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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:15:54 UTC

Update Date

2022-03-07 02:55:59 UTC

HMDB ID

HMDB0038917

Secondary Accession Numbers

HMDB38917

Metabolite Identification

Common Name

Armillarivin

Description

Armillarivin 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 significant number of articles have been published on Armillarivin.

Structure

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


  Mrv0541 05061310442D          

 28 31  0  0  0  0            999 V2000
   -1.4606    1.4957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7863    1.5151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2702    2.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0897    2.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5079    0.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6180    0.0598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1896   -0.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8695    0.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2455    2.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1480    1.9572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3548   -0.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7036    0.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0567    0.7584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935    0.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7509   -0.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6711    1.4877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3853   -0.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7092    1.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1423    0.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4079    0.8198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3380    0.2864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9862    1.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467    1.5184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7404   -1.3375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5551   -0.4486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8241   -1.2904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2232   -0.3182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0950    1.0748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 12  1  1  0  0  0  0
 12  5  2  0  0  0  0
 13  6  1  0  0  0  0
 13  8  1  0  0  0  0
 14  6  2  0  0  0  0
 14 11  1  0  0  0  0
 15  5  1  0  0  0  0
 15  7  2  0  0  0  0
 16  9  1  0  0  0  0
 16 13  1  0  0  0  0
 17  7  1  0  0  0  0
 18 10  1  0  0  0  0
 19 12  1  0  0  0  0
 19 17  2  0  0  0  0
 20 14  1  0  0  0  0
 20 18  1  0  0  0  0
 21 19  1  0  0  0  0
 22  2  1  0  0  0  0
 22  3  1  0  0  0  0
 22  8  1  0  0  0  0
 22  9  1  0  0  0  0
 23  4  1  0  0  0  0
 23 10  1  0  0  0  0
 23 16  1  0  0  0  0
 23 20  1  0  0  0  0
 24 11  2  0  0  0  0
 25 15  1  0  0  0  0
 26 17  1  0  0  0  0
 27 21  2  0  0  0  0
 28 18  1  0  0  0  0
 28 21  1  0  0  0  0
M  END

HMDB0038917
     RDKit          3D
Armillarivin
 56 59  0  0  0  0  0  0  0  0999 V2000
   -5.3611    1.3955    1.4864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4050    0.5364    0.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6418    0.2106   -0.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7181   -0.5857   -1.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9738   -0.8978   -1.9385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5572   -1.0380   -1.9332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3088   -0.7131   -1.3747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1745   -1.2117   -1.9774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2264    0.0790   -0.2602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9760    0.4525    0.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9490    1.1934    1.4046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7088    0.0745   -0.0569 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5323    0.4617    0.5835 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5412    1.0634   -0.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1902   -0.2776   -0.4124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6587   -0.9986   -1.6601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6462   -0.3842   -0.3126 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4092    0.8965   -0.6902 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8144    0.4570   -0.2450 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7674    1.6283   -0.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3009   -0.6544   -1.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5373    0.0062    1.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2187   -0.7698    0.9940 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3714   -0.6468    2.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0628   -0.6298    2.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2152   -0.5057    3.2604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0183   -0.4945    3.1361 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4080   -0.7307    0.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8943    2.3858    1.3086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4351    1.6686    1.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9843    0.8791    2.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5553    0.5804    0.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5008   -1.7076   -1.6552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5787   -1.6610   -2.8062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2282   -1.1346   -1.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6569    1.1053    1.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0252    1.4159   -1.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1007    1.8821    0.1473 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0279   -1.8528   -1.4026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5144   -1.4055   -2.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1289   -0.3050   -2.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0211   -1.1332   -1.0734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1182    1.7463   -0.0718 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3856    1.0745   -1.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7918    1.2017   -0.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7270    2.1000   -1.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5678    2.3419    0.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9779   -1.6447   -0.7231 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8793   -0.5311   -2.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4102   -0.6755   -1.1457 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2785    0.9029    1.7680 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3232   -0.5986    1.6144 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5716   -1.8504    0.9740 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8211   -0.5673    3.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6581   -0.4255    4.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0852   -1.7083    0.6459 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  2  0
 25 28  1  0
  9  2  1  0
 28 13  1  0
 28 15  1  0
 23 17  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  5 33  1  0
  6 34  1  0
  8 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  0
 21 49  1  0
 21 50  1  0
 22 51  1  0
 22 52  1  0
 23 53  1  0
 24 54  1  0
 26 55  1  0
 28 56  1  0
M  END


  Mrv0541 05061310442D          

 28 31  0  0  0  0            999 V2000
   -1.4606    1.4957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7863    1.5151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2702    2.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0897    2.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5079    0.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6180    0.0598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1896   -0.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8695    0.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2455    2.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1480    1.9572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3548   -0.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7036    0.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0567    0.7584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935    0.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7509   -0.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6711    1.4877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3853   -0.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7092    1.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1423    0.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4079    0.8198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3380    0.2864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9862    1.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467    1.5184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7404   -1.3375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5551   -0.4486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8241   -1.2904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2232   -0.3182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0950    1.0748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 12  1  1  0  0  0  0
 12  5  2  0  0  0  0
 13  6  1  0  0  0  0
 13  8  1  0  0  0  0
 14  6  2  0  0  0  0
 14 11  1  0  0  0  0
 15  5  1  0  0  0  0
 15  7  2  0  0  0  0
 16  9  1  0  0  0  0
 16 13  1  0  0  0  0
 17  7  1  0  0  0  0
 18 10  1  0  0  0  0
 19 12  1  0  0  0  0
 19 17  2  0  0  0  0
 20 14  1  0  0  0  0
 20 18  1  0  0  0  0
 21 19  1  0  0  0  0
 22  2  1  0  0  0  0
 22  3  1  0  0  0  0
 22  8  1  0  0  0  0
 22  9  1  0  0  0  0
 23  4  1  0  0  0  0
 23 10  1  0  0  0  0
 23 16  1  0  0  0  0
 23 20  1  0  0  0  0
 24 11  2  0  0  0  0
 25 15  1  0  0  0  0
 26 17  1  0  0  0  0
 27 21  2  0  0  0  0
 28 18  1  0  0  0  0
 28 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038917

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C1C(C=O)=CC1CC(C)(C)CC21

> <INCHI_IDENTIFIER>
InChI=1S/C23H28O5/c1-12-5-15(25)7-17(26)19(12)21(27)28-18-10-23(4)16-9-22(2,3)8-13(16)6-14(11-24)20(18)23/h5-7,11,13,16,18,20,25-26H,8-10H2,1-4H3

> <INCHI_KEY>
NFCOJBIECSQMAM-UHFFFAOYSA-N

> <FORMULA>
C23H28O5

> <MOLECULAR_WEIGHT>
384.4654

> <EXACT_MASS>
384.193674006

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
42.351304387699855

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-formyl-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>
3.77

> <JCHEM_LOGP>
4.877060330666667

> <ALOGPS_LOGS>
-4.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.558151991629083

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.699804477583715

> <JCHEM_PKA_STRONGEST_BASIC>
-4.002807740555437

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
106.90369999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.67e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038917
     RDKit          3D
Armillarivin
 56 59  0  0  0  0  0  0  0  0999 V2000
   -5.3611    1.3955    1.4864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4050    0.5364    0.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6418    0.2106   -0.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7181   -0.5857   -1.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9738   -0.8978   -1.9385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5572   -1.0380   -1.9332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3088   -0.7131   -1.3747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1745   -1.2117   -1.9774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2264    0.0790   -0.2602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9760    0.4525    0.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9490    1.1934    1.4046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7088    0.0745   -0.0569 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5323    0.4617    0.5835 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5412    1.0634   -0.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1902   -0.2776   -0.4124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6587   -0.9986   -1.6601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6462   -0.3842   -0.3126 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4092    0.8965   -0.6902 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8144    0.4570   -0.2450 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7674    1.6283   -0.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3009   -0.6544   -1.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5373    0.0062    1.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2187   -0.7698    0.9940 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3714   -0.6468    2.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0628   -0.6298    2.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2152   -0.5057    3.2604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0183   -0.4945    3.1361 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4080   -0.7307    0.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8943    2.3858    1.3086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4351    1.6686    1.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9843    0.8791    2.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5553    0.5804    0.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5008   -1.7076   -1.6552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5787   -1.6610   -2.8062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2282   -1.1346   -1.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6569    1.1053    1.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0252    1.4159   -1.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1007    1.8821    0.1473 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0279   -1.8528   -1.4026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5144   -1.4055   -2.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1289   -0.3050   -2.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0211   -1.1332   -1.0734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1182    1.7463   -0.0718 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3856    1.0745   -1.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7918    1.2017   -0.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7270    2.1000   -1.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5678    2.3419    0.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9779   -1.6447   -0.7231 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8793   -0.5311   -2.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4102   -0.6755   -1.1457 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2785    0.9029    1.7680 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3232   -0.5986    1.6144 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5716   -1.8504    0.9740 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8211   -0.5673    3.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6581   -0.4255    4.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0852   -1.7083    0.6459 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  2  0
 25 28  1  0
  9  2  1  0
 28 13  1  0
 28 15  1  0
 23 17  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  5 33  1  0
  6 34  1  0
  8 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  0
 21 49  1  0
 21 50  1  0
 22 51  1  0
 22 52  1  0
 23 53  1  0
 24 54  1  0
 26 55  1  0
 28 56  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      -2.726   2.792   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.934   2.828   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.971   4.650   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.901   4.306   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.681   0.977   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.887   0.112   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.087  -1.623   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.223   1.680   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.058   3.882   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.143   3.653   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.529  -1.135   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.180   1.320   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.706   1.416   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.348   0.169   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.135  -0.494   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.986   2.777   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.586  -1.280   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.324   2.349   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.132   0.192   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.628   1.530   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.631   0.535   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.441   3.204   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.447   2.834   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.249  -2.497   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -6.636  -0.837   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -1.538  -2.409   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.417  -0.594   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -0.177   2.006   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   22                                                            
CONECT    3   22                                                            
CONECT    4   23                                                            
CONECT    5   12   15                                                       
CONECT    6   13   14                                                       
CONECT    7   15   17                                                       
CONECT    8   13   22                                                       
CONECT    9   16   22                                                       
CONECT   10   18   23                                                       
CONECT   11   14   24                                                       
CONECT   12    1    5   19                                                  
CONECT   13    6    8   16                                                  
CONECT   14    6   11   20                                                  
CONECT   15    5    7   25                                                  
CONECT   16    9   13   23                                                  
CONECT   17    7   19   26                                                  
CONECT   18   10   20   28                                                  
CONECT   19   12   17   21                                                  
CONECT   20   14   18   23                                                  
CONECT   21   19   27   28                                                  
CONECT   22    2    3    8    9                                             
CONECT   23    4   10   16   20                                             
CONECT   24   11                                                            
CONECT   25   15                                                            
CONECT   26   17                                                            
CONECT   27   21                                                            
CONECT   28   18   21                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

COMPND    HMDB0038917
HETATM    1  C1  UNL     1      -5.361   1.396   1.486  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.405   0.536   0.281  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.642   0.211  -0.277  1.00  0.00           C  
HETATM    4  C4  UNL     1      -6.718  -0.586  -1.397  1.00  0.00           C  
HETATM    5  O1  UNL     1      -7.974  -0.898  -1.938  1.00  0.00           O  
HETATM    6  C5  UNL     1      -5.557  -1.038  -1.933  1.00  0.00           C  
HETATM    7  C6  UNL     1      -4.309  -0.713  -1.375  1.00  0.00           C  
HETATM    8  O2  UNL     1      -3.175  -1.212  -1.977  1.00  0.00           O  
HETATM    9  C7  UNL     1      -4.226   0.079  -0.260  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.976   0.453   0.366  1.00  0.00           C  
HETATM   11  O3  UNL     1      -2.949   1.193   1.405  1.00  0.00           O  
HETATM   12  O4  UNL     1      -1.709   0.075  -0.057  1.00  0.00           O  
HETATM   13  C9  UNL     1      -0.532   0.462   0.584  1.00  0.00           C  
HETATM   14  C10 UNL     1       0.541   1.063  -0.325  1.00  0.00           C  
HETATM   15  C11 UNL     1       1.190  -0.278  -0.412  1.00  0.00           C  
HETATM   16  C12 UNL     1       0.659  -0.999  -1.660  1.00  0.00           C  
HETATM   17  C13 UNL     1       2.646  -0.384  -0.313  1.00  0.00           C  
HETATM   18  C14 UNL     1       3.409   0.896  -0.690  1.00  0.00           C  
HETATM   19  C15 UNL     1       4.814   0.457  -0.245  1.00  0.00           C  
HETATM   20  C16 UNL     1       5.767   1.628  -0.276  1.00  0.00           C  
HETATM   21  C17 UNL     1       5.301  -0.654  -1.116  1.00  0.00           C  
HETATM   22  C18 UNL     1       4.537   0.006   1.168  1.00  0.00           C  
HETATM   23  C19 UNL     1       3.219  -0.770   0.994  1.00  0.00           C  
HETATM   24  C20 UNL     1       2.371  -0.647   2.167  1.00  0.00           C  
HETATM   25  C21 UNL     1       1.063  -0.630   2.069  1.00  0.00           C  
HETATM   26  C22 UNL     1       0.215  -0.506   3.260  1.00  0.00           C  
HETATM   27  O5  UNL     1      -1.018  -0.494   3.136  1.00  0.00           O  
HETATM   28  C23 UNL     1       0.408  -0.731   0.773  1.00  0.00           C  
HETATM   29  H1  UNL     1      -4.894   2.386   1.309  1.00  0.00           H  
HETATM   30  H2  UNL     1      -6.435   1.669   1.751  1.00  0.00           H  
HETATM   31  H3  UNL     1      -4.984   0.879   2.392  1.00  0.00           H  
HETATM   32  H4  UNL     1      -7.555   0.580   0.164  1.00  0.00           H  
HETATM   33  H5  UNL     1      -8.501  -1.708  -1.655  1.00  0.00           H  
HETATM   34  H6  UNL     1      -5.579  -1.661  -2.806  1.00  0.00           H  
HETATM   35  H7  UNL     1      -2.228  -1.135  -1.791  1.00  0.00           H  
HETATM   36  H8  UNL     1      -0.657   1.105   1.482  1.00  0.00           H  
HETATM   37  H9  UNL     1       0.025   1.416  -1.266  1.00  0.00           H  
HETATM   38  H10 UNL     1       1.101   1.882   0.147  1.00  0.00           H  
HETATM   39  H11 UNL     1       0.028  -1.853  -1.403  1.00  0.00           H  
HETATM   40  H12 UNL     1       1.514  -1.406  -2.265  1.00  0.00           H  
HETATM   41  H13 UNL     1       0.129  -0.305  -2.342  1.00  0.00           H  
HETATM   42  H14 UNL     1       3.021  -1.133  -1.073  1.00  0.00           H  
HETATM   43  H15 UNL     1       3.118   1.746  -0.072  1.00  0.00           H  
HETATM   44  H16 UNL     1       3.386   1.074  -1.777  1.00  0.00           H  
HETATM   45  H17 UNL     1       6.792   1.202  -0.150  1.00  0.00           H  
HETATM   46  H18 UNL     1       5.727   2.100  -1.261  1.00  0.00           H  
HETATM   47  H19 UNL     1       5.568   2.342   0.548  1.00  0.00           H  
HETATM   48  H20 UNL     1       4.978  -1.645  -0.723  1.00  0.00           H  
HETATM   49  H21 UNL     1       4.879  -0.531  -2.128  1.00  0.00           H  
HETATM   50  H22 UNL     1       6.410  -0.676  -1.146  1.00  0.00           H  
HETATM   51  H23 UNL     1       4.279   0.903   1.768  1.00  0.00           H  
HETATM   52  H24 UNL     1       5.323  -0.599   1.614  1.00  0.00           H  
HETATM   53  H25 UNL     1       3.572  -1.850   0.974  1.00  0.00           H  
HETATM   54  H26 UNL     1       2.821  -0.567   3.142  1.00  0.00           H  
HETATM   55  H27 UNL     1       0.658  -0.426   4.230  1.00  0.00           H  
HETATM   56  H28 UNL     1      -0.085  -1.708   0.646  1.00  0.00           H  
CONECT    1    2   29   30   31
CONECT    2    3    3    9
CONECT    3    4   32
CONECT    4    5    6    6
CONECT    5   33
CONECT    6    7   34
CONECT    7    8    9    9
CONECT    8   35
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   13
CONECT   13   14   28   36
CONECT   14   15   37   38
CONECT   15   16   17   28
CONECT   16   39   40   41
CONECT   17   18   23   42
CONECT   18   19   43   44
CONECT   19   20   21   22
CONECT   20   45   46   47
CONECT   21   48   49   50
CONECT   22   23   51   52
CONECT   23   24   53
CONECT   24   25   25   54
CONECT   25   26   28
CONECT   26   27   27   55
CONECT   28   56
END

HMDB0038917
     RDKit          3D
Armillarivin
 56 59  0  0  0  0  0  0  0  0999 V2000
   -5.3611    1.3955    1.4864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4050    0.5364    0.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6418    0.2106   -0.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7181   -0.5857   -1.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9738   -0.8978   -1.9385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5572   -1.0380   -1.9332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3088   -0.7131   -1.3747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1745   -1.2117   -1.9774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2264    0.0790   -0.2602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9760    0.4525    0.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9490    1.1934    1.4046 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7088    0.0745   -0.0569 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5323    0.4617    0.5835 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5412    1.0634   -0.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1902   -0.2776   -0.4124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6587   -0.9986   -1.6601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6462   -0.3842   -0.3126 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4092    0.8965   -0.6902 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8144    0.4570   -0.2450 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7674    1.6283   -0.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3009   -0.6544   -1.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5373    0.0062    1.1683 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2187   -0.7698    0.9940 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3714   -0.6468    2.1667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0628   -0.6298    2.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2152   -0.5057    3.2604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0183   -0.4945    3.1361 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4080   -0.7307    0.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8943    2.3858    1.3086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4351    1.6686    1.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9843    0.8791    2.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5553    0.5804    0.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5008   -1.7076   -1.6552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5787   -1.6610   -2.8062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2282   -1.1346   -1.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6569    1.1053    1.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0252    1.4159   -1.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1007    1.8821    0.1473 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0279   -1.8528   -1.4026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5144   -1.4055   -2.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1289   -0.3050   -2.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0211   -1.1332   -1.0734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1182    1.7463   -0.0718 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3856    1.0745   -1.7772 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7918    1.2017   -0.1504 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7270    2.1000   -1.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5678    2.3419    0.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9779   -1.6447   -0.7231 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8793   -0.5311   -2.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4102   -0.6755   -1.1457 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2785    0.9029    1.7680 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3232   -0.5986    1.6144 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5716   -1.8504    0.9740 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8211   -0.5673    3.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6581   -0.4255    4.2300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0852   -1.7083    0.6459 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  2  0
 25 28  1  0
  9  2  1  0
 28 13  1  0
 28 15  1  0
 23 17  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  5 33  1  0
  6 34  1  0
  8 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
 21 48  1  0
 21 49  1  0
 21 50  1  0
 22 51  1  0
 22 52  1  0
 23 53  1  0
 24 54  1  0
 26 55  1  0
 28 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Formyl-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

C₂₃H₂₈O₅

Average Molecular Weight

384.4654

Monoisotopic Molecular Weight

384.193674006

IUPAC Name

3-formyl-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

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

CAS Registry Number

135247-97-1

SMILES

CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C1C(C=O)=CC1CC(C)(C)CC21

InChI Identifier

InChI=1S/C23H28O5/c1-12-5-15(25)7-17(26)19(12)21(27)28-18-10-23(4)16-9-22(2,3)8-13(16)6-14(11-24)20(18)23/h5-7,11,13,16,18,20,25-26H,8-10H2,1-4H3

InChI Key

NFCOJBIECSQMAM-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
Resorcinol
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Toluene
Phenol
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aldehyde
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: HMDB0038917)

Source

Endogenous

Endogenous (HMDB: HMDB0038917)

Plant

Plant (HMDB: HMDB0038917)

Animal

Animal (HMDB: HMDB0038917)

Exogenous

Food

Food (HMDB: HMDB0038917)

Vegetable

Mushroom

Exogenous (HMDB: HMDB0038917)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0038917)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0038917)

Lipid metabolism pathway (HMDB: HMDB0038917)

Cellular process

Cell signaling (HMDB: HMDB0038917)

Biochemical process

Lipid transport (HMDB: HMDB0038917)

Role

Biological role

Energy source (HMDB: HMDB0038917)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0038917)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	159 - 172 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.21 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	0.017 g/L	ALOGPS
logP	3.77	ALOGPS
logP	4.88	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	8.7	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	106.9 m³·mol⁻¹	ChemAxon
Polarizability	42.35 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]+	186.699	31661259
DarkChem	[M-H]-	185.829	31661259
DeepCCS	[M-2H]-	224.064	30932474
DeepCCS	[M+Na]+	199.293	30932474
AllCCS	[M+H]+	194.4	32859911
AllCCS	[M+H-H2O]+	192.0	32859911
AllCCS	[M+NH4]+	196.7	32859911
AllCCS	[M+Na]+	197.3	32859911
AllCCS	[M-H]-	196.4	32859911
AllCCS	[M+Na-2H]-	196.6	32859911
AllCCS	[M+HCOO]-	196.8	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.	7.57 minutes	32390414
Predicted by Siyang on May 30, 2022	17.7234 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.09 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2955.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	378.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	218.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	177.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	503.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	896.1 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	947.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	77.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1402.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	559.9 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	1881.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	541.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	550.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	294.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	256.9 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	26.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Armillarivin	CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C1C(C=O)=CC1CC(C)(C)CC21	4123.2	Standard polar	33892256
Armillarivin	CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C1C(C=O)=CC1CC(C)(C)CC21	2748.5	Standard non polar	33892256
Armillarivin	CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C1C(C=O)=CC1CC(C)(C)CC21	3125.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Armillarivin,1TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C=O)C12	3227.6	Semi standard non polar	33892256
Armillarivin,1TMS,isomer #2	CC1=CC(O)=CC(O[Si](C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C=O)C12	3192.7	Semi standard non polar	33892256
Armillarivin,2TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C=O)C12	3250.8	Semi standard non polar	33892256
Armillarivin,1TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C=O)C12	3442.6	Semi standard non polar	33892256
Armillarivin,1TBDMS,isomer #2	CC1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=C(C=O)C12	3406.3	Semi standard non polar	33892256
Armillarivin,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=C(C=O)C12	3654.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Armillarivin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f7c-1921000000-599cec08d570dc0ad927	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Armillarivin GC-MS (2 TMS) - 70eV, Positive	splash10-000l-1950110000-4865aef9adfb6f1b17ec	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Armillarivin 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 - Armillarivin 10V, Positive-QTOF	splash10-000i-0439000000-a09231d868b877a61d06	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillarivin 20V, Positive-QTOF	splash10-0uxr-0953000000-89ef4a2067604adb080f	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillarivin 40V, Positive-QTOF	splash10-0udi-2910000000-dae424cc6cf5bda32a36	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillarivin 10V, Negative-QTOF	splash10-001i-0229000000-b209c00ac580055c1089	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillarivin 20V, Negative-QTOF	splash10-00si-0926000000-d2ea6d0fc734d18ba59c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillarivin 40V, Negative-QTOF	splash10-00di-2920000000-ec363da0b7c1951b6480	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillarivin 10V, Positive-QTOF	splash10-000i-0869000000-f7314a5e31de0522e528	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillarivin 20V, Positive-QTOF	splash10-0gc9-2945000000-00e2180a120f2a6bd6c6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillarivin 40V, Positive-QTOF	splash10-0pbi-1920000000-edae8435a4206adc198a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillarivin 10V, Negative-QTOF	splash10-01c0-0904000000-00f04b36257385d08a35	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillarivin 20V, Negative-QTOF	splash10-00di-2921000000-291dd6ad9075b3012787	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Armillarivin 40V, Negative-QTOF	splash10-00dl-8931000000-14fb3f5e1641dd26d857	2021-09-22	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

FDB018381

KNApSAcK ID

C00055512

Chemspider ID

35014691

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

78171719

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1872671

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 Armillarivin (HMDB0038917)

MOL for HMDB0038917 (Armillarivin)

3D MOL for HMDB0038917 (Armillarivin)

3D SDF for HMDB0038917 (Armillarivin)

3D-SDF for HMDB0038917 (Armillarivin)

PDB for HMDB0038917 (Armillarivin)

3D PDB for HMDB0038917 (Armillarivin)

SMILES for HMDB0038917 (Armillarivin)

INCHI for HMDB0038917 (Armillarivin)

Structure for HMDB0038917 (Armillarivin)

3D Structure for HMDB0038917 (Armillarivin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra