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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:43:07 UTC

Update Date

2022-03-07 02:54:57 UTC

HMDB ID

HMDB0036562

Secondary Accession Numbers

HMDB36562

Metabolite Identification

Common Name

Aucubin

Description

Aucubin is found in common verbena. Aucubin is a monoterpenoid based compound. Aucubin, like all iridoids, has a cyclopentan-[C]-pyran skeleton. Iridoids can consist of ten, nine, or rarely eight carbons in which C11 is more frequently missing than C10. Aucubin has 10 carbons with the C11 carbon missing. The stereochemical configurations at C5 and C9 lead to cis fused rings, which are common to all iridoids containing carbocylclic- or seco-skeleton in non-rearranged form. Oxidative cleavage at C7-C8 bond affords secoiridoids. The last steps in the biosynthesis of iridoids usually consist of O-glycosylation and O-alkylation. Aucubin, a glycoside iridoid, has an O-linked glucose moiety. Aucubin is an iridoid glycoside. Iridoids are commonly found in plants and function as defensive compounds. Irioids decrease the growth rates of many generalist herbivores. Aucubin is found in the leaves of Aucuba japonica (Cornaceae), Eucommia ulmoides (Eucommiaceae), and Plantago asiatic (Plantaginaceae), etc, plants used in traditional Chinese and folk medicine. Aucubin was found to protect against liver damage induced by carbon tetrachloride or alpha-amanitin in mice and rats when 80 mg/kg was dosed intraperitoneally. Geranyl pyrophosphate is the precursor for iridoids. Geranyl phosphate is generated through the mevalonate pathway or the methylerythritol phosphate pathway. The initial steps of the pathway involve the fusion of three molecules of acetyl-CoA to produce the C6 compound 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA). HMG-CoA is then reduced in two steps by the enzyme HMG-CoA reductase. The resulting mevalonate is then sequentially phosphorylated by two separate kinases, mevalonate kinase and phosphomevalonate kinase, to form 5-pyrophosphomevalonate. Phosphosphomevalonate decarboxylase through a concerted decarboxylation reaction affords isopentenyl pyrophosphate (IPP). IPP is the basic C5 building block that is added to prenyl phosphate cosubstrates to form longer chains. IPP is isomerized to the allylic ester dimethylallyl pyrophosphate (DMAPP) by IPP isomerase. Through a multistep process, including the dephosphorylation DMAPP, IPP and DMAPP are combinded to from the C10 compound geranyl pyrophosphate (GPP). Geranyl pyrophosphate is a major branch point for terpenoid synthesis. The cyclizaton reaction to form the iridoid pyrane ring may result from one of two routes: route 1 - a hydride nucleophillic attack on C1 will lead to 1-O-carbonyl atom attack on C3, yielding the lactone ring; route 2 - loss of proton from carbon 4 leads to the formation of a double bond C3-C4; consequently the 3-0-carbonyl atom will attach to C1

Structure

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

HMDB0036562
     RDKit          3D
Aucubin
 46 48  0  0  0  0  0  0  0  0999 V2000
    1.6773    0.4050    2.0485 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4436    1.3108    1.3379 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9716    0.6191    0.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2666    0.4699   -0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4684   -0.2785   -1.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7015    0.5508   -2.4663 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1794   -1.0540   -1.4655 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7313   -1.3855   -2.8151 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4390   -1.6846   -2.8839 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7156   -1.6403   -1.6868 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9305   -0.6066   -0.6932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1998    0.2061   -0.8350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0182    0.0002    0.2800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1682   -0.6010   -0.1617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2264   -0.6567    0.7007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3205   -1.4877    0.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8911   -2.7729   -0.2012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7341    0.7354    1.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0661    0.8035    2.3859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6798    1.7602    0.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7141    2.0933   -0.6774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2924    1.2299    1.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3276    0.8910    2.4248 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2212    0.0409   -0.9676 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5972    0.6646    3.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.6477    2.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8396    2.1962    1.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0775    0.8276    0.5062 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3143   -0.9789   -1.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8026    0.0185   -3.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1575   -1.9148   -0.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3756   -1.3869   -3.6479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9762   -1.9499   -3.8339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9426   -1.1492    0.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5189   -0.7450    0.9678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9141   -1.1333    1.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5633   -0.9817   -0.9059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2283   -1.5678    0.7098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1297   -2.8119   -0.8433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6376    0.9195    0.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7293    0.0404    2.9192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8473    2.6496    1.2912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6449    2.2802   -0.9510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5373    2.0393    0.9678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8152    1.5852    2.9152 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0962    0.8021   -1.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 11 24  1  0
 24  3  1  0
 24  7  1  0
 22 13  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  4 28  1  0
  5 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
 11 34  1  0
 13 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
 23 45  1  0
 24 46  1  0
M  END


  Mrv1652307201900032D          

 24 26  0  0  0  0            999 V2000
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1536    3.5881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279    3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.0709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    5.6479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  6  3  2  0  0  0  0
  6  4  1  0  0  0  0
  7  1  1  0  0  0  0
  8  3  1  0  0  0  0
  8  7  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  9  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 10  1  0  0  0  0
 15 13  1  0  0  0  0
 16  4  1  0  0  0  0
 17  5  1  0  0  0  0
 18  8  1  0  0  0  0
 19 11  1  0  0  0  0
 20 12  1  0  0  0  0
 21 13  1  0  0  0  0
 22  2  1  0  0  0  0
 22 14  1  0  0  0  0
 23  9  1  0  0  0  0
 23 15  1  0  0  0  0
 24 14  1  0  0  0  0
 24 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036562

> <DATABASE_NAME>
hmdb

> <SMILES>
OCC1OC(OC2OC=CC3C(O)C=C(CO)C23)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O9/c16-4-6-3-8(18)7-1-2-22-14(10(6)7)24-15-13(21)12(20)11(19)9(5-17)23-15/h1-3,7-21H,4-5H2

