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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:06:49 UTC

Update Date

2021-09-14 14:57:42 UTC

HMDB ID

HMDB0060912

Secondary Accession Numbers

HMDB60912

Metabolite Identification

Common Name

9-alpha,10-alpha-epoxyhexahydrocannabinol

Description

9-alpha,10-alpha-epoxyhexahydrocannabinol, also known as AATTH, belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. 9-alpha,10-alpha-epoxyhexahydrocannabinol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HMDB0060912
     RDKit          3D
9-alpha,10-alpha-epoxyhexahydrocannabinol
 54 57  0  0  0  0  0  0  0  0999 V2000
    6.4751    0.6419   -0.0815 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3806   -0.3706   -1.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4814   -1.5264   -0.9443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0385   -1.2905   -0.7658 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6259   -0.4358    0.4020 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1116   -0.3321    0.4473 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3735   -1.2435    1.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0136   -1.1499    1.1962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7009   -2.0867    1.9166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6816   -0.1549    0.5410 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0548    0.7672   -0.1729 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4510    0.6728   -0.2155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5456    1.8124   -0.8691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9443    2.0140   -0.7679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1842    2.7907    0.5075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3739    2.8458   -1.9346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5872    0.6524   -0.7353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0843    0.7010   -0.8733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7921    0.1635    0.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3078   -1.2149    0.6668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1251   -2.4168    0.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6466   -1.4486    1.8747 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8413   -1.3447    0.7549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1581   -0.0117    0.5552 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9910    1.6038   -0.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5733    0.9399    0.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2224    0.2942    0.9356 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0452    0.1647   -2.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4107   -0.7978   -1.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6208   -2.2019   -1.8499 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8469   -2.1954   -0.1091 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5675   -2.3030   -0.5563 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5155   -0.9751   -1.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9863    0.6205    0.3209 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0174   -0.8976    1.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8892   -2.0393    1.6792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3072   -2.8495    2.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0445    1.3938   -0.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4246    2.4689    1.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9622    3.8618    0.2866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2119    2.7355    0.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3724    3.3098   -1.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3993    2.2129   -2.8372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6538    3.6933   -2.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1506    0.0502   -1.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3994    0.0369   -1.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4767    1.6952   -1.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8796    0.0754    0.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7491    0.8578    1.2104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5134   -2.9362    1.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4460   -3.1530   -0.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9847   -2.1334   -0.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4029   -2.2458    0.3026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4026    0.6788    1.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 12  6  1  0
 24 17  1  0
 24 10  1  0
 23 20  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  7 36  1  0
  9 37  1  0
 12 38  1  0
 15 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
 23 53  1  0
 24 54  1  0
M  END


  Mrv0541 07091309062D          

 24 27  0  0  0  0            999 V2000
    7.4913   -1.7982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4796    0.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5273    0.9830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6381   -1.4079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7214   -1.5018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0797   -2.0204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3098   -1.7241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6682   -2.2427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6902    0.0540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0486   -0.4646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2566   -2.4650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7699   -1.1314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8983   -1.9463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4601   -0.2423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4867   -2.1686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0000   -0.8350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5884   -1.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3584   -1.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9468   -1.5759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1017    0.2763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1769   -1.2796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8451   -2.6872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8717   -0.0201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3052   -2.0945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
 10  9  1  0  0  0  0
 13  8  1  0  0  0  0
 13 11  2  0  0  0  0
 13 12  1  0  0  0  0
 14  9  1  0  0  0  0
 15 11  1  0  0  0  0
 16 12  2  0  0  0  0
 17 14  1  0  0  0  0
 18 15  2  0  0  0  0
 18 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 17  1  0  0  0  0
 20  2  1  0  0  0  0
 20  3  1  0  0  0  0
 20 14  1  0  0  0  0
 21  4  1  0  0  0  0
 21 10  1  0  0  0  0
 21 19  1  0  0  0  0
 22 15  1  0  0  0  0
 23 16  1  0  0  0  0
 23 20  1  0  0  0  0
 24 19  1  0  0  0  0
 24 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060912

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCC1=CC(O)=C2C3C4OC4(C)CCC3C(C)(C)OC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O3/c1-5-6-7-8-13-11-15(22)18-16(12-13)23-20(2,3)14-9-10-21(4)19(24-21)17(14)18/h11-12,14,17,19,22H,5-10H2,1-4H3

> <INCHI_KEY>
VSQGBNUBIDZRPJ-UHFFFAOYSA-N

> <FORMULA>
C21H30O3

> <MOLECULAR_WEIGHT>
330.4611

> <EXACT_MASS>
330.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
39.5983661624988

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9,9,13-trimethyl-5-pentyl-8,14-dioxatetracyclo[8.5.0.0²,⁷.0¹³,¹⁵]pentadeca-2,4,6-trien-3-ol

> <ALOGPS_LOGP>
5.60

> <JCHEM_LOGP>
5.121329329

> <ALOGPS_LOGS>
-5.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.900698416633276

> <JCHEM_PKA_STRONGEST_BASIC>
-4.142420664829111

> <JCHEM_POLAR_SURFACE_AREA>
41.99

> <JCHEM_REFRACTIVITY>
95.41699999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.89e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9,9,13-trimethyl-5-pentyl-8,14-dioxatetracyclo[8.5.0.0²,⁷.0¹³,¹⁵]pentadeca-2,4,6-trien-3-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060912
     RDKit          3D
9-alpha,10-alpha-epoxyhexahydrocannabinol
 54 57  0  0  0  0  0  0  0  0999 V2000
    6.4751    0.6419   -0.0815 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3806   -0.3706   -1.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4814   -1.5264   -0.9443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0385   -1.2905   -0.7658 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6259   -0.4358    0.4020 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1116   -0.3321    0.4473 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3735   -1.2435    1.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0136   -1.1499    1.1962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7009   -2.0867    1.9166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6816   -0.1549    0.5410 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0548    0.7672   -0.1729 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4510    0.6728   -0.2155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5456    1.8124   -0.8691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9443    2.0140   -0.7679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1842    2.7907    0.5075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3739    2.8458   -1.9346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5872    0.6524   -0.7353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0843    0.7010   -0.8733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7921    0.1635    0.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3078   -1.2149    0.6668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1251   -2.4168    0.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6466   -1.4486    1.8747 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8413   -1.3447    0.7549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1581   -0.0117    0.5552 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9910    1.6038   -0.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5733    0.9399    0.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2224    0.2942    0.9356 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0452    0.1647   -2.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4107   -0.7978   -1.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6208   -2.2019   -1.8499 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8469   -2.1954   -0.1091 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5675   -2.3030   -0.5563 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5155   -0.9751   -1.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0174   -0.8976    1.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3072   -2.8495    2.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0445    1.3938   -0.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4246    2.4689    1.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9622    3.8618    0.2866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2119    2.7355    0.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3724    3.3098   -1.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3993    2.2129   -2.8372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6538    3.6933   -2.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1506    0.0502   -1.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3994    0.0369   -1.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4767    1.6952   -1.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8796    0.0754    0.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7491    0.8578    1.2104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5134   -2.9362    1.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4460   -3.1530   -0.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9847   -2.1334   -0.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4029   -2.2458    0.3026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4026    0.6788    1.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 12  6  1  0
 24 17  1  0
 24 10  1  0
 23 20  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  7 36  1  0
  9 37  1  0
 12 38  1  0
 15 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
 23 53  1  0
 24 54  1  0
M  END

HEADER    PROTEIN                                 09-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-13         0                                  
HETATM    1  C   UNK     0      13.984  -3.357   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.762   1.527   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.718   1.835   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.191  -2.628   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.547  -2.803   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.349  -3.771   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.912  -3.218   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.714  -4.186   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.288   0.101   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.091  -0.867   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.079  -4.601   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.037  -2.112   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.277  -3.633   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.726  -0.452   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.642  -4.048   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.600  -1.559   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.965  -1.974   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.402  -2.527   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.767  -2.942   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.923   0.516   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.330  -2.389   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.444  -5.016   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.361  -0.038   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.570  -3.910   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2   20                                                            
CONECT    3   20                                                            
CONECT    4   21                                                            
CONECT    5    1    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7   13                                                       
CONECT    9   10   14                                                       
CONECT   10    9   21                                                       
CONECT   11   13   15                                                       
CONECT   12   13   16                                                       
CONECT   13    8   11   12                                                  
CONECT   14    9   17   20                                                  
CONECT   15   11   18   22                                                  
CONECT   16   12   18   23                                                  
CONECT   17   14   18   19                                                  
CONECT   18   15   16   17                                                  
CONECT   19   17   21   24                                                  
CONECT   20    2    3   14   23                                             
CONECT   21    4   10   19   24                                             
CONECT   22   15                                                            
CONECT   23   16   20                                                       
CONECT   24   19   21                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0060912
HETATM    1  C1  UNL     1       6.475   0.642  -0.082  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.381  -0.371  -1.159  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.481  -1.526  -0.944  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.038  -1.290  -0.766  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.626  -0.436   0.402  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.112  -0.332   0.447  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.373  -1.243   1.154  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.014  -1.150   1.196  1.00  0.00           C  
HETATM    9  O1  UNL     1      -0.701  -2.087   1.917  1.00  0.00           O  
HETATM   10  C9  UNL     1      -0.682  -0.155   0.541  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.055   0.767  -0.173  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.451   0.673  -0.216  1.00  0.00           C  
HETATM   13  O2  UNL     1      -0.546   1.812  -0.869  1.00  0.00           O  
HETATM   14  C12 UNL     1      -1.944   2.014  -0.768  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.184   2.791   0.507  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.374   2.846  -1.935  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.587   0.652  -0.735  1.00  0.00           C  
HETATM   18  C16 UNL     1      -4.084   0.701  -0.873  1.00  0.00           C  
HETATM   19  C17 UNL     1      -4.792   0.164   0.350  1.00  0.00           C  
HETATM   20  C18 UNL     1      -4.308  -1.215   0.667  1.00  0.00           C  
HETATM   21  C19 UNL     1      -5.125  -2.417   0.201  1.00  0.00           C  
HETATM   22  O3  UNL     1      -3.647  -1.449   1.875  1.00  0.00           O  
HETATM   23  C20 UNL     1      -2.841  -1.345   0.755  1.00  0.00           C  
HETATM   24  C21 UNL     1      -2.158  -0.012   0.555  1.00  0.00           C  
HETATM   25  H1  UNL     1       5.991   1.604  -0.365  1.00  0.00           H  
HETATM   26  H2  UNL     1       7.573   0.940   0.012  1.00  0.00           H  
HETATM   27  H3  UNL     1       6.222   0.294   0.936  1.00  0.00           H  
HETATM   28  H4  UNL     1       6.045   0.165  -2.087  1.00  0.00           H  
HETATM   29  H5  UNL     1       7.411  -0.798  -1.340  1.00  0.00           H  
HETATM   30  H6  UNL     1       5.621  -2.202  -1.850  1.00  0.00           H  
HETATM   31  H7  UNL     1       5.847  -2.195  -0.109  1.00  0.00           H  
HETATM   32  H8  UNL     1       3.568  -2.303  -0.556  1.00  0.00           H  
HETATM   33  H9  UNL     1       3.516  -0.975  -1.709  1.00  0.00           H  
HETATM   34  H10 UNL     1       3.986   0.620   0.321  1.00  0.00           H  
HETATM   35  H11 UNL     1       4.017  -0.898   1.326  1.00  0.00           H  
HETATM   36  H12 UNL     1       1.889  -2.039   1.679  1.00  0.00           H  
HETATM   37  H13 UNL     1      -0.307  -2.850   2.428  1.00  0.00           H  
HETATM   38  H14 UNL     1       2.044   1.394  -0.775  1.00  0.00           H  
HETATM   39  H15 UNL     1      -1.425   2.469   1.262  1.00  0.00           H  
HETATM   40  H16 UNL     1      -1.962   3.862   0.287  1.00  0.00           H  
HETATM   41  H17 UNL     1      -3.212   2.736   0.865  1.00  0.00           H  
HETATM   42  H18 UNL     1      -3.372   3.310  -1.801  1.00  0.00           H  
HETATM   43  H19 UNL     1      -2.399   2.213  -2.837  1.00  0.00           H  
HETATM   44  H20 UNL     1      -1.654   3.693  -2.021  1.00  0.00           H  
HETATM   45  H21 UNL     1      -2.151   0.050  -1.560  1.00  0.00           H  
HETATM   46  H22 UNL     1      -4.399   0.037  -1.731  1.00  0.00           H  
HETATM   47  H23 UNL     1      -4.477   1.695  -1.102  1.00  0.00           H  
HETATM   48  H24 UNL     1      -5.880   0.075   0.068  1.00  0.00           H  
HETATM   49  H25 UNL     1      -4.749   0.858   1.210  1.00  0.00           H  
HETATM   50  H26 UNL     1      -5.513  -2.936   1.112  1.00  0.00           H  
HETATM   51  H27 UNL     1      -4.446  -3.153  -0.304  1.00  0.00           H  
HETATM   52  H28 UNL     1      -5.985  -2.133  -0.407  1.00  0.00           H  
HETATM   53  H29 UNL     1      -2.403  -2.246   0.303  1.00  0.00           H  
HETATM   54  H30 UNL     1      -2.403   0.679   1.396  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   28   29
CONECT    3    4   30   31
CONECT    4    5   32   33
CONECT    5    6   34   35
CONECT    6    7    7   12
CONECT    7    8   36
CONECT    8    9   10   10
CONECT    9   37
CONECT   10   11   24
CONECT   11   12   12   13
CONECT   12   38
CONECT   13   14
CONECT   14   15   16   17
CONECT   15   39   40   41
CONECT   16   42   43   44
CONECT   17   18   24   45
CONECT   18   19   46   47
CONECT   19   20   48   49
CONECT   20   21   22   23
CONECT   21   50   51   52
CONECT   22   23
CONECT   23   24   53
CONECT   24   54
END

HMDB0060912
     RDKit          3D
9-alpha,10-alpha-epoxyhexahydrocannabinol
 54 57  0  0  0  0  0  0  0  0999 V2000
    6.4751    0.6419   -0.0815 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3806   -0.3706   -1.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4814   -1.5264   -0.9443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0385   -1.2905   -0.7658 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6259   -0.4358    0.4020 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1116   -0.3321    0.4473 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3735   -1.2435    1.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0136   -1.1499    1.1962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7009   -2.0867    1.9166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6816   -0.1549    0.5410 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0548    0.7672   -0.1729 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4510    0.6728   -0.2155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5456    1.8124   -0.8691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9443    2.0140   -0.7679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1842    2.7907    0.5075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3739    2.8458   -1.9346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5872    0.6524   -0.7353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0843    0.7010   -0.8733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7921    0.1635    0.3495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3078   -1.2149    0.6668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1251   -2.4168    0.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6466   -1.4486    1.8747 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8413   -1.3447    0.7549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1581   -0.0117    0.5552 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9910    1.6038   -0.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5733    0.9399    0.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2224    0.2942    0.9356 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0452    0.1647   -2.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4107   -0.7978   -1.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6208   -2.2019   -1.8499 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8469   -2.1954   -0.1091 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5675   -2.3030   -0.5563 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5155   -0.9751   -1.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9863    0.6205    0.3209 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0174   -0.8976    1.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8892   -2.0393    1.6792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3072   -2.8495    2.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0445    1.3938   -0.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4246    2.4689    1.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9622    3.8618    0.2866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2119    2.7355    0.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3724    3.3098   -1.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3993    2.2129   -2.8372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6538    3.6933   -2.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1506    0.0502   -1.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3994    0.0369   -1.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4767    1.6952   -1.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8796    0.0754    0.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7491    0.8578    1.2104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5134   -2.9362    1.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4460   -3.1530   -0.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9847   -2.1334   -0.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4029   -2.2458    0.3026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4026    0.6788    1.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 12  6  1  0
 24 17  1  0
 24 10  1  0
 23 20  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  7 36  1  0
  9 37  1  0
 12 38  1  0
 15 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
 23 53  1  0
 24 54  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
9-a,10-a-Epoxyhexahydrocannabinol	Generator
9-Α,10-α-epoxyhexahydrocannabinol	Generator
4-O-Acetyl-1,5-anhydro-2,3,6-trideoxy-3-trifluoroacetamidohex-1-enitol	HMDB
AATTH	HMDB

Chemical Formula

C₂₁H₃₀O₃

Average Molecular Weight

330.4611

Monoisotopic Molecular Weight

330.219494826

IUPAC Name

9,9,13-trimethyl-5-pentyl-8,14-dioxatetracyclo[8.5.0.0²,⁷.0¹³,¹⁵]pentadeca-2,4,6-trien-3-ol

Traditional Name

9,9,13-trimethyl-5-pentyl-8,14-dioxatetracyclo[8.5.0.0²,⁷.0¹³,¹⁵]pentadeca-2,4,6-trien-3-ol

CAS Registry Number

Not Available

SMILES

CCCCCC1=CC(O)=C2C3C4OC4(C)CCC3C(C)(C)OC2=C1

InChI Identifier

InChI=1S/C21H30O3/c1-5-6-7-8-13-11-15(22)18-16(12-13)23-20(2,3)14-9-10-21(4)19(24-21)17(14)18/h11-12,14,17,19,22H,5-10H2,1-4H3

InChI Key

VSQGBNUBIDZRPJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

2,2-dimethyl-1-benzopyrans

Alternative Parents

Substituents

2,2-dimethyl-1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Oxepane
Alkyl aryl ether
Benzenoid
Oxacycle
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0060912)
Liver (HMDB: HMDB0060912)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060912)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060912)

Cellular substructure

Cytoplasm (HMDB: HMDB0060912)
Membrane (HMDB: HMDB0060912)

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
Water Solubility	0.0019 g/L	ALOGPS
logP	5.6	ALOGPS
logP	5.12	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	9.9	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	41.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	95.42 m³·mol⁻¹	ChemAxon
Polarizability	39.6 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	181.73	31661259
DarkChem	[M-H]-	178.222	31661259
DeepCCS	[M+H]+	190.836	30932474
DeepCCS	[M-H]-	188.478	30932474
DeepCCS	[M-2H]-	221.667	30932474
DeepCCS	[M+Na]+	196.929	30932474
AllCCS	[M+H]+	183.6	32859911
AllCCS	[M+H-H2O]+	180.6	32859911
AllCCS	[M+NH4]+	186.4	32859911
AllCCS	[M+Na]+	187.2	32859911
AllCCS	[M-H]-	191.5	32859911
AllCCS	[M+Na-2H]-	191.9	32859911
AllCCS	[M+HCOO]-	192.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
9-alpha,10-alpha-epoxyhexahydrocannabinol	CCCCCC1=CC(O)=C2C3C4OC4(C)CCC3C(C)(C)OC2=C1	3291.1	Standard polar	33892256
9-alpha,10-alpha-epoxyhexahydrocannabinol	CCCCCC1=CC(O)=C2C3C4OC4(C)CCC3C(C)(C)OC2=C1	2492.4	Standard non polar	33892256
9-alpha,10-alpha-epoxyhexahydrocannabinol	CCCCCC1=CC(O)=C2C3C4OC4(C)CCC3C(C)(C)OC2=C1	2632.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
9-alpha,10-alpha-epoxyhexahydrocannabinol,1TMS,isomer #1	CCCCCC1=CC2=C(C(O[Si](C)(C)C)=C1)C1C(CCC3(C)OC13)C(C)(C)O2	2412.6	Semi standard non polar	33892256
9-alpha,10-alpha-epoxyhexahydrocannabinol,1TBDMS,isomer #1	CCCCCC1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1)C1C(CCC3(C)OC13)C(C)(C)O2	2633.3	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 - 9-alpha,10-alpha-epoxyhexahydrocannabinol GC-MS (Non-derivatized) - 70eV, Positive	splash10-06dl-5393000000-d3cbbfbd6398e124a2a2	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9-alpha,10-alpha-epoxyhexahydrocannabinol GC-MS (1 TMS) - 70eV, Positive	splash10-008j-3019000000-a6c6e191d36386bbaee1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9-alpha,10-alpha-epoxyhexahydrocannabinol 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 - 9-alpha,10-alpha-epoxyhexahydrocannabinol 10V, Positive-QTOF	splash10-001i-0119000000-6e8d5e495ba842352b0d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-alpha,10-alpha-epoxyhexahydrocannabinol 20V, Positive-QTOF	splash10-06z0-4693000000-9a70297c6126bff36b13	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-alpha,10-alpha-epoxyhexahydrocannabinol 40V, Positive-QTOF	splash10-0a4l-9420000000-091575b50da2814dcdb3	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-alpha,10-alpha-epoxyhexahydrocannabinol 10V, Negative-QTOF	splash10-004i-0009000000-0a6ca3cf16464ed1e833	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-alpha,10-alpha-epoxyhexahydrocannabinol 20V, Negative-QTOF	splash10-004i-0209000000-70499fa05a92fdc2463c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-alpha,10-alpha-epoxyhexahydrocannabinol 40V, Negative-QTOF	splash10-01t9-1900000000-0447fd17ec6f5d063299	2017-10-06	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

125763

PDB ID

Not Available

ChEBI ID

Not Available

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 9-alpha,10-alpha-epoxyhexahydrocannabinol (HMDB0060912)

MOL for HMDB0060912 (9-alpha,10-alpha-epoxyhexahydrocannabinol)

3D MOL for HMDB0060912 (9-alpha,10-alpha-epoxyhexahydrocannabinol)

3D SDF for HMDB0060912 (9-alpha,10-alpha-epoxyhexahydrocannabinol)

3D-SDF for HMDB0060912 (9-alpha,10-alpha-epoxyhexahydrocannabinol)

PDB for HMDB0060912 (9-alpha,10-alpha-epoxyhexahydrocannabinol)

3D PDB for HMDB0060912 (9-alpha,10-alpha-epoxyhexahydrocannabinol)

SMILES for HMDB0060912 (9-alpha,10-alpha-epoxyhexahydrocannabinol)

INCHI for HMDB0060912 (9-alpha,10-alpha-epoxyhexahydrocannabinol)

Structure for HMDB0060912 (9-alpha,10-alpha-epoxyhexahydrocannabinol)

3D Structure for HMDB0060912 (9-alpha,10-alpha-epoxyhexahydrocannabinol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra