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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:34:30 UTC

Update Date

2022-03-07 02:56:49 UTC

HMDB ID

HMDB0040953

Secondary Accession Numbers

HMDB40953

Metabolite Identification

Common Name

Tussilagone

Description

Tussilagone belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a significant number of articles have been published on Tussilagone.

Structure

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


  Mrv0541 05061312162D          

 28 29  0  0  0  0            999 V2000
   -0.5768   -0.0742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1381    0.3382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1381    1.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5768    1.5756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5768    2.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9142   -1.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3792   -0.7988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0754    0.0838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2903    0.3382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2903    1.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0754    1.4175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5607    0.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3857    0.7507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1381   -1.3116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5768   -0.8992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7894   -1.2821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8518    1.5756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1863   -0.9706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5667    1.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2802    1.5756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5667    0.3382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9953    1.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7088    1.5756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9953    0.3382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5988   -1.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4237   -1.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1863   -2.4006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4237    1.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  1  0  0  0  0
  1 15  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 17  1  0  0  0  0
  4  5  2  0  0  0  0
  4 10  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 18  1  0  0  0  0
  8  9  1  0  0  0  0
  8 12  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 19  1  0  0  0  0
 18 25  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 28  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
M  END

HMDB0040953
     RDKit          3D
Tussilagone
 62 63  0  0  0  0  0  0  0  0999 V2000
    0.8890   -1.9645    1.5720 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2545   -1.0556    0.8463 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8572   -0.2911   -0.2455 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2068   -0.5505   -0.4740 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2145    0.4008   -0.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8358    1.5538   -0.0726 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5815    0.0058   -0.6445 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5619    0.8756   -0.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2638    2.2827   -0.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9758    0.4698   -0.8385 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8538    0.7102    0.3661 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0981   -0.4722   -1.5265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3651   -0.6699   -1.3708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8224   -2.0520   -1.7834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3116   -2.2396   -1.6193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1287   -3.1558   -1.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9214   -0.2494   -0.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1740   -0.7740    1.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2064    0.3913    2.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2633    1.6042    1.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7723    2.6627    1.6057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9928    1.2563    0.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4322    1.7110    0.0802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5516    3.2107    0.2008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2161    1.0232    1.0170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2767    0.2164    0.6718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1158   -0.5199    1.6566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5311    0.1121   -0.5586 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4048   -2.4979    2.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9304   -2.1562    1.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7740    0.8048    0.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8206   -1.0136   -0.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8416    2.3115    0.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2189    2.8736   -0.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6180    2.7393   -0.9736 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9606   -0.5845   -1.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3464    1.0602   -1.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6482   -0.0559    0.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2410    0.7214    1.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3370    1.7249    0.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3691    0.4044   -2.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5550   -1.3517   -2.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8555    0.0281   -2.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6236   -2.2285   -2.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5619   -3.1737   -2.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8921   -1.4358   -2.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6285   -2.4511   -0.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4079   -4.1094   -1.5963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0091   -3.1106   -1.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4468   -3.2985   -0.0226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9568   -0.6350    0.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6817   -1.6105    1.6663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0490    0.3233    2.8297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2786    0.4072    2.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4718    1.6961   -0.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8346    1.4588   -0.9244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3310    3.6019    1.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5645    3.4907   -0.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8683    3.6463   -0.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5854   -0.7177    2.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0237    0.1213    1.8275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5061   -1.4747    1.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
  3 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 18  2  1  0
 22 17  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  7 32  1  0
  9 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
 22 55  1  0
 23 56  1  0
 24 57  1  0
 24 58  1  0
 24 59  1  0
 27 60  1  0
 27 61  1  0
 27 62  1  0
M  END


  Mrv0541 05061312162D          

 28 29  0  0  0  0            999 V2000
   -0.5768   -0.0742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1381    0.3382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1381    1.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5768    1.5756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5768    2.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9142   -1.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3792   -0.7988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0754    0.0838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2903    0.3382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2903    1.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0754    1.4175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5607    0.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3857    0.7507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1381   -1.3116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5768   -0.8992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7894   -1.2821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8518    1.5756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1863   -0.9706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5667    1.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2802    1.5756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5667    0.3382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9953    1.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7088    1.5756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9953    0.3382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5988   -1.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4237   -1.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1863   -2.4006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4237    1.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  1  0  0  0  0
  1 15  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 17  1  0  0  0  0
  4  5  2  0  0  0  0
  4 10  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 18  1  0  0  0  0
  8  9  1  0  0  0  0
  8 12  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 19  1  0  0  0  0
 18 25  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 20 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 28  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040953

> <DATABASE_NAME>
hmdb

> <SMILES>
CC\C(C)=C\C(=O)OC1CC(C(C)C)C2C(CC(=O)C2C(C)OC(C)=O)C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C23H34O5/c1-8-13(4)9-21(26)28-20-11-17(12(2)3)23-18(14(20)5)10-19(25)22(23)15(6)27-16(7)24/h9,12,15,17-18,20,22-23H,5,8,10-11H2,1-4,6-7H3/b13-9+

> <INCHI_KEY>
CFUPNMDNSQIWBB-UKTHLTGXSA-N

> <FORMULA>
C23H34O5

> <MOLECULAR_WEIGHT>
390.5131

> <EXACT_MASS>
390.240624198

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
43.97682865583954

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[1-(acetyloxy)ethyl]-4-methylidene-2-oxo-7-(propan-2-yl)-octahydro-1H-inden-5-yl (2E)-3-methylpent-2-enoate

> <ALOGPS_LOGP>
3.96

> <JCHEM_LOGP>
4.395476534333333

> <ALOGPS_LOGS>
-5.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.16527458479212

> <JCHEM_PKA_STRONGEST_BASIC>
-6.546206721942806

> <JCHEM_POLAR_SURFACE_AREA>
69.67

> <JCHEM_REFRACTIVITY>
107.95839999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.66e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[1-(acetyloxy)ethyl]-7-isopropyl-4-methylidene-2-oxo-hexahydro-1H-inden-5-yl (2E)-3-methylpent-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040953
     RDKit          3D
Tussilagone
 62 63  0  0  0  0  0  0  0  0999 V2000
    0.8890   -1.9645    1.5720 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2545   -1.0556    0.8463 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8572   -0.2911   -0.2455 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2068   -0.5505   -0.4740 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2145    0.4008   -0.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8358    1.5538   -0.0726 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5815    0.0058   -0.6445 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5619    0.8756   -0.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2638    2.2827   -0.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9758    0.4698   -0.8385 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8538    0.7102    0.3661 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0981   -0.4722   -1.5265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3651   -0.6699   -1.3708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8224   -2.0520   -1.7834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3116   -2.2396   -1.6193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1287   -3.1558   -1.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9214   -0.2494   -0.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1740   -0.7740    1.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2064    0.3913    2.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2633    1.6042    1.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7723    2.6627    1.6057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9928    1.2563    0.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4322    1.7110    0.0802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5516    3.2107    0.2008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2161    1.0232    1.0170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2767    0.2164    0.6718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1158   -0.5199    1.6566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5311    0.1121   -0.5586 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4048   -2.4979    2.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9304   -2.1562    1.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7740    0.8048    0.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8206   -1.0136   -0.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8416    2.3115    0.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2189    2.8736   -0.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6180    2.7393   -0.9736 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9606   -0.5845   -1.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3464    1.0602   -1.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6482   -0.0559    0.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2410    0.7214    1.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3370    1.7249    0.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3691    0.4044   -2.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5550   -1.3517   -2.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8555    0.0281   -2.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6236   -2.2285   -2.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5619   -3.1737   -2.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8921   -1.4358   -2.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6285   -2.4511   -0.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4079   -4.1094   -1.5963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0091   -3.1106   -1.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4468   -3.2985   -0.0226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9568   -0.6350    0.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6817   -1.6105    1.6663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0490    0.3233    2.8297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2786    0.4072    2.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4718    1.6961   -0.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8346    1.4588   -0.9244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3310    3.6019    1.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5645    3.4907   -0.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8683    3.6463   -0.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5854   -0.7177    2.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0237    0.1213    1.8275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5061   -1.4747    1.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
  3 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 18  2  1  0
 22 17  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  7 32  1  0
  9 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
 22 55  1  0
 23 56  1  0
 24 57  1  0
 24 58  1  0
 24 59  1  0
 27 60  1  0
 27 61  1  0
 27 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      -1.077  -0.139   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.258   0.631   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.258   2.171   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.077   2.941   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.077   4.481   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.573  -2.417   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.441  -1.491   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.874   0.156   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.409   0.631   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.409   2.171   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.874   2.646   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.780   1.401   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -6.320   1.401   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.258  -2.448   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.077  -1.679   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.474  -2.393   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.590   2.941   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -5.948  -1.812   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.925   2.171   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.256   2.941   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.925   0.631   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.591   2.171   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.923   2.941   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.591   0.631   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.718  -3.147   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -8.258  -3.147   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -5.948  -4.481   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       8.258   2.171   0.000  0.00  0.00           C+0
CONECT    1    2    9   15                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4                                                            
CONECT    6    7                                                            
CONECT    7    6    8   18                                                  
CONECT    8    7    9   12                                                  
CONECT    9    1    8   10                                                  
CONECT   10    4    9   11                                                  
CONECT   11   10   12                                                       
CONECT   12    8   11   13                                                  
CONECT   13   12                                                            
CONECT   14   15                                                            
CONECT   15    1   14   16                                                  
CONECT   16   15                                                            
CONECT   17    3   19                                                       
CONECT   18    7   25                                                       
CONECT   19   17   20   21                                                  
CONECT   20   19   22                                                       
CONECT   21   19                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22   28                                                       
CONECT   24   22                                                            
CONECT   25   18   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   23                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

COMPND    HMDB0040953
HETATM    1  C1  UNL     1       0.889  -1.964   1.572  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.254  -1.056   0.846  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.857  -0.291  -0.245  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.207  -0.550  -0.474  1.00  0.00           O  
HETATM    5  C4  UNL     1       3.215   0.401  -0.383  1.00  0.00           C  
HETATM    6  O2  UNL     1       2.836   1.554  -0.073  1.00  0.00           O  
HETATM    7  C5  UNL     1       4.582   0.006  -0.644  1.00  0.00           C  
HETATM    8  C6  UNL     1       5.562   0.876  -0.569  1.00  0.00           C  
HETATM    9  C7  UNL     1       5.264   2.283  -0.211  1.00  0.00           C  
HETATM   10  C8  UNL     1       6.976   0.470  -0.839  1.00  0.00           C  
HETATM   11  C9  UNL     1       7.854   0.710   0.366  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.098  -0.472  -1.526  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.365  -0.670  -1.371  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.822  -2.052  -1.783  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.312  -2.240  -1.619  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.129  -3.156  -1.054  1.00  0.00           C  
HETATM   17  C15 UNL     1      -1.921  -0.249  -0.041  1.00  0.00           C  
HETATM   18  C16 UNL     1      -1.174  -0.774   1.144  1.00  0.00           C  
HETATM   19  C17 UNL     1      -1.206   0.391   2.145  1.00  0.00           C  
HETATM   20  C18 UNL     1      -1.263   1.604   1.293  1.00  0.00           C  
HETATM   21  O3  UNL     1      -0.772   2.663   1.606  1.00  0.00           O  
HETATM   22  C19 UNL     1      -1.993   1.256   0.080  1.00  0.00           C  
HETATM   23  C20 UNL     1      -3.432   1.711   0.080  1.00  0.00           C  
HETATM   24  C21 UNL     1      -3.552   3.211   0.201  1.00  0.00           C  
HETATM   25  O4  UNL     1      -4.216   1.023   1.017  1.00  0.00           O  
HETATM   26  C22 UNL     1      -5.277   0.216   0.672  1.00  0.00           C  
HETATM   27  C23 UNL     1      -6.116  -0.520   1.657  1.00  0.00           C  
HETATM   28  O5  UNL     1      -5.531   0.112  -0.559  1.00  0.00           O  
HETATM   29  H1  UNL     1       0.405  -2.498   2.361  1.00  0.00           H  
HETATM   30  H2  UNL     1       1.930  -2.156   1.341  1.00  0.00           H  
HETATM   31  H3  UNL     1       0.774   0.805   0.016  1.00  0.00           H  
HETATM   32  H4  UNL     1       4.821  -1.014  -0.907  1.00  0.00           H  
HETATM   33  H5  UNL     1       4.842   2.311   0.825  1.00  0.00           H  
HETATM   34  H6  UNL     1       6.219   2.874  -0.194  1.00  0.00           H  
HETATM   35  H7  UNL     1       4.618   2.739  -0.974  1.00  0.00           H  
HETATM   36  H8  UNL     1       6.961  -0.584  -1.165  1.00  0.00           H  
HETATM   37  H9  UNL     1       7.346   1.060  -1.700  1.00  0.00           H  
HETATM   38  H10 UNL     1       8.648  -0.056   0.364  1.00  0.00           H  
HETATM   39  H11 UNL     1       7.241   0.721   1.278  1.00  0.00           H  
HETATM   40  H12 UNL     1       8.337   1.725   0.289  1.00  0.00           H  
HETATM   41  H13 UNL     1       0.369   0.404  -2.182  1.00  0.00           H  
HETATM   42  H14 UNL     1       0.555  -1.352  -2.050  1.00  0.00           H  
HETATM   43  H15 UNL     1      -1.855   0.028  -2.098  1.00  0.00           H  
HETATM   44  H16 UNL     1      -1.624  -2.229  -2.882  1.00  0.00           H  
HETATM   45  H17 UNL     1      -3.562  -3.174  -2.207  1.00  0.00           H  
HETATM   46  H18 UNL     1      -3.892  -1.436  -2.126  1.00  0.00           H  
HETATM   47  H19 UNL     1      -3.628  -2.451  -0.595  1.00  0.00           H  
HETATM   48  H20 UNL     1      -1.408  -4.109  -1.596  1.00  0.00           H  
HETATM   49  H21 UNL     1      -0.009  -3.111  -1.179  1.00  0.00           H  
HETATM   50  H22 UNL     1      -1.447  -3.298  -0.023  1.00  0.00           H  
HETATM   51  H23 UNL     1      -2.957  -0.635   0.033  1.00  0.00           H  
HETATM   52  H24 UNL     1      -1.682  -1.611   1.666  1.00  0.00           H  
HETATM   53  H25 UNL     1      -2.049   0.323   2.830  1.00  0.00           H  
HETATM   54  H26 UNL     1      -0.279   0.407   2.750  1.00  0.00           H  
HETATM   55  H27 UNL     1      -1.472   1.696  -0.823  1.00  0.00           H  
HETATM   56  H28 UNL     1      -3.835   1.459  -0.924  1.00  0.00           H  
HETATM   57  H29 UNL     1      -3.331   3.602   1.189  1.00  0.00           H  
HETATM   58  H30 UNL     1      -4.564   3.491  -0.081  1.00  0.00           H  
HETATM   59  H31 UNL     1      -2.868   3.646  -0.566  1.00  0.00           H  
HETATM   60  H32 UNL     1      -5.585  -0.718   2.595  1.00  0.00           H  
HETATM   61  H33 UNL     1      -7.024   0.121   1.828  1.00  0.00           H  
HETATM   62  H34 UNL     1      -6.506  -1.475   1.232  1.00  0.00           H  
CONECT    1    2    2   29   30
CONECT    2    3   18
CONECT    3    4   12   31
CONECT    4    5
CONECT    5    6    6    7
CONECT    7    8    8   32
CONECT    8    9   10
CONECT    9   33   34   35
CONECT   10   11   36   37
CONECT   11   38   39   40
CONECT   12   13   41   42
CONECT   13   14   17   43
CONECT   14   15   16   44
CONECT   15   45   46   47
CONECT   16   48   49   50
CONECT   17   18   22   51
CONECT   18   19   52
CONECT   19   20   53   54
CONECT   20   21   21   22
CONECT   22   23   55
CONECT   23   24   25   56
CONECT   24   57   58   59
CONECT   25   26
CONECT   26   27   28   28
CONECT   27   60   61   62
END

HMDB0040953
     RDKit          3D
Tussilagone
 62 63  0  0  0  0  0  0  0  0999 V2000
    0.8890   -1.9645    1.5720 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2545   -1.0556    0.8463 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8572   -0.2911   -0.2455 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2068   -0.5505   -0.4740 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2145    0.4008   -0.3832 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8358    1.5538   -0.0726 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5815    0.0058   -0.6445 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5619    0.8756   -0.5691 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2638    2.2827   -0.2109 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9758    0.4698   -0.8385 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8538    0.7102    0.3661 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0981   -0.4722   -1.5265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3651   -0.6699   -1.3708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8224   -2.0520   -1.7834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3116   -2.2396   -1.6193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1287   -3.1558   -1.0544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9214   -0.2494   -0.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1740   -0.7740    1.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2064    0.3913    2.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2633    1.6042    1.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7723    2.6627    1.6057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9928    1.2563    0.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4322    1.7110    0.0802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5516    3.2107    0.2008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2161    1.0232    1.0170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2767    0.2164    0.6718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1158   -0.5199    1.6566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5311    0.1121   -0.5586 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4048   -2.4979    2.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9304   -2.1562    1.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7740    0.8048    0.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8206   -1.0136   -0.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8416    2.3115    0.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2189    2.8736   -0.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6180    2.7393   -0.9736 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9606   -0.5845   -1.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3464    1.0602   -1.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6482   -0.0559    0.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2410    0.7214    1.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3370    1.7249    0.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3691    0.4044   -2.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5550   -1.3517   -2.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8555    0.0281   -2.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6236   -2.2285   -2.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5619   -3.1737   -2.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8921   -1.4358   -2.1257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6285   -2.4511   -0.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4079   -4.1094   -1.5963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0091   -3.1106   -1.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4468   -3.2985   -0.0226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9568   -0.6350    0.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6817   -1.6105    1.6663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0490    0.3233    2.8297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2786    0.4072    2.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4718    1.6961   -0.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8346    1.4588   -0.9244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3310    3.6019    1.1885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5645    3.4907   -0.0806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8683    3.6463   -0.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5854   -0.7177    2.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0237    0.1213    1.8275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5061   -1.4747    1.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
  3 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 13 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 18  2  1  0
 22 17  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  7 32  1  0
  9 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
 22 55  1  0
 23 56  1  0
 24 57  1  0
 24 58  1  0
 24 59  1  0
 27 60  1  0
 27 61  1  0
 27 62  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Farfaratin	HMDB
1-[1-(Acetyloxy)ethyl]-4-methylidene-2-oxo-7-(propan-2-yl)-octahydro-1H-inden-5-yl (2E)-3-methylpent-2-enoic acid	Generator
(7R,14R)-14-Acetoxy-7-((2'e)-3'-methylpent-2'-enoyloxy)-oplopanone	MeSH
14-Acetoxy-7-(3'-ethylcrotonoyloxy)-notonipetranone	MeSH
14-Acetoxy-7b-(3'-ethylcrotonoyloxy)-notonipetranone	MeSH
Tussilagone	MeSH
9a-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one 4-acetate	Generator
9a-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one 4-acetic acid	Generator
9alpha-(3-Methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one 4-acetic acid	Generator
9Α-(3-methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one 4-acetate	Generator
9Α-(3-methyl-2E-pentenoyloxy)-4S-hydroxy-10(14)-oplopen-3-one 4-acetic acid	Generator

Chemical Formula

C₂₃H₃₄O₅

Average Molecular Weight

390.5131

Monoisotopic Molecular Weight

390.240624198

IUPAC Name

1-[1-(acetyloxy)ethyl]-4-methylidene-2-oxo-7-(propan-2-yl)-octahydro-1H-inden-5-yl (2E)-3-methylpent-2-enoate

Traditional Name

1-[1-(acetyloxy)ethyl]-7-isopropyl-4-methylidene-2-oxo-hexahydro-1H-inden-5-yl (2E)-3-methylpent-2-enoate

CAS Registry Number

104012-37-5

SMILES

CC\C(C)=C\C(=O)OC1CC(C(C)C)C2C(CC(=O)C2C(C)OC(C)=O)C1=C

InChI Identifier

InChI=1S/C23H34O5/c1-8-13(4)9-21(26)28-20-11-17(12(2)3)23-18(14(20)5)10-19(25)22(23)15(6)27-16(7)24/h9,12,15,17-18,20,22-23H,5,8,10-11H2,1-4,6-7H3/b13-9+

InChI Key

CFUPNMDNSQIWBB-UKTHLTGXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Oplopane sesquiterpenoid
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty acyl
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Cyclic ketone
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0040953)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040953)

Source

Endogenous

Endogenous (HMDB: HMDB0040953)

Plant

Plant (HMDB: HMDB0040953)

Animal

Animal (HMDB: HMDB0040953)

Exogenous

Food

Food (HMDB: HMDB0040953)

Tea

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0040953)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0040953)

Cellular process

Cell signaling (HMDB: HMDB0040953)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0040953)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0040953)

Nutrient

Nutrient (HMDB: HMDB0040953)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0040953)

Emulsifier (HMDB: HMDB0040953)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	100 - 101 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.089 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	0.0027 g/L	ALOGPS
logP	3.96	ALOGPS
logP	4.4	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	19.17	ChemAxon
pKa (Strongest Basic)	-6.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	69.67 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	107.96 m³·mol⁻¹	ChemAxon
Polarizability	43.98 Å³	ChemAxon
Number of Rings	2	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]+	194.322	31661259
DarkChem	[M-H]-	187.855	31661259
DeepCCS	[M+H]+	202.736	30932474
DeepCCS	[M-H]-	200.378	30932474
DeepCCS	[M-2H]-	233.858	30932474
DeepCCS	[M+Na]+	209.086	30932474
AllCCS	[M+H]+	197.5	32859911
AllCCS	[M+H-H2O]+	195.3	32859911
AllCCS	[M+NH4]+	199.5	32859911
AllCCS	[M+Na]+	200.1	32859911
AllCCS	[M-H]-	195.6	32859911
AllCCS	[M+Na-2H]-	196.8	32859911
AllCCS	[M+HCOO]-	198.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tussilagone	CC\C(C)=C\C(=O)OC1CC(C(C)C)C2C(CC(=O)C2C(C)OC(C)=O)C1=C	3368.4	Standard polar	33892256
Tussilagone	CC\C(C)=C\C(=O)OC1CC(C(C)C)C2C(CC(=O)C2C(C)OC(C)=O)C1=C	2427.0	Standard non polar	33892256
Tussilagone	CC\C(C)=C\C(=O)OC1CC(C(C)C)C2C(CC(=O)C2C(C)OC(C)=O)C1=C	2471.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tussilagone,1TMS,isomer #1	C=C1C(OC(=O)/C=C(\C)CC)CC(C(C)C)C2C(C(C)OC(C)=O)=C(O[Si](C)(C)C)CC12	2582.8	Semi standard non polar	33892256
Tussilagone,1TMS,isomer #1	C=C1C(OC(=O)/C=C(\C)CC)CC(C(C)C)C2C(C(C)OC(C)=O)=C(O[Si](C)(C)C)CC12	2622.0	Standard non polar	33892256
Tussilagone,1TMS,isomer #2	C=C1C(OC(=O)/C=C(\C)CC)CC(C(C)C)C2C1C=C(O[Si](C)(C)C)C2C(C)OC(C)=O	2532.6	Semi standard non polar	33892256
Tussilagone,1TMS,isomer #2	C=C1C(OC(=O)/C=C(\C)CC)CC(C(C)C)C2C1C=C(O[Si](C)(C)C)C2C(C)OC(C)=O	2596.1	Standard non polar	33892256
Tussilagone,1TBDMS,isomer #1	C=C1C(OC(=O)/C=C(\C)CC)CC(C(C)C)C2C(C(C)OC(C)=O)=C(O[Si](C)(C)C(C)(C)C)CC12	2783.2	Semi standard non polar	33892256
Tussilagone,1TBDMS,isomer #1	C=C1C(OC(=O)/C=C(\C)CC)CC(C(C)C)C2C(C(C)OC(C)=O)=C(O[Si](C)(C)C(C)(C)C)CC12	2831.4	Standard non polar	33892256
Tussilagone,1TBDMS,isomer #2	C=C1C(OC(=O)/C=C(\C)CC)CC(C(C)C)C2C1C=C(O[Si](C)(C)C(C)(C)C)C2C(C)OC(C)=O	2737.0	Semi standard non polar	33892256
Tussilagone,1TBDMS,isomer #2	C=C1C(OC(=O)/C=C(\C)CC)CC(C(C)C)C2C1C=C(O[Si](C)(C)C(C)(C)C)C2C(C)OC(C)=O	2764.0	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tussilagone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-7195000000-dafd6bcde25680a7933e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tussilagone 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 - Tussilagone 10V, Positive-QTOF	splash10-052e-8039000000-b36cbbf403995c06f288	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tussilagone 20V, Positive-QTOF	splash10-0pb9-9021000000-244d8ac8eb2ebcd7accb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tussilagone 40V, Positive-QTOF	splash10-0pbi-9020000000-fac7c6b5476c989c8559	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tussilagone 10V, Negative-QTOF	splash10-000m-3029000000-cc27d7bfdedf1be0fd1c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tussilagone 20V, Negative-QTOF	splash10-052g-7196000000-b72b479fc0e0efe7c218	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tussilagone 40V, Negative-QTOF	splash10-052e-7090000000-f0c13261c10949ebf3ba	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tussilagone 10V, Positive-QTOF	splash10-002r-0090000000-b075c0a89c9622fc55ec	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tussilagone 20V, Positive-QTOF	splash10-0002-0391000000-de73ab31b89043a1fcb0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tussilagone 40V, Positive-QTOF	splash10-05no-9240000000-368855e350e7563e39ec	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tussilagone 10V, Negative-QTOF	splash10-001r-1093000000-78557e1f844456105034	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tussilagone 20V, Negative-QTOF	splash10-0btj-6392000000-8d5ae20280d274812a16	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tussilagone 40V, Negative-QTOF	splash10-0a4i-7191000000-5e1b8f0852d951b8061c	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB020801

KNApSAcK ID

C00056379

Chemspider ID

35015056

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13919184

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1888071

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 Tussilagone (HMDB0040953)

MOL for HMDB0040953 (Tussilagone)

3D MOL for HMDB0040953 (Tussilagone)

3D SDF for HMDB0040953 (Tussilagone)

3D-SDF for HMDB0040953 (Tussilagone)

PDB for HMDB0040953 (Tussilagone)

3D PDB for HMDB0040953 (Tussilagone)

SMILES for HMDB0040953 (Tussilagone)

INCHI for HMDB0040953 (Tussilagone)

Structure for HMDB0040953 (Tussilagone)

3D Structure for HMDB0040953 (Tussilagone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra