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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 03:05:58 UTC

Update Date

2021-09-23 03:05:58 UTC

HMDB ID

HMDB0301857

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Arctiopicrin

Description

Arctiopicrin belongs to germacranolides and derivatives class of compounds. Those are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Arctiopicrin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Arctiopicrin can be found in burdock, which makes arctiopicrin a potential biomarker for the consumption of this food product.

Structure

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

HMDB0301857
     RDKit          3D
Arctiopicrin
 51 52  0  0  0  0  0  0  0  0999 V2000
   -1.4428   -2.7227   -1.4603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2618   -2.1947   -1.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9151   -2.5007   -2.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0017   -2.9663   -3.2498 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0550   -2.1795   -1.3303 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6663   -1.1939   -0.3992 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2885   -1.5406    0.9097 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2107   -0.8406    1.5193 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7245   -1.3463    2.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0832   -1.5798    2.7570 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7440    0.4217    0.9309 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9340    1.5668    1.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2636    2.3651    0.4154 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0187    2.1328    0.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4340    2.9855   -1.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1347    1.0945    0.6089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4380    0.1476   -0.4229 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8438    0.0826   -0.2824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7138    0.4332   -1.3043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730    0.8114   -2.3793 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1741    0.3835   -1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7318   -0.9841   -0.8719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7067    1.4136   -0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2094    1.2467    1.0703 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1545   -1.2201   -0.2894 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2692   -2.4496   -0.8275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6253   -3.4444   -2.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0187   -0.2316   -0.8136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8977   -2.4779    1.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2421   -2.3078    3.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5370   -0.5451    3.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4938   -1.3598    1.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8168    0.4215   -0.1563 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8158    0.4631    1.2917 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2418    1.2657    2.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6651    2.2542    1.9982 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8566    3.1667   -0.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8337    4.0207   -1.0128 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7034    2.5933   -2.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6630    3.0676   -0.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6918    1.6247    1.1680 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6313    0.4663    1.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2399    0.5044   -1.4610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6297    0.6693   -2.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5271   -1.6496   -1.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8272   -0.8755   -0.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3017   -1.3906    0.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8251    1.2608   -0.1818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5648    2.4417   -0.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4224    0.3217    1.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0999   -1.6255    0.7140 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  2  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 17 25  1  0
 25  2  1  0
 25  6  1  0
  1 26  1  0
  1 27  1  0
  6 28  1  6
  7 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 15 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  6
 21 44  1  0
 22 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
 25 51  1  1
M  END


  Mrv0541 02241220542D          

 25 26  0  0  1  0            999 V2000
    0.0244    0.0423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4369    0.7568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1014    1.5105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2574    0.8430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8094    0.2299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0934    2.5463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 12 20  1  0  0  0  0
  4 20  1  0  0  0  0
 20 21  1  1  0  0  0
  2 21  1  0  0  0  0
 21 22  2  0  0  0  0
 10 23  1  0  0  0  0
  6 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0301857

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(CO)C(=O)O[C@H]1C\C(C)=C\CC\C(CO)=C\[C@H]2OC(=O)C(=C)[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O6/c1-11-5-4-6-14(10-21)8-16-17(13(3)19(23)25-16)15(7-11)24-18(22)12(2)9-20/h5,8,12,15-17,20-21H,3-4,6-7,9-10H2,1-2H3/b11-5+,14-8-/t12?,15-,16+,17+/m0/s1

> <INCHI_KEY>
VOOFFTMORIBISQ-UMRVURNHSA-N

> <FORMULA>
C19H26O6

> <MOLECULAR_WEIGHT>
350.4061

> <EXACT_MASS>
350.172938564

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
36.34875687163985

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4S,11aR)-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl 3-hydroxy-2-methylpropanoate

> <ALOGPS_LOGP>
1.53

> <JCHEM_LOGP>
1.594110069000001

> <ALOGPS_LOGS>
-2.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.89264238533444

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.19448414100946

> <JCHEM_PKA_STRONGEST_BASIC>
-2.692959934342225

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
93.4194

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.75e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
arctiopicrin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0301857
     RDKit          3D
Arctiopicrin
 51 52  0  0  0  0  0  0  0  0999 V2000
   -1.4428   -2.7227   -1.4603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2618   -2.1947   -1.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9151   -2.5007   -2.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0017   -2.9663   -3.2498 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0550   -2.1795   -1.3303 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6663   -1.1939   -0.3992 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2885   -1.5406    0.9097 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2107   -0.8406    1.5193 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7245   -1.3463    2.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0832   -1.5798    2.7570 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7440    0.4217    0.9309 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9340    1.5668    1.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2636    2.3651    0.4154 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0187    2.1328    0.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4340    2.9855   -1.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1347    1.0945    0.6089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4380    0.1476   -0.4229 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8438    0.0826   -0.2824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7138    0.4332   -1.3043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730    0.8114   -2.3793 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1741    0.3835   -1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7318   -0.9841   -0.8719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7067    1.4136   -0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2094    1.2467    1.0703 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1545   -1.2201   -0.2894 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2692   -2.4496   -0.8275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6253   -3.4444   -2.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0187   -0.2316   -0.8136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8977   -2.4779    1.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2421   -2.3078    3.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5370   -0.5451    3.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4938   -1.3598    1.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8168    0.4215   -0.1563 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8158    0.4631    1.2917 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2418    1.2657    2.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6651    2.2542    1.9982 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8566    3.1667   -0.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8337    4.0207   -1.0128 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7034    2.5933   -2.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6630    3.0676   -0.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6918    1.6247    1.1680 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6313    0.4663    1.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2399    0.5044   -1.4610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6297    0.6693   -2.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5271   -1.6496   -1.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8272   -0.8755   -0.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3017   -1.3906    0.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8251    1.2608   -0.1818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5648    2.4417   -0.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4224    0.3217    1.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0999   -1.6255    0.7140 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  2  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 17 25  1  0
 25  2  1  0
 25  6  1  0
  1 26  1  0
  1 27  1  0
  6 28  1  6
  7 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 15 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  6
 21 44  1  0
 22 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
 25 51  1  1
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  O   UNK     0       0.046   0.079   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.816   1.413   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.189   2.820   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.335   3.080   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.668   5.390   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.669   3.080   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.347   1.574   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.378   0.429   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.041   4.753   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   20                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   24                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   23                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20   12    4   21                                                  
CONECT   21   20    2   22                                                  
CONECT   22   21                                                            
CONECT   23   10                                                            
CONECT   24    6   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

COMPND    HMDB0301857
HETATM    1  C1  UNL     1      -1.443  -2.723  -1.460  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.262  -2.195  -1.286  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.915  -2.501  -2.088  1.00  0.00           C  
HETATM    4  O1  UNL     1       1.002  -2.966  -3.250  1.00  0.00           O  
HETATM    5  O2  UNL     1       2.055  -2.180  -1.330  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.666  -1.194  -0.399  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.289  -1.541   0.910  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.211  -0.841   1.519  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.724  -1.346   2.841  1.00  0.00           C  
HETATM   10  O3  UNL     1       5.083  -1.580   2.757  1.00  0.00           O  
HETATM   11  C8  UNL     1       3.744   0.422   0.931  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.934   1.567   1.501  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.264   2.365   0.415  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.019   2.133   0.039  1.00  0.00           C  
HETATM   15  C12 UNL     1       0.434   2.986  -1.058  1.00  0.00           C  
HETATM   16  C13 UNL     1       0.135   1.095   0.609  1.00  0.00           C  
HETATM   17  C14 UNL     1      -0.438   0.148  -0.423  1.00  0.00           C  
HETATM   18  O4  UNL     1      -1.844   0.083  -0.282  1.00  0.00           O  
HETATM   19  C15 UNL     1      -2.714   0.433  -1.304  1.00  0.00           C  
HETATM   20  O5  UNL     1      -2.173   0.811  -2.379  1.00  0.00           O  
HETATM   21  C16 UNL     1      -4.174   0.383  -1.182  1.00  0.00           C  
HETATM   22  C17 UNL     1      -4.732  -0.984  -0.872  1.00  0.00           C  
HETATM   23  C18 UNL     1      -4.707   1.414  -0.202  1.00  0.00           C  
HETATM   24  O6  UNL     1      -4.209   1.247   1.070  1.00  0.00           O  
HETATM   25  C19 UNL     1       0.155  -1.220  -0.289  1.00  0.00           C  
HETATM   26  H1  UNL     1      -2.269  -2.450  -0.828  1.00  0.00           H  
HETATM   27  H2  UNL     1      -1.625  -3.444  -2.240  1.00  0.00           H  
HETATM   28  H3  UNL     1       2.019  -0.232  -0.814  1.00  0.00           H  
HETATM   29  H4  UNL     1       1.898  -2.478   1.353  1.00  0.00           H  
HETATM   30  H5  UNL     1       3.242  -2.308   3.104  1.00  0.00           H  
HETATM   31  H6  UNL     1       3.537  -0.545   3.587  1.00  0.00           H  
HETATM   32  H7  UNL     1       5.494  -1.360   1.906  1.00  0.00           H  
HETATM   33  H8  UNL     1       3.817   0.422  -0.156  1.00  0.00           H  
HETATM   34  H9  UNL     1       4.816   0.463   1.292  1.00  0.00           H  
HETATM   35  H10 UNL     1       2.242   1.266   2.301  1.00  0.00           H  
HETATM   36  H11 UNL     1       3.665   2.254   1.998  1.00  0.00           H  
HETATM   37  H12 UNL     1       2.857   3.167  -0.066  1.00  0.00           H  
HETATM   38  H13 UNL     1       0.834   4.021  -1.013  1.00  0.00           H  
HETATM   39  H14 UNL     1       0.703   2.593  -2.054  1.00  0.00           H  
HETATM   40  H15 UNL     1      -0.663   3.068  -0.912  1.00  0.00           H  
HETATM   41  H16 UNL     1      -0.692   1.625   1.168  1.00  0.00           H  
HETATM   42  H17 UNL     1       0.631   0.466   1.373  1.00  0.00           H  
HETATM   43  H18 UNL     1      -0.240   0.504  -1.461  1.00  0.00           H  
HETATM   44  H19 UNL     1      -4.630   0.669  -2.171  1.00  0.00           H  
HETATM   45  H20 UNL     1      -4.527  -1.650  -1.732  1.00  0.00           H  
HETATM   46  H21 UNL     1      -5.827  -0.875  -0.795  1.00  0.00           H  
HETATM   47  H22 UNL     1      -4.302  -1.391   0.069  1.00  0.00           H  
HETATM   48  H23 UNL     1      -5.825   1.261  -0.182  1.00  0.00           H  
HETATM   49  H24 UNL     1      -4.565   2.442  -0.580  1.00  0.00           H  
HETATM   50  H25 UNL     1      -4.422   0.322   1.352  1.00  0.00           H  
HETATM   51  H26 UNL     1      -0.100  -1.625   0.714  1.00  0.00           H  
CONECT    1    2    2   26   27
CONECT    2    3   25
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   25   28
CONECT    7    8    8   29
CONECT    8    9   11
CONECT    9   10   30   31
CONECT   10   32
CONECT   11   12   33   34
CONECT   12   13   35   36
CONECT   13   14   14   37
CONECT   14   15   16
CONECT   15   38   39   40
CONECT   16   17   41   42
CONECT   17   18   25   43
CONECT   18   19
CONECT   19   20   20   21
CONECT   21   22   23   44
CONECT   22   45   46   47
CONECT   23   24   48   49
CONECT   24   50
CONECT   25   51
END

HMDB0301857
     RDKit          3D
Arctiopicrin
 51 52  0  0  0  0  0  0  0  0999 V2000
   -1.4428   -2.7227   -1.4603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2618   -2.1947   -1.2856 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9151   -2.5007   -2.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0017   -2.9663   -3.2498 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0550   -2.1795   -1.3303 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6663   -1.1939   -0.3992 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2885   -1.5406    0.9097 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2107   -0.8406    1.5193 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7245   -1.3463    2.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0832   -1.5798    2.7570 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7440    0.4217    0.9309 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9340    1.5668    1.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2636    2.3651    0.4154 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0187    2.1328    0.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4340    2.9855   -1.0576 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1347    1.0945    0.6089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4380    0.1476   -0.4229 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8438    0.0826   -0.2824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7138    0.4332   -1.3043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730    0.8114   -2.3793 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1741    0.3835   -1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7318   -0.9841   -0.8719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7067    1.4136   -0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2094    1.2467    1.0703 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1545   -1.2201   -0.2894 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2692   -2.4496   -0.8275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6253   -3.4444   -2.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0187   -0.2316   -0.8136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8977   -2.4779    1.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2421   -2.3078    3.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5370   -0.5451    3.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4938   -1.3598    1.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8168    0.4215   -0.1563 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8158    0.4631    1.2917 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2418    1.2657    2.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6651    2.2542    1.9982 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8566    3.1667   -0.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8337    4.0207   -1.0128 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7034    2.5933   -2.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6630    3.0676   -0.9122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6918    1.6247    1.1680 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6313    0.4663    1.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2399    0.5044   -1.4610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6297    0.6693   -2.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5271   -1.6496   -1.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8272   -0.8755   -0.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3017   -1.3906    0.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8251    1.2608   -0.1818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5648    2.4417   -0.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4224    0.3217    1.3524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0999   -1.6255    0.7140 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  2  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 17 25  1  0
 25  2  1  0
 25  6  1  0
  1 26  1  0
  1 27  1  0
  6 28  1  6
  7 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 15 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  6
 21 44  1  0
 22 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
 25 51  1  1
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₉H₂₆O₆

Average Molecular Weight

350.4061

Monoisotopic Molecular Weight

350.172938564

IUPAC Name

(3aR,4S,11aR)-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl 3-hydroxy-2-methylpropanoate

Traditional Name

arctiopicrin

CAS Registry Number

Not Available

SMILES

CC(CO)C(=O)O[C@H]1C\C(C)=C\CC\C(CO)=C\[C@H]2OC(=O)C(=C)[C@H]12

InChI Identifier

InChI=1S/C19H26O6/c1-11-5-4-6-14(10-21)8-16-17(13(3)19(23)25-16)15(7-11)24-18(22)12(2)9-20/h5,8,12,15-17,20-21H,3-4,6-7,9-10H2,1-2H3/b11-5+,14-8-/t12?,15-,16+,17+/m0/s1

InChI Key

VOOFFTMORIBISQ-UMRVURNHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Germacrane sesquiterpenoid
Sesquiterpenoid
Beta-hydroxy acid
Dicarboxylic acid or derivatives
Gamma butyrolactone
Hydroxy acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Primary alcohol
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

germacranolide (CHEBI:2810 )
Germacrenes (C09297 )

Ontology

Not Available

Burdock (FooDB: FOOD00017)

Process

Not Available

Role

Biological role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

antibiotic (HMDB: HMDB0301857)

Agriculture

Pesticide

Insecticide

pesticide (HMDB: HMDB0301857)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.53	ALOGPS
logP	1.59	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	6.19	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	93.42 m³·mol⁻¹	ChemAxon
Polarizability	36.35 Å³	ChemAxon
Number of Rings	2	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]+	184.868	32859911
AllCCS	[M+H-H2O]+	182.023	32859911
AllCCS	[M+Na]+	188.248	32859911
AllCCS	[M+NH4]+	187.495	32859911
AllCCS	[M-H]-	184.551	32859911
AllCCS	[M+Na-2H]-	185.001	32859911
AllCCS	[M+HCOO]-	185.633	32859911
DeepCCS	[M-2H]-	225.384	30932474
DeepCCS	[M+Na]+	201.171	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 - Arctiopicrin 10V, Negative-QTOF	splash10-0002-0019000000-9f11535b555d9419b4e5	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arctiopicrin 20V, Negative-QTOF	splash10-0pwa-4159000000-cab34407a76bf2e6749c	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arctiopicrin 40V, Negative-QTOF	splash10-0pbi-5930000000-0035e2e8f0c39f71f7fd	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arctiopicrin 10V, Negative-QTOF	splash10-000j-9232000000-7f20cecc951b6e6d5860	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arctiopicrin 20V, Negative-QTOF	splash10-00dr-9010000000-5b615e6bc4cc8f907e64	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arctiopicrin 40V, Negative-QTOF	splash10-05mk-4090000000-bfdd537bdd238ce9c5bc	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arctiopicrin 10V, Positive-QTOF	splash10-0f89-2039000000-68c42594e4b85bd072bc	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arctiopicrin 20V, Positive-QTOF	splash10-00ns-6197000000-e93d0da833f4bb338a3e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arctiopicrin 40V, Positive-QTOF	splash10-052r-9110000000-d5cd0917bfa8221b6edc	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arctiopicrin 10V, Positive-QTOF	splash10-0002-0090000000-ec632ef45f55ea86b2c7	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arctiopicrin 20V, Positive-QTOF	splash10-0002-0090000000-9aea08757b7861de4ebd	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arctiopicrin 40V, Positive-QTOF	splash10-006t-4090000000-e0691aedac3acf6bd88f	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281423

PDB ID

Not Available

ChEBI ID

2810

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1814231

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Arctiopicrin (HMDB0301857)

MOL for HMDB0301857 (Arctiopicrin)

3D MOL for HMDB0301857 (Arctiopicrin)

3D SDF for HMDB0301857 (Arctiopicrin)

3D-SDF for HMDB0301857 (Arctiopicrin)

PDB for HMDB0301857 (Arctiopicrin)

3D PDB for HMDB0301857 (Arctiopicrin)

SMILES for HMDB0301857 (Arctiopicrin)

INCHI for HMDB0301857 (Arctiopicrin)

Structure for HMDB0301857 (Arctiopicrin)

3D Structure for HMDB0301857 (Arctiopicrin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra