669   1.303   0.124  1.00  0.00           C  
HETATM   27  O7  UNL     1       7.844   1.454   0.841  1.00  0.00           O  
HETATM   28  C21 UNL     1       6.142   0.040  -0.097  1.00  0.00           C  
HETATM   29  C22 UNL     1       4.970  -0.128  -0.810  1.00  0.00           C  
HETATM   30  C23 UNL     1      -1.284  -0.197  -1.115  1.00  0.00           C  
HETATM   31  H1  UNL     1      -2.106  -3.543  -1.492  1.00  0.00           H  
HETATM   32  H2  UNL     1      -0.353  -2.904  -1.412  1.00  0.00           H  
HETATM   33  H3  UNL     1      -2.261   1.766  -0.907  1.00  0.00           H  
HETATM   34  H4  UNL     1      -2.050   1.402   1.370  1.00  0.00           H  
HETATM   35  H5  UNL     1      -4.381   3.049   1.332  1.00  0.00           H  
HETATM   36  H6  UNL     1      -5.856   2.060   1.000  1.00  0.00           H  
HETATM   37  H7  UNL     1      -5.567   2.202  -1.074  1.00  0.00           H  
HETATM   38  H8  UNL     1      -5.727  -0.163   1.995  1.00  0.00           H  
HETATM   39  H9  UNL     1      -0.412  -3.252   2.065  1.00  0.00           H  
HETATM   40  H10 UNL     1      -1.791  -2.755   3.057  1.00  0.00           H  
HETATM   41  H11 UNL     1      -2.073  -3.507   1.406  1.00  0.00           H  
HETATM   42  H12 UNL     1       0.527  -2.041   0.633  1.00  0.00           H  
HETATM   43  H13 UNL     1       0.551  -0.667   1.734  1.00  0.00           H  
HETATM   44  H14 UNL     1      -0.086   0.885   0.252  1.00  0.00           H  
HETATM   45  H15 UNL     1       3.098  -0.143  -2.566  1.00  0.00           H  
HETATM   46  H16 UNL     1       3.008   1.695  -2.761  1.00  0.00           H  
HETATM   47  H17 UNL     1       4.391   3.189  -1.448  1.00  0.00           H  
HETATM   48  H18 UNL     1       6.475   3.388  -0.172  1.00  0.00           H  
HETATM   49  H19 UNL     1       7.934   1.575   1.825  1.00  0.00           H  
HETATM   50  H20 UNL     1       6.662  -0.833   0.299  1.00  0.00           H  
HETATM   51  H21 UNL     1       4.549  -1.107  -0.989  1.00  0.00           H  
HETATM   52  H22 UNL     1      -1.014   0.189  -2.144  1.00  0.00           H  
CONECT    1    2    2   31   32
CONECT    2    3   30
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   30   33
CONECT    7    8   14   34
CONECT    8    9   11   11
CONECT    9   10   35   36
CONECT   10   37
CONECT   11   12   38
CONECT   12   13   13   14
CONECT   14   15   15
CONECT   15   16   17
CONECT   16   39   40   41
CONECT   17   18   42   43
CONECT   18   19   30   44
CONECT   19   20
CONECT   20   21   21   22
CONECT   22   23   45   46
CONECT   23   24   24   29
CONECT   24   25   47
CONECT   25   26   26   48
CONECT   26   27   28
CONECT   27   49
CONECT   28   29   29   50
CONECT   29   51
CONECT   30   52
END

HMDB0035828
     RDKit          3D
Lactupicrin
 52 55  0  0  0  0  0  0  0  0999 V2000
   -1.4233   -2.7140   -1.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9251   -1.4964   -1.2604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3638   -1.2501   -1.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3276   -2.0667   -1.1616 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5174    0.1483   -1.3384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4083    0.6952   -0.6489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6215    0.6092    0.8475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0739    0.9242    1.0996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7829    2.1838    0.7649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7090    2.3689   -0.6092 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6629   -0.1014    1.6881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7241   -1.1744    1.8939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9850   -2.2978    2.4365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4414   -0.7392    1.3722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3410   -1.4707    1.3891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4303   -2.8298    1.9912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0146   -1.1094    0.8817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0907   -0.1219   -0.2234 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0555   -0.1393   -1.0599 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9258    0.9417   -1.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6462    1.9249   -0.4408 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1044    0.8384   -2.0537 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3559    1.0225   -1.2883 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8583    2.2895   -1.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0375    2.4242   -0.3622 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6689    1.3029    0.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8444    1.4535    0.8407 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1418    0.0396   -0.0971 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9705   -0.1281   -0.8100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2841   -0.1973   -1.1149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1056   -3.5434   -1.4921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3533   -2.9040   -1.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2606    1.7663   -0.9069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0497    1.4018    1.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3814    3.0491    1.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8559    2.0600    1.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5670    2.2021   -1.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7271   -0.1634    1.9946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4116   -3.2520    2.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7912   -2.7549    3.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0727   -3.5066    1.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5266   -2.0409    0.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5506   -0.6673    1.7339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0864    0.8850    0.2516 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0985   -0.1432   -2.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0077    1.6948   -2.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3910    3.1893   -1.4483 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4750    3.3884   -0.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9336    1.5753    1.8251 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6621   -0.8327    0.2991 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5495   -1.1073   -0.9890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0144    0.1894   -2.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  2  0
 18 30  1  0
 30  2  1  0
 30  6  1  0
 14  7  1  0
 29 23  1  0
  1 31  1  0
  1 32  1  0
  6 33  1  0
  7 34  1  0
  9 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 22 45  1  0
 22 46  1  0
 24 47  1  0
 25 48  1  0
 27 49  1  0
 28 50  1  0
 29 51  1  0
 30 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Intybin	HMDB, MeSH
Lactucopicrin	HMDB
9-(Hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-2H,3H,3ah,4H,5H,7H,9ah,9BH-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetic acid	Generator
Lactucopicrin3,3a,4,5,9a,9b-hexahydro-4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methyleneazuleno(4,5-b)furan-2,7-dione p-hydroxyphenylacetate hydrate	MeSH

Chemical Formula

C₂₃H₂₂O₇

Average Molecular Weight

410.4166

Monoisotopic Molecular Weight

410.136553058

IUPAC Name

9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate

Traditional Name

9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate

CAS Registry Number

65725-11-3

SMILES

CC1=C2C(C3OC(=O)C(=C)C3C(C1)OC(=O)CC1=CC=C(O)C=C1)C(CO)=CC2=O

InChI Identifier

InChI=1S/C23H22O7/c1-11-7-17(29-18(27)8-13-3-5-15(25)6-4-13)20-12(2)23(28)30-22(20)21-14(10-24)9-16(26)19(11)21/h3-6,9,17,20-22,24-25H,2,7-8,10H2,1H3

InChI Key

UMVSOHBRAQTGQI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

1-hydroxy-2-unsubstituted benzenoids

Direct Parent

1-hydroxy-2-unsubstituted benzenoids

Alternative Parents

Substituents

1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Primary alcohol
Organooxygen 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: HMDB0035828)

Source

Endogenous

Endogenous (HMDB: HMDB0035828)

Plant

Plant (HMDB: HMDB0035828)
Coffea (HMDB: HMDB0035828)

Animal

Animal (HMDB: HMDB0035828)

Exogenous

Food

Food (HMDB: HMDB0035828)

Vegetable

Leaf vegetable

Root vegetable

Chicory (FooDB: FOOD00049)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0035828)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0035828)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0035828)

Lipid metabolism pathway (HMDB: HMDB0035828)

Cellular process

Cell signaling (HMDB: HMDB0035828)

Biochemical process

Lipid transport (HMDB: HMDB0035828)

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	132 - 178 °C	Not Available
Boiling Point	686.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	3777 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.240 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.088 g/L	ALOGPS
logP	1.99	ALOGPS
logP	1.95	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	6.52	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	107.72 m³·mol⁻¹	ChemAxon
Polarizability	41.18 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]+	196.161	31661259
DarkChem	[M-H]-	189.672	31661259
DeepCCS	[M+H]+	192.335	30932474
DeepCCS	[M-H]-	189.977	30932474
DeepCCS	[M-2H]-	224.044	30932474
DeepCCS	[M+Na]+	199.188	30932474
AllCCS	[M+H]+	197.3	32859911
AllCCS	[M+H-H2O]+	194.9	32859911
AllCCS	[M+NH4]+	199.5	32859911
AllCCS	[M+Na]+	200.2	32859911
AllCCS	[M-H]-	194.4	32859911
AllCCS	[M+Na-2H]-	194.5	32859911
AllCCS	[M+HCOO]-	194.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.83 minutes	32390414
Predicted by Siyang on May 30, 2022	12.4439 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.63 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2449.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	214.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	170.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	164.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	94.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	501.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	512.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	119.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	999.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	483.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1475.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	329.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	391.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	290.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	155.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	86.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lactupicrin	CC1=C2C(C3OC(=O)C(=C)C3C(C1)OC(=O)CC1=CC=C(O)C=C1)C(CO)=CC2=O	5226.5	Standard polar	33892256
Lactupicrin	CC1=C2C(C3OC(=O)C(=C)C3C(C1)OC(=O)CC1=CC=C(O)C=C1)C(CO)=CC2=O	3254.5	Standard non polar	33892256
Lactupicrin	CC1=C2C(C3OC(=O)C(=C)C3C(C1)OC(=O)CC1=CC=C(O)C=C1)C(CO)=CC2=O	3873.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lactupicrin,1TMS,isomer #1	C=C1C(=O)OC2C3C(CO)=CC(=O)C3=C(C)CC(OC(=O)CC3=CC=C(O[Si](C)(C)C)C=C3)C12	3608.1	Semi standard non polar	33892256
Lactupicrin,1TMS,isomer #2	C=C1C(=O)OC2C3C(CO[Si](C)(C)C)=CC(=O)C3=C(C)CC(OC(=O)CC3=CC=C(O)C=C3)C12	3567.0	Semi standard non polar	33892256
Lactupicrin,2TMS,isomer #1	C=C1C(=O)OC2C3C(CO[Si](C)(C)C)=CC(=O)C3=C(C)CC(OC(=O)CC3=CC=C(O[Si](C)(C)C)C=C3)C12	3620.3	Semi standard non polar	33892256
Lactupicrin,1TBDMS,isomer #1	C=C1C(=O)OC2C3C(CO)=CC(=O)C3=C(C)CC(OC(=O)CC3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)C12	3784.8	Semi standard non polar	33892256
Lactupicrin,1TBDMS,isomer #2	C=C1C(=O)OC2C3C(CO[Si](C)(C)C(C)(C)C)=CC(=O)C3=C(C)CC(OC(=O)CC3=CC=C(O)C=C3)C12	3769.8	Semi standard non polar	33892256
Lactupicrin,2TBDMS,isomer #1	C=C1C(=O)OC2C3C(CO[Si](C)(C)C(C)(C)C)=CC(=O)C3=C(C)CC(OC(=O)CC3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)C12	3991.9	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 - Lactupicrin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-1902000000-447da619a6ca571ad014	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lactupicrin GC-MS (2 TMS) - 70eV, Positive	splash10-004i-1920210000-c224ca80e51775b73faa	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lactupicrin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lactupicrin 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 - Lactupicrin 10V, Positive-QTOF	splash10-01p6-0449400000-0930a4dc1fe6b942c8df	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lactupicrin 20V, Positive-QTOF	splash10-052r-0964000000-d7776f7f46c493e2bfbb	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lactupicrin 40V, Positive-QTOF	splash10-0a4r-2930000000-33f79bf051b7b71011fc	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lactupicrin 10V, Negative-QTOF	splash10-0a4i-0367900000-596fcf399a87d2bc872b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lactupicrin 20V, Negative-QTOF	splash10-0a7i-0596100000-f219cb9416848503d0df	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lactupicrin 40V, Negative-QTOF	splash10-001i-1960000000-0202858172af131c5198	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lactupicrin 10V, Negative-QTOF	splash10-0a6r-0591600000-872925ccdb6386245209	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lactupicrin 20V, Negative-QTOF	splash10-0a4i-0980100000-302d9ac7f387b3c8e311	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lactupicrin 40V, Negative-QTOF	splash10-0a6v-0291000000-6eb4afe572f7ac2b5c38	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lactupicrin 10V, Positive-QTOF	splash10-0a4i-0090000000-b2357ac73f1167a2b48d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lactupicrin 20V, Positive-QTOF	splash10-0a4l-0290000000-a2ea6f22cbd95999d34d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lactupicrin 40V, Positive-QTOF	splash10-004i-8892000000-59de1dd3685ff0a79fb2	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3482908

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1699951

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Lactupicrin (HMDB0035828)

MOL for HMDB0035828 (Lactupicrin)

3D MOL for HMDB0035828 (Lactupicrin)

3D SDF for HMDB0035828 (Lactupicrin)

3D-SDF for HMDB0035828 (Lactupicrin)

PDB for HMDB0035828 (Lactupicrin)

3D PDB for HMDB0035828 (Lactupicrin)

SMILES for HMDB0035828 (Lactupicrin)

INCHI for HMDB0035828 (Lactupicrin)

Structure for HMDB0035828 (Lactupicrin)

3D Structure for HMDB0035828 (Lactupicrin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra