Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:04:56 UTC

Update Date

2022-03-07 02:55:53 UTC

HMDB ID

HMDB0038742

Secondary Accession Numbers

HMDB38742

Metabolite Identification

Common Name

Armillasin

Description

Armillasin 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 Armillasin.

Structure

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


  Mrv0541 05061310372D          

 27 30  0  0  0  0            999 V2000
   -1.2154   -1.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3497    0.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8336   -0.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6532   -0.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1815    1.7412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3570    1.7105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2626   -0.1156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9444    1.2774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4330    0.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8090   -0.2789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7115   -0.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4584   -0.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6202    1.0426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5056    0.6728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2346    0.3132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1401    1.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2727    0.5424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8971    0.3053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0928    0.1215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5497    0.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4102    0.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9714    0.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3099    0.8565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5788    1.6983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1502   -0.6669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667    1.5425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4685    0.7262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
 12  1  1  0  0  0  0
 12  7  2  0  0  0  0
 13  5  1  0  0  0  0
 13  9  1  0  0  0  0
 14  7  1  0  0  0  0
 14  8  2  0  0  0  0
 15 10  1  0  0  0  0
 15 13  1  0  0  0  0
 16  8  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  1  0  0  0  0
 18 16  2  0  0  0  0
 19 18  1  0  0  0  0
 20  2  1  0  0  0  0
 20  3  1  0  0  0  0
 20  9  1  0  0  0  0
 20 10  1  0  0  0  0
 21  4  1  0  0  0  0
 21 11  1  0  0  0  0
 21 15  1  0  0  0  0
 22  6  1  0  0  0  0
 22 17  1  0  0  0  0
 22 21  1  0  0  0  0
 23 14  1  0  0  0  0
 24 16  1  0  0  0  0
 25 19  2  0  0  0  0
 26 22  1  0  0  0  0
 27 17  1  0  0  0  0
 27 19  1  0  0  0  0
M  END

HMDB0038742
     RDKit          3D
Armillasin
 55 58  0  0  0  0  0  0  0  0999 V2000
    5.5057   -1.2415   -1.5919 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1208   -0.0914   -0.7849 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0910    0.7757   -0.3396 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7401    1.8763    0.4305 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7223    2.7661    0.8892 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4394    2.1023    0.7476 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4561    1.2299    0.3005 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1791    1.5413    0.6708 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7966    0.1377   -0.4627 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7490   -0.7761   -0.9286 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0874   -1.7893   -1.6395 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4077   -0.6604   -0.6787 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4294   -1.5491   -1.1371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3836   -2.1229    0.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5792   -1.3743   -0.5329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7457   -2.2656   -0.9251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9799   -0.2518    0.3570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0547   -0.5564    1.3331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7561    0.7843    1.5685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6953    1.1284    3.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1604    0.6666    1.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9966    1.7841    0.7139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6290    0.8902   -0.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5926    1.4128   -1.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7585    0.5404   -1.9050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8067   -0.9087   -1.7278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1917   -1.5698   -2.9018 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2614   -2.2169   -1.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6129   -1.2280   -1.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0658   -1.1889   -2.6073 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1351    0.6145   -0.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1332    2.5527    1.7908 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1964    2.9747    1.3535 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3070    1.1559    0.5299 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8243   -2.3946   -1.7448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0268   -1.7699    1.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743   -3.2100   -0.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0116   -2.8824   -0.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5461   -1.6085   -1.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3582   -2.9346   -1.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0844    0.1745    0.8325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7546   -1.3365    1.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5639   -0.8930    2.2901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3615    1.9945    3.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6739    1.4443    3.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0301    0.2350    3.5939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2398    1.1255    0.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4490   -0.3998    0.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8853    1.1629    1.7501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5947    2.6483    0.4388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0411    2.0488    1.2264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5317    0.5164   -0.9744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4586    2.4553   -1.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0163    0.9430   -2.5630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7611   -2.4621   -2.9804 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
  9  2  1  0
 26 13  1  0
 26 15  1  0
 23 17  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  5 32  1  0
  6 33  1  0
  8 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 18 42  1  0
 18 43  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
 21 47  1  0
 21 48  1  0
 21 49  1  0
 22 50  1  0
 22 51  1  0
 23 52  1  0
 24 53  1  0
 25 54  1  0
 27 55  1  0
M  END


  Mrv0541 05061310372D          

 27 30  0  0  0  0            999 V2000
   -1.2154   -1.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3497    0.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8336   -0.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6532   -0.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1815    1.7412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3570    1.7105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2626   -0.1156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9444    1.2774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4330    0.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8090   -0.2789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7115   -0.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4584   -0.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6202    1.0426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5056    0.6728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2346    0.3132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1401    1.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2727    0.5424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8971    0.3053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0928    0.1215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5497    0.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4102    0.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9714    0.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3099    0.8565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5788    1.6983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1502   -0.6669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667    1.5425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4685    0.7262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
 12  1  1  0  0  0  0
 12  7  2  0  0  0  0
 13  5  1  0  0  0  0
 13  9  1  0  0  0  0
 14  7  1  0  0  0  0
 14  8  2  0  0  0  0
 15 10  1  0  0  0  0
 15 13  1  0  0  0  0
 16  8  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  1  0  0  0  0
 18 16  2  0  0  0  0
 19 18  1  0  0  0  0
 20  2  1  0  0  0  0
 20  3  1  0  0  0  0
 20  9  1  0  0  0  0
 20 10  1  0  0  0  0
 21  4  1  0  0  0  0
 21 11  1  0  0  0  0
 21 15  1  0  0  0  0
 22  6  1  0  0  0  0
 22 17  1  0  0  0  0
 22 21  1  0  0  0  0
 23 14  1  0  0  0  0
 24 16  1  0  0  0  0
 25 19  2  0  0  0  0
 26 22  1  0  0  0  0
 27 17  1  0  0  0  0
 27 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038742

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=CC12O

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O5/c1-12-7-14(23)8-16(24)18(12)19(25)27-17-11-21(4)15-10-20(2,3)9-13(15)5-6-22(17,21)26/h5-8,13,15,17,23-24,26H,9-11H2,1-4H3

> <INCHI_KEY>
AFPPVJHFFGBKOB-UHFFFAOYSA-N

> <FORMULA>
C22H28O5

> <MOLECULAR_WEIGHT>
372.4547

> <EXACT_MASS>
372.193674006

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
40.75105105863582

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2a-hydroxy-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate

> <ALOGPS_LOGP>
3.68

> <JCHEM_LOGP>
4.831091597333334

> <ALOGPS_LOGS>
-3.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.554908855716997

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.697540911126874

> <JCHEM_PKA_STRONGEST_BASIC>
-3.612866087656098

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
102.97299999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.75e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2a-hydroxy-6,6,7b-trimethyl-1H,2H,4aH,5H,7H,7aH-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038742
     RDKit          3D
Armillasin
 55 58  0  0  0  0  0  0  0  0999 V2000
    5.5057   -1.2415   -1.5919 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1208   -0.0914   -0.7849 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0910    0.7757   -0.3396 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7401    1.8763    0.4305 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7223    2.7661    0.8892 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4394    2.1023    0.7476 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4561    1.2299    0.3005 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1791    1.5413    0.6708 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7966    0.1377   -0.4627 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7490   -0.7761   -0.9286 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0874   -1.7893   -1.6395 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4077   -0.6604   -0.6787 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4294   -1.5491   -1.1371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3836   -2.1229    0.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5792   -1.3743   -0.5329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7457   -2.2656   -0.9251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9799   -0.2518    0.3570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0547   -0.5564    1.3331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7561    0.7843    1.5685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6953    1.1284    3.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1604    0.6666    1.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9966    1.7841    0.7139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6290    0.8902   -0.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5926    1.4128   -1.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7585    0.5404   -1.9050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8067   -0.9087   -1.7278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1917   -1.5698   -2.9018 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2614   -2.2169   -1.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6129   -1.2280   -1.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0658   -1.1889   -2.6073 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1351    0.6145   -0.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1332    2.5527    1.7908 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1964    2.9747    1.3535 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3070    1.1559    0.5299 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8243   -2.3946   -1.7448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0268   -1.7699    1.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743   -3.2100   -0.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0116   -2.8824   -0.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5461   -1.6085   -1.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3582   -2.9346   -1.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0844    0.1745    0.8325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7546   -1.3365    1.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5639   -0.8930    2.2901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3615    1.9945    3.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6739    1.4443    3.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0301    0.2350    3.5939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2398    1.1255    0.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4490   -0.3998    0.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8853    1.1629    1.7501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5947    2.6483    0.4388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0411    2.0488    1.2264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5317    0.5164   -0.9744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4586    2.4553   -1.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0163    0.9430   -2.5630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7611   -2.4621   -2.9804 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
  9  2  1  0
 26 13  1  0
 26 15  1  0
 23 17  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  5 32  1  0
  6 33  1  0
  8 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 18 42  1  0
 18 43  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
 21 47  1  0
 21 48  1  0
 21 49  1  0
 22 50  1  0
 22 51  1  0
 23 52  1  0
 24 53  1  0
 25 54  1  0
 27 55  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      -2.269  -2.031   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.986   0.534   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.023  -1.288   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.953  -0.944   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.939   3.250   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.400   3.193   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.224  -0.216   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.630   2.384   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.275   1.682   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.110  -0.521   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.195  -0.292   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.722  -0.559   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.758   1.946   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.677   1.256   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.038   0.585   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.128   2.042   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.376   1.012   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.675   0.570   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.173   0.227   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.493   0.158   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.499   0.528   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.680   1.832   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -6.178   1.599   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -1.080   3.170   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.280  -1.245   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       2.551   2.879   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.875   1.356   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   20                                                            
CONECT    3   20                                                            
CONECT    4   21                                                            
CONECT    5    6   13                                                       
CONECT    6    5   22                                                       
CONECT    7   12   14                                                       
CONECT    8   14   16                                                       
CONECT    9   13   20                                                       
CONECT   10   15   20                                                       
CONECT   11   17   21                                                       
CONECT   12    1    7   18                                                  
CONECT   13    5    9   15                                                  
CONECT   14    7    8   23                                                  
CONECT   15   10   13   21                                                  
CONECT   16    8   18   24                                                  
CONECT   17   11   22   27                                                  
CONECT   18   12   16   19                                                  
CONECT   19   18   25   27                                                  
CONECT   20    2    3    9   10                                             
CONECT   21    4   11   15   22                                             
CONECT   22    6   17   21   26                                             
CONECT   23   14                                                            
CONECT   24   16                                                            
CONECT   25   19                                                            
CONECT   26   22                                                            
CONECT   27   17   19                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

COMPND    HMDB0038742
HETATM    1  C1  UNL     1       5.506  -1.242  -1.592  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.121  -0.091  -0.785  1.00  0.00           C  
HETATM    3  C3  UNL     1       6.091   0.776  -0.340  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.740   1.876   0.430  1.00  0.00           C  
HETATM    5  O1  UNL     1       6.722   2.766   0.889  1.00  0.00           O  
HETATM    6  C5  UNL     1       4.439   2.102   0.748  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.456   1.230   0.300  1.00  0.00           C  
HETATM    8  O2  UNL     1       2.179   1.541   0.671  1.00  0.00           O  
HETATM    9  C7  UNL     1       3.797   0.138  -0.463  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.749  -0.776  -0.929  1.00  0.00           C  
HETATM   11  O3  UNL     1       3.087  -1.789  -1.639  1.00  0.00           O  
HETATM   12  O4  UNL     1       1.408  -0.660  -0.679  1.00  0.00           O  
HETATM   13  C9  UNL     1       0.429  -1.549  -1.137  1.00  0.00           C  
HETATM   14  C10 UNL     1      -0.384  -2.123   0.021  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.579  -1.374  -0.533  1.00  0.00           C  
HETATM   16  C12 UNL     1      -2.746  -2.266  -0.925  1.00  0.00           C  
HETATM   17  C13 UNL     1      -1.980  -0.252   0.357  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.055  -0.556   1.333  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.756   0.784   1.569  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.695   1.128   3.033  1.00  0.00           C  
HETATM   21  C17 UNL     1      -5.160   0.667   1.057  1.00  0.00           C  
HETATM   22  C18 UNL     1      -2.997   1.784   0.714  1.00  0.00           C  
HETATM   23  C19 UNL     1      -2.629   0.890  -0.443  1.00  0.00           C  
HETATM   24  C20 UNL     1      -1.593   1.413  -1.321  1.00  0.00           C  
HETATM   25  C21 UNL     1      -0.758   0.540  -1.905  1.00  0.00           C  
HETATM   26  C22 UNL     1      -0.807  -0.909  -1.728  1.00  0.00           C  
HETATM   27  O5  UNL     1      -1.192  -1.570  -2.902  1.00  0.00           O  
HETATM   28  H1  UNL     1       5.261  -2.217  -1.085  1.00  0.00           H  
HETATM   29  H2  UNL     1       6.613  -1.228  -1.761  1.00  0.00           H  
HETATM   30  H3  UNL     1       5.066  -1.189  -2.607  1.00  0.00           H  
HETATM   31  H4  UNL     1       7.135   0.615  -0.581  1.00  0.00           H  
HETATM   32  H5  UNL     1       7.133   2.553   1.791  1.00  0.00           H  
HETATM   33  H6  UNL     1       4.196   2.975   1.353  1.00  0.00           H  
HETATM   34  H7  UNL     1       1.307   1.156   0.530  1.00  0.00           H  
HETATM   35  H8  UNL     1       0.824  -2.395  -1.745  1.00  0.00           H  
HETATM   36  H9  UNL     1      -0.027  -1.770   1.011  1.00  0.00           H  
HETATM   37  H10 UNL     1      -0.574  -3.210  -0.047  1.00  0.00           H  
HETATM   38  H11 UNL     1      -3.012  -2.882  -0.069  1.00  0.00           H  
HETATM   39  H12 UNL     1      -3.546  -1.609  -1.300  1.00  0.00           H  
HETATM   40  H13 UNL     1      -2.358  -2.935  -1.735  1.00  0.00           H  
HETATM   41  H14 UNL     1      -1.084   0.175   0.833  1.00  0.00           H  
HETATM   42  H15 UNL     1      -3.755  -1.336   1.043  1.00  0.00           H  
HETATM   43  H16 UNL     1      -2.564  -0.893   2.290  1.00  0.00           H  
HETATM   44  H17 UNL     1      -4.362   1.994   3.195  1.00  0.00           H  
HETATM   45  H18 UNL     1      -2.674   1.444   3.301  1.00  0.00           H  
HETATM   46  H19 UNL     1      -4.030   0.235   3.594  1.00  0.00           H  
HETATM   47  H20 UNL     1      -5.240   1.126   0.039  1.00  0.00           H  
HETATM   48  H21 UNL     1      -5.449  -0.400   0.923  1.00  0.00           H  
HETATM   49  H22 UNL     1      -5.885   1.163   1.750  1.00  0.00           H  
HETATM   50  H23 UNL     1      -3.595   2.648   0.439  1.00  0.00           H  
HETATM   51  H24 UNL     1      -2.041   2.049   1.226  1.00  0.00           H  
HETATM   52  H25 UNL     1      -3.532   0.516  -0.974  1.00  0.00           H  
HETATM   53  H26 UNL     1      -1.459   2.455  -1.528  1.00  0.00           H  
HETATM   54  H27 UNL     1       0.016   0.943  -2.563  1.00  0.00           H  
HETATM   55  H28 UNL     1      -0.761  -2.462  -2.980  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3    3    9
CONECT    3    4   31
CONECT    4    5    6    6
CONECT    5   32
CONECT    6    7   33
CONECT    7    8    9    9
CONECT    8   34
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   13
CONECT   13   14   26   35
CONECT   14   15   36   37
CONECT   15   16   17   26
CONECT   16   38   39   40
CONECT   17   18   23   41
CONECT   18   19   42   43
CONECT   19   20   21   22
CONECT   20   44   45   46
CONECT   21   47   48   49
CONECT   22   23   50   51
CONECT   23   24   52
CONECT   24   25   25   53
CONECT   25   26   54
CONECT   26   27
CONECT   27   55
END

HMDB0038742
     RDKit          3D
Armillasin
 55 58  0  0  0  0  0  0  0  0999 V2000
    5.5057   -1.2415   -1.5919 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1208   -0.0914   -0.7849 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0910    0.7757   -0.3396 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7401    1.8763    0.4305 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7223    2.7661    0.8892 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4394    2.1023    0.7476 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4561    1.2299    0.3005 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1791    1.5413    0.6708 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7966    0.1377   -0.4627 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7490   -0.7761   -0.9286 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0874   -1.7893   -1.6395 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4077   -0.6604   -0.6787 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4294   -1.5491   -1.1371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3836   -2.1229    0.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5792   -1.3743   -0.5329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7457   -2.2656   -0.9251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9799   -0.2518    0.3570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0547   -0.5564    1.3331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7561    0.7843    1.5685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6953    1.1284    3.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1604    0.6666    1.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9966    1.7841    0.7139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6290    0.8902   -0.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5926    1.4128   -1.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7585    0.5404   -1.9050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8067   -0.9087   -1.7278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1917   -1.5698   -2.9018 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2614   -2.2169   -1.0855 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6129   -1.2280   -1.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0658   -1.1889   -2.6073 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1351    0.6145   -0.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1332    2.5527    1.7908 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1964    2.9747    1.3535 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3070    1.1559    0.5299 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8243   -2.3946   -1.7448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0268   -1.7699    1.0108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743   -3.2100   -0.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0116   -2.8824   -0.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5461   -1.6085   -1.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3582   -2.9346   -1.7355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0844    0.1745    0.8325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7546   -1.3365    1.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5639   -0.8930    2.2901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3615    1.9945    3.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6739    1.4443    3.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0301    0.2350    3.5939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2398    1.1255    0.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4490   -0.3998    0.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8853    1.1629    1.7501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5947    2.6483    0.4388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0411    2.0488    1.2264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5317    0.5164   -0.9744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4586    2.4553   -1.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0163    0.9430   -2.5630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7611   -2.4621   -2.9804 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
  9  2  1  0
 26 13  1  0
 26 15  1  0
 23 17  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  5 32  1  0
  6 33  1  0
  8 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 18 42  1  0
 18 43  1  0
 20 44  1  0
 20 45  1  0
 20 46  1  0
 21 47  1  0
 21 48  1  0
 21 49  1  0
 22 50  1  0
 22 51  1  0
 23 52  1  0
 24 53  1  0
 25 54  1  0
 27 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2a-Hydroxy-6,6,7b-trimethyl-1H,2H,2ah,4ah,5H,6H,7H,7ah,7BH-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoic acid	HMDB

Chemical Formula

C₂₂H₂₈O₅

Average Molecular Weight

372.4547

Monoisotopic Molecular Weight

372.193674006

IUPAC Name

2a-hydroxy-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate

Traditional Name

2a-hydroxy-6,6,7b-trimethyl-1H,2H,4aH,5H,7H,7aH-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate

CAS Registry Number

139051-16-4

SMILES

CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=CC12O

InChI Identifier

InChI=1S/C22H28O5/c1-12-7-14(23)8-16(24)18(12)19(25)27-17-11-21(4)15-10-20(2,3)9-13(15)5-6-22(17,21)26/h5-8,13,15,17,23-24,26H,9-11H2,1-4H3

InChI Key

AFPPVJHFFGBKOB-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
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
O-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Benzoate ester
Salicylic acid or derivatives
Benzoic acid or derivatives
M-cresol
Benzoyl
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Toluene
Phenol
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Tertiary alcohol
Carboxylic acid ester
Cyclobutanol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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: HMDB0038742)

Source

Endogenous

Endogenous (HMDB: HMDB0038742)

Plant

Plant (HMDB: HMDB0038742)

Animal

Animal (HMDB: HMDB0038742)

Exogenous

Food

Food (HMDB: HMDB0038742)

Vegetable

Mushroom

Exogenous (HMDB: HMDB0038742)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0038742)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0038742)

Lipid metabolism pathway (HMDB: HMDB0038742)

Cellular process

Cell signaling (HMDB: HMDB0038742)

Biochemical process

Lipid transport (HMDB: HMDB0038742)

Role

Biological role

Energy source (HMDB: HMDB0038742)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0038742)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	179 - 181 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	2.38 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	0.048 g/L	ALOGPS
logP	3.68	ALOGPS
logP	4.83	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	8.7	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	102.97 m³·mol⁻¹	ChemAxon
Polarizability	40.75 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
DarkChem	[M+H]+	185.822	31661259
DarkChem	[M-H]-	180.927	31661259
DeepCCS	[M-2H]-	215.511	30932474
DeepCCS	[M+Na]+	190.739	30932474
AllCCS	[M+H]+	191.9	32859911
AllCCS	[M+H-H2O]+	189.4	32859911
AllCCS	[M+NH4]+	194.3	32859911
AllCCS	[M+Na]+	194.9	32859911
AllCCS	[M-H]-	194.0	32859911
AllCCS	[M+Na-2H]-	194.1	32859911
AllCCS	[M+HCOO]-	194.4	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.	7.08 minutes	32390414
Predicted by Siyang on May 30, 2022	13.6756 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.25 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2496.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	219.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	183.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	152.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	228.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	797.8 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	671.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	76.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1105.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	465.8 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	1615.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	435.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	440.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	219.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	158.0 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	13.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Armillasin	CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=CC12O	3758.4	Standard polar	33892256
Armillasin	CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=CC12O	2798.8	Standard non polar	33892256
Armillasin	CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=CC12O	2933.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Armillasin,1TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=CC12O	3007.5	Semi standard non polar	33892256
Armillasin,1TMS,isomer #2	CC1=CC(O)=CC(O[Si](C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=CC12O	2974.4	Semi standard non polar	33892256
Armillasin,1TMS,isomer #3	CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=CC12O[Si](C)(C)C	2999.7	Semi standard non polar	33892256
Armillasin,2TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=CC12O	3012.9	Semi standard non polar	33892256
Armillasin,2TMS,isomer #2	CC1=CC(O[Si](C)(C)C)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=CC12O[Si](C)(C)C	3004.0	Semi standard non polar	33892256
Armillasin,2TMS,isomer #3	CC1=CC(O)=CC(O[Si](C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=CC12O[Si](C)(C)C	3004.4	Semi standard non polar	33892256
Armillasin,3TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=CC12O[Si](C)(C)C	3023.8	Semi standard non polar	33892256
Armillasin,1TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=CC12O	3240.8	Semi standard non polar	33892256
Armillasin,1TBDMS,isomer #2	CC1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=CC12O	3185.2	Semi standard non polar	33892256
Armillasin,1TBDMS,isomer #3	CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=CC12O[Si](C)(C)C(C)(C)C	3230.6	Semi standard non polar	33892256
Armillasin,2TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=CC12O	3442.5	Semi standard non polar	33892256
Armillasin,2TBDMS,isomer #2	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=CC12O[Si](C)(C)C(C)(C)C	3456.3	Semi standard non polar	33892256
Armillasin,2TBDMS,isomer #3	CC1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=CC12O[Si](C)(C)C(C)(C)C	3423.0	Semi standard non polar	33892256
Armillasin,3TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=CC12O[Si](C)(C)C(C)(C)C	3618.8	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 - Armillasin GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-1900000000-1b14c75c172157b0b929	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Armillasin GC-MS (3 TMS) - 70eV, Positive	splash10-0002-1090010000-72d805139281745cfdec	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Armillasin 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 - Armillasin 10V, Positive-QTOF	splash10-00di-0439000000-eef51c1def02a0c2d331	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillasin 20V, Positive-QTOF	splash10-0zfr-0922000000-a1c7c18fd1ba7124ecb0	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillasin 40V, Positive-QTOF	splash10-0zfr-4900000000-ba4b72f28f775e68c8e2	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillasin 10V, Negative-QTOF	splash10-00di-0419000000-b41ab66703d52409e000	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillasin 20V, Negative-QTOF	splash10-00di-0924000000-1741464462e8f1399f66	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillasin 40V, Negative-QTOF	splash10-00di-1910000000-4fe4c5952722660951c7	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillasin 10V, Positive-QTOF	splash10-05fr-0559000000-952dc88bd9e9e4e64bae	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillasin 20V, Positive-QTOF	splash10-0ue9-1903000000-dcac5128cbf376468174	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillasin 40V, Positive-QTOF	splash10-0kai-4900000000-38b0a755feaf20efa389	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillasin 10V, Negative-QTOF	splash10-00di-0109000000-ce68e1efbeac23eefc7e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillasin 20V, Negative-QTOF	splash10-00di-1931000000-c878a6401c215b488a18	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillasin 40V, Negative-QTOF	splash10-00xu-9810000000-4dc021886f8636589ef2	2021-09-25	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

FDB018153

KNApSAcK ID

C00055508

Chemspider ID

35014648

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752445

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1870851

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 Armillasin (HMDB0038742)

MOL for HMDB0038742 (Armillasin)

3D MOL for HMDB0038742 (Armillasin)

3D SDF for HMDB0038742 (Armillasin)

3D-SDF for HMDB0038742 (Armillasin)

PDB for HMDB0038742 (Armillasin)

3D PDB for HMDB0038742 (Armillasin)

SMILES for HMDB0038742 (Armillasin)

INCHI for HMDB0038742 (Armillasin)

Structure for HMDB0038742 (Armillasin)

3D Structure for HMDB0038742 (Armillasin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra