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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 19:56:10 UTC

Update Date

2021-09-23 19:56:10 UTC

HMDB ID

HMDB0302705

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Laurenoniolide

Description

Laurenoniolide 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. Laurenoniolide is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Laurenoniolide can be found in sweet bay, which makes laurenoniolide a potential biomarker for the consumption of this food product.

Structure

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

  Mrv1533007131513432D          

 26 27  0  0  1  0            999 V2000
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9440    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0396    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0945    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0862    1.6455    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
 10  1  1  0  0  0  0
 10  6  1  0  0  0  0
 10  8  2  0  0  0  0
 11  2  1  0  0  0  0
 11  7  2  0  0  0  0
 11  9  1  0  0  0  0
 12  3  2  0  0  0  0
 13  4  1  0  0  0  0
 14  8  1  0  0  0  0
 15  9  1  0  0  0  0
 16 12  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 12  1  0  0  0  0
 18 13  2  0  0  0  0
 19 17  2  0  0  0  0
 20 13  1  0  0  0  0
 14 20  1  6  0  0  0
 21 15  1  0  0  0  0
 21 17  1  0  0  0  0
 22  7  1  0  0  0  0
 23  8  1  0  0  0  0
 14 24  1  1  0  0  0
 15 25  1  1  0  0  0
 16 26  1  6  0  0  0
M  END

HMDB0302705
     RDKit          3D
Laurenoniolide
 43 44  0  0  0  0  0  0  0  0999 V2000
    2.6302   -2.3818    0.5656 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3564   -2.1550    0.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5114   -3.1422   -0.3932 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8257   -4.1955   -1.0017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8021   -2.7152   -0.2412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8149   -1.3275    0.0417 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9008   -1.0925    1.0586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0271   -0.4270    0.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1263   -1.2355   -0.2797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1287    0.8749    0.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1097    1.7573    0.8769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0522    2.1963   -0.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2285    2.3418    0.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3731    3.5737    1.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2057    1.4661    0.5629 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1537    0.2007   -0.2342 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4900   -0.1323   -0.5622 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9125   -0.2601   -1.8783 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3039   -0.6076   -2.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0952   -0.0776   -2.8203 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5495   -0.9340    0.5190 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1194   -3.3158    0.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2469   -1.6334    1.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0293   -0.8343   -0.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5529   -0.6083    1.9709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3328   -2.0786    1.4191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0859   -0.7691   -0.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1204   -2.2839    0.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9623   -1.1860   -1.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9855    1.3398   -0.2451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6461    2.7006    1.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6429    1.3826    1.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0071    1.5541   -1.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3177    3.2190   -0.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4286    3.9329    1.3361 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2525    3.3252    2.5152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3224    4.3710    1.1156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0926    1.6849    1.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6024    0.3181   -1.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7252    0.1051   -2.9996 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3138   -1.6591   -2.6515 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9963   -0.6064   -1.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5533   -0.6853    1.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 16 21  1  0
 21  2  1  0
 21  6  1  0
  1 22  1  0
  1 23  1  0
  6 24  1  6
  7 25  1  0
  7 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  6
 19 40  1  0
 19 41  1  0
 19 42  1  0
 21 43  1  1
M  END

  Mrv1533007131513432D          

 26 27  0  0  1  0            999 V2000
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9440    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0396    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0945    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0862    1.6455    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
 10  1  1  0  0  0  0
 10  6  1  0  0  0  0
 10  8  2  0  0  0  0
 11  2  1  0  0  0  0
 11  7  2  0  0  0  0
 11  9  1  0  0  0  0
 12  3  2  0  0  0  0
 13  4  1  0  0  0  0
 14  8  1  0  0  0  0
 15  9  1  0  0  0  0
 16 12  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 12  1  0  0  0  0
 18 13  2  0  0  0  0
 19 17  2  0  0  0  0
 20 13  1  0  0  0  0
 14 20  1  6  0  0  0
 21 15  1  0  0  0  0
 21 17  1  0  0  0  0
 22  7  1  0  0  0  0
 23  8  1  0  0  0  0
 14 24  1  1  0  0  0
 15 25  1  1  0  0  0
 16 26  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0302705

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]\C1=C(C)/C[C@]2([H])OC(=O)C(=C)[C@@]2([H])[C@]([H])(OC(C)=O)\C([H])=C(C)\CC1

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O4/c1-10-6-5-7-11(2)9-15-16(12(3)17(19)21-15)14(8-10)20-13(4)18/h7-8,14-16H,3,5-6,9H2,1-2,4H3/b10-8+,11-7+/t14-,15+,16+/m1/s1

> <INCHI_KEY>
ORJVLIMAQARNOU-SYQXSARVSA-N

> <FORMULA>
C17H22O4

> <MOLECULAR_WEIGHT>
290.359

> <EXACT_MASS>
290.151809188

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
31.034676302302536

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4R,11aS)-6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,7H,8H,11H,11aH-cyclodeca[b]furan-4-yl acetate

> <ALOGPS_LOGP>
3.31

> <JCHEM_LOGP>
2.9121302570000003

> <ALOGPS_LOGS>
-3.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.6367313516367235

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
80.6686

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.33e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
laurenobiolide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302705
     RDKit          3D
Laurenoniolide
 43 44  0  0  0  0  0  0  0  0999 V2000
    2.6302   -2.3818    0.5656 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3564   -2.1550    0.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5114   -3.1422   -0.3932 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8257   -4.1955   -1.0017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8021   -2.7152   -0.2412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8149   -1.3275    0.0417 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9008   -1.0925    1.0586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0271   -0.4270    0.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1263   -1.2355   -0.2797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1287    0.8749    0.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1097    1.7573    0.8769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0522    2.1963   -0.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2285    2.3418    0.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3731    3.5737    1.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2057    1.4661    0.5629 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1537    0.2007   -0.2342 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4900   -0.1323   -0.5622 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9125   -0.2601   -1.8783 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3039   -0.6076   -2.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0952   -0.0776   -2.8203 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5495   -0.9340    0.5190 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1194   -3.3158    0.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2469   -1.6334    1.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0293   -0.8343   -0.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5529   -0.6083    1.9709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3328   -2.0786    1.4191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0859   -0.7691   -0.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1204   -2.2839    0.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9623   -1.1860   -1.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9855    1.3398   -0.2451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6461    2.7006    1.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6429    1.3826    1.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0071    1.5541   -1.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3177    3.2190   -0.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4286    3.9329    1.3361 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2525    3.3252    2.5152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3224    4.3710    1.1156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0926    1.6849    1.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6024    0.3181   -1.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7252    0.1051   -2.9996 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3138   -1.6591   -2.6515 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9963   -0.6064   -1.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5533   -0.6853    1.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 16 21  1  0
 21  2  1  0
 21  6  1  0
  1 22  1  0
  1 23  1  0
  6 24  1  6
  7 25  1  0
  7 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  6
 19 40  1  0
 19 41  1  0
 19 42  1  0
 21 43  1  1
M  END

HEADER    PROTEIN                                 13-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUL-15         0                                  
HETATM    1  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.762   1.246   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.941   3.481   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.465   2.016   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.000   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.370   0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.000   6.160   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -3.910   0.770   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.465  -0.476   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0       4.001  -2.310   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       4.001   0.770   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       2.667   3.080   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       1.334   0.770   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.161   3.072   0.000  0.00  0.00           H+0
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4   13                                                            
CONECT    5    6    7                                                       
CONECT    6    5   10                                                       
CONECT    7    5   11   22                                                  
CONECT    8   10   14   23                                                  
CONECT    9   11   15                                                       
CONECT   10    1    6    8                                                  
CONECT   11    2    7    9                                                  
CONECT   12    3   16   17                                                  
CONECT   13    4   18   20                                                  
CONECT   14    8   16   20   24                                             
CONECT   15    9   16   21   25                                             
CONECT   16   12   14   15   26                                             
CONECT   17   12   19   21                                                  
CONECT   18   13                                                            
CONECT   19   17                                                            
CONECT   20   13   14                                                       
CONECT   21   15   17                                                       
CONECT   22    7                                                            
CONECT   23    8                                                            
CONECT   24   14                                                            
CONECT   25   15                                                            
CONECT   26   16                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

COMPND    HMDB0302705
HETATM    1  C1  UNL     1       2.630  -2.382   0.566  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.356  -2.155   0.268  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.511  -3.142  -0.393  1.00  0.00           C  
HETATM    4  O1  UNL     1       0.826  -4.195  -1.002  1.00  0.00           O  
HETATM    5  O2  UNL     1      -0.802  -2.715  -0.241  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.815  -1.328   0.042  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.901  -1.093   1.059  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.027  -0.427   0.367  1.00  0.00           C  
HETATM    9  C7  UNL     1      -4.126  -1.235  -0.280  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.129   0.875   0.280  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.110   1.757   0.877  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.052   2.196  -0.145  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.229   2.342   0.597  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.373   3.574   1.423  1.00  0.00           C  
HETATM   15  C13 UNL     1       1.206   1.466   0.563  1.00  0.00           C  
HETATM   16  C14 UNL     1       1.154   0.201  -0.234  1.00  0.00           C  
HETATM   17  O3  UNL     1       2.490  -0.132  -0.562  1.00  0.00           O  
HETATM   18  C15 UNL     1       2.913  -0.260  -1.878  1.00  0.00           C  
HETATM   19  C16 UNL     1       4.304  -0.608  -2.259  1.00  0.00           C  
HETATM   20  O4  UNL     1       2.095  -0.078  -2.820  1.00  0.00           O  
HETATM   21  C17 UNL     1       0.549  -0.934   0.519  1.00  0.00           C  
HETATM   22  H1  UNL     1       3.119  -3.316   0.335  1.00  0.00           H  
HETATM   23  H2  UNL     1       3.247  -1.633   1.060  1.00  0.00           H  
HETATM   24  H3  UNL     1      -1.029  -0.834  -0.934  1.00  0.00           H  
HETATM   25  H4  UNL     1      -1.553  -0.608   1.971  1.00  0.00           H  
HETATM   26  H5  UNL     1      -2.333  -2.079   1.419  1.00  0.00           H  
HETATM   27  H6  UNL     1      -5.086  -0.769  -0.009  1.00  0.00           H  
HETATM   28  H7  UNL     1      -4.120  -2.284   0.091  1.00  0.00           H  
HETATM   29  H8  UNL     1      -3.962  -1.186  -1.385  1.00  0.00           H  
HETATM   30  H9  UNL     1      -3.985   1.340  -0.245  1.00  0.00           H  
HETATM   31  H10 UNL     1      -2.646   2.701   1.209  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.643   1.383   1.799  1.00  0.00           H  
HETATM   33  H12 UNL     1      -1.007   1.554  -1.020  1.00  0.00           H  
HETATM   34  H13 UNL     1      -1.318   3.219  -0.529  1.00  0.00           H  
HETATM   35  H14 UNL     1       1.429   3.933   1.336  1.00  0.00           H  
HETATM   36  H15 UNL     1       0.252   3.325   2.515  1.00  0.00           H  
HETATM   37  H16 UNL     1      -0.322   4.371   1.116  1.00  0.00           H  
HETATM   38  H17 UNL     1       2.093   1.685   1.149  1.00  0.00           H  
HETATM   39  H18 UNL     1       0.602   0.318  -1.183  1.00  0.00           H  
HETATM   40  H19 UNL     1       4.725   0.105  -3.000  1.00  0.00           H  
HETATM   41  H20 UNL     1       4.314  -1.659  -2.651  1.00  0.00           H  
HETATM   42  H21 UNL     1       4.996  -0.606  -1.393  1.00  0.00           H  
HETATM   43  H22 UNL     1       0.553  -0.685   1.603  1.00  0.00           H  
CONECT    1    2    2   22   23
CONECT    2    3   21
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   21   24
CONECT    7    8   25   26
CONECT    8    9   10   10
CONECT    9   27   28   29
CONECT   10   11   30
CONECT   11   12   31   32
CONECT   12   13   33   34
CONECT   13   14   15   15
CONECT   14   35   36   37
CONECT   15   16   38
CONECT   16   17   21   39
CONECT   17   18
CONECT   18   19   20   20
CONECT   19   40   41   42
CONECT   21   43
END

HMDB0302705
     RDKit          3D
Laurenoniolide
 43 44  0  0  0  0  0  0  0  0999 V2000
    2.6302   -2.3818    0.5656 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3564   -2.1550    0.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5114   -3.1422   -0.3932 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8257   -4.1955   -1.0017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8021   -2.7152   -0.2412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8149   -1.3275    0.0417 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9008   -1.0925    1.0586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0271   -0.4270    0.3671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1263   -1.2355   -0.2797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1287    0.8749    0.2804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1097    1.7573    0.8769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0522    2.1963   -0.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2285    2.3418    0.5974 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3731    3.5737    1.4226 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2057    1.4661    0.5629 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1537    0.2007   -0.2342 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4900   -0.1323   -0.5622 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9125   -0.2601   -1.8783 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3039   -0.6076   -2.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0952   -0.0776   -2.8203 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5495   -0.9340    0.5190 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1194   -3.3158    0.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2469   -1.6334    1.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0293   -0.8343   -0.9339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5529   -0.6083    1.9709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3328   -2.0786    1.4191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0859   -0.7691   -0.0089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1204   -2.2839    0.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9623   -1.1860   -1.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9855    1.3398   -0.2451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6461    2.7006    1.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6429    1.3826    1.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0071    1.5541   -1.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3177    3.2190   -0.5289 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4286    3.9329    1.3361 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2525    3.3252    2.5152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3224    4.3710    1.1156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0926    1.6849    1.1492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6024    0.3181   -1.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7252    0.1051   -2.9996 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3138   -1.6591   -2.6515 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9963   -0.6064   -1.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5533   -0.6853    1.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 16 21  1  0
 21  2  1  0
 21  6  1  0
  1 22  1  0
  1 23  1  0
  6 24  1  6
  7 25  1  0
  7 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  6
 19 40  1  0
 19 41  1  0
 19 42  1  0
 21 43  1  1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3AR,4R,11as)-6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3ah,4H,7H,8H,11H,11ah-cyclodeca[b]furan-4-yl acetic acid	Generator

Chemical Formula

C₁₇H₂₂O₄

Average Molecular Weight

290.359

Monoisotopic Molecular Weight

290.151809188

IUPAC Name

(3aR,4R,11aS)-6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,7H,8H,11H,11aH-cyclodeca[b]furan-4-yl acetate

Traditional Name

laurenobiolide

CAS Registry Number

Not Available

SMILES

[H]\C1=C(C)/C[C@]2([H])OC(=O)C(=C)[C@@]2([H])[C@]([H])(OC(C)=O)\C([H])=C(C)\CC1

InChI Identifier

InChI=1S/C17H22O4/c1-10-6-5-7-11(2)9-15-16(12(3)17(19)21-15)14(8-10)20-13(4)18/h7-8,14-16H,3,5-6,9H2,1-2,4H3/b10-8+,11-7+/t14-,15+,16+/m1/s1

InChI Key

ORJVLIMAQARNOU-SYQXSARVSA-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
Dicarboxylic acid or derivatives
Gamma butyrolactone
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Germacrenes (C09492 )

Ontology

Not Available

Exogenous (HMDB: HMDB0302705)

Food

Herb and spice

Herb

Sweet bay (FooDB: FOOD00097)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.31	ALOGPS
logP	2.91	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	80.67 m³·mol⁻¹	ChemAxon
Polarizability	31.03 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]+	170.086	32859911
AllCCS	[M+H-H2O]+	166.738	32859911
AllCCS	[M+Na]+	174.082	32859911
AllCCS	[M+NH4]+	173.19	32859911
AllCCS	[M-H]-	173.721	32859911
AllCCS	[M+Na-2H]-	173.821	32859911
AllCCS	[M+HCOO]-	174.056	32859911
DeepCCS	[M+H]+	176.128	30932474
DeepCCS	[M-H]-	174.191	30932474
DeepCCS	[M-2H]-	207.43	30932474
DeepCCS	[M+Na]+	182.04	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 - Laurenoniolide 10V, Positive-QTOF	splash10-0006-0090000000-5dd05d95f16c803a4875	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laurenoniolide 20V, Positive-QTOF	splash10-003s-1690000000-603db850d843dbf236f2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laurenoniolide 40V, Positive-QTOF	splash10-0ftf-9840000000-ddd7810d621ff43e3546	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laurenoniolide 10V, Negative-QTOF	splash10-000j-0090000000-0c6ee6f48041152fa721	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laurenoniolide 20V, Negative-QTOF	splash10-000b-2090000000-be7ce9b54e80ed94245f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laurenoniolide 40V, Negative-QTOF	splash10-0kfx-8940000000-c75c9d4e3c2cbee283e2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laurenoniolide 10V, Positive-QTOF	splash10-001i-0090000000-325b4e1f7e836a7f8719	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laurenoniolide 20V, Positive-QTOF	splash10-001i-1390000000-8c6faede2b22e0e18a72	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laurenoniolide 40V, Positive-QTOF	splash10-0006-9530000000-2ca0b5ea0809e2d24125	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laurenoniolide 10V, Negative-QTOF	splash10-000i-0090000000-eb9a1f7c498492c2f394	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laurenoniolide 20V, Negative-QTOF	splash10-0a4i-9080000000-c9304d328da27b5e9d99	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Laurenoniolide 40V, Negative-QTOF	splash10-0a4l-9030000000-013c73286a3484eb11da	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

5281475

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1857081

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Laurenoniolide (HMDB0302705)

MOL for HMDB0302705 (Laurenoniolide)

3D MOL for HMDB0302705 (Laurenoniolide)

3D SDF for HMDB0302705 (Laurenoniolide)

3D-SDF for HMDB0302705 (Laurenoniolide)

PDB for HMDB0302705 (Laurenoniolide)

3D PDB for HMDB0302705 (Laurenoniolide)

SMILES for HMDB0302705 (Laurenoniolide)

INCHI for HMDB0302705 (Laurenoniolide)

Structure for HMDB0302705 (Laurenoniolide)

3D Structure for HMDB0302705 (Laurenoniolide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra