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

2012-09-11 21:47:55 UTC

Update Date

2022-03-07 02:55:00 UTC

HMDB ID

HMDB0036636

Secondary Accession Numbers

HMDB36636

Metabolite Identification

Common Name

Methuyl tanshinonate

Description

Methuyl tanshinonate belongs to the class of organic compounds known as tanshinones, isotanshinones, and derivatives. These are a group of abietane-type norditerpenoid quinones. Methuyl tanshinonate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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


  Mrv0541 05061309152D          

 25 28  0  0  0  0            999 V2000
   -0.8637    2.7283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7119   -0.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4209   -0.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2475    2.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4354    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8399    0.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520    0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278    1.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5867    1.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574    2.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035    1.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5596    1.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838    0.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4672    2.1038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914    1.8134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9990    2.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111    2.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475    1.3279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7094    0.3328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9960    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7187    3.5104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3429    3.2200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4249    0.7436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7075   -0.4922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962    0.8215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  7  6  2  0  0  0  0
  8  4  1  0  0  0  0
 10  1  1  0  0  0  0
 10  9  2  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 13 11  2  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
 15 12  2  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 12  1  0  0  0  0
 18 14  2  0  0  0  0
 20  2  1  0  0  0  0
 20  8  1  0  0  0  0
 20 13  1  0  0  0  0
 20 19  1  0  0  0  0
 21 16  2  0  0  0  0
 22 17  2  0  0  0  0
 23 19  2  0  0  0  0
 24  3  1  0  0  0  0
 24 19  1  0  0  0  0
 25  9  1  0  0  0  0
 25 18  1  0  0  0  0
M  END

HMDB0036636
     RDKit          3D
Methuyl tanshinonate
 43 46  0  0  0  0  0  0  0  0999 V2000
   -4.5133    2.5173    0.7625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5980    1.4404    0.7576 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5772    0.5527   -0.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3982    0.7681   -1.2344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6734   -0.5881   -0.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9803   -1.3289   -1.7029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8060   -1.5203    0.7850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9617   -2.7319    0.5423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4769   -2.3671    0.4016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2651   -0.9628   -0.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2737   -0.1154   -0.3924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9767    1.1800   -0.7575 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3057    1.6579   -0.7617 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3455    0.8324   -0.3924 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0612   -0.4790   -0.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1145   -1.3931    0.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9176   -2.5826    0.7139 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5028   -0.8732    0.3623 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4188   -1.6407    0.6959 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7417    0.5029   -0.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8905    1.2636   -0.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2830    0.7894    0.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4825    2.5100   -0.5679 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1862    2.5326   -0.7146 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7153    1.3406   -0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3817    2.3371    0.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9269    2.7250    1.7717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0226    3.4471    0.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5939   -2.2203   -1.5501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0340   -1.6554   -2.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5436   -0.6595   -2.3932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3860   -0.9779    1.6542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8367   -1.8382    0.9310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2964   -3.2775   -0.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1401   -3.4432    1.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1007   -2.5033    1.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0112   -3.1045   -0.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8125    1.8105   -1.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5397    2.6899   -1.0526 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6771    0.1695   -0.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3004    0.1871    1.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9566    1.6462    0.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1255    3.3626   -0.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  1  0
 11  5  1  0
 25 14  1  0
 15 10  1  0
 25 20  2  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  6 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 12 38  1  0
 13 39  1  0
 22 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
M  END


  Mrv0541 05061309152D          

 25 28  0  0  0  0            999 V2000
   -0.8637    2.7283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7119   -0.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4209   -0.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2475    2.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4354    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8399    0.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520    0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278    1.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5867    1.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574    2.0770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035    1.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5596    1.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838    0.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4672    2.1038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914    1.8134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9990    2.7345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111    2.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475    1.3279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7094    0.3328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9960    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7187    3.5104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3429    3.2200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4249    0.7436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7075   -0.4922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962    0.8215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  7  6  2  0  0  0  0
  8  4  1  0  0  0  0
 10  1  1  0  0  0  0
 10  9  2  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 13 11  2  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
 15 12  2  0  0  0  0
 16 14  1  0  0  0  0
 17 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 12  1  0  0  0  0
 18 14  2  0  0  0  0
 20  2  1  0  0  0  0
 20  8  1  0  0  0  0
 20 13  1  0  0  0  0
 20 19  1  0  0  0  0
 21 16  2  0  0  0  0
 22 17  2  0  0  0  0
 23 19  2  0  0  0  0
 24  3  1  0  0  0  0
 24 19  1  0  0  0  0
 25  9  1  0  0  0  0
 25 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036636

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)C1(C)CCCC2=C1C=CC1=C2C(=O)C(=O)C2=C1OC=C2C

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O5/c1-10-9-25-18-12-6-7-13-11(15(12)17(22)16(21)14(10)18)5-4-8-20(13,2)19(23)24-3/h6-7,9H,4-5,8H2,1-3H3

> <INCHI_KEY>
YFDKIHAZVQFLRC-UHFFFAOYSA-N

> <FORMULA>
C20H18O5

> <MOLECULAR_WEIGHT>
338.3539

> <EXACT_MASS>
338.115423686

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
35.988440934245915

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 6,14-dimethyl-16,17-dioxo-12-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),2(7),8,11(15),13-pentaene-6-carboxylate

> <ALOGPS_LOGP>
3.46

> <JCHEM_LOGP>
3.8692811853333335

> <ALOGPS_LOGS>
-4.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.657815313461834

> <JCHEM_POLAR_SURFACE_AREA>
73.58

> <JCHEM_REFRACTIVITY>
91.57529999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.77e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 6,14-dimethyl-16,17-dioxo-12-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),2(7),8,11(15),13-pentaene-6-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036636
     RDKit          3D
Methuyl tanshinonate
 43 46  0  0  0  0  0  0  0  0999 V2000
   -4.5133    2.5173    0.7625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5980    1.4404    0.7576 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5772    0.5527   -0.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3982    0.7681   -1.2344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6734   -0.5881   -0.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9803   -1.3289   -1.7029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8060   -1.5203    0.7850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9617   -2.7319    0.5423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4769   -2.3671    0.4016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2651   -0.9628   -0.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2737   -0.1154   -0.3924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9767    1.1800   -0.7575 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3057    1.6579   -0.7617 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3455    0.8324   -0.3924 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0612   -0.4790   -0.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1145   -1.3931    0.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9176   -2.5826    0.7139 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5028   -0.8732    0.3623 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4188   -1.6407    0.6959 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7417    0.5029   -0.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8905    1.2636   -0.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2830    0.7894    0.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4825    2.5100   -0.5679 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1862    2.5326   -0.7146 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7153    1.3406   -0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3817    2.3371    0.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9269    2.7250    1.7717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0226    3.4471    0.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5939   -2.2203   -1.5501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0340   -1.6554   -2.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5436   -0.6595   -2.3932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3860   -0.9779    1.6542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8367   -1.8382    0.9310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2964   -3.2775   -0.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1401   -3.4432    1.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1007   -2.5033    1.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0112   -3.1045   -0.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8125    1.8105   -1.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5397    2.6899   -1.0526 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6771    0.1695   -0.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3004    0.1871    1.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9566    1.6462    0.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1255    3.3626   -0.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  1  0
 11  5  1  0
 25 14  1  0
 15 10  1  0
 25 20  2  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  6 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 12 38  1  0
 13 39  1  0
 22 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  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      -1.612   5.093   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.929  -0.051   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.119  -1.692   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.929   4.020   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.413   4.291   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.434   0.759   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.950   0.488   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.452   2.572   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.095   2.398   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.667   3.877   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.420   3.114   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.911   2.208   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.943   1.665   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.872   3.927   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.904   3.385   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.865   5.104   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.381   4.833   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.395   2.479   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.791   0.621   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.459   1.394   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.342   6.553   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.373   6.011   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      10.126   1.388   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       8.787  -0.919   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.180   1.533   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   20                                                            
CONECT    3   24                                                            
CONECT    4    5    8                                                       
CONECT    5    4   11                                                       
CONECT    6    7   12                                                       
CONECT    7    6   13                                                       
CONECT    8    4   20                                                       
CONECT    9   10   25                                                       
CONECT   10    1    9   14                                                  
CONECT   11    5   13   15                                                  
CONECT   12    6   15   18                                                  
CONECT   13    7   11   20                                                  
CONECT   14   10   16   18                                                  
CONECT   15   11   12   17                                                  
CONECT   16   14   17   21                                                  
CONECT   17   15   16   22                                                  
CONECT   18   12   14   25                                                  
CONECT   19   20   23   24                                                  
CONECT   20    2    8   13   19                                             
CONECT   21   16                                                            
CONECT   22   17                                                            
CONECT   23   19                                                            
CONECT   24    3   19                                                       
CONECT   25    9   18                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0036636
HETATM    1  C1  UNL     1      -4.513   2.517   0.763  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.598   1.440   0.758  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.577   0.553  -0.310  1.00  0.00           C  
HETATM    4  O2  UNL     1      -4.398   0.768  -1.234  1.00  0.00           O  
HETATM    5  C3  UNL     1      -2.673  -0.588  -0.411  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.980  -1.329  -1.703  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.806  -1.520   0.785  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.962  -2.732   0.542  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.477  -2.367   0.402  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.265  -0.963  -0.019  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.274  -0.115  -0.392  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.977   1.180  -0.758  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.306   1.658  -0.762  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.345   0.832  -0.392  1.00  0.00           C  
HETATM   15  C13 UNL     1       1.061  -0.479  -0.021  1.00  0.00           C  
HETATM   16  C14 UNL     1       2.114  -1.393   0.372  1.00  0.00           C  
HETATM   17  O3  UNL     1       1.918  -2.583   0.714  1.00  0.00           O  
HETATM   18  C15 UNL     1       3.503  -0.873   0.362  1.00  0.00           C  
HETATM   19  O4  UNL     1       4.419  -1.641   0.696  1.00  0.00           O  
HETATM   20  C16 UNL     1       3.742   0.503  -0.033  1.00  0.00           C  
HETATM   21  C17 UNL     1       4.891   1.264  -0.142  1.00  0.00           C  
HETATM   22  C18 UNL     1       6.283   0.789   0.153  1.00  0.00           C  
HETATM   23  C19 UNL     1       4.482   2.510  -0.568  1.00  0.00           C  
HETATM   24  O5  UNL     1       3.186   2.533  -0.715  1.00  0.00           O  
HETATM   25  C20 UNL     1       2.715   1.341  -0.400  1.00  0.00           C  
HETATM   26  H1  UNL     1      -5.382   2.337   0.097  1.00  0.00           H  
HETATM   27  H2  UNL     1      -4.927   2.725   1.772  1.00  0.00           H  
HETATM   28  H3  UNL     1      -4.023   3.447   0.355  1.00  0.00           H  
HETATM   29  H4  UNL     1      -3.594  -2.220  -1.550  1.00  0.00           H  
HETATM   30  H5  UNL     1      -2.034  -1.655  -2.203  1.00  0.00           H  
HETATM   31  H6  UNL     1      -3.544  -0.659  -2.393  1.00  0.00           H  
HETATM   32  H7  UNL     1      -2.386  -0.978   1.654  1.00  0.00           H  
HETATM   33  H8  UNL     1      -3.837  -1.838   0.931  1.00  0.00           H  
HETATM   34  H9  UNL     1      -2.296  -3.277  -0.382  1.00  0.00           H  
HETATM   35  H10 UNL     1      -2.140  -3.443   1.375  1.00  0.00           H  
HETATM   36  H11 UNL     1      -0.101  -2.503   1.460  1.00  0.00           H  
HETATM   37  H12 UNL     1       0.011  -3.104  -0.240  1.00  0.00           H  
HETATM   38  H13 UNL     1      -1.812   1.810  -1.044  1.00  0.00           H  
HETATM   39  H14 UNL     1       0.540   2.690  -1.053  1.00  0.00           H  
HETATM   40  H15 UNL     1       6.677   0.170  -0.660  1.00  0.00           H  
HETATM   41  H16 UNL     1       6.300   0.187   1.088  1.00  0.00           H  
HETATM   42  H17 UNL     1       6.957   1.646   0.316  1.00  0.00           H  
HETATM   43  H18 UNL     1       5.126   3.363  -0.760  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6    7   11
CONECT    6   29   30   31
CONECT    7    8   32   33
CONECT    8    9   34   35
CONECT    9   10   36   37
CONECT   10   11   11   15
CONECT   11   12
CONECT   12   13   13   38
CONECT   13   14   39
CONECT   14   15   15   25
CONECT   15   16
CONECT   16   17   17   18
CONECT   18   19   19   20
CONECT   20   21   25   25
CONECT   21   22   23   23
CONECT   22   40   41   42
CONECT   23   24   43
CONECT   24   25
END

HMDB0036636
     RDKit          3D
Methuyl tanshinonate
 43 46  0  0  0  0  0  0  0  0999 V2000
   -4.5133    2.5173    0.7625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5980    1.4404    0.7576 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5772    0.5527   -0.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3982    0.7681   -1.2344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6734   -0.5881   -0.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9803   -1.3289   -1.7029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8060   -1.5203    0.7850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9617   -2.7319    0.5423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4769   -2.3671    0.4016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2651   -0.9628   -0.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2737   -0.1154   -0.3924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9767    1.1800   -0.7575 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3057    1.6579   -0.7617 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3455    0.8324   -0.3924 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0612   -0.4790   -0.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1145   -1.3931    0.3720 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9176   -2.5826    0.7139 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5028   -0.8732    0.3623 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4188   -1.6407    0.6959 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7417    0.5029   -0.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8905    1.2636   -0.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2830    0.7894    0.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4825    2.5100   -0.5679 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1862    2.5326   -0.7146 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7153    1.3406   -0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3817    2.3371    0.0975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9269    2.7250    1.7717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0226    3.4471    0.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5939   -2.2203   -1.5501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0340   -1.6554   -2.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5436   -0.6595   -2.3932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3860   -0.9779    1.6542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8367   -1.8382    0.9310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2964   -3.2775   -0.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1401   -3.4432    1.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1007   -2.5033    1.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0112   -3.1045   -0.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8125    1.8105   -1.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5397    2.6899   -1.0526 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6771    0.1695   -0.6597 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3004    0.1871    1.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9566    1.6462    0.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1255    3.3626   -0.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 23 24  1  0
 24 25  1  0
 11  5  1  0
 25 14  1  0
 15 10  1  0
 25 20  2  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  6 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 12 38  1  0
 13 39  1  0
 22 40  1  0
 22 41  1  0
 22 42  1  0
 23 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Methuyl tanshinonic acid	Generator
Methyl 6,14-dimethyl-16,17-dioxo-12-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),2(7),8,11(15),13-pentaene-6-carboxylic acid	Generator

Chemical Formula

C₂₀H₁₈O₅

Average Molecular Weight

338.3539

Monoisotopic Molecular Weight

338.115423686

IUPAC Name

methyl 6,14-dimethyl-16,17-dioxo-12-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),2(7),8,11(15),13-pentaene-6-carboxylate

Traditional Name

methyl 6,14-dimethyl-16,17-dioxo-12-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1(10),2(7),8,11(15),13-pentaene-6-carboxylate

CAS Registry Number

18887-19-9

SMILES

COC(=O)C1(C)CCCC2=C1C=CC1=C2C(=O)C(=O)C2=C1OC=C2C

InChI Identifier

InChI=1S/C20H18O5/c1-10-9-25-18-12-6-7-13-11(15(12)17(22)16(21)14(10)18)5-4-8-20(13,2)19(23)24-3/h6-7,9H,4-5,8H2,1-3H3

InChI Key

YFDKIHAZVQFLRC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tanshinones, isotanshinones, and derivatives. These are a group of abietane-type norditerpenoid quinones.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Tanshinones, isotanshinones, and derivatives

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0036636)
Cell membrane (HMDB: HMDB0036636)

Cellular substructure

Extracellular (HMDB: HMDB0036636)
Membrane (HMDB: HMDB0036636)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036636)

Source

Endogenous

Endogenous (HMDB: HMDB0036636)

Plant

Plant (HMDB: HMDB0036636)

Animal

Animal (HMDB: HMDB0036636)

Exogenous

Food

Food (HMDB: HMDB0036636)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0036636)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0036636)

Cellular process

Cell signaling (HMDB: HMDB0036636)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0036636)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036636)

Nutrient

Nutrient (HMDB: HMDB0036636)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036636)

Emulsifier (HMDB: HMDB0036636)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	175 - 176 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.018 g/L	ALOGPS
logP	3.46	ALOGPS
logP	3.87	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	73.58 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	91.58 m³·mol⁻¹	ChemAxon
Polarizability	35.99 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]+	180.422	31661259
DarkChem	[M-H]-	179.566	31661259
DeepCCS	[M+H]+	177.145	30932474
DeepCCS	[M-H]-	174.787	30932474
DeepCCS	[M-2H]-	209.111	30932474
DeepCCS	[M+Na]+	185.402	30932474
AllCCS	[M+H]+	179.3	32859911
AllCCS	[M+H-H2O]+	176.2	32859911
AllCCS	[M+NH4]+	182.2	32859911
AllCCS	[M+Na]+	183.0	32859911
AllCCS	[M-H]-	186.1	32859911
AllCCS	[M+Na-2H]-	185.8	32859911
AllCCS	[M+HCOO]-	185.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methuyl tanshinonate	COC(=O)C1(C)CCCC2=C1C=CC1=C2C(=O)C(=O)C2=C1OC=C2C	3968.6	Standard polar	33892256
Methuyl tanshinonate	COC(=O)C1(C)CCCC2=C1C=CC1=C2C(=O)C(=O)C2=C1OC=C2C	2640.9	Standard non polar	33892256
Methuyl tanshinonate	COC(=O)C1(C)CCCC2=C1C=CC1=C2C(=O)C(=O)C2=C1OC=C2C	2975.1	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 - Methuyl tanshinonate GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-0094000000-5575ab9274450376cbd6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methuyl tanshinonate 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 - Methuyl tanshinonate 10V, Positive-QTOF	splash10-000i-0009000000-518cc91621784f3cdb12	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methuyl tanshinonate 20V, Positive-QTOF	splash10-052r-1059000000-7c9442b1ed33fd954395	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methuyl tanshinonate 40V, Positive-QTOF	splash10-0udu-3090000000-346e4ab8d2f49e050421	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methuyl tanshinonate 10V, Negative-QTOF	splash10-000i-0009000000-2ef93dc4b089f05b0b35	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methuyl tanshinonate 20V, Negative-QTOF	splash10-000i-0009000000-2d1be7ca5864d2f860e1	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methuyl tanshinonate 40V, Negative-QTOF	splash10-056r-1093000000-661d8a816955f77859f4	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methuyl tanshinonate 10V, Positive-QTOF	splash10-004r-0097000000-605adc09a24abf121930	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methuyl tanshinonate 20V, Positive-QTOF	splash10-004i-0091000000-8bda5ca2a8f714a607b5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methuyl tanshinonate 40V, Positive-QTOF	splash10-0w59-0191000000-63c66a1ca329da85a898	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methuyl tanshinonate 10V, Negative-QTOF	splash10-002r-0079000000-3e370463dd1c6dd3b229	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methuyl tanshinonate 20V, Negative-QTOF	splash10-004i-0090000000-99a1efa42b4c4ca3538d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methuyl tanshinonate 40V, Negative-QTOF	splash10-01ti-0091000000-2b5195239d42c6076750	2021-09-24	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

FDB015556

KNApSAcK ID

Not Available

Chemspider ID

542418

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

624381

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 Methuyl tanshinonate (HMDB0036636)

MOL for HMDB0036636 (Methuyl tanshinonate)

3D MOL for HMDB0036636 (Methuyl tanshinonate)

3D SDF for HMDB0036636 (Methuyl tanshinonate)

3D-SDF for HMDB0036636 (Methuyl tanshinonate)

PDB for HMDB0036636 (Methuyl tanshinonate)

3D PDB for HMDB0036636 (Methuyl tanshinonate)

SMILES for HMDB0036636 (Methuyl tanshinonate)

INCHI for HMDB0036636 (Methuyl tanshinonate)

Structure for HMDB0036636 (Methuyl tanshinonate)

3D Structure for HMDB0036636 (Methuyl tanshinonate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra