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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 20:56:23 UTC

Update Date

2021-09-23 20:56:23 UTC

HMDB ID

HMDB0302821

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Manoyl oxide

Description

Manoyl oxide, also known as (-)-ent-13-epi-manoyl oxide, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Manoyl oxide is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Manoyl oxide can be found in pot marjoram, which makes manoyl oxide a potential biomarker for the consumption of this food product.

Structure

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

HMDB0302821
     RDKit          3D
Manoyl oxide
 55 57  0  0  0  0  0  0  0  0999 V2000
    5.4704    0.1523    0.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5930   -0.2629   -0.4240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1582   -0.5514   -0.0524 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0991   -2.0478    0.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8671    0.1935    1.1896 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4048    0.3381    1.5166 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6038   -0.1101    0.3295 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2205    0.4274   -0.8937 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6221    1.8645   -0.8641 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3901    0.2216   -2.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9999    0.7526   -1.8829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5602   -0.1515   -0.7866 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0461   -0.1694   -0.7705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4694   -0.8753   -2.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6863    1.1912   -0.8232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5460   -1.0283    0.3362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8612   -0.8896    1.6476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3640   -0.9641    1.4801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8727    0.1150    0.4979 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1783    1.4146    1.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4030   -0.3048   -1.1390 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1905    0.3011    1.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4850    0.3498    0.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9055   -0.4026   -1.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1089   -2.5057    0.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5326   -2.6044   -0.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6774   -2.2162    1.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3865    1.1941    1.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3348   -0.3414    2.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2342    1.3616    1.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1048   -0.3326    2.3694 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7307   -1.2364    0.2918 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5771    2.3575    0.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9877    2.4878   -1.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6696    2.0384   -1.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8941    0.7632   -2.9710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3392   -0.8772   -2.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9277    1.7906   -1.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6099    0.6011   -2.7958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2528   -1.1964   -1.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7075   -1.6248   -2.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4497   -1.3734   -1.9469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5697   -0.1090   -2.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3213    1.2881    0.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4410    1.2902   -1.6587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9888    2.0185   -0.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6403   -0.8885    0.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4226   -2.1026    0.0087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1468   -1.7573    2.2796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1741    0.0134    2.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1336   -1.9343    0.9969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8509   -0.9127    2.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7678    1.3648    2.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2532    1.5805    1.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7493    2.2994    0.6806 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  6
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  1
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  1
  8 21  1  0
 21  3  1  0
 19  7  1  0
 19 12  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  4 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  6
  9 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  6
 14 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 20 53  1  0
 20 54  1  0
 20 55  1  0
M  END


  Mrv0541 02241221322D          

 21 23  0  0  1  0            999 V2000
    3.6020    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3977    1.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2732    1.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7429    0.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4425    0.4624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7429    0.7998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
  2 11  1  0  0  0  0
  8 12  1  0  0  0  0
  8 13  1  0  0  0  0
  4 14  1  1  0  0  0
  3 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  1 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  2  0  0  0  0
 17 20  1  6  0  0  0
  2 21  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0302821

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)CCC[C@]2(C)[C@@H]1CC[C@]1(C)O[C@](C)(CC[C@@H]21)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O/c1-7-18(4)13-9-16-19(5)12-8-11-17(2,3)15(19)10-14-20(16,6)21-18/h7,15-16H,1,8-14H2,2-6H3/t15-,16+,18+,19-,20+/m1/s1

> <INCHI_KEY>
IGGWKHQYMAJOHK-QVHQYWGISA-N

> <FORMULA>
C20H34O

> <MOLECULAR_WEIGHT>
290.4834

> <EXACT_MASS>
290.26096571

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
36.02868978900422

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,4aS,6aR,10aR,10bS)-3-ethenyl-3,4a,7,7,10a-pentamethyl-dodecahydro-1H-naphtho[2,1-b]pyran

> <ALOGPS_LOGP>
5.39

> <JCHEM_LOGP>
5.498561761333333

> <ALOGPS_LOGS>
-6.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.235396953661379

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
89.4728

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.42e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4aS,6aR,10aR,10bS)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1H-naphtho[2,1-b]pyran

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0302821
     RDKit          3D
Manoyl oxide
 55 57  0  0  0  0  0  0  0  0999 V2000
    5.4704    0.1523    0.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5930   -0.2629   -0.4240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1582   -0.5514   -0.0524 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0991   -2.0478    0.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8671    0.1935    1.1896 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4048    0.3381    1.5166 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6038   -0.1101    0.3295 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2205    0.4274   -0.8937 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6221    1.8645   -0.8641 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3901    0.2216   -2.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9999    0.7526   -1.8829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5602   -0.1515   -0.7866 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0461   -0.1694   -0.7705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4694   -0.8753   -2.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6863    1.1912   -0.8232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5460   -1.0283    0.3362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8612   -0.8896    1.6476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3640   -0.9641    1.4801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8727    0.1150    0.4979 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1783    1.4146    1.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4030   -0.3048   -1.1390 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1905    0.3011    1.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4850    0.3498    0.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9055   -0.4026   -1.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1089   -2.5057    0.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5326   -2.6044   -0.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6774   -2.2162    1.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3865    1.1941    1.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3348   -0.3414    2.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2342    1.3616    1.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1048   -0.3326    2.3694 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7307   -1.2364    0.2918 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5771    2.3575    0.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9877    2.4878   -1.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6696    2.0384   -1.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8941    0.7632   -2.9710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3392   -0.8772   -2.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9277    1.7906   -1.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6099    0.6011   -2.7958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2528   -1.1964   -1.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7075   -1.6248   -2.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4497   -1.3734   -1.9469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5697   -0.1090   -2.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3213    1.2881    0.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4410    1.2902   -1.6587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9888    2.0185   -0.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6403   -0.8885    0.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4226   -2.1026    0.0087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1468   -1.7573    2.2796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1741    0.0134    2.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1336   -1.9343    0.9969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8509   -0.9127    2.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7678    1.3648    2.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2532    1.5805    1.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7493    2.2994    0.6806 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  6
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  1
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  1
  8 21  1  0
 21  3  1  0
 19  7  1  0
 19 12  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  4 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  6
  9 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  6
 14 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 20 53  1  0
 20 54  1  0
 20 55  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       6.724   2.104   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.742   2.920   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.510   3.643   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.853   0.047   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.159   0.863   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.853   1.493   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
CONECT    1    2   17                                                       
CONECT    2    1    3   11   21                                             
CONECT    3    2    4   15                                                  
CONECT    4    3    5    9   14                                             
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   12   13                                             
CONECT    9    8    4   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10    2                                                       
CONECT   12    8                                                            
CONECT   13    8                                                            
CONECT   14    4                                                            
CONECT   15    3   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    1   18   20                                             
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17                                                            
CONECT   21    2                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0302821
HETATM    1  C1  UNL     1       5.470   0.152   0.464  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.593  -0.263  -0.424  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.158  -0.551  -0.052  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.099  -2.048   0.277  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.867   0.194   1.190  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.405   0.338   1.517  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.604  -0.110   0.329  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.221   0.427  -0.894  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.622   1.865  -0.864  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.390   0.222  -2.161  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.000   0.753  -1.883  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.560  -0.151  -0.787  1.00  0.00           C  
HETATM   13  C13 UNL     1      -3.046  -0.169  -0.771  1.00  0.00           C  
HETATM   14  C14 UNL     1      -3.469  -0.875  -2.076  1.00  0.00           C  
HETATM   15  C15 UNL     1      -3.686   1.191  -0.823  1.00  0.00           C  
HETATM   16  C16 UNL     1      -3.546  -1.028   0.336  1.00  0.00           C  
HETATM   17  C17 UNL     1      -2.861  -0.890   1.648  1.00  0.00           C  
HETATM   18  C18 UNL     1      -1.364  -0.964   1.480  1.00  0.00           C  
HETATM   19  C19 UNL     1      -0.873   0.115   0.498  1.00  0.00           C  
HETATM   20  C20 UNL     1      -1.178   1.415   1.146  1.00  0.00           C  
HETATM   21  O1  UNL     1       2.403  -0.305  -1.139  1.00  0.00           O  
HETATM   22  H1  UNL     1       5.190   0.301   1.493  1.00  0.00           H  
HETATM   23  H2  UNL     1       6.485   0.350   0.170  1.00  0.00           H  
HETATM   24  H3  UNL     1       4.906  -0.403  -1.451  1.00  0.00           H  
HETATM   25  H4  UNL     1       4.109  -2.506   0.294  1.00  0.00           H  
HETATM   26  H5  UNL     1       2.533  -2.604  -0.509  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.677  -2.216   1.296  1.00  0.00           H  
HETATM   28  H7  UNL     1       3.387   1.194   1.163  1.00  0.00           H  
HETATM   29  H8  UNL     1       3.335  -0.341   2.045  1.00  0.00           H  
HETATM   30  H9  UNL     1       1.234   1.362   1.840  1.00  0.00           H  
HETATM   31  H10 UNL     1       1.105  -0.333   2.369  1.00  0.00           H  
HETATM   32  H11 UNL     1       0.731  -1.236   0.292  1.00  0.00           H  
HETATM   33  H12 UNL     1       1.577   2.357   0.099  1.00  0.00           H  
HETATM   34  H13 UNL     1       0.988   2.488  -1.564  1.00  0.00           H  
HETATM   35  H14 UNL     1       2.670   2.038  -1.254  1.00  0.00           H  
HETATM   36  H15 UNL     1       0.894   0.763  -2.971  1.00  0.00           H  
HETATM   37  H16 UNL     1       0.339  -0.877  -2.367  1.00  0.00           H  
HETATM   38  H17 UNL     1      -0.928   1.791  -1.560  1.00  0.00           H  
HETATM   39  H18 UNL     1      -1.610   0.601  -2.796  1.00  0.00           H  
HETATM   40  H19 UNL     1      -1.253  -1.196  -1.102  1.00  0.00           H  
HETATM   41  H20 UNL     1      -2.707  -1.625  -2.377  1.00  0.00           H  
HETATM   42  H21 UNL     1      -4.450  -1.373  -1.947  1.00  0.00           H  
HETATM   43  H22 UNL     1      -3.570  -0.109  -2.878  1.00  0.00           H  
HETATM   44  H23 UNL     1      -4.321   1.288   0.104  1.00  0.00           H  
HETATM   45  H24 UNL     1      -4.441   1.290  -1.659  1.00  0.00           H  
HETATM   46  H25 UNL     1      -2.989   2.019  -0.961  1.00  0.00           H  
HETATM   47  H26 UNL     1      -4.640  -0.889   0.436  1.00  0.00           H  
HETATM   48  H27 UNL     1      -3.423  -2.103   0.009  1.00  0.00           H  
HETATM   49  H28 UNL     1      -3.147  -1.757   2.280  1.00  0.00           H  
HETATM   50  H29 UNL     1      -3.174   0.013   2.222  1.00  0.00           H  
HETATM   51  H30 UNL     1      -1.134  -1.934   0.997  1.00  0.00           H  
HETATM   52  H31 UNL     1      -0.851  -0.913   2.437  1.00  0.00           H  
HETATM   53  H32 UNL     1      -0.768   1.365   2.198  1.00  0.00           H  
HETATM   54  H33 UNL     1      -2.253   1.580   1.277  1.00  0.00           H  
HETATM   55  H34 UNL     1      -0.749   2.299   0.681  1.00  0.00           H  
CONECT    1    2    2   22   23
CONECT    2    3   24
CONECT    3    4    5   21
CONECT    4   25   26   27
CONECT    5    6   28   29
CONECT    6    7   30   31
CONECT    7    8   19   32
CONECT    8    9   10   21
CONECT    9   33   34   35
CONECT   10   11   36   37
CONECT   11   12   38   39
CONECT   12   13   19   40
CONECT   13   14   15   16
CONECT   14   41   42   43
CONECT   15   44   45   46
CONECT   16   17   47   48
CONECT   17   18   49   50
CONECT   18   19   51   52
CONECT   19   20
CONECT   20   53   54   55
END

HMDB0302821
     RDKit          3D
Manoyl oxide
 55 57  0  0  0  0  0  0  0  0999 V2000
    5.4704    0.1523    0.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5930   -0.2629   -0.4240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1582   -0.5514   -0.0524 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0991   -2.0478    0.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8671    0.1935    1.1896 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4048    0.3381    1.5166 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6038   -0.1101    0.3295 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2205    0.4274   -0.8937 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6221    1.8645   -0.8641 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3901    0.2216   -2.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9999    0.7526   -1.8829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5602   -0.1515   -0.7866 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0461   -0.1694   -0.7705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4694   -0.8753   -2.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6863    1.1912   -0.8232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5460   -1.0283    0.3362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8612   -0.8896    1.6476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3640   -0.9641    1.4801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8727    0.1150    0.4979 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1783    1.4146    1.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4030   -0.3048   -1.1390 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1905    0.3011    1.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4850    0.3498    0.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9055   -0.4026   -1.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1089   -2.5057    0.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5326   -2.6044   -0.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6774   -2.2162    1.2961 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3865    1.1941    1.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3348   -0.3414    2.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2342    1.3616    1.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1048   -0.3326    2.3694 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7307   -1.2364    0.2918 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5771    2.3575    0.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9877    2.4878   -1.5635 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6696    2.0384   -1.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8941    0.7632   -2.9710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3392   -0.8772   -2.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9277    1.7906   -1.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6099    0.6011   -2.7958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2528   -1.1964   -1.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7075   -1.6248   -2.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4497   -1.3734   -1.9469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5697   -0.1090   -2.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3213    1.2881    0.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4410    1.2902   -1.6587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9888    2.0185   -0.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6403   -0.8885    0.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4226   -2.1026    0.0087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1468   -1.7573    2.2796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1741    0.0134    2.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1336   -1.9343    0.9969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8509   -0.9127    2.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7678    1.3648    2.1980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2532    1.5805    1.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7493    2.2994    0.6806 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  6
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  1
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  1
  8 21  1  0
 21  3  1  0
 19  7  1  0
 19 12  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  4 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  6
  9 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  6
 14 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  0
 15 45  1  0
 15 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 20 53  1  0
 20 54  1  0
 20 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-ent-13-Epi-manoyl oxide	ChEBI
ent-13-Epi-manoyl oxide	ChEBI

Chemical Formula

C₂₀H₃₄O

Average Molecular Weight

290.4834

Monoisotopic Molecular Weight

290.26096571

IUPAC Name

(3R,4aS,6aR,10aR,10bS)-3-ethenyl-3,4a,7,7,10a-pentamethyl-dodecahydro-1H-naphtho[2,1-b]pyran

Traditional Name

(3R,4aS,6aR,10aR,10bS)-3-ethenyl-3,4a,7,7,10a-pentamethyl-octahydro-1H-naphtho[2,1-b]pyran

CAS Registry Number

Not Available

SMILES

CC1(C)CCC[C@]2(C)[C@@H]1CC[C@]1(C)O[C@](C)(CC[C@@H]21)C=C

InChI Identifier

InChI=1S/C20H34O/c1-7-18(4)13-9-16-19(5)12-8-11-17(2,3)15(19)10-14-20(16,6)21-18/h7,15-16H,1,8-14H2,2-6H3/t15-,16+,18+,19-,20+/m1/s1

InChI Key

IGGWKHQYMAJOHK-QVHQYWGISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Polycyclic triterpenoid
Triterpenoid
Naphthopyran
Naphthalene
Pyran
Oxane
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Pot marjoram (FooDB: FOOD00123)

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	5.39	ALOGPS
logP	5.5	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	89.47 m³·mol⁻¹	ChemAxon
Polarizability	36.03 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	174.504	32859911
AllCCS	[M+H-H2O]+	171.406	32859911
AllCCS	[M+Na]+	178.204	32859911
AllCCS	[M+NH4]+	177.378	32859911
AllCCS	[M-H]-	184.465	32859911
AllCCS	[M+Na-2H]-	184.975	32859911
AllCCS	[M+HCOO]-	185.671	32859911
DeepCCS	[M-2H]-	214.306	30932474
DeepCCS	[M+Na]+	189.519	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 - Manoyl oxide 10V, Positive-QTOF	splash10-0006-2090000000-36130687587e7a35c0f9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Manoyl oxide 20V, Positive-QTOF	splash10-06di-4190000000-20a9456ee3f6d23bc143	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Manoyl oxide 40V, Positive-QTOF	splash10-0fsl-9720000000-1a78aa01433124242789	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Manoyl oxide 10V, Negative-QTOF	splash10-000i-1090000000-8a0ec2e1bc3422a5e45f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Manoyl oxide 20V, Negative-QTOF	splash10-0079-2090000000-d6a76a2375356cd027fd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Manoyl oxide 40V, Negative-QTOF	splash10-067i-9180000000-852dce52d465e592cac5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Manoyl oxide 10V, Positive-QTOF	splash10-0006-0190000000-9486bb3027a48d7f4c4c	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Manoyl oxide 20V, Positive-QTOF	splash10-0f7c-2890000000-c6bfd9c68ced20ea1e3c	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Manoyl oxide 40V, Positive-QTOF	splash10-004l-9410000000-a3ebe4156caa4dabcf84	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Manoyl oxide 10V, Negative-QTOF	splash10-000i-0090000000-e782630883d1b4130674	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Manoyl oxide 20V, Negative-QTOF	splash10-000i-0090000000-e782630883d1b4130674	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Manoyl oxide 40V, Negative-QTOF	splash10-000i-0090000000-99a63f34a8259abb7fc3	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

FDB006376

KNApSAcK ID

C00043487

Chemspider ID

4956187

KEGG Compound ID

Not Available

BioCyc ID

CPD-20258

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

138224

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Manoyl oxide (HMDB0302821)

MOL for HMDB0302821 (Manoyl oxide)

3D MOL for HMDB0302821 (Manoyl oxide)

3D SDF for HMDB0302821 (Manoyl oxide)

3D-SDF for HMDB0302821 (Manoyl oxide)

PDB for HMDB0302821 (Manoyl oxide)

3D PDB for HMDB0302821 (Manoyl oxide)

SMILES for HMDB0302821 (Manoyl oxide)

INCHI for HMDB0302821 (Manoyl oxide)

Structure for HMDB0302821 (Manoyl oxide)

3D Structure for HMDB0302821 (Manoyl oxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra