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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:18:25 UTC

Update Date

2022-03-07 02:54:07 UTC

HMDB ID

HMDB0034464

Secondary Accession Numbers

HMDB34464

Metabolite Identification

Common Name

Austinol

Description

Austinol belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. Austinol is an extremely weak basic (essentially neutral) compound (based on its pKa). Metabolite of Emericella nidulans, Emericella dentata, Aspergillus variecolor and Aspergillus ustus.

Structure

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


  Mrv0541 05061307502D          

 33 37  0  0  0  0            999 V2000
    3.6719    1.6446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7541    0.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3722   -1.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7100   -0.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7026   -1.1807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0898    0.1511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9565    2.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0093    1.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1954    1.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8010   -0.6719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6148   -0.5373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3816    0.8724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8571    0.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3792   -1.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5328    0.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5677    0.7377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9665    1.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7131   -1.0715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0447    0.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4287   -0.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2774   -0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1120    1.1906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9052    0.2349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4091   -0.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5435   -0.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3468    0.6388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5155   -1.2632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8547    0.0711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2507   -0.6298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0990   -1.6283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2144    2.1360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2426   -0.2680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2618    1.0219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  2  0  0  0  0
 11 10  1  0  0  0  0
 12  1  1  0  0  0  0
 13  2  2  0  0  0  0
 14  3  1  0  0  0  0
 15  8  1  0  0  0  0
 16 12  2  0  0  0  0
 17 16  1  0  0  0  0
 20  4  1  0  0  0  0
 20  5  1  0  0  0  0
 21  6  1  0  0  0  0
 21 10  1  0  0  0  0
 21 16  1  0  0  0  0
 22  7  1  0  0  0  0
 22 13  1  0  0  0  0
 22 17  1  0  0  0  0
 23  9  1  0  0  0  0
 23 11  1  0  0  0  0
 23 12  1  0  0  0  0
 23 20  1  0  0  0  0
 24 13  1  0  0  0  0
 24 18  1  0  0  0  0
 24 21  1  0  0  0  0
 25 14  1  0  0  0  0
 25 19  1  0  0  0  0
 25 24  1  0  0  0  0
 26 15  2  0  0  0  0
 27 18  2  0  0  0  0
 28 19  2  0  0  0  0
 29 25  1  0  0  0  0
 30 14  1  0  0  0  0
 30 18  1  0  0  0  0
 31 17  1  0  0  0  0
 32 15  1  0  0  0  0
 32 20  1  0  0  0  0
 33 19  1  0  0  0  0
 33 22  1  0  0  0  0
M  END

HMDB0034464
     RDKit          3D
Austinol
 63 67  0  0  0  0  0  0  0  0999 V2000
   -2.3727   -0.2593   -2.3874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1124   -0.3678   -1.0997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1647   -1.6734   -0.4077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6098   -2.7760   -1.3706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2212   -1.5738    0.5463 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3490   -0.3976    1.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8557   -0.4560    2.4458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8951    0.9064    0.7860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6856    1.8712    1.7434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9616    1.4852   -0.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9115    2.3983    0.5961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2503    2.2881   -1.0621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9133    1.9634   -1.0771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0767    2.5870   -1.7112 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7448    0.7751   -0.2130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4177    0.6111    0.4252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4395    0.8549    1.9292 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6051    1.5744   -0.1395 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9235    1.3635    0.5415 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4891   -0.0451    0.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3092   -0.2502    1.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4998   -0.7891    1.5515 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1337   -1.2367    0.3250 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2476   -1.7393    0.3095 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3868   -1.0543   -0.8216 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4330    0.0052   -0.8280 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7445   -0.0501   -2.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2781    1.2651   -0.7699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4348   -1.0431    0.2152 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7501   -2.5088    0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1104   -0.7590    0.2614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8517   -1.9296    0.1991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9336   -2.4941    1.4872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6297   -1.1228   -2.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3227    0.7150   -2.8528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8471   -2.8812   -2.1816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7104   -3.7283   -0.8254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5777   -2.5308   -1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1680    1.6779    2.5629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4830    0.6306   -0.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4053    3.0359   -0.1918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6715    1.8655    1.1747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3039    3.1073    1.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5217    0.4057    2.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2194    0.2809    2.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3884    1.9268    2.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2676    2.5941    0.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7914    1.4457   -1.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    2.1460    0.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9052    1.6510    1.6171 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8850    0.0648    2.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0652   -0.9192    2.4888 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3613   -0.6947   -2.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7563   -0.5002   -2.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6611    0.9789   -2.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5046    1.6174    0.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3022    1.0674   -1.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8412    2.0090   -1.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1613   -3.1326    0.7382 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4888   -2.8395   -0.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8321   -2.7246    0.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3931   -2.7697   -0.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3964   -1.9222    2.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 20 29  1  0
 29 30  1  0
 29 31  2  0
 31 32  1  0
 32 33  1  0
 15  2  1  0
 31 16  1  0
 32  3  1  0
 15  8  1  0
 26 20  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 11 43  1  0
 17 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 21 51  1  0
 22 52  1  0
 27 53  1  0
 27 54  1  0
 27 55  1  0
 28 56  1  0
 28 57  1  0
 28 58  1  0
 30 59  1  0
 30 60  1  0
 30 61  1  0
 32 62  1  0
 33 63  1  0
M  END


  Mrv0541 05061307502D          

 33 37  0  0  0  0            999 V2000
    3.6719    1.6446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7541    0.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3722   -1.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7100   -0.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7026   -1.1807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0898    0.1511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9565    2.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0093    1.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1954    1.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8010   -0.6719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6148   -0.5373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3816    0.8724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8571    0.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3792   -1.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5328    0.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5677    0.7377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9665    1.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7131   -1.0715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0447    0.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4287   -0.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2774   -0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1120    1.1906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9052    0.2349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4091   -0.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5435   -0.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3468    0.6388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5155   -1.2632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8547    0.0711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2507   -0.6298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0990   -1.6283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2144    2.1360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2426   -0.2680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2618    1.0219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  2  0  0  0  0
 11 10  1  0  0  0  0
 12  1  1  0  0  0  0
 13  2  2  0  0  0  0
 14  3  1  0  0  0  0
 15  8  1  0  0  0  0
 16 12  2  0  0  0  0
 17 16  1  0  0  0  0
 20  4  1  0  0  0  0
 20  5  1  0  0  0  0
 21  6  1  0  0  0  0
 21 10  1  0  0  0  0
 21 16  1  0  0  0  0
 22  7  1  0  0  0  0
 22 13  1  0  0  0  0
 22 17  1  0  0  0  0
 23  9  1  0  0  0  0
 23 11  1  0  0  0  0
 23 12  1  0  0  0  0
 23 20  1  0  0  0  0
 24 13  1  0  0  0  0
 24 18  1  0  0  0  0
 24 21  1  0  0  0  0
 25 14  1  0  0  0  0
 25 19  1  0  0  0  0
 25 24  1  0  0  0  0
 26 15  2  0  0  0  0
 27 18  2  0  0  0  0
 28 19  2  0  0  0  0
 29 25  1  0  0  0  0
 30 14  1  0  0  0  0
 30 18  1  0  0  0  0
 31 17  1  0  0  0  0
 32 15  1  0  0  0  0
 32 20  1  0  0  0  0
 33 19  1  0  0  0  0
 33 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034464

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1OC(=O)C23C(=C)C(C)(OC(=O)C12O)C(O)C1=C(C)C2(CCC31C)C=CC(=O)OC2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C25H30O8/c1-12-16-17(27)22(7)13(2)24(18(28)31-14(3)25(24,30)19(29)33-22)21(16,6)10-11-23(12)9-8-15(26)32-20(23,4)5/h8-9,14,17,27,30H,2,10-11H2,1,3-7H3

> <INCHI_KEY>
DNKFADXVMUNRRM-UHFFFAOYSA-N

> <FORMULA>
C25H30O8

> <MOLECULAR_WEIGHT>
458.5009

> <EXACT_MASS>
458.194067936

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
45.548013601963625

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8',12'-dihydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-2,6-dihydro-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione

> <ALOGPS_LOGP>
2.13

> <JCHEM_LOGP>
1.662103973333334

> <ALOGPS_LOGS>
-3.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.328454660557899

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.787206581508324

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5307128875628324

> <JCHEM_POLAR_SURFACE_AREA>
119.36000000000001

> <JCHEM_REFRACTIVITY>
115.75819999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.50e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8',12'-dihydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034464
     RDKit          3D
Austinol
 63 67  0  0  0  0  0  0  0  0999 V2000
   -2.3727   -0.2593   -2.3874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1124   -0.3678   -1.0997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1647   -1.6734   -0.4077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6098   -2.7760   -1.3706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2212   -1.5738    0.5463 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3490   -0.3976    1.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8557   -0.4560    2.4458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8951    0.9064    0.7860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6856    1.8712    1.7434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9616    1.4852   -0.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9115    2.3983    0.5961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2503    2.2881   -1.0621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9133    1.9634   -1.0771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0767    2.5870   -1.7112 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7448    0.7751   -0.2130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4177    0.6111    0.4252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4395    0.8549    1.9292 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6051    1.5744   -0.1395 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9235    1.3635    0.5415 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4891   -0.0451    0.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3092   -0.2502    1.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4998   -0.7891    1.5515 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1337   -1.2367    0.3250 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2476   -1.7393    0.3095 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3868   -1.0543   -0.8216 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4330    0.0052   -0.8280 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7445   -0.0501   -2.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2781    1.2651   -0.7699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4348   -1.0431    0.2152 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7501   -2.5088    0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1104   -0.7590    0.2614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8517   -1.9296    0.1991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9336   -2.4941    1.4872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6297   -1.1228   -2.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3227    0.7150   -2.8528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8471   -2.8812   -2.1816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7104   -3.7283   -0.8254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5777   -2.5308   -1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1680    1.6779    2.5629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4830    0.6306   -0.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4053    3.0359   -0.1918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6715    1.8655    1.1747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3039    3.1073    1.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5217    0.4057    2.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2194    0.2809    2.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3884    1.9268    2.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2676    2.5941    0.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7914    1.4457   -1.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    2.1460    0.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9052    1.6510    1.6171 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8850    0.0648    2.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0652   -0.9192    2.4888 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3613   -0.6947   -2.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7563   -0.5002   -2.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6611    0.9789   -2.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5046    1.6174    0.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3022    1.0674   -1.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8412    2.0090   -1.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1613   -3.1326    0.7382 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4888   -2.8395   -0.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8321   -2.7246    0.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3931   -2.7697   -0.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3964   -1.9222    2.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 20 29  1  0
 29 30  1  0
 29 31  2  0
 31 32  1  0
 32 33  1  0
 15  2  1  0
 31 16  1  0
 32  3  1  0
 15  8  1  0
 26 20  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 11 43  1  0
 17 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 21 51  1  0
 22 52  1  0
 27 53  1  0
 27 54  1  0
 27 55  1  0
 28 56  1  0
 28 57  1  0
 28 58  1  0
 30 59  1  0
 30 60  1  0
 30 61  1  0
 32 62  1  0
 33 63  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.854   3.070   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.274   1.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.695  -2.908   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.925  -1.507   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.778  -2.204   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.768   0.282   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.786   3.735   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.351   2.131   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.831   1.880   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.228  -1.254   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.748  -1.003   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.312   1.629   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.600   0.640   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.708  -2.272   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.328   0.941   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.793   1.377   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.671   2.518   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.198  -2.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.083   0.424   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.267  -0.752   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.251  -0.064   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.076   2.222   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.290   0.438   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.630  -0.516   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.014  -0.759   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      11.847   1.193   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       4.696  -2.358   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -1.595   0.133   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -0.468  -1.176   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.051  -3.039   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       4.134   3.987   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       9.786  -0.500   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       0.489   1.908   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   13                                                            
CONECT    3   14                                                            
CONECT    4   20                                                            
CONECT    5   20                                                            
CONECT    6   21                                                            
CONECT    7   22                                                            
CONECT    8    9   15                                                       
CONECT    9    8   23                                                       
CONECT   10   11   21                                                       
CONECT   11   10   23                                                       
CONECT   12    1   16   23                                                  
CONECT   13    2   22   24                                                  
CONECT   14    3   25   30                                                  
CONECT   15    8   26   32                                                  
CONECT   16   12   17   21                                                  
CONECT   17   16   22   31                                                  
CONECT   18   24   27   30                                                  
CONECT   19   25   28   33                                                  
CONECT   20    4    5   23   32                                             
CONECT   21    6   10   16   24                                             
CONECT   22    7   13   17   33                                             
CONECT   23    9   11   12   20                                             
CONECT   24   13   18   21   25                                             
CONECT   25   14   19   24   29                                             
CONECT   26   15                                                            
CONECT   27   18                                                            
CONECT   28   19                                                            
CONECT   29   25                                                            
CONECT   30   14   18                                                       
CONECT   31   17                                                            
CONECT   32   15   20                                                       
CONECT   33   19   22                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

COMPND    HMDB0034464
HETATM    1  C1  UNL     1      -2.373  -0.259  -2.387  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.112  -0.368  -1.100  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.165  -1.673  -0.408  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.610  -2.776  -1.371  1.00  0.00           C  
HETATM    5  O1  UNL     1      -3.221  -1.574   0.546  1.00  0.00           O  
HETATM    6  C5  UNL     1      -3.349  -0.398   1.308  1.00  0.00           C  
HETATM    7  O2  UNL     1      -3.856  -0.456   2.446  1.00  0.00           O  
HETATM    8  C6  UNL     1      -2.895   0.906   0.786  1.00  0.00           C  
HETATM    9  O3  UNL     1      -2.686   1.871   1.743  1.00  0.00           O  
HETATM   10  C7  UNL     1      -3.962   1.485  -0.146  1.00  0.00           C  
HETATM   11  C8  UNL     1      -4.912   2.398   0.596  1.00  0.00           C  
HETATM   12  O4  UNL     1      -3.250   2.288  -1.062  1.00  0.00           O  
HETATM   13  C9  UNL     1      -1.913   1.963  -1.077  1.00  0.00           C  
HETATM   14  O5  UNL     1      -1.077   2.587  -1.711  1.00  0.00           O  
HETATM   15  C10 UNL     1      -1.745   0.775  -0.213  1.00  0.00           C  
HETATM   16  C11 UNL     1      -0.418   0.611   0.425  1.00  0.00           C  
HETATM   17  C12 UNL     1      -0.440   0.855   1.929  1.00  0.00           C  
HETATM   18  C13 UNL     1       0.605   1.574  -0.140  1.00  0.00           C  
HETATM   19  C14 UNL     1       1.924   1.363   0.541  1.00  0.00           C  
HETATM   20  C15 UNL     1       2.489  -0.045   0.324  1.00  0.00           C  
HETATM   21  C16 UNL     1       3.309  -0.250   1.576  1.00  0.00           C  
HETATM   22  C17 UNL     1       4.500  -0.789   1.551  1.00  0.00           C  
HETATM   23  C18 UNL     1       5.134  -1.237   0.325  1.00  0.00           C  
HETATM   24  O6  UNL     1       6.248  -1.739   0.310  1.00  0.00           O  
HETATM   25  O7  UNL     1       4.387  -1.054  -0.822  1.00  0.00           O  
HETATM   26  C19 UNL     1       3.433   0.005  -0.828  1.00  0.00           C  
HETATM   27  C20 UNL     1       2.744  -0.050  -2.172  1.00  0.00           C  
HETATM   28  C21 UNL     1       4.278   1.265  -0.770  1.00  0.00           C  
HETATM   29  C22 UNL     1       1.435  -1.043   0.215  1.00  0.00           C  
HETATM   30  C23 UNL     1       1.750  -2.509   0.037  1.00  0.00           C  
HETATM   31  C24 UNL     1       0.110  -0.759   0.261  1.00  0.00           C  
HETATM   32  C25 UNL     1      -0.852  -1.930   0.199  1.00  0.00           C  
HETATM   33  O8  UNL     1      -0.934  -2.494   1.487  1.00  0.00           O  
HETATM   34  H1  UNL     1      -2.630  -1.123  -2.964  1.00  0.00           H  
HETATM   35  H2  UNL     1      -2.323   0.715  -2.853  1.00  0.00           H  
HETATM   36  H3  UNL     1      -1.847  -2.881  -2.182  1.00  0.00           H  
HETATM   37  H4  UNL     1      -2.710  -3.728  -0.825  1.00  0.00           H  
HETATM   38  H5  UNL     1      -3.578  -2.531  -1.833  1.00  0.00           H  
HETATM   39  H6  UNL     1      -3.168   1.678   2.563  1.00  0.00           H  
HETATM   40  H7  UNL     1      -4.483   0.631  -0.616  1.00  0.00           H  
HETATM   41  H8  UNL     1      -5.405   3.036  -0.192  1.00  0.00           H  
HETATM   42  H9  UNL     1      -5.672   1.865   1.175  1.00  0.00           H  
HETATM   43  H10 UNL     1      -4.304   3.107   1.195  1.00  0.00           H  
HETATM   44  H11 UNL     1       0.522   0.406   2.325  1.00  0.00           H  
HETATM   45  H12 UNL     1      -1.219   0.281   2.456  1.00  0.00           H  
HETATM   46  H13 UNL     1      -0.388   1.927   2.193  1.00  0.00           H  
HETATM   47  H14 UNL     1       0.268   2.594   0.161  1.00  0.00           H  
HETATM   48  H15 UNL     1       0.791   1.446  -1.199  1.00  0.00           H  
HETATM   49  H16 UNL     1       2.593   2.146   0.072  1.00  0.00           H  
HETATM   50  H17 UNL     1       1.905   1.651   1.617  1.00  0.00           H  
HETATM   51  H18 UNL     1       2.885   0.065   2.534  1.00  0.00           H  
HETATM   52  H19 UNL     1       5.065  -0.919   2.489  1.00  0.00           H  
HETATM   53  H20 UNL     1       3.361  -0.695  -2.852  1.00  0.00           H  
HETATM   54  H21 UNL     1       1.756  -0.500  -2.161  1.00  0.00           H  
HETATM   55  H22 UNL     1       2.661   0.979  -2.571  1.00  0.00           H  
HETATM   56  H23 UNL     1       4.505   1.617   0.234  1.00  0.00           H  
HETATM   57  H24 UNL     1       5.302   1.067  -1.228  1.00  0.00           H  
HETATM   58  H25 UNL     1       3.841   2.009  -1.466  1.00  0.00           H  
HETATM   59  H26 UNL     1       1.161  -3.133   0.738  1.00  0.00           H  
HETATM   60  H27 UNL     1       1.489  -2.840  -0.989  1.00  0.00           H  
HETATM   61  H28 UNL     1       2.832  -2.725   0.109  1.00  0.00           H  
HETATM   62  H29 UNL     1      -0.393  -2.770  -0.412  1.00  0.00           H  
HETATM   63  H30 UNL     1      -0.396  -1.922   2.081  1.00  0.00           H  
CONECT    1    2    2   34   35
CONECT    2    3   15
CONECT    3    4    5   32
CONECT    4   36   37   38
CONECT    5    6
CONECT    6    7    7    8
CONECT    8    9   10   15
CONECT    9   39
CONECT   10   11   12   40
CONECT   11   41   42   43
CONECT   12   13
CONECT   13   14   14   15
CONECT   15   16
CONECT   16   17   18   31
CONECT   17   44   45   46
CONECT   18   19   47   48
CONECT   19   20   49   50
CONECT   20   21   26   29
CONECT   21   22   22   51
CONECT   22   23   52
CONECT   23   24   24   25
CONECT   25   26
CONECT   26   27   28
CONECT   27   53   54   55
CONECT   28   56   57   58
CONECT   29   30   31   31
CONECT   30   59   60   61
CONECT   31   32
CONECT   32   33   62
CONECT   33   63
END

HMDB0034464
     RDKit          3D
Austinol
 63 67  0  0  0  0  0  0  0  0999 V2000
   -2.3727   -0.2593   -2.3874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1124   -0.3678   -1.0997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1647   -1.6734   -0.4077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6098   -2.7760   -1.3706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2212   -1.5738    0.5463 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3490   -0.3976    1.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8557   -0.4560    2.4458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8951    0.9064    0.7860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6856    1.8712    1.7434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9616    1.4852   -0.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9115    2.3983    0.5961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2503    2.2881   -1.0621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9133    1.9634   -1.0771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0767    2.5870   -1.7112 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7448    0.7751   -0.2130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4177    0.6111    0.4252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4395    0.8549    1.9292 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6051    1.5744   -0.1395 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9235    1.3635    0.5415 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4891   -0.0451    0.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3092   -0.2502    1.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4998   -0.7891    1.5515 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1337   -1.2367    0.3250 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2476   -1.7393    0.3095 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3868   -1.0543   -0.8216 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4330    0.0052   -0.8280 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7445   -0.0501   -2.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2781    1.2651   -0.7699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4348   -1.0431    0.2152 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7501   -2.5088    0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1104   -0.7590    0.2614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8517   -1.9296    0.1991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9336   -2.4941    1.4872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6297   -1.1228   -2.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3227    0.7150   -2.8528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8471   -2.8812   -2.1816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7104   -3.7283   -0.8254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5777   -2.5308   -1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1680    1.6779    2.5629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4830    0.6306   -0.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4053    3.0359   -0.1918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6715    1.8655    1.1747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3039    3.1073    1.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5217    0.4057    2.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2194    0.2809    2.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3884    1.9268    2.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2676    2.5941    0.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7914    1.4457   -1.1995 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    2.1460    0.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9052    1.6510    1.6171 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8850    0.0648    2.5337 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0652   -0.9192    2.4888 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3613   -0.6947   -2.8522 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7563   -0.5002   -2.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6611    0.9789   -2.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5046    1.6174    0.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3022    1.0674   -1.2282 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8412    2.0090   -1.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1613   -3.1326    0.7382 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4888   -2.8395   -0.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8321   -2.7246    0.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3931   -2.7697   -0.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3964   -1.9222    2.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 20 29  1  0
 29 30  1  0
 29 31  2  0
 31 32  1  0
 32 33  1  0
 15  2  1  0
 31 16  1  0
 32  3  1  0
 15  8  1  0
 26 20  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
  9 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 11 43  1  0
 17 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 21 51  1  0
 22 52  1  0
 27 53  1  0
 27 54  1  0
 27 55  1  0
 28 56  1  0
 28 57  1  0
 28 58  1  0
 30 59  1  0
 30 60  1  0
 30 61  1  0
 32 62  1  0
 33 63  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Austinol	MeSH
Dehydroaustinol	MeSH

Chemical Formula

C₂₅H₃₀O₈

Average Molecular Weight

458.5009

Monoisotopic Molecular Weight

458.194067936

IUPAC Name

8',12'-dihydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-2,6-dihydro-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione

Traditional Name

8',12'-dihydroxy-2,2,2',6',9',13'-hexamethyl-16'-methylidene-10',14'-dioxaspiro[pyran-3,5'-tetracyclo[7.6.1.0¹,¹².0²,⁷]hexadecan]-6'-ene-6,11',15'-trione

CAS Registry Number

72040-27-8

SMILES

CC1OC(=O)C23C(=C)C(C)(OC(=O)C12O)C(O)C1=C(C)C2(CCC31C)C=CC(=O)OC2(C)C

InChI Identifier

InChI=1S/C25H30O8/c1-12-16-17(27)22(7)13(2)24(18(28)31-14(3)25(24,30)19(29)33-22)21(16,6)10-11-23(12)9-8-15(26)32-20(23,4)5/h8-9,14,17,27,30H,2,10-11H2,1,3-7H3

InChI Key

DNKFADXVMUNRRM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furopyrans

Sub Class

Not Available

Direct Parent

Furopyrans

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0034464)

Cellular substructure

Source

Endogenous

Endogenous (HMDB: HMDB0034464)

Exogenous

Food

Food (HMDB: HMDB0034464)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0034464)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0034464)

Nutrient

Nutrient (HMDB: HMDB0034464)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0034464)

Emulsifier (HMDB: HMDB0034464)

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	0.15 g/L	ALOGPS
logP	2.13	ALOGPS
logP	1.66	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	10.79	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	115.76 m³·mol⁻¹	ChemAxon
Polarizability	45.55 Å³	ChemAxon
Number of Rings	5	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
DarkChem	[M+H]+	205.341	31661259
DarkChem	[M-H]-	196.077	31661259
DeepCCS	[M-2H]-	231.799	30932474
DeepCCS	[M+Na]+	207.223	30932474
AllCCS	[M+H]+	204.4	32859911
AllCCS	[M+H-H2O]+	202.3	32859911
AllCCS	[M+NH4]+	206.4	32859911
AllCCS	[M+Na]+	206.9	32859911
AllCCS	[M-H]-	212.6	32859911
AllCCS	[M+Na-2H]-	213.6	32859911
AllCCS	[M+HCOO]-	214.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Austinol	CC1OC(=O)C23C(=C)C(C)(OC(=O)C12O)C(O)C1=C(C)C2(CCC31C)C=CC(=O)OC2(C)C	3821.0	Standard polar	33892256
Austinol	CC1OC(=O)C23C(=C)C(C)(OC(=O)C12O)C(O)C1=C(C)C2(CCC31C)C=CC(=O)OC2(C)C	2795.8	Standard non polar	33892256
Austinol	CC1OC(=O)C23C(=C)C(C)(OC(=O)C12O)C(O)C1=C(C)C2(CCC31C)C=CC(=O)OC2(C)C	3616.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Austinol,1TMS,isomer #1	C=C1C2(C)OC(=O)C3(O[Si](C)(C)C)C(C)OC(=O)C13C1(C)CCC3(C=CC(=O)OC3(C)C)C(C)=C1C2O	3421.4	Semi standard non polar	33892256
Austinol,1TMS,isomer #2	C=C1C2(C)OC(=O)C3(O)C(C)OC(=O)C13C1(C)CCC3(C=CC(=O)OC3(C)C)C(C)=C1C2O[Si](C)(C)C	3371.1	Semi standard non polar	33892256
Austinol,2TMS,isomer #1	C=C1C2(C)OC(=O)C3(O[Si](C)(C)C)C(C)OC(=O)C13C1(C)CCC3(C=CC(=O)OC3(C)C)C(C)=C1C2O[Si](C)(C)C	3379.2	Semi standard non polar	33892256
Austinol,1TBDMS,isomer #1	C=C1C2(C)OC(=O)C3(O[Si](C)(C)C(C)(C)C)C(C)OC(=O)C13C1(C)CCC3(C=CC(=O)OC3(C)C)C(C)=C1C2O	3649.6	Semi standard non polar	33892256
Austinol,1TBDMS,isomer #2	C=C1C2(C)OC(=O)C3(O)C(C)OC(=O)C13C1(C)CCC3(C=CC(=O)OC3(C)C)C(C)=C1C2O[Si](C)(C)C(C)(C)C	3591.2	Semi standard non polar	33892256
Austinol,2TBDMS,isomer #1	C=C1C2(C)OC(=O)C3(O[Si](C)(C)C(C)(C)C)C(C)OC(=O)C13C1(C)CCC3(C=CC(=O)OC3(C)C)C(C)=C1C2O[Si](C)(C)C(C)(C)C	3836.2	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 - Austinol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-0091300000-47e68609e84a76fd034c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Austinol GC-MS (2 TMS) - 70eV, Positive	splash10-06dr-5014190000-81cad28c2b4253746324	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Austinol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Austinol 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 - Austinol 10V, Positive-QTOF	splash10-0a4j-0004900000-59b20501baab42acff37	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Austinol 20V, Positive-QTOF	splash10-052e-0019400000-d0dd7935e6cf2372c290	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Austinol 40V, Positive-QTOF	splash10-0udl-9208100000-6a80e186802edeb6b812	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Austinol 10V, Negative-QTOF	splash10-0bt9-0000900000-a83418b75c732a655ca1	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Austinol 20V, Negative-QTOF	splash10-08fr-0001900000-88682b6d4ab7611661d5	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Austinol 40V, Negative-QTOF	splash10-014l-1109000000-0491f21835a15aac45e8	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Austinol 10V, Negative-QTOF	splash10-0a4i-0000900000-27765c5f554803eaf083	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Austinol 20V, Negative-QTOF	splash10-0bt9-0000900000-ba7512b7d18e9022d9ee	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Austinol 40V, Negative-QTOF	splash10-0a4i-3001900000-0d210593f94c8acdb179	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Austinol 10V, Positive-QTOF	splash10-0a4i-0001900000-cddf9b40a5ddc252815c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Austinol 20V, Positive-QTOF	splash10-05nb-0006900000-53cecb43c3c527c6d569	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Austinol 40V, Positive-QTOF	splash10-0f6y-5903300000-e7aa1f952015ceb62b4a	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012873

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

73745644

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Austinol (HMDB0034464)

MOL for HMDB0034464 (Austinol)

3D MOL for HMDB0034464 (Austinol)

3D SDF for HMDB0034464 (Austinol)

3D-SDF for HMDB0034464 (Austinol)

PDB for HMDB0034464 (Austinol)

3D PDB for HMDB0034464 (Austinol)

SMILES for HMDB0034464 (Austinol)

INCHI for HMDB0034464 (Austinol)

Structure for HMDB0034464 (Austinol)

3D Structure for HMDB0034464 (Austinol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra