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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:00:19 UTC

Update Date

2022-03-07 02:54:20 UTC

HMDB ID

HMDB0035062

Secondary Accession Numbers

HMDB35062

Metabolite Identification

Common Name

Arnamiol

Description

Arnamiol belongs to the class of organic compounds known as melleolides and analogues. Melleolides and analogues are compounds with a structure characterized by the presence of a 2-hydroxy-4-methoxy-6-methylbenzoic acid derivative linked to a 3,6,6,7b-tetramethyl-cyclobuta[e]indene moiety. Based on a literature review a small amount of articles have been published on Arnamiol.

Structure

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


  Mrv0541 05061308132D          

 31 34  0  0  0  0            999 V2000
   -0.8971    0.5197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3497    0.5391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8336    1.5152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6532    1.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2347   -2.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6261   -1.8455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4330   -0.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8090    1.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7115    0.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9182   -1.5842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1401   -0.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6202   -0.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3570   -0.8855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2346    0.5118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8218   -1.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1874   -1.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2727    0.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5788   -0.8733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9714   -0.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9444   -0.4524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1815   -0.9162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2254   -0.6896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5497    0.7406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4102    0.5424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5056    0.1522    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3039   -2.3135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2606   -2.2664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5671   -1.6455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7867   -1.2942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9917   -1.4246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4685    0.0988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11  1  1  0  0  0  0
 12  7  1  0  0  0  0
 13 10  1  0  0  0  0
 14  8  1  0  0  0  0
 14 12  1  0  0  0  0
 15  6  2  0  0  0  0
 16  6  1  0  0  0  0
 17  9  1  0  0  0  0
 18 11  2  0  0  0  0
 18 15  1  0  0  0  0
 19 13  2  0  0  0  0
 19 17  1  0  0  0  0
 20 11  1  0  0  0  0
 20 16  2  0  0  0  0
 21 12  1  0  0  0  0
 21 13  1  0  0  0  0
 22 18  1  0  0  0  0
 23  2  1  0  0  0  0
 23  3  1  0  0  0  0
 23  7  1  0  0  0  0
 23  8  1  0  0  0  0
 24  4  1  0  0  0  0
 24  9  1  0  0  0  0
 24 14  1  0  0  0  0
 24 19  1  0  0  0  0
 25 20  1  0  0  0  0
 26 10  1  0  0  0  0
 27 15  1  0  0  0  0
 28 21  1  0  0  0  0
 29 22  2  0  0  0  0
 30  5  1  0  0  0  0
 30 16  1  0  0  0  0
 31 17  1  0  0  0  0
 31 22  1  0  0  0  0
M  END

HMDB0035062
     RDKit          3D
Arnamiol
 62 65  0  0  0  0  0  0  0  0999 V2000
    8.4068   -1.5088    0.7092 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9238   -0.2371    0.4019 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5916    0.1301    0.3929 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6047   -0.7643    0.6982 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2330   -0.3816    0.6876 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3234   -1.3553    1.0089 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8590    0.8995    0.3701 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4671    1.3065    0.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1943    2.5279    0.0453 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3609    0.5563    0.6274 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0443    1.0664    0.5782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7998    0.7464    1.7933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2837   -0.4416    1.0450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4857   -1.7004    1.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9121    0.2384   -0.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4909   -0.1174   -1.3449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1096    0.5737   -2.6207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2323    1.1663   -3.1381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5055   -1.1782   -1.4021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4932   -0.7295   -2.3170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1169   -1.5965   -0.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6241   -1.4718   -0.1690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0016   -0.2807    0.6867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9750    0.6091   -0.0109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6204   -0.7615    1.9586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6602    0.4188    0.9494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7573   -0.7552    1.0821 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8792    1.7947    0.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5086    3.2034   -0.2895 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1970    1.4056    0.0783 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4293    2.5888   -0.3205 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.4170   -1.6911    0.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7141   -2.2814    0.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4117   -1.6341    1.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8482   -1.7856    0.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3619   -1.2525    1.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0505    2.1384    0.2923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5785    1.4950    2.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1376    0.4574    2.6343 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2326   -1.6199    2.0867 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0968   -1.9359    0.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1348   -2.5651    1.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6918   -0.2055   -3.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3059    1.3103   -2.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5200    0.7438   -3.9814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0847   -2.0949   -1.8920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9386    0.0899   -1.9953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8369   -2.6500    0.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0415   -2.4178    0.2757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0071   -1.4343   -1.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4819    1.3582   -0.6637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6853    0.0587   -0.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6104    1.1581    0.7360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1275   -0.2429    2.8019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7302   -0.5927    1.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4590   -1.8464    2.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7898    0.9977    1.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3961    1.1119    0.1527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9839   -1.3295    1.9799 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0546    3.6836    0.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9239    3.2382   -1.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4755    3.7860   -0.4816 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
 26 27  1  0
  7 28  1  0
 28 29  1  0
 28 30  2  0
 30 31  1  0
 30  3  1  0
 15 11  1  0
 27 21  1  0
 27 13  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  6 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 14 40  1  0
 14 41  1  0
 14 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 19 46  1  0
 20 47  1  0
 21 48  1  0
 22 49  1  0
 22 50  1  0
 24 51  1  0
 24 52  1  0
 24 53  1  0
 25 54  1  0
 25 55  1  0
 25 56  1  0
 26 57  1  0
 26 58  1  0
 27 59  1  0
 29 60  1  0
 29 61  1  0
 29 62  1  0
M  END


  Mrv0541 05061308132D          

 31 34  0  0  0  0            999 V2000
   -0.8971    0.5197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3497    0.5391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8336    1.5152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6532    1.3308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2347   -2.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6261   -1.8455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4330   -0.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8090    1.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7115    0.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9182   -1.5842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1401   -0.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6202   -0.2176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3570   -0.8855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2346    0.5118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8218   -1.6617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1874   -1.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2727    0.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5788   -0.8733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9714   -0.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9444   -0.4524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1815   -0.9162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2254   -0.6896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5497    0.7406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4102    0.5424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5056    0.1522    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3039   -2.3135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2606   -2.2664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5671   -1.6455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7867   -1.2942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9917   -1.4246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4685    0.0988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11  1  1  0  0  0  0
 12  7  1  0  0  0  0
 13 10  1  0  0  0  0
 14  8  1  0  0  0  0
 14 12  1  0  0  0  0
 15  6  2  0  0  0  0
 16  6  1  0  0  0  0
 17  9  1  0  0  0  0
 18 11  2  0  0  0  0
 18 15  1  0  0  0  0
 19 13  2  0  0  0  0
 19 17  1  0  0  0  0
 20 11  1  0  0  0  0
 20 16  2  0  0  0  0
 21 12  1  0  0  0  0
 21 13  1  0  0  0  0
 22 18  1  0  0  0  0
 23  2  1  0  0  0  0
 23  3  1  0  0  0  0
 23  7  1  0  0  0  0
 23  8  1  0  0  0  0
 24  4  1  0  0  0  0
 24  9  1  0  0  0  0
 24 14  1  0  0  0  0
 24 19  1  0  0  0  0
 25 20  1  0  0  0  0
 26 10  1  0  0  0  0
 27 15  1  0  0  0  0
 28 21  1  0  0  0  0
 29 22  2  0  0  0  0
 30  5  1  0  0  0  0
 30 16  1  0  0  0  0
 31 17  1  0  0  0  0
 31 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035062

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(Cl)C(C)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4C(O)C(CO)=C23)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H31ClO6/c1-11-18(15(27)6-16(30-5)20(11)25)22(29)31-17-9-24(4)14-8-23(2,3)7-12(14)21(28)13(10-26)19(17)24/h6,12,14,17,21,26-28H,7-10H2,1-5H3

> <INCHI_KEY>
OMAGQTXDHXASNM-UHFFFAOYSA-N

> <FORMULA>
C24H31ClO6

> <MOLECULAR_WEIGHT>
450.952

> <EXACT_MASS>
450.180916431

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
48.80536670635909

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,4H,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate

> <ALOGPS_LOGP>
3.41

> <JCHEM_LOGP>
4.194590127999999

> <ALOGPS_LOGS>
-4.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.19222938893536

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.324084973317882

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7730707526470066

> <JCHEM_POLAR_SURFACE_AREA>
96.22

> <JCHEM_REFRACTIVITY>
118.26859999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.66e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,4H,4aH,5H,7H,7aH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035062
     RDKit          3D
Arnamiol
 62 65  0  0  0  0  0  0  0  0999 V2000
    8.4068   -1.5088    0.7092 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9238   -0.2371    0.4019 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5916    0.1301    0.3929 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6047   -0.7643    0.6982 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2330   -0.3816    0.6876 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3234   -1.3553    1.0089 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8590    0.8995    0.3701 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4671    1.3065    0.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1943    2.5279    0.0453 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3609    0.5563    0.6274 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0443    1.0664    0.5782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7998    0.7464    1.7933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2837   -0.4416    1.0450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4857   -1.7004    1.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9121    0.2384   -0.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4909   -0.1174   -1.3449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1096    0.5737   -2.6207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2323    1.1663   -3.1381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5055   -1.1782   -1.4021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4932   -0.7295   -2.3170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1169   -1.5965   -0.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6241   -1.4718   -0.1690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0016   -0.2807    0.6867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9750    0.6091   -0.0109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6204   -0.7615    1.9586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6602    0.4188    0.9494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7573   -0.7552    1.0821 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8792    1.7947    0.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5086    3.2034   -0.2895 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1970    1.4056    0.0783 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4293    2.5888   -0.3205 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.4170   -1.6911    0.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7141   -2.2814    0.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4117   -1.6341    1.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8482   -1.7856    0.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3619   -1.2525    1.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0505    2.1384    0.2923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5785    1.4950    2.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1376    0.4574    2.6343 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2326   -1.6199    2.0867 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0968   -1.9359    0.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1348   -2.5651    1.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6918   -0.2055   -3.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3059    1.3103   -2.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5200    0.7438   -3.9814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0847   -2.0949   -1.8920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9386    0.0899   -1.9953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8369   -2.6500    0.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0415   -2.4178    0.2757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0071   -1.4343   -1.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4819    1.3582   -0.6637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6853    0.0587   -0.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6104    1.1581    0.7360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1275   -0.2429    2.8019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7302   -0.5927    1.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4590   -1.8464    2.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7898    0.9977    1.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3961    1.1119    0.1527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9839   -1.3295    1.9799 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0546    3.6836    0.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9239    3.2382   -1.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4755    3.7860   -0.4816 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
 26 27  1  0
  7 28  1  0
 28 29  1  0
 28 30  2  0
 30 31  1  0
 30  3  1  0
 15 11  1  0
 27 21  1  0
 27 13  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  6 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 14 40  1  0
 14 41  1  0
 14 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 19 46  1  0
 20 47  1  0
 21 48  1  0
 22 49  1  0
 22 50  1  0
 24 51  1  0
 24 52  1  0
 24 53  1  0
 25 54  1  0
 25 55  1  0
 25 56  1  0
 26 57  1  0
 26 58  1  0
 27 59  1  0
 29 60  1  0
 29 61  1  0
 29 62  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      -1.675   0.970   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.986   1.006   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.023   2.828   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.953   2.484   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.038  -4.131   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.035  -3.445   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.275  -0.142   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.110   2.061   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.195   1.832   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.581  -2.957   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.128  -0.502   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.758  -0.406   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.400  -1.653   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.038   0.955   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.534  -3.102   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.083  -2.316   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.376   0.528   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.080  -1.630   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.680  -0.292   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.630  -0.844   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.939  -1.710   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.421  -1.287   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.493   1.382   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.499   1.012   0.000  0.00  0.00           C+0
HETATM   25 Cl   UNK     0      -4.677   0.284   0.000  0.00  0.00          Cl+0
HETATM   26  O   UNK     0       4.301  -4.319   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -0.486  -4.231   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       6.659  -3.072   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       1.469  -2.416   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -5.585  -2.659   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.875   0.184   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   23                                                            
CONECT    3   23                                                            
CONECT    4   24                                                            
CONECT    5   30                                                            
CONECT    6   15   16                                                       
CONECT    7   12   23                                                       
CONECT    8   14   23                                                       
CONECT    9   17   24                                                       
CONECT   10   13   26                                                       
CONECT   11    1   18   20                                                  
CONECT   12    7   14   21                                                  
CONECT   13   10   19   21                                                  
CONECT   14    8   12   24                                                  
CONECT   15    6   18   27                                                  
CONECT   16    6   20   30                                                  
CONECT   17    9   19   31                                                  
CONECT   18   11   15   22                                                  
CONECT   19   13   17   24                                                  
CONECT   20   11   16   25                                                  
CONECT   21   12   13   28                                                  
CONECT   22   18   29   31                                                  
CONECT   23    2    3    7    8                                             
CONECT   24    4    9   14   19                                             
CONECT   25   20                                                            
CONECT   26   10                                                            
CONECT   27   15                                                            
CONECT   28   21                                                            
CONECT   29   22                                                            
CONECT   30    5   16                                                       
CONECT   31   17   22                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

COMPND    HMDB0035062
HETATM    1  C1  UNL     1       8.407  -1.509   0.709  1.00  0.00           C  
HETATM    2  O1  UNL     1       7.924  -0.237   0.402  1.00  0.00           O  
HETATM    3  C2  UNL     1       6.592   0.130   0.393  1.00  0.00           C  
HETATM    4  C3  UNL     1       5.605  -0.764   0.698  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.233  -0.382   0.688  1.00  0.00           C  
HETATM    6  O2  UNL     1       3.323  -1.355   1.009  1.00  0.00           O  
HETATM    7  C5  UNL     1       3.859   0.899   0.370  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.467   1.307   0.354  1.00  0.00           C  
HETATM    9  O3  UNL     1       2.194   2.528   0.045  1.00  0.00           O  
HETATM   10  O4  UNL     1       1.361   0.556   0.627  1.00  0.00           O  
HETATM   11  C7  UNL     1       0.044   1.066   0.578  1.00  0.00           C  
HETATM   12  C8  UNL     1      -0.800   0.746   1.793  1.00  0.00           C  
HETATM   13  C9  UNL     1      -1.284  -0.442   1.045  1.00  0.00           C  
HETATM   14  C10 UNL     1      -0.486  -1.700   1.244  1.00  0.00           C  
HETATM   15  C11 UNL     1      -0.912   0.238  -0.221  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.491  -0.117  -1.345  1.00  0.00           C  
HETATM   17  C13 UNL     1      -1.110   0.574  -2.621  1.00  0.00           C  
HETATM   18  O5  UNL     1      -2.232   1.166  -3.138  1.00  0.00           O  
HETATM   19  C14 UNL     1      -2.506  -1.178  -1.402  1.00  0.00           C  
HETATM   20  O6  UNL     1      -3.493  -0.729  -2.317  1.00  0.00           O  
HETATM   21  C15 UNL     1      -3.117  -1.596  -0.124  1.00  0.00           C  
HETATM   22  C16 UNL     1      -4.624  -1.472  -0.169  1.00  0.00           C  
HETATM   23  C17 UNL     1      -5.002  -0.281   0.687  1.00  0.00           C  
HETATM   24  C18 UNL     1      -5.975   0.609  -0.011  1.00  0.00           C  
HETATM   25  C19 UNL     1      -5.620  -0.761   1.959  1.00  0.00           C  
HETATM   26  C20 UNL     1      -3.660   0.419   0.949  1.00  0.00           C  
HETATM   27  C21 UNL     1      -2.757  -0.755   1.082  1.00  0.00           C  
HETATM   28  C22 UNL     1       4.879   1.795   0.062  1.00  0.00           C  
HETATM   29  C23 UNL     1       4.509   3.203  -0.289  1.00  0.00           C  
HETATM   30  C24 UNL     1       6.197   1.406   0.078  1.00  0.00           C  
HETATM   31 CL1  UNL     1       7.429   2.589  -0.320  1.00  0.00          CL  
HETATM   32  H1  UNL     1       9.417  -1.691   0.279  1.00  0.00           H  
HETATM   33  H2  UNL     1       7.714  -2.281   0.316  1.00  0.00           H  
HETATM   34  H3  UNL     1       8.412  -1.634   1.820  1.00  0.00           H  
HETATM   35  H4  UNL     1       5.848  -1.786   0.955  1.00  0.00           H  
HETATM   36  H5  UNL     1       2.362  -1.253   1.046  1.00  0.00           H  
HETATM   37  H6  UNL     1       0.051   2.138   0.292  1.00  0.00           H  
HETATM   38  H7  UNL     1      -1.578   1.495   2.039  1.00  0.00           H  
HETATM   39  H8  UNL     1      -0.138   0.457   2.634  1.00  0.00           H  
HETATM   40  H9  UNL     1       0.233  -1.620   2.087  1.00  0.00           H  
HETATM   41  H10 UNL     1       0.097  -1.936   0.330  1.00  0.00           H  
HETATM   42  H11 UNL     1      -1.135  -2.565   1.484  1.00  0.00           H  
HETATM   43  H12 UNL     1      -0.692  -0.205  -3.294  1.00  0.00           H  
HETATM   44  H13 UNL     1      -0.306   1.310  -2.439  1.00  0.00           H  
HETATM   45  H14 UNL     1      -2.520   0.744  -3.981  1.00  0.00           H  
HETATM   46  H15 UNL     1      -2.085  -2.095  -1.892  1.00  0.00           H  
HETATM   47  H16 UNL     1      -3.939   0.090  -1.995  1.00  0.00           H  
HETATM   48  H17 UNL     1      -2.837  -2.650   0.114  1.00  0.00           H  
HETATM   49  H18 UNL     1      -5.041  -2.418   0.276  1.00  0.00           H  
HETATM   50  H19 UNL     1      -5.007  -1.434  -1.190  1.00  0.00           H  
HETATM   51  H20 UNL     1      -5.482   1.358  -0.664  1.00  0.00           H  
HETATM   52  H21 UNL     1      -6.685   0.059  -0.662  1.00  0.00           H  
HETATM   53  H22 UNL     1      -6.610   1.158   0.736  1.00  0.00           H  
HETATM   54  H23 UNL     1      -5.127  -0.243   2.802  1.00  0.00           H  
HETATM   55  H24 UNL     1      -6.730  -0.593   1.985  1.00  0.00           H  
HETATM   56  H25 UNL     1      -5.459  -1.846   2.062  1.00  0.00           H  
HETATM   57  H26 UNL     1      -3.790   0.998   1.881  1.00  0.00           H  
HETATM   58  H27 UNL     1      -3.396   1.112   0.153  1.00  0.00           H  
HETATM   59  H28 UNL     1      -2.984  -1.330   1.980  1.00  0.00           H  
HETATM   60  H29 UNL     1       4.055   3.684   0.594  1.00  0.00           H  
HETATM   61  H30 UNL     1       3.924   3.238  -1.217  1.00  0.00           H  
HETATM   62  H31 UNL     1       5.476   3.786  -0.482  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3
CONECT    3    4    4   30
CONECT    4    5   35
CONECT    5    6    7    7
CONECT    6   36
CONECT    7    8   28
CONECT    8    9    9   10
CONECT   10   11
CONECT   11   12   15   37
CONECT   12   13   38   39
CONECT   13   14   15   27
CONECT   14   40   41   42
CONECT   15   16   16
CONECT   16   17   19
CONECT   17   18   43   44
CONECT   18   45
CONECT   19   20   21   46
CONECT   20   47
CONECT   21   22   27   48
CONECT   22   23   49   50
CONECT   23   24   25   26
CONECT   24   51   52   53
CONECT   25   54   55   56
CONECT   26   27   57   58
CONECT   27   59
CONECT   28   29   30   30
CONECT   29   60   61   62
CONECT   30   31
END

HMDB0035062
     RDKit          3D
Arnamiol
 62 65  0  0  0  0  0  0  0  0999 V2000
    8.4068   -1.5088    0.7092 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9238   -0.2371    0.4019 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5916    0.1301    0.3929 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6047   -0.7643    0.6982 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2330   -0.3816    0.6876 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3234   -1.3553    1.0089 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8590    0.8995    0.3701 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4671    1.3065    0.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1943    2.5279    0.0453 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3609    0.5563    0.6274 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0443    1.0664    0.5782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7998    0.7464    1.7933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2837   -0.4416    1.0450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4857   -1.7004    1.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9121    0.2384   -0.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4909   -0.1174   -1.3449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1096    0.5737   -2.6207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2323    1.1663   -3.1381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5055   -1.1782   -1.4021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4932   -0.7295   -2.3170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1169   -1.5965   -0.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6241   -1.4718   -0.1690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0016   -0.2807    0.6867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9750    0.6091   -0.0109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6204   -0.7615    1.9586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6602    0.4188    0.9494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7573   -0.7552    1.0821 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8792    1.7947    0.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5086    3.2034   -0.2895 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1970    1.4056    0.0783 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4293    2.5888   -0.3205 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.4170   -1.6911    0.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7141   -2.2814    0.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4117   -1.6341    1.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8482   -1.7856    0.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3619   -1.2525    1.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0505    2.1384    0.2923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5785    1.4950    2.0385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1376    0.4574    2.6343 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2326   -1.6199    2.0867 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0968   -1.9359    0.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1348   -2.5651    1.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6918   -0.2055   -3.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3059    1.3103   -2.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5200    0.7438   -3.9814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0847   -2.0949   -1.8920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9386    0.0899   -1.9953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8369   -2.6500    0.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0415   -2.4178    0.2757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0071   -1.4343   -1.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4819    1.3582   -0.6637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6853    0.0587   -0.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6104    1.1581    0.7360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1275   -0.2429    2.8019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7302   -0.5927    1.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4590   -1.8464    2.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7898    0.9977    1.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3961    1.1119    0.1527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9839   -1.3295    1.9799 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0546    3.6836    0.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9239    3.2382   -1.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4755    3.7860   -0.4816 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
 26 27  1  0
  7 28  1  0
 28 29  1  0
 28 30  2  0
 30 31  1  0
 30  3  1  0
 15 11  1  0
 27 21  1  0
 27 13  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  6 36  1  0
 11 37  1  0
 12 38  1  0
 12 39  1  0
 14 40  1  0
 14 41  1  0
 14 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 19 46  1  0
 20 47  1  0
 21 48  1  0
 22 49  1  0
 22 50  1  0
 24 51  1  0
 24 52  1  0
 24 53  1  0
 25 54  1  0
 25 55  1  0
 25 56  1  0
 26 57  1  0
 26 58  1  0
 27 59  1  0
 29 60  1  0
 29 61  1  0
 29 62  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,4H,4ah,5H,6H,7H,7ah,7BH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoic acid	HMDB

Chemical Formula

C₂₄H₃₁ClO₆

Average Molecular Weight

450.952

Monoisotopic Molecular Weight

450.180916431

IUPAC Name

4-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,4H,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate

Traditional Name

4-hydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,4H,4aH,5H,7H,7aH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate

CAS Registry Number

102092-23-9

SMILES

COC1=C(Cl)C(C)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4C(O)C(CO)=C23)C(O)=C1

InChI Identifier

InChI=1S/C24H31ClO6/c1-11-18(15(27)6-16(30-5)20(11)25)22(29)31-17-9-24(4)14-8-23(2,3)7-12(14)21(28)13(10-26)19(17)24/h6,12,14,17,21,26-28H,7-10H2,1-5H3

InChI Key

OMAGQTXDHXASNM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as melleolides and analogues. Melleolides and analogues are compounds with a structure characterized by the presence of a 2-hydroxy-4-methoxy-6-methylbenzoic acid derivative linked to a 3,6,6,7b-tetramethyl-cyclobuta[e]indene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Melleolides and analogues

Alternative Parents

Substituents

Melleolide-skeleton
O-hydroxybenzoic acid ester
P-methoxybenzoic acid or derivatives
Benzoate ester
Methoxyphenol
Salicylic acid or derivatives
3-halobenzoic acid or derivatives
Halobenzoic acid or derivatives
Benzoic acid or derivatives
Benzoyl
Phenoxy compound
4-chlorophenol
Anisole
Phenol ether
M-cresol
4-halophenol
Methoxybenzene
Alkyl aryl ether
Chlorobenzene
1-hydroxy-2-unsubstituted benzenoid
Toluene
Halobenzene
Phenol
Aryl chloride
Benzenoid
Aryl halide
Monocyclic benzene moiety
Vinylogous acid
Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Ether
Organohalogen compound
Organochloride
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organic oxide
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035062)

Source

Endogenous

Endogenous (HMDB: HMDB0035062)

Plant

Plant (HMDB: HMDB0035062)

Animal

Animal (HMDB: HMDB0035062)

Exogenous

Food

Food (HMDB: HMDB0035062)

Vegetable

Mushroom

Exogenous (HMDB: HMDB0035062)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0035062)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0035062)

Lipid metabolism pathway (HMDB: HMDB0035062)

Cellular process

Cell signaling (HMDB: HMDB0035062)

Biochemical process

Lipid transport (HMDB: HMDB0035062)

Role

Biological role

Energy source (HMDB: HMDB0035062)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035062)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	132 - 134 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.051 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0057 g/L	ALOGPS
logP	3.41	ALOGPS
logP	4.19	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	9.32	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	118.27 m³·mol⁻¹	ChemAxon
Polarizability	48.81 Å³	ChemAxon
Number of Rings	4	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
DeepCCS	[M-2H]-	239.289	30932474
DeepCCS	[M+Na]+	214.714	30932474
AllCCS	[M+H]+	204.7	32859911
AllCCS	[M+H-H2O]+	202.8	32859911
AllCCS	[M+NH4]+	206.5	32859911
AllCCS	[M+Na]+	207.0	32859911
AllCCS	[M-H]-	207.1	32859911
AllCCS	[M+Na-2H]-	207.8	32859911
AllCCS	[M+HCOO]-	208.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.89 minutes	32390414
Predicted by Siyang on May 30, 2022	15.7022 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.99 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	37.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3040.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	252.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	214.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	178.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	213.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	769.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	909.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	82.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1228.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	554.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1897.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	497.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	503.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	216.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	226.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	9.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Arnamiol	COC1=C(Cl)C(C)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4C(O)C(CO)=C23)C(O)=C1	4111.5	Standard polar	33892256
Arnamiol	COC1=C(Cl)C(C)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4C(O)C(CO)=C23)C(O)=C1	3071.6	Standard non polar	33892256
Arnamiol	COC1=C(Cl)C(C)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4C(O)C(CO)=C23)C(O)=C1	3389.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Arnamiol,1TMS,isomer #1	COC1=CC(O)=C(C(=O)OC2CC3(C)C2=C(CO)C(O[Si](C)(C)C)C2CC(C)(C)CC23)C(C)=C1Cl	3320.8	Semi standard non polar	33892256
Arnamiol,1TMS,isomer #2	COC1=CC(O)=C(C(=O)OC2CC3(C)C2=C(CO[Si](C)(C)C)C(O)C2CC(C)(C)CC23)C(C)=C1Cl	3347.4	Semi standard non polar	33892256
Arnamiol,1TMS,isomer #3	COC1=CC(O[Si](C)(C)C)=C(C(=O)OC2CC3(C)C2=C(CO)C(O)C2CC(C)(C)CC23)C(C)=C1Cl	3443.8	Semi standard non polar	33892256
Arnamiol,2TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C(C(=O)OC2CC3(C)C2=C(CO)C(O[Si](C)(C)C)C2CC(C)(C)CC23)C(C)=C1Cl	3309.4	Semi standard non polar	33892256
Arnamiol,2TMS,isomer #2	COC1=CC(O)=C(C(=O)OC2CC3(C)C2=C(CO[Si](C)(C)C)C(O[Si](C)(C)C)C2CC(C)(C)CC23)C(C)=C1Cl	3271.2	Semi standard non polar	33892256
Arnamiol,2TMS,isomer #3	COC1=CC(O[Si](C)(C)C)=C(C(=O)OC2CC3(C)C2=C(CO[Si](C)(C)C)C(O)C2CC(C)(C)CC23)C(C)=C1Cl	3344.5	Semi standard non polar	33892256
Arnamiol,3TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C(C(=O)OC2CC3(C)C2=C(CO[Si](C)(C)C)C(O[Si](C)(C)C)C2CC(C)(C)CC23)C(C)=C1Cl	3289.4	Semi standard non polar	33892256
Arnamiol,1TBDMS,isomer #1	COC1=CC(O)=C(C(=O)OC2CC3(C)C2=C(CO)C(O[Si](C)(C)C(C)(C)C)C2CC(C)(C)CC23)C(C)=C1Cl	3552.7	Semi standard non polar	33892256
Arnamiol,1TBDMS,isomer #2	COC1=CC(O)=C(C(=O)OC2CC3(C)C2=C(CO[Si](C)(C)C(C)(C)C)C(O)C2CC(C)(C)CC23)C(C)=C1Cl	3591.2	Semi standard non polar	33892256
Arnamiol,1TBDMS,isomer #3	COC1=CC(O[Si](C)(C)C(C)(C)C)=C(C(=O)OC2CC3(C)C2=C(CO)C(O)C2CC(C)(C)CC23)C(C)=C1Cl	3686.4	Semi standard non polar	33892256
Arnamiol,2TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C(C(=O)OC2CC3(C)C2=C(CO)C(O[Si](C)(C)C(C)(C)C)C2CC(C)(C)CC23)C(C)=C1Cl	3770.2	Semi standard non polar	33892256
Arnamiol,2TBDMS,isomer #2	COC1=CC(O)=C(C(=O)OC2CC3(C)C2=C(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2CC(C)(C)CC23)C(C)=C1Cl	3736.5	Semi standard non polar	33892256
Arnamiol,2TBDMS,isomer #3	COC1=CC(O[Si](C)(C)C(C)(C)C)=C(C(=O)OC2CC3(C)C2=C(CO[Si](C)(C)C(C)(C)C)C(O)C2CC(C)(C)CC23)C(C)=C1Cl	3810.0	Semi standard non polar	33892256
Arnamiol,3TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C(C(=O)OC2CC3(C)C2=C(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C2CC(C)(C)CC23)C(C)=C1Cl	3949.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Arnamiol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-4591400000-291d854e56fbddc2734c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arnamiol GC-MS (3 TMS) - 70eV, Positive	splash10-0udi-5119018000-d656c6caf93093692ca8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arnamiol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Arnamiol 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 - Arnamiol 10V, Positive-QTOF	splash10-0fsi-0120900000-154722e354ceb958bceb	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arnamiol 20V, Positive-QTOF	splash10-015a-1671900000-65b6bc1b93a86989f8ec	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arnamiol 40V, Positive-QTOF	splash10-00kb-2940100000-a41bc8969de8aa85d592	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arnamiol 10V, Negative-QTOF	splash10-0002-0120900000-a6fa9cfbc05fe2aa3d3b	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arnamiol 20V, Negative-QTOF	splash10-0gis-0420900000-59557273dbe5f07764be	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arnamiol 40V, Negative-QTOF	splash10-00di-0950000000-ac1121496bd9fa8b79e3	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arnamiol 10V, Positive-QTOF	splash10-0udi-0140900000-1d7174adedee5dfa9102	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arnamiol 20V, Positive-QTOF	splash10-0002-3934500000-4d68169cf23897a5fe1d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arnamiol 40V, Positive-QTOF	splash10-0532-6963200000-533c643bbec1dd128506	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arnamiol 10V, Negative-QTOF	splash10-0002-0110900000-fd876e6d9cb668b8fe66	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arnamiol 20V, Negative-QTOF	splash10-007k-0460900000-10064748727e7ed1258a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Arnamiol 40V, Negative-QTOF	splash10-053r-9822100000-605f0c039fb8cd5087ee	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB013685

KNApSAcK ID

C00021472

Chemspider ID

28576292

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71317588

PDB ID

Not Available

ChEBI ID

169640

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1847421

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Arnamiol (HMDB0035062)

MOL for HMDB0035062 (Arnamiol)

3D MOL for HMDB0035062 (Arnamiol)

3D SDF for HMDB0035062 (Arnamiol)

3D-SDF for HMDB0035062 (Arnamiol)

PDB for HMDB0035062 (Arnamiol)

3D PDB for HMDB0035062 (Arnamiol)

SMILES for HMDB0035062 (Arnamiol)

INCHI for HMDB0035062 (Arnamiol)

Structure for HMDB0035062 (Arnamiol)

3D Structure for HMDB0035062 (Arnamiol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra