NP-MRD: Showing NP-Card for 12-methoxycarnosic acid (NP0030638)

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Record Information

Version

2.0

Created at

2021-06-19 21:56:27 UTC

Updated at

2021-06-29 23:58:44 UTC

NP-MRD ID

NP0030638

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-methoxycarnosic acid

Provided By

JEOL Database JEOL Logo

Description

12-Methoxy-cis-carnosic acid belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 12-methoxycarnosic acid is found in Hyptis martiusii, Perovskia scrophularifolia, Salvia officinalis and Rosmarinus officinalis . 12-methoxycarnosic acid was first documented in 2004 (PMID: 15561190). Based on a literature review very few articles have been published on 12-Methoxy-cis-carnosic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123563D          

 55 57  0  0  0  0            999 V2000
   -3.2805    1.4253   -2.9228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3582    0.4729   -3.4641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6518   -0.1202   -2.4431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1023   -1.2938   -1.8379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3737   -1.9963   -2.2822 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4079   -2.0611   -1.1544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0776   -3.3970   -2.8275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3164   -1.8167   -0.8004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1035   -1.2155   -0.3954 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3627   -0.0486   -1.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4292    0.4634   -2.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0092    1.5672   -2.7653 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7020    0.6287   -0.6133 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4296    2.1368   -0.4164 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9336    3.0738   -1.0179 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5309    2.3982    0.5620 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7052    0.4026   -1.7820 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1458    0.8124   -1.4905 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6860    0.1744   -0.2206 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8100    0.4468    1.0179 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4081   -0.3513    2.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9278    1.9320    1.4363 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3053    0.0454    0.7352 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1075   -1.4874    0.7636 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6321   -1.8450    0.7498 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -5.3474   -2.4900   -1.5195 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1604   -1.5206    1.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  1  0  0  0  0
  4  3  2  0  0  0  0
 18 17  1  0  0  0  0
  3 11  1  0  0  0  0
 11 10  2  0  0  0  0
 19 20  1  0  0  0  0
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 13 10  1  0  0  0  0
  4  5  1  0  0  0  0
 23 24  1  0  0  0  0
  5  6  1  0  0  0  0
 24 25  1  0  0  0  0
  5  7  1  0  0  0  0
 25  9  1  0  0  0  0
  3  2  1  0  0  0  0
 20 23  1  0  0  0  0
  2  1  1  0  0  0  0
 13 17  1  0  0  0  0
 20 21  1  1  0  0  0
 10  9  1  0  0  0  0
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 13 23  1  0  0  0  0
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  9  8  2  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
  8  4  1  0  0  0  0
 14 16  1  0  0  0  0
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  8 36  1  0  0  0  0
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  5 29  1  6  0  0  0
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 16 38  1  0  0  0  0
M  END

     RDKit          3D

 55 57  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306192123563D          

 55 57  0  0  0  0            999 V2000
   -3.2805    1.4253   -2.9228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3582    0.4729   -3.4641 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5925    1.6296   -3.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4400    3.3722    0.5178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3909    0.9433   -2.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7064   -0.6596   -2.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2273    1.9025   -1.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7772    0.5116   -2.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7722   -0.9075   -0.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7081    0.5356   -0.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5601   -1.4075    1.9594 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3936    0.0373    2.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7614   -0.2884    3.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7209    2.6294    0.6260 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2474    2.1616    2.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9444    2.1656    1.7757 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7168    0.4370    1.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5201   -1.9298    1.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6202   -1.9611   -0.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5427   -2.9372    0.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1604   -1.5206    1.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  1  0  0  0  0
  4  3  2  0  0  0  0
 18 17  1  0  0  0  0
  3 11  1  0  0  0  0
 11 10  2  0  0  0  0
 19 20  1  0  0  0  0
 11 12  1  0  0  0  0
 13 10  1  0  0  0  0
  4  5  1  0  0  0  0
 23 24  1  0  0  0  0
  5  6  1  0  0  0  0
 24 25  1  0  0  0  0
  5  7  1  0  0  0  0
 25  9  1  0  0  0  0
  3  2  1  0  0  0  0
 20 23  1  0  0  0  0
  2  1  1  0  0  0  0
 13 17  1  0  0  0  0
 20 21  1  1  0  0  0
 10  9  1  0  0  0  0
 20 22  1  0  0  0  0
 13 23  1  0  0  0  0
 23 51  1  1  0  0  0
  9  8  2  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
  8  4  1  0  0  0  0
 14 16  1  0  0  0  0
 18 41  1  0  0  0  0
 18 42  1  0  0  0  0
 19 43  1  0  0  0  0
 19 44  1  0  0  0  0
 17 39  1  0  0  0  0
 17 40  1  0  0  0  0
 24 52  1  0  0  0  0
 24 53  1  0  0  0  0
 25 54  1  0  0  0  0
 25 55  1  0  0  0  0
  8 36  1  0  0  0  0
 12 37  1  0  0  0  0
  5 29  1  6  0  0  0
  6 30  1  0  0  0  0
  6 31  1  0  0  0  0
  6 32  1  0  0  0  0
  7 33  1  0  0  0  0
  7 34  1  0  0  0  0
  7 35  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
 21 45  1  0  0  0  0
 21 46  1  0  0  0  0
 21 47  1  0  0  0  0
 22 48  1  0  0  0  0
 22 49  1  0  0  0  0
 22 50  1  0  0  0  0
 16 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0030638

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@]12C3=C(O[H])C(OC([H])([H])[H])=C(C([H])=C3C([H])([H])C([H])([H])[C@@]1([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])C2([H])[H])C([H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O4/c1-12(2)14-11-13-7-8-15-20(3,4)9-6-10-21(15,19(23)24)16(13)17(22)18(14)25-5/h11-12,15,22H,6-10H2,1-5H3,(H,23,24)/t15-,21-/m0/s1

> <INCHI_KEY>
QQNSARJGBPMQDI-BTYIYWSLSA-N

> <FORMULA>
C21H30O4

> <MOLECULAR_WEIGHT>
346.467

> <EXACT_MASS>
346.214409446

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
39.23008319165385

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4aS,10aS)-5-hydroxy-6-methoxy-1,1-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-4a-carboxylic acid

> <ALOGPS_LOGP>
4.68

> <JCHEM_LOGP>
5.287528140666668

> <ALOGPS_LOGS>
-4.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.954102851953087

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.331572871998162

> <JCHEM_PKA_STRONGEST_BASIC>
-4.884940048366394

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
97.8881

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.04e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4aS,10aS)-5-hydroxy-7-isopropyl-6-methoxy-1,1-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 55 57  0  0  0  0  0  0  0  0999 V2000
   -3.2805    1.4253   -2.9228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3582    0.4729   -3.4641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6518   -0.1202   -2.4431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1023   -1.2938   -1.8379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3737   -1.9963   -2.2822 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4079   -2.0611   -1.1544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0776   -3.3970   -2.8275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3164   -1.8167   -0.8004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1035   -1.2155   -0.3954 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3627   -0.0486   -1.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4292    0.4634   -2.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0092    1.5672   -2.7653 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7020    0.6287   -0.6133 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4296    2.1368   -0.4164 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9336    3.0738   -1.0179 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5309    2.3982    0.5620 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7052    0.4026   -1.7820 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1458    0.8124   -1.4905 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6860    0.1744   -0.2206 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8100    0.4468    1.0179 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4081   -0.3513    2.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9278    1.9320    1.4363 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3053    0.0454    0.7352 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1075   -1.4874    0.7636 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6321   -1.8450    0.7498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0033    0.9493   -2.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8331    1.8642   -3.7588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7564    2.2339   -2.4018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8339   -1.4345   -3.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3474   -2.4900   -1.5195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0654   -2.6792   -0.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6257   -1.0613   -0.7632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3467   -3.3528   -3.6426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9907   -3.8570   -3.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6774   -4.0631   -2.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6431   -2.7223   -0.2900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5925    1.6296   -3.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4400    3.3722    0.5178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3909    0.9433   -2.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7064   -0.6596   -2.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2273    1.9025   -1.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7772    0.5116   -2.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7722   -0.9075   -0.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7081    0.5356   -0.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5601   -1.4075    1.9594 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3936    0.0373    2.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7614   -0.2884    3.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7209    2.6294    0.6260 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2474    2.1616    2.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9444    2.1656    1.7757 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7168    0.4370    1.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5201   -1.9298    1.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6202   -1.9611   -0.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5427   -2.9372    0.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1604   -1.5206    1.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  1  0
  4  3  2  0
 18 17  1  0
  3 11  1  0
 11 10  2  0
 19 20  1  0
 11 12  1  0
 13 10  1  0
  4  5  1  0
 23 24  1  0
  5  6  1  0
 24 25  1  0
  5  7  1  0
 25  9  1  0
  3  2  1  0
 20 23  1  0
  2  1  1  0
 13 17  1  0
 20 21  1  1
 10  9  1  0
 20 22  1  0
 13 23  1  0
 23 51  1  1
  9  8  2  0
 13 14  1  1
 14 15  2  0
  8  4  1  0
 14 16  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 19 44  1  0
 17 39  1  0
 17 40  1  0
 24 52  1  0
 24 53  1  0
 25 54  1  0
 25 55  1  0
  8 36  1  0
 12 37  1  0
  5 29  1  6
  6 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  7 35  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 21 45  1  0
 21 46  1  0
 21 47  1  0
 22 48  1  0
 22 49  1  0
 22 50  1  0
 16 38  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.281   1.425  -2.923  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.358   0.473  -3.464  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.652  -0.120  -2.443  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.102  -1.294  -1.838  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.374  -1.996  -2.282  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.408  -2.061  -1.154  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.078  -3.397  -2.828  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.316  -1.817  -0.800  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.104  -1.216  -0.395  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.363  -0.049  -1.026  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.429   0.463  -2.069  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.009   1.567  -2.765  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.702   0.629  -0.613  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.430   2.137  -0.416  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.934   3.074  -1.018  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.531   2.398   0.562  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.705   0.403  -1.782  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.146   0.812  -1.490  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.686   0.174  -0.221  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.810   0.447   1.018  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.408  -0.351   2.205  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.928   1.932   1.436  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.305   0.045   0.735  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.107  -1.487   0.764  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.632  -1.845   0.750  0.00  0.00           C+0
HETATM   26  H   UNK     0      -4.003   0.949  -2.252  0.00  0.00           H+0
HETATM   27  H   UNK     0      -3.833   1.864  -3.759  0.00  0.00           H+0
HETATM   28  H   UNK     0      -2.756   2.234  -2.402  0.00  0.00           H+0
HETATM   29  H   UNK     0      -3.834  -1.435  -3.103  0.00  0.00           H+0
HETATM   30  H   UNK     0      -5.347  -2.490  -1.520  0.00  0.00           H+0
HETATM   31  H   UNK     0      -4.065  -2.679  -0.318  0.00  0.00           H+0
HETATM   32  H   UNK     0      -4.626  -1.061  -0.763  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.347  -3.353  -3.643  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.991  -3.857  -3.221  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.677  -4.063  -2.055  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.643  -2.722  -0.290  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.593   1.630  -3.545  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.440   3.372   0.518  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.391   0.943  -2.683  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.706  -0.660  -2.063  0.00  0.00           H+0
HETATM   41  H   UNK     0       4.227   1.903  -1.434  0.00  0.00           H+0
HETATM   42  H   UNK     0       4.777   0.512  -2.336  0.00  0.00           H+0
HETATM   43  H   UNK     0       4.772  -0.908  -0.385  0.00  0.00           H+0
HETATM   44  H   UNK     0       5.708   0.536  -0.048  0.00  0.00           H+0
HETATM   45  H   UNK     0       4.560  -1.408   1.959  0.00  0.00           H+0
HETATM   46  H   UNK     0       5.394   0.037   2.489  0.00  0.00           H+0
HETATM   47  H   UNK     0       3.761  -0.288   3.087  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.721   2.629   0.626  0.00  0.00           H+0
HETATM   49  H   UNK     0       3.247   2.162   2.264  0.00  0.00           H+0
HETATM   50  H   UNK     0       4.944   2.166   1.776  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.717   0.437   1.578  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.520  -1.930   1.675  0.00  0.00           H+0
HETATM   53  H   UNK     0       2.620  -1.961  -0.082  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.543  -2.937   0.699  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.160  -1.521   1.686  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2    3    1                                                       
CONECT    3    4   11    2                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6    7   29                                             
CONECT    6    5   30   31   32                                             
CONECT    7    5   33   34   35                                             
CONECT    8    9    4   36                                                  
CONECT    9   25   10    8                                                  
CONECT   10   11   13    9                                                  
CONECT   11    3   10   12                                                  
CONECT   12   11   37                                                       
CONECT   13   10   17   23   14                                             
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   38                                                       
CONECT   17   18   13   39   40                                             
CONECT   18   19   17   41   42                                             
CONECT   19   18   20   43   44                                             
CONECT   20   19   23   21   22                                             
CONECT   21   20   45   46   47                                             
CONECT   22   20   48   49   50                                             
CONECT   23   24   20   13   51                                             
CONECT   24   23   25   52   53                                             
CONECT   25   24    9   54   55                                             
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    5                                                            
CONECT   30    6                                                            
CONECT   31    6                                                            
CONECT   32    6                                                            
CONECT   33    7                                                            
CONECT   34    7                                                            
CONECT   35    7                                                            
CONECT   36    8                                                            
CONECT   37   12                                                            
CONECT   38   16                                                            
CONECT   39   17                                                            
CONECT   40   17                                                            
CONECT   41   18                                                            
CONECT   42   18                                                            
CONECT   43   19                                                            
CONECT   44   19                                                            
CONECT   45   21                                                            
CONECT   46   21                                                            
CONECT   47   21                                                            
CONECT   48   22                                                            
CONECT   49   22                                                            
CONECT   50   22                                                            
CONECT   51   23                                                            
CONECT   52   24                                                            
CONECT   53   24                                                            
CONECT   54   25                                                            
CONECT   55   25                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  114    0
END

RDKit          3D

55 57  0  0  0  0  0  0  0  0999 V2000
   -3.2805    1.4253   -2.9228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3582    0.4729   -3.4641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6518   -0.1202   -2.4431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1023   -1.2938   -1.8379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3737   -1.9963   -2.2822 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4079   -2.0611   -1.1544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0776   -3.3970   -2.8275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3164   -1.8167   -0.8004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1035   -1.2155   -0.3954 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3627   -0.0486   -1.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4292    0.4634   -2.0692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0092    1.5672   -2.7653 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7020    0.6287   -0.6133 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4296    2.1368   -0.4164 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9336    3.0738   -1.0179 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5309    2.3982    0.5620 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1458    0.8124   -1.4905 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6860    0.1744   -0.2206 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8100    0.4468    1.0179 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4081   -0.3513    2.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9278    1.9320    1.4363 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3053    0.0454    0.7352 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1075   -1.4874    0.7636 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6321   -1.8450    0.7498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0033    0.9493   -2.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8331    1.8642   -3.7588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7564    2.2339   -2.4018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8339   -1.4345   -3.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3474   -2.4900   -1.5195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0654   -2.6792   -0.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6257   -1.0613   -0.7632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3467   -3.3528   -3.6426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9907   -3.8570   -3.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6774   -4.0631   -2.0555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6431   -2.7223   -0.2900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5925    1.6296   -3.5453 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4400    3.3722    0.5178 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3909    0.9433   -2.6827 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7064   -0.6596   -2.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2273    1.9025   -1.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7772    0.5116   -2.3356 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7722   -0.9075   -0.3854 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7081    0.5356   -0.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5601   -1.4075    1.9594 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3936    0.0373    2.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7614   -0.2884    3.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7209    2.6294    0.6260 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2474    2.1616    2.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9444    2.1656    1.7757 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7168    0.4370    1.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5201   -1.9298    1.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6202   -1.9611   -0.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5427   -2.9372    0.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1604   -1.5206    1.6858 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  1  0
  4  3  2  0
 18 17  1  0
  3 11  1  0
 11 10  2  0
 19 20  1  0
 11 12  1  0
 13 10  1  0
  4  5  1  0
 23 24  1  0
  5  6  1  0
 24 25  1  0
  5  7  1  0
 25  9  1  0
  3  2  1  0
 20 23  1  0
  2  1  1  0
 13 17  1  0
 20 21  1  1
 10  9  1  0
 20 22  1  0
 13 23  1  0
 23 51  1  1
  9  8  2  0
 13 14  1  1
 14 15  2  0
  8  4  1  0
 14 16  1  0
 18 41  1  0
 18 42  1  0
 19 43  1  0
 19 44  1  0
 17 39  1  0
 17 40  1  0
 24 52  1  0
 24 53  1  0
 25 54  1  0
 25 55  1  0
  8 36  1  0
 12 37  1  0
  5 29  1  6
  6 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  7 35  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 21 45  1  0
 21 46  1  0
 21 47  1  0
 22 48  1  0
 22 49  1  0
 22 50  1  0
 16 38  1  0
M  END

View in JSmol

Synonyms

Value	Source
12-Methoxy-cis-carnosate	Generator

Chemical Formula

C₂₁H₃₀O₄

Average Mass

346.4670 Da

Monoisotopic Mass

346.21441 Da

IUPAC Name

(4aS,10aS)-5-hydroxy-6-methoxy-1,1-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-4a-carboxylic acid

Traditional Name

(4aS,10aS)-5-hydroxy-7-isopropyl-6-methoxy-1,1-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-4a-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)[C@]12C3=C(O[H])C(OC([H])([H])[H])=C(C([H])=C3C([H])([H])C([H])([H])[C@@]1([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])C2([H])[H])C([H])(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C21H30O4/c1-12(2)14-11-13-7-8-15-20(3,4)9-6-10-21(15,19(23)24)16(13)17(22)18(14)25-5/h11-12,15,22H,6-10H2,1-5H3,(H,23,24)/t15-,21-/m0/s1

InChI Key

QQNSARJGBPMQDI-BTYIYWSLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Medusantha martiusii	JEOL database	Araujo, E. C. C., et al, Magn. Reson. Chem. 42,1049 (2004)
Perovskia scrophularifolia	Plant	KNApSAcK
Salvia officinalis	Plant	KNApSAcK
Salvia rosmarinus	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Abietane diterpenoid
Diterpenoid
Hydrophenanthrene
Phenanthrene
1-naphthalenecarboxylic acid
1-naphthalenecarboxylic acid or derivatives
Tetralin
Cumene
Phenol ether
Anisole
Alkyl aryl ether
Phenol
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Ether
Carboxylic acid
Organooxygen compound
Organic oxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.68	ALOGPS
logP	5.29	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	4.33	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	97.89 m³·mol⁻¹	ChemAxon
Polarizability	39.23 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101371515

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Oluwatuyi M, Kaatz GW, Gibbons S: Antibacterial and resistance modifying activity of Rosmarinus officinalis. Phytochemistry. 2004 Dec;65(24):3249-54. doi: 10.1016/j.phytochem.2004.10.009. [PubMed:15561190 ]
Araujo, E. C. C., et al. (2004). Araujo, E. C. C., et al, Magn. Reson. Chem. 42,1049 (2004). Mag. Reson. Chem..

Showing NP-Card for 12-methoxycarnosic acid (NP0030638)

MOL for NP0030638 (12-methoxycarnosic acid)

3D MOL for NP0030638 (12-methoxycarnosic acid)

3D SDF for NP0030638 (12-methoxycarnosic acid)

3D-SDF for NP0030638 (12-methoxycarnosic acid)

PDB for NP0030638 (12-methoxycarnosic acid)

3D PDB for NP0030638 (12-methoxycarnosic acid)

SMILES for NP0030638 (12-methoxycarnosic acid)

INCHI for NP0030638 (12-methoxycarnosic acid)

Structure for NP0030638 (12-methoxycarnosic acid)

3D Structure for NP0030638 (12-methoxycarnosic acid)