> <INCHI_KEY>
RJWJHRPNHPHBRN-UHFFFAOYSA-N

> <FORMULA>
C15H22O9

> <MOLECULAR_WEIGHT>
346.3298

> <EXACT_MASS>
346.126382302

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
33.65277119493116

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[5-hydroxy-7-(hydroxymethyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-2.14

> <JCHEM_LOGP>
-3.181869902333333

> <ALOGPS_LOGS>
-0.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.17414390825667

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.204139846240158

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7414455018345434

> <JCHEM_POLAR_SURFACE_AREA>
149.07

> <JCHEM_REFRACTIVITY>
79.1768

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.00e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
aucubin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036562
     RDKit          3D
Aucubin
 46 48  0  0  0  0  0  0  0  0999 V2000
    1.6773    0.4050    2.0485 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4436    1.3108    1.3379 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9716    0.6191    0.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2666    0.4699   -0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4684   -0.2785   -1.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7015    0.5508   -2.4663 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1794   -1.0540   -1.4655 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7313   -1.3855   -2.8151 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4390   -1.6846   -2.8839 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7156   -1.6403   -1.6868 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9305   -0.6066   -0.6932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1998    0.2061   -0.8350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0182    0.0002    0.2800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1682   -0.6010   -0.1617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2264   -0.6567    0.7007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3205   -1.4877    0.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8911   -2.7729   -0.2012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7341    0.7354    1.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0661    0.8035    2.3859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6798    1.7602    0.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7141    2.0933   -0.6774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2924    1.2299    1.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3276    0.8910    2.4248 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2212    0.0409   -0.9676 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5972    0.6646    3.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.6477    2.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8396    2.1962    1.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0775    0.8276    0.5062 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3143   -0.9789   -1.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8026    0.0185   -3.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1575   -1.9148   -0.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3756   -1.3869   -3.6479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9762   -1.9499   -3.8339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9426   -1.1492    0.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5189   -0.7450    0.9678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9141   -1.1333    1.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5633   -0.9817   -0.9059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2283   -1.5678    0.7098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1297   -2.8119   -0.8433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6376    0.9195    0.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7293    0.0404    2.9192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8473    2.6496    1.2912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6449    2.2802   -0.9510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5373    2.0393    0.9678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8152    1.5852    2.9152 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0962    0.8021   -1.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 11 24  1  0
 24  3  1  0
 24  7  1  0
 22 13  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  4 28  1  0
  5 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
 11 34  1  0
 13 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
 23 45  1  0
 24 46  1  0
M  END

HEADER    PROTEIN                                 20-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUL-19         0                                  
HETATM    1  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.744   5.553   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.865   5.923   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.268   4.089   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.268   1.597   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.531   6.693   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.531   8.233   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.198   9.003   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.864   8.233   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.864   6.693   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.287   6.698   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       9.199   6.693   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -0.744   0.132   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       7.865   9.003   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.198  10.543   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.530   9.003   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.864   3.613   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.198   5.923   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.530   5.923   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1   22                                                       
CONECT    3    6    8                                                       
CONECT    4    6   16                                                       
CONECT    5    9   17                                                       
CONECT    6    3    4   10                                                  
CONECT    7    1    8   10                                                  
CONECT    8    3    7   18                                                  
CONECT    9    5   11   23                                                  
CONECT   10    6    7   14                                                  
CONECT   11    9   12   19                                                  
CONECT   12   11   13   20                                                  
CONECT   13   12   15   21                                                  
CONECT   14   10   22   24                                                  
CONECT   15   13   23   24                                                  
CONECT   16    4                                                            
CONECT   17    5                                                            
CONECT   18    8                                                            
CONECT   19   11                                                            
CONECT   20   12                                                            
CONECT   21   13                                                            
CONECT   22    2   14                                                       
CONECT   23    9   15                                                       
CONECT   24   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0036562
HETATM    1  O1  UNL     1       1.677   0.405   2.048  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.444   1.311   1.338  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.972   0.619   0.134  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.267   0.470  -0.117  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.468  -0.278  -1.413  1.00  0.00           C  
HETATM    6  O2  UNL     1       4.702   0.551  -2.466  1.00  0.00           O  
HETATM    7  C5  UNL     1       3.179  -1.054  -1.466  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.731  -1.385  -2.815  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.439  -1.685  -2.884  1.00  0.00           C  
HETATM   10  O3  UNL     1       0.716  -1.640  -1.687  1.00  0.00           O  
HETATM   11  C8  UNL     1       0.930  -0.607  -0.693  1.00  0.00           C  
HETATM   12  O4  UNL     1      -0.200   0.206  -0.835  1.00  0.00           O  
HETATM   13  C9  UNL     1      -1.018   0.000   0.280  1.00  0.00           C  
HETATM   14  O5  UNL     1      -2.168  -0.601  -0.162  1.00  0.00           O  
HETATM   15  C10 UNL     1      -3.226  -0.657   0.701  1.00  0.00           C  
HETATM   16  C11 UNL     1      -4.321  -1.488   0.068  1.00  0.00           C  
HETATM   17  O6  UNL     1      -3.891  -2.773  -0.201  1.00  0.00           O  
HETATM   18  C12 UNL     1      -3.734   0.735   1.054  1.00  0.00           C  
HETATM   19  O7  UNL     1      -4.066   0.803   2.386  1.00  0.00           O  
HETATM   20  C13 UNL     1      -2.680   1.760   0.654  1.00  0.00           C  
HETATM   21  O8  UNL     1      -2.714   2.093  -0.677  1.00  0.00           O  
HETATM   22  C14 UNL     1      -1.292   1.230   1.048  1.00  0.00           C  
HETATM   23  O9  UNL     1      -1.328   0.891   2.425  1.00  0.00           O  
HETATM   24  C15 UNL     1       2.221   0.041  -0.968  1.00  0.00           C  
HETATM   25  H1  UNL     1       1.597   0.665   3.017  1.00  0.00           H  
HETATM   26  H2  UNL     1       3.279   1.648   2.020  1.00  0.00           H  
HETATM   27  H3  UNL     1       1.840   2.196   1.029  1.00  0.00           H  
HETATM   28  H4  UNL     1       5.078   0.828   0.506  1.00  0.00           H  
HETATM   29  H5  UNL     1       5.314  -0.979  -1.217  1.00  0.00           H  
HETATM   30  H6  UNL     1       4.803   0.018  -3.293  1.00  0.00           H  
HETATM   31  H7  UNL     1       3.158  -1.915  -0.804  1.00  0.00           H  
HETATM   32  H8  UNL     1       3.376  -1.387  -3.648  1.00  0.00           H  
HETATM   33  H9  UNL     1       0.976  -1.950  -3.834  1.00  0.00           H  
HETATM   34  H10 UNL     1       0.943  -1.149   0.277  1.00  0.00           H  
HETATM   35  H11 UNL     1      -0.519  -0.745   0.968  1.00  0.00           H  
HETATM   36  H12 UNL     1      -2.914  -1.133   1.646  1.00  0.00           H  
HETATM   37  H13 UNL     1      -4.563  -0.982  -0.906  1.00  0.00           H  
HETATM   38  H14 UNL     1      -5.228  -1.568   0.710  1.00  0.00           H  
HETATM   39  H15 UNL     1      -3.130  -2.812  -0.843  1.00  0.00           H  
HETATM   40  H16 UNL     1      -4.638   0.920   0.454  1.00  0.00           H  
HETATM   41  H17 UNL     1      -3.729   0.040   2.919  1.00  0.00           H  
HETATM   42  H18 UNL     1      -2.847   2.650   1.291  1.00  0.00           H  
HETATM   43  H19 UNL     1      -3.645   2.280  -0.951  1.00  0.00           H  
HETATM   44  H20 UNL     1      -0.537   2.039   0.968  1.00  0.00           H  
HETATM   45  H21 UNL     1      -1.815   1.585   2.915  1.00  0.00           H  
HETATM   46  H22 UNL     1       2.096   0.802  -1.802  1.00  0.00           H  
CONECT    1    2   25
CONECT    2    3   26   27
CONECT    3    4    4   24
CONECT    4    5   28
CONECT    5    6    7   29
CONECT    6   30
CONECT    7    8   24   31
CONECT    8    9    9   32
CONECT    9   10   33
CONECT   10   11
CONECT   11   12   24   34
CONECT   12   13
CONECT   13   14   22   35
CONECT   14   15
CONECT   15   16   18   36
CONECT   16   17   37   38
CONECT   17   39
CONECT   18   19   20   40
CONECT   19   41
CONECT   20   21   22   42
CONECT   21   43
CONECT   22   23   44
CONECT   23   45
CONECT   24   46
END

HMDB0036562
     RDKit          3D
Aucubin
 46 48  0  0  0  0  0  0  0  0999 V2000
    1.6773    0.4050    2.0485 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4436    1.3108    1.3379 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9716    0.6191    0.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2666    0.4699   -0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4684   -0.2785   -1.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7015    0.5508   -2.4663 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1794   -1.0540   -1.4655 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7313   -1.3855   -2.8151 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4390   -1.6846   -2.8839 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7156   -1.6403   -1.6868 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9305   -0.6066   -0.6932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1998    0.2061   -0.8350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0182    0.0002    0.2800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1682   -0.6010   -0.1617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2264   -0.6567    0.7007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3205   -1.4877    0.0681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8911   -2.7729   -0.2012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7341    0.7354    1.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0661    0.8035    2.3859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6798    1.7602    0.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7141    2.0933   -0.6774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2924    1.2299    1.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3276    0.8910    2.4248 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2212    0.0409   -0.9676 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5972    0.6646    3.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.6477    2.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8396    2.1962    1.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0775    0.8276    0.5062 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3143   -0.9789   -1.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8026    0.0185   -3.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1575   -1.9148   -0.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3756   -1.3869   -3.6479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9762   -1.9499   -3.8339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9426   -1.1492    0.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5189   -0.7450    0.9678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9141   -1.1333    1.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5633   -0.9817   -0.9059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2283   -1.5678    0.7098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1297   -2.8119   -0.8433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6376    0.9195    0.4539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7293    0.0404    2.9192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8473    2.6496    1.2912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6449    2.2802   -0.9510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5373    2.0393    0.9678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8152    1.5852    2.9152 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0962    0.8021   -1.8018 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 11 24  1  0
 24  3  1  0
 24  7  1  0
 22 13  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  4 28  1  0
  5 29  1  0
  6 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
 11 34  1  0
 13 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
 23 45  1  0
 24 46  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Aucuboside	HMDB
Rhimantin	HMDB
Rhinanthin	HMDB

Chemical Formula

C₁₅H₂₂O₉

Average Molecular Weight

346.3298

Monoisotopic Molecular Weight

346.126382302

IUPAC Name

2-{[5-hydroxy-7-(hydroxymethyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

aucubin

CAS Registry Number

479-98-1

SMILES

OCC1OC(OC2OC=CC3C(O)C=C(CO)C23)C(O)C(O)C1O

InChI Identifier

InChI=1S/C15H22O9/c16-4-6-3-8(18)7-1-2-22-14(10(6)7)24-15-13(21)12(20)11(19)9(5-17)23-15/h1-3,7-21H,4-5H2

InChI Key

RJWJHRPNHPHBRN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoid o-glycosides. These are iridoid monoterpenes containing a glycosyl (usually a pyranosyl) moiety linked to the iridoid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Iridoid O-glycosides

Alternative Parents

Substituents

Iridoid o-glycoside
Hexose monosaccharide
Glycosyl compound
Iridoid-skeleton
O-glycosyl compound
Bicyclic monoterpenoid
Monoterpenoid
Monosaccharide
Oxane
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Hydrocarbon derivative
Primary alcohol
Organic oxygen compound
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036562)

Source

Endogenous

Endogenous (HMDB: HMDB0036562)

Plant

Plant (HMDB: HMDB0036562)

Animal

Animal (HMDB: HMDB0036562)

Exogenous

Food

Food (HMDB: HMDB0036562)

Herb and spice

Herb

Common verbena (FooDB: FOOD00196)

Exogenous (HMDB: HMDB0036562)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036562)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036562)

Lipid metabolism pathway (HMDB: HMDB0036562)

Cellular process

Cell signaling (HMDB: HMDB0036562)

Biochemical process

Lipid transport (HMDB: HMDB0036562)

Role

Industrial applicationBiological role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	181 °C	Not Available
Boiling Point	669.02 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	356 mg/mL at 20 °C	Not Available
LogP	-4.103 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	50 g/L	ALOGPS
logP	-2.1	ALOGPS
logP	-3.2	ChemAxon
logS	-0.84	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	149.07 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	79.18 m³·mol⁻¹	ChemAxon
Polarizability	33.65 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	178.748	31661259
DarkChem	[M-H]-	169.883	31661259
DeepCCS	[M-2H]-	208.195	30932474
DeepCCS	[M+Na]+	183.463	30932474
AllCCS	[M+H]+	180.0	32859911
AllCCS	[M+H-H2O]+	177.0	32859911
AllCCS	[M+NH4]+	182.7	32859911
AllCCS	[M+Na]+	183.5	32859911
AllCCS	[M-H]-	178.2	32859911
AllCCS	[M+Na-2H]-	177.7	32859911
AllCCS	[M+HCOO]-	177.3	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.	1.82 minutes	32390414
Predicted by Siyang on May 30, 2022	10.0905 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.41 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	260.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1097.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	219.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	58.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	177.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	54.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	294.3 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	293.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	591.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	651.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	104.1 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	899.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	210.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	203.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	500.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	387.1 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	230.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Aucubin	OCC1OC(OC2OC=CC3C(O)C=C(CO)C23)C(O)C(O)C1O	3842.3	Standard polar	33892256
Aucubin	OCC1OC(OC2OC=CC3C(O)C=C(CO)C23)C(O)C(O)C1O	2998.0	Standard non polar	33892256
Aucubin	OCC1OC(OC2OC=CC3C(O)C=C(CO)C23)C(O)C(O)C1O	3068.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Aucubin,1TMS,isomer #1	C[Si](C)(C)OCC1OC(OC2OC=CC3C(O)C=C(CO)C23)C(O)C(O)C1O	3036.7	Semi standard non polar	33892256
Aucubin,1TMS,isomer #2	C[Si](C)(C)OC1C=C(CO)C2C(OC3OC(CO)C(O)C(O)C3O)OC=CC12	3045.2	Semi standard non polar	33892256
Aucubin,1TMS,isomer #3	C[Si](C)(C)OCC1=CC(O)C2C=COC(OC3OC(CO)C(O)C(O)C3O)C12	3030.2	Semi standard non polar	33892256
Aucubin,1TMS,isomer #4	C[Si](C)(C)OC1C(OC2OC=CC3C(O)C=C(CO)C23)OC(CO)C(O)C1O	3004.2	Semi standard non polar	33892256
Aucubin,1TMS,isomer #5	C[Si](C)(C)OC1C(O)C(CO)OC(OC2OC=CC3C(O)C=C(CO)C23)C1O	2986.2	Semi standard non polar	33892256
Aucubin,1TMS,isomer #6	C[Si](C)(C)OC1C(CO)OC(OC2OC=CC3C(O)C=C(CO)C23)C(O)C1O	2991.9	Semi standard non polar	33892256
Aucubin,2TMS,isomer #1	C[Si](C)(C)OCC1OC(OC2OC=CC3C(O[Si](C)(C)C)C=C(CO)C23)C(O)C(O)C1O	3002.6	Semi standard non polar	33892256
Aucubin,2TMS,isomer #10	C[Si](C)(C)OCC1=CC(O)C2C=COC(OC3OC(CO)C(O[Si](C)(C)C)C(O)C3O)C12	2953.1	Semi standard non polar	33892256
Aucubin,2TMS,isomer #11	C[Si](C)(C)OCC1=CC(O)C2C=COC(OC3OC(CO)C(O)C(O[Si](C)(C)C)C3O)C12	2948.3	Semi standard non polar	33892256
Aucubin,2TMS,isomer #12	C[Si](C)(C)OCC1=CC(O)C2C=COC(OC3OC(CO)C(O)C(O)C3O[Si](C)(C)C)C12	2955.1	Semi standard non polar	33892256
Aucubin,2TMS,isomer #13	C[Si](C)(C)OC1C(CO)OC(OC2OC=CC3C(O)C=C(CO)C23)C(O[Si](C)(C)C)C1O	2947.4	Semi standard non polar	33892256
Aucubin,2TMS,isomer #14	C[Si](C)(C)OC1C(OC2OC=CC3C(O)C=C(CO)C23)OC(CO)C(O)C1O[Si](C)(C)C	2962.6	Semi standard non polar	33892256
Aucubin,2TMS,isomer #15	C[Si](C)(C)OC1C(CO)OC(OC2OC=CC3C(O)C=C(CO)C23)C(O)C1O[Si](C)(C)C	2956.6	Semi standard non polar	33892256
Aucubin,2TMS,isomer #2	C[Si](C)(C)OCC1=CC(O)C2C=COC(OC3OC(CO[Si](C)(C)C)C(O)C(O)C3O)C12	2979.0	Semi standard non polar	33892256
Aucubin,2TMS,isomer #3	C[Si](C)(C)OCC1OC(OC2OC=CC3C(O)C=C(CO)C23)C(O[Si](C)(C)C)C(O)C1O	2981.6	Semi standard non polar	33892256
Aucubin,2TMS,isomer #4	C[Si](C)(C)OCC1OC(OC2OC=CC3C(O)C=C(CO)C23)C(O)C(O[Si](C)(C)C)C1O	2977.0	Semi standard non polar	33892256
Aucubin,2TMS,isomer #5	C[Si](C)(C)OCC1OC(OC2OC=CC3C(O)C=C(CO)C23)C(O)C(O)C1O[Si](C)(C)C	2979.7	Semi standard non polar	33892256
Aucubin,2TMS,isomer #6	C[Si](C)(C)OCC1=CC(O[Si](C)(C)C)C2C=COC(OC3OC(CO)C(O)C(O)C3O)C12	2988.7	Semi standard non polar	33892256
Aucubin,2TMS,isomer #7	C[Si](C)(C)OC1C=C(CO)C2C(OC3OC(CO)C(O[Si](C)(C)C)C(O)C3O)OC=CC12	2978.7	Semi standard non polar	33892256
Aucubin,2TMS,isomer #8	C[Si](C)(C)OC1C=C(CO)C2C(OC3OC(CO)C(O)C(O[Si](C)(C)C)C3O)OC=CC12	2970.8	Semi standard non polar	33892256
Aucubin,2TMS,isomer #9	C[Si](C)(C)OC1C=C(CO)C2C(OC3OC(CO)C(O)C(O)C3O[Si](C)(C)C)OC=CC12	2994.6	Semi standard non polar	33892256
Aucubin,3TMS,isomer #1	C[Si](C)(C)OCC1=CC(O[Si](C)(C)C)C2C=COC(OC3OC(CO[Si](C)(C)C)C(O)C(O)C3O)C12	2918.0	Semi standard non polar	33892256
Aucubin,3TMS,isomer #10	C[Si](C)(C)OCC1OC(OC2OC=CC3C(O)C=C(CO)C23)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C	2923.1	Semi standard non polar	33892256
Aucubin,3TMS,isomer #11	C[Si](C)(C)OCC1=CC(O[Si](C)(C)C)C2C=COC(OC3OC(CO)C(O[Si](C)(C)C)C(O)C3O)C12	2947.0	Semi standard non polar	33892256
Aucubin,3TMS,isomer #12	C[Si](C)(C)OCC1=CC(O[Si](C)(C)C)C2C=COC(OC3OC(CO)C(O)C(O[Si](C)(C)C)C3O)C12	2935.5	Semi standard non polar	33892256
Aucubin,3TMS,isomer #13	C[Si](C)(C)OCC1=CC(O[Si](C)(C)C)C2C=COC(OC3OC(CO)C(O)C(O)C3O[Si](C)(C)C)C12	2927.9	Semi standard non polar	33892256
Aucubin,3TMS,isomer #14	C[Si](C)(C)OC1C=C(CO)C2C(OC3OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O)OC=CC12	2944.4	Semi standard non polar	33892256
Aucubin,3TMS,isomer #15	C[Si](C)(C)OC1C=C(CO)C2C(OC3OC(CO)C(O[Si](C)(C)C)C(O)C3O[Si](C)(C)C)OC=CC12	2940.4	Semi standard non polar	33892256
Aucubin,3TMS,isomer #16	C[Si](C)(C)OC1C=C(CO)C2C(OC3OC(CO)C(O)C(O[Si](C)(C)C)C3O[Si](C)(C)C)OC=CC12	2938.7	Semi standard non polar	33892256
Aucubin,3TMS,isomer #17	C[Si](C)(C)OCC1=CC(O)C2C=COC(OC3OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O)C12	2900.1	Semi standard non polar	33892256
Aucubin,3TMS,isomer #18	C[Si](C)(C)OCC1=CC(O)C2C=COC(OC3OC(CO)C(O[Si](C)(C)C)C(O)C3O[Si](C)(C)C)C12	2897.6	Semi standard non polar	33892256
Aucubin,3TMS,isomer #19	C[Si](C)(C)OCC1=CC(O)C2C=COC(OC3OC(CO)C(O)C(O[Si](C)(C)C)C3O[Si](C)(C)C)C12	2887.0	Semi standard non polar	33892256
Aucubin,3TMS,isomer #2	C[Si](C)(C)OCC1OC(OC2OC=CC3C(O[Si](C)(C)C)C=C(CO)C23)C(O[Si](C)(C)C)C(O)C1O	2945.6	Semi standard non polar	33892256
Aucubin,3TMS,isomer #20	C[Si](C)(C)OC1C(CO)OC(OC2OC=CC3C(O)C=C(CO)C23)C(O[Si](C)(C)C)C1O[Si](C)(C)C	2916.0	Semi standard non polar	33892256
Aucubin,3TMS,isomer #3	C[Si](C)(C)OCC1OC(OC2OC=CC3C(O[Si](C)(C)C)C=C(CO)C23)C(O)C(O[Si](C)(C)C)C1O	2934.1	Semi standard non polar	33892256
Aucubin,3TMS,isomer #4	C[Si](C)(C)OCC1OC(OC2OC=CC3C(O[Si](C)(C)C)C=C(CO)C23)C(O)C(O)C1O[Si](C)(C)C	2948.7	Semi standard non polar	33892256
Aucubin,3TMS,isomer #5	C[Si](C)(C)OCC1=CC(O)C2C=COC(OC3OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C3O)C12	2916.5	Semi standard non polar	33892256
Aucubin,3TMS,isomer #6	C[Si](C)(C)OCC1=CC(O)C2C=COC(OC3OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C3O)C12	2901.1	Semi standard non polar	33892256
Aucubin,3TMS,isomer #7	C[Si](C)(C)OCC1=CC(O)C2C=COC(OC3OC(CO[Si](C)(C)C)C(O)C(O)C3O[Si](C)(C)C)C12	2907.0	Semi standard non polar	33892256
Aucubin,3TMS,isomer #8	C[Si](C)(C)OCC1OC(OC2OC=CC3C(O)C=C(CO)C23)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O	2902.7	Semi standard non polar	33892256
Aucubin,3TMS,isomer #9	C[Si](C)(C)OCC1OC(OC2OC=CC3C(O)C=C(CO)C23)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C	2926.9	Semi standard non polar	33892256
Aucubin,4TMS,isomer #1	C[Si](C)(C)OCC1=CC(O[Si](C)(C)C)C2C=COC(OC3OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C3O)C12	2893.6	Semi standard non polar	33892256
Aucubin,4TMS,isomer #10	C[Si](C)(C)OCC1OC(OC2OC=CC3C(O)C=C(CO)C23)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C	2878.5	Semi standard non polar	33892256
Aucubin,4TMS,isomer #11	C[Si](C)(C)OCC1=CC(O[Si](C)(C)C)C2C=COC(OC3OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O)C12	2877.3	Semi standard non polar	33892256
Aucubin,4TMS,isomer #12	C[Si](C)(C)OCC1=CC(O[Si](C)(C)C)C2C=COC(OC3OC(CO)C(O[Si](C)(C)C)C(O)C3O[Si](C)(C)C)C12	2886.6	Semi standard non polar	33892256
Aucubin,4TMS,isomer #13	C[Si](C)(C)OCC1=CC(O[Si](C)(C)C)C2C=COC(OC3OC(CO)C(O)C(O[Si](C)(C)C)C3O[Si](C)(C)C)C12	2848.0	Semi standard non polar	33892256
Aucubin,4TMS,isomer #14	C[Si](C)(C)OC1C=C(CO)C2C(OC3OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O[Si](C)(C)C)OC=CC12	2884.3	Semi standard non polar	33892256
Aucubin,4TMS,isomer #15	C[Si](C)(C)OCC1=CC(O)C2C=COC(OC3OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O[Si](C)(C)C)C12	2834.5	Semi standard non polar	33892256
Aucubin,4TMS,isomer #2	C[Si](C)(C)OCC1=CC(O[Si](C)(C)C)C2C=COC(OC3OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C3O)C12	2857.5	Semi standard non polar	33892256
Aucubin,4TMS,isomer #3	C[Si](C)(C)OCC1=CC(O[Si](C)(C)C)C2C=COC(OC3OC(CO[Si](C)(C)C)C(O)C(O)C3O[Si](C)(C)C)C12	2870.8	Semi standard non polar	33892256
Aucubin,4TMS,isomer #4	C[Si](C)(C)OCC1OC(OC2OC=CC3C(O[Si](C)(C)C)C=C(CO)C23)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O	2866.8	Semi standard non polar	33892256
Aucubin,4TMS,isomer #5	C[Si](C)(C)OCC1OC(OC2OC=CC3C(O[Si](C)(C)C)C=C(CO)C23)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C	2892.0	Semi standard non polar	33892256
Aucubin,4TMS,isomer #6	C[Si](C)(C)OCC1OC(OC2OC=CC3C(O[Si](C)(C)C)C=C(CO)C23)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C	2894.0	Semi standard non polar	33892256
Aucubin,4TMS,isomer #7	C[Si](C)(C)OCC1=CC(O)C2C=COC(OC3OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O)C12	2846.1	Semi standard non polar	33892256
Aucubin,4TMS,isomer #8	C[Si](C)(C)OCC1=CC(O)C2C=COC(OC3OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C3O[Si](C)(C)C)C12	2837.7	Semi standard non polar	33892256
Aucubin,4TMS,isomer #9	C[Si](C)(C)OCC1=CC(O)C2C=COC(OC3OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C3O[Si](C)(C)C)C12	2809.5	Semi standard non polar	33892256
Aucubin,5TMS,isomer #1	C[Si](C)(C)OCC1=CC(O[Si](C)(C)C)C2C=COC(OC3OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O)C12	2772.3	Semi standard non polar	33892256
Aucubin,5TMS,isomer #2	C[Si](C)(C)OCC1=CC(O[Si](C)(C)C)C2C=COC(OC3OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C3O[Si](C)(C)C)C12	2774.8	Semi standard non polar	33892256
Aucubin,5TMS,isomer #3	C[Si](C)(C)OCC1=CC(O[Si](C)(C)C)C2C=COC(OC3OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C3O[Si](C)(C)C)C12	2736.3	Semi standard non polar	33892256
Aucubin,5TMS,isomer #4	C[Si](C)(C)OCC1OC(OC2OC=CC3C(O[Si](C)(C)C)C=C(CO)C23)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C	2791.4	Semi standard non polar	33892256
Aucubin,5TMS,isomer #5	C[Si](C)(C)OCC1=CC(O)C2C=COC(OC3OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O[Si](C)(C)C)C12	2747.9	Semi standard non polar	33892256
Aucubin,5TMS,isomer #6	C[Si](C)(C)OCC1=CC(O[Si](C)(C)C)C2C=COC(OC3OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O[Si](C)(C)C)C12	2736.0	Semi standard non polar	33892256
Aucubin,6TMS,isomer #1	C[Si](C)(C)OCC1=CC(O[Si](C)(C)C)C2C=COC(OC3OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O[Si](C)(C)C)C12	2682.2	Semi standard non polar	33892256
Aucubin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1OC(OC2OC=CC3C(O)C=C(CO)C23)C(O)C(O)C1O	3261.1	Semi standard non polar	33892256
Aucubin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1C=C(CO)C2C(OC3OC(CO)C(O)C(O)C3O)OC=CC12	3308.8	Semi standard non polar	33892256
Aucubin,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCC1=CC(O)C2C=COC(OC3OC(CO)C(O)C(O)C3O)C12	3265.7	Semi standard non polar	33892256
Aucubin,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1C(OC2OC=CC3C(O)C=C(CO)C23)OC(CO)C(O)C1O	3266.0	Semi standard non polar	33892256
Aucubin,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1C(O)C(CO)OC(OC2OC=CC3C(O)C=C(CO)C23)C1O	3258.6	Semi standard non polar	33892256
Aucubin,1TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1C(CO)OC(OC2OC=CC3C(O)C=C(CO)C23)C(O)C1O	3255.0	Semi standard non polar	33892256
Aucubin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1OC(OC2OC=CC3C(O[Si](C)(C)C(C)(C)C)C=C(CO)C23)C(O)C(O)C1O	3437.5	Semi standard non polar	33892256
Aucubin,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OCC1=CC(O)C2C=COC(OC3OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C3O)C12	3425.0	Semi standard non polar	33892256
Aucubin,2TBDMS,isomer #11	CC(C)(C)[Si](C)(C)OCC1=CC(O)C2C=COC(OC3OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C3O)C12	3428.6	Semi standard non polar	33892256
Aucubin,2TBDMS,isomer #12	CC(C)(C)[Si](C)(C)OCC1=CC(O)C2C=COC(OC3OC(CO)C(O)C(O)C3O[Si](C)(C)C(C)(C)C)C12	3421.6	Semi standard non polar	33892256
Aucubin,2TBDMS,isomer #13	CC(C)(C)[Si](C)(C)OC1C(CO)OC(OC2OC=CC3C(O)C=C(CO)C23)C(O[Si](C)(C)C(C)(C)C)C1O	3405.8	Semi standard non polar	33892256
Aucubin,2TBDMS,isomer #14	CC(C)(C)[Si](C)(C)OC1C(OC2OC=CC3C(O)C=C(CO)C23)OC(CO)C(O)C1O[Si](C)(C)C(C)(C)C	3416.1	Semi standard non polar	33892256
Aucubin,2TBDMS,isomer #15	CC(C)(C)[Si](C)(C)OC1C(CO)OC(OC2OC=CC3C(O)C=C(CO)C23)C(O)C1O[Si](C)(C)C(C)(C)C	3408.3	Semi standard non polar	33892256
Aucubin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC1=CC(O)C2C=COC(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C3O)C12	3420.5	Semi standard non polar	33892256
Aucubin,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCC1OC(OC2OC=CC3C(O)C=C(CO)C23)C(O[Si](C)(C)C(C)(C)C)C(O)C1O	3412.7	Semi standard non polar	33892256
Aucubin,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OCC1OC(OC2OC=CC3C(O)C=C(CO)C23)C(O)C(O[Si](C)(C)C(C)(C)C)C1O	3420.3	Semi standard non polar	33892256
Aucubin,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OCC1OC(OC2OC=CC3C(O)C=C(CO)C23)C(O)C(O)C1O[Si](C)(C)C(C)(C)C	3404.5	Semi standard non polar	33892256
Aucubin,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OCC1=CC(O[Si](C)(C)C(C)(C)C)C2C=COC(OC3OC(CO)C(O)C(O)C3O)C12	3483.8	Semi standard non polar	33892256
Aucubin,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1C=C(CO)C2C(OC3OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C3O)OC=CC12	3442.6	Semi standard non polar	33892256
Aucubin,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC1C=C(CO)C2C(OC3OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C3O)OC=CC12	3453.4	Semi standard non polar	33892256
Aucubin,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1C=C(CO)C2C(OC3OC(CO)C(O)C(O)C3O[Si](C)(C)C(C)(C)C)OC=CC12	3446.1	Semi standard non polar	33892256
Aucubin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CC(O[Si](C)(C)C(C)(C)C)C2C=COC(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C3O)C12	3613.4	Semi standard non polar	33892256
Aucubin,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OCC1OC(OC2OC=CC3C(O)C=C(CO)C23)C(O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C	3574.3	Semi standard non polar	33892256
Aucubin,3TBDMS,isomer #11	CC(C)(C)[Si](C)(C)OCC1=CC(O[Si](C)(C)C(C)(C)C)C2C=COC(OC3OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C3O)C12	3632.4	Semi standard non polar	33892256
Aucubin,3TBDMS,isomer #12	CC(C)(C)[Si](C)(C)OCC1=CC(O[Si](C)(C)C(C)(C)C)C2C=COC(OC3OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C3O)C12	3639.1	Semi standard non polar	33892256
Aucubin,3TBDMS,isomer #13	CC(C)(C)[Si](C)(C)OCC1=CC(O[Si](C)(C)C(C)(C)C)C2C=COC(OC3OC(CO)C(O)C(O)C3O[Si](C)(C)C(C)(C)C)C12	3626.5	Semi standard non polar	33892256
Aucubin,3TBDMS,isomer #14	CC(C)(C)[Si](C)(C)OC1C=C(CO)C2C(OC3OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C3O)OC=CC12	3594.0	Semi standard non polar	33892256
Aucubin,3TBDMS,isomer #15	CC(C)(C)[Si](C)(C)OC1C=C(CO)C2C(OC3OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C3O[Si](C)(C)C(C)(C)C)OC=CC12	3583.2	Semi standard non polar	33892256
Aucubin,3TBDMS,isomer #16	CC(C)(C)[Si](C)(C)OC1C=C(CO)C2C(OC3OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C)OC=CC12	3589.3	Semi standard non polar	33892256
Aucubin,3TBDMS,isomer #17	CC(C)(C)[Si](C)(C)OCC1=CC(O)C2C=COC(OC3OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C3O)C12	3565.4	Semi standard non polar	33892256
Aucubin,3TBDMS,isomer #18	CC(C)(C)[Si](C)(C)OCC1=CC(O)C2C=COC(OC3OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C3O[Si](C)(C)C(C)(C)C)C12	3560.4	Semi standard non polar	33892256
Aucubin,3TBDMS,isomer #19	CC(C)(C)[Si](C)(C)OCC1=CC(O)C2C=COC(OC3OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C)C12	3562.6	Semi standard non polar	33892256
Aucubin,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC1OC(OC2OC=CC3C(O[Si](C)(C)C(C)(C)C)C=C(CO)C23)C(O[Si](C)(C)C(C)(C)C)C(O)C1O	3581.3	Semi standard non polar	33892256
Aucubin,3TBDMS,isomer #20	CC(C)(C)[Si](C)(C)OC1C(CO)OC(OC2OC=CC3C(O)C=C(CO)C23)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C	3537.5	Semi standard non polar	33892256
Aucubin,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCC1OC(OC2OC=CC3C(O[Si](C)(C)C(C)(C)C)C=C(CO)C23)C(O)C(O[Si](C)(C)C(C)(C)C)C1O	3607.5	Semi standard non polar	33892256
Aucubin,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OCC1OC(OC2OC=CC3C(O[Si](C)(C)C(C)(C)C)C=C(CO)C23)C(O)C(O)C1O[Si](C)(C)C(C)(C)C	3582.3	Semi standard non polar	33892256
Aucubin,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OCC1=CC(O)C2C=COC(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C3O)C12	3570.8	Semi standard non polar	33892256
Aucubin,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OCC1=CC(O)C2C=COC(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C3O)C12	3585.6	Semi standard non polar	33892256
Aucubin,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OCC1=CC(O)C2C=COC(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C3O[Si](C)(C)C(C)(C)C)C12	3572.4	Semi standard non polar	33892256
Aucubin,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OCC1OC(OC2OC=CC3C(O)C=C(CO)C23)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O	3564.6	Semi standard non polar	33892256
Aucubin,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OCC1OC(OC2OC=CC3C(O)C=C(CO)C23)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C	3558.5	Semi standard non polar	33892256
Aucubin,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CC(O[Si](C)(C)C(C)(C)C)C2C=COC(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C3O)C12	3784.7	Semi standard non polar	33892256
Aucubin,4TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OCC1OC(OC2OC=CC3C(O)C=C(CO)C23)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C	3733.9	Semi standard non polar	33892256
Aucubin,4TBDMS,isomer #11	CC(C)(C)[Si](C)(C)OCC1=CC(O[Si](C)(C)C(C)(C)C)C2C=COC(OC3OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C3O)C12	3770.1	Semi standard non polar	33892256
Aucubin,4TBDMS,isomer #12	CC(C)(C)[Si](C)(C)OCC1=CC(O[Si](C)(C)C(C)(C)C)C2C=COC(OC3OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C3O[Si](C)(C)C(C)(C)C)C12	3756.2	Semi standard non polar	33892256
Aucubin,4TBDMS,isomer #13	CC(C)(C)[Si](C)(C)OCC1=CC(O[Si](C)(C)C(C)(C)C)C2C=COC(OC3OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C)C12	3765.7	Semi standard non polar	33892256
Aucubin,4TBDMS,isomer #14	CC(C)(C)[Si](C)(C)OC1C=C(CO)C2C(OC3OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C)OC=CC12	3715.3	Semi standard non polar	33892256
Aucubin,4TBDMS,isomer #15	CC(C)(C)[Si](C)(C)OCC1=CC(O)C2C=COC(OC3OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C)C12	3692.8	Semi standard non polar	33892256
Aucubin,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OCC1=CC(O[Si](C)(C)C(C)(C)C)C2C=COC(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C3O)C12	3808.0	Semi standard non polar	33892256
Aucubin,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OCC1=CC(O[Si](C)(C)C(C)(C)C)C2C=COC(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C3O[Si](C)(C)C(C)(C)C)C12	3785.4	Semi standard non polar	33892256
Aucubin,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OCC1OC(OC2OC=CC3C(O[Si](C)(C)C(C)(C)C)C=C(CO)C23)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O	3758.1	Semi standard non polar	33892256
Aucubin,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OCC1OC(OC2OC=CC3C(O[Si](C)(C)C(C)(C)C)C=C(CO)C23)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C	3757.2	Semi standard non polar	33892256
Aucubin,4TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OCC1OC(OC2OC=CC3C(O[Si](C)(C)C(C)(C)C)C=C(CO)C23)C(O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C	3771.7	Semi standard non polar	33892256
Aucubin,4TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OCC1=CC(O)C2C=COC(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C3O)C12	3753.2	Semi standard non polar	33892256
Aucubin,4TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OCC1=CC(O)C2C=COC(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C3O[Si](C)(C)C(C)(C)C)C12	3743.5	Semi standard non polar	33892256
Aucubin,4TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OCC1=CC(O)C2C=COC(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C)C12	3747.8	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 - Aucubin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00or-4719000000-a03c5ea19b82d7991f35	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aucubin GC-MS (4 TMS) - 70eV, Positive	splash10-01b9-2252049000-fb4fdbe14aa2fef93db3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aucubin 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 - Aucubin 10V, Positive-QTOF	splash10-02vr-0904000000-0dc8cc1fee5ec1d7b66a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aucubin 20V, Positive-QTOF	splash10-014i-0901000000-23ae99445d0f902ebb10	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aucubin 40V, Positive-QTOF	splash10-014i-1900000000-0197bf91c00175908c8f	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aucubin 10V, Negative-QTOF	splash10-00nb-0917000000-5b5a2c303dee5ed5b778	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aucubin 20V, Negative-QTOF	splash10-0159-1901000000-dcbc777e43693cc64c6f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aucubin 40V, Negative-QTOF	splash10-001l-5900000000-66eed55623a37e730cdc	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aucubin 10V, Negative-QTOF	splash10-0002-0209000000-6d1f85d0258419cba6e0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aucubin 20V, Negative-QTOF	splash10-005a-5925000000-7b6e750efe6aab6eda8d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aucubin 40V, Negative-QTOF	splash10-0uxr-6910000000-9a98e60322aa35e884b0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aucubin 10V, Positive-QTOF	splash10-00mk-0709000000-9b62837c71245c712dd9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aucubin 20V, Positive-QTOF	splash10-00kb-0901000000-8bd04921ef01bfdb1bb4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aucubin 40V, Positive-QTOF	splash10-07bs-4900000000-1f7344e04d4a474d0b71	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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

Aucubin

METLIN ID

Not Available

PubChem Compound

348157

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1509131

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Hung JY, Yang CJ, Tsai YM, Huang HW, Huang MS: Antiproliferative activity of aucubin is through cell cycle arrest and apoptosis in human non-small cell lung cancer A549 cells. Clin Exp Pharmacol Physiol. 2008 Sep;35(9):995-1001. doi: 10.1111/j.1440-1681.2008.04935.x. Epub 2008 Apr 21. [PubMed:18430063 ]
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 Aucubin (HMDB0036562)

MOL for HMDB0036562 (Aucubin)

3D MOL for HMDB0036562 (Aucubin)

3D SDF for HMDB0036562 (Aucubin)

3D-SDF for HMDB0036562 (Aucubin)

PDB for HMDB0036562 (Aucubin)

3D PDB for HMDB0036562 (Aucubin)

SMILES for HMDB0036562 (Aucubin)

INCHI for HMDB0036562 (Aucubin)

Structure for HMDB0036562 (Aucubin)

3D Structure for HMDB0036562 (Aucubin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra