NP-MRD: Showing NP-Card for 7alpha-methoxyrosmanol (NP0031793)

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Record Information

Version

2.0

Created at

2021-06-19 22:46:29 UTC

Updated at

2021-06-30 00:00:36 UTC

NP-MRD ID

NP0031793

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7alpha-methoxyrosmanol

Provided By

JEOL Database JEOL Logo

Description

7-Methoxyrosmanol belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. 7alpha-methoxyrosmanol is found in Lepechinia urbanii, Salvia aurea, Salvia canariensis, Salvia columbariae, Salvia dorrii, Salvia mellifera, Salvia munzii, Salvia officinalis , Salvia pachyphylla, Rosmarinus officinalis and Salvinia molesta. 7alpha-methoxyrosmanol was first documented in 2003 (PMID: 12624814). Based on a literature review a small amount of articles have been published on 7-Methoxyrosmanol (PMID: 33228164) (PMID: 25200369) (PMID: 17190465) (PMID: 15050633).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100463D          

 54 57  0  0  0  0            999 V2000
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   -2.0352   -0.0434    2.7086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9236   -0.6515    2.0394 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3535   -0.9225    0.6023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4371   -1.8025    0.3830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8752   -2.1415   -0.9054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0637   -3.0674   -1.1068 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6096   -4.5282   -1.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2077   -2.8430   -0.1092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1469   -1.6082   -1.9717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4015   -1.9186   -3.2869 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9393    1.5437   -1.3424 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8452    2.7100   -0.9695 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2542    3.5231    0.1703 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0686    2.6749    1.4429 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.4556    2.3613    2.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4817   -0.4323    1.6907 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6521   -0.2429    0.3362 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5689   -0.7332   -0.3008 O   0  0  0  0  0  0  0  0  0  0  0  0
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 12 14  2  0  0  0  0
 17 16  1  0  0  0  0
 12 13  1  0  0  0  0
 15 14  1  0  0  0  0
  6  7  1  0  0  0  0
 22 23  1  0  0  0  0
  7  8  1  0  0  0  0
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  7  9  1  0  0  0  0
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  4  5  2  0  0  0  0
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  4  3  1  0  0  0  0
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  5  6  1  0  0  0  0
  3  2  1  0  0  0  0
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  6 10  2  0  0  0  0
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  5 31  1  0  0  0  0
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  7 32  1  6  0  0  0
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  1 29  1  0  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306202100463D          

 54 57  0  0  0  0            999 V2000
   -2.1073   -0.3972    4.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0352   -0.0434    2.7086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9236   -0.6515    2.0394 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -6.0863   -3.4295   -0.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9390   -3.1489    0.9072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9206   -2.7383   -3.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9071   -0.6936   -3.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4629    0.9666   -2.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0431    1.9736   -1.8100 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9713    3.3577   -1.8456 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8458    2.3451   -0.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2878    3.9349   -0.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9028    4.3845    0.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8824    4.4484    2.7252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1600    2.9912    3.4205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6632    3.8524    2.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3729    1.8623    3.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0198    3.2861    2.2225 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0722    1.7331    1.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8576    1.7893    1.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4501    0.6382    3.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 14  2  0  0  0  0
 17 16  1  0  0  0  0
 12 13  1  0  0  0  0
 15 14  1  0  0  0  0
  6  7  1  0  0  0  0
 22 23  1  0  0  0  0
  7  8  1  0  0  0  0
 18 19  1  0  0  0  0
  7  9  1  0  0  0  0
 19 22  1  0  0  0  0
 19 20  1  1  0  0  0
 14  4  1  0  0  0  0
 22 53  1  6  0  0  0
 15 16  1  0  0  0  0
 19 21  1  0  0  0  0
  4  5  2  0  0  0  0
 10 11  1  0  0  0  0
 15 22  1  0  0  0  0
  4  3  1  0  0  0  0
  3 23  1  0  0  0  0
  5  6  1  0  0  0  0
  3  2  1  0  0  0  0
  2  1  1  0  0  0  0
  6 10  2  0  0  0  0
 23 24  1  0  0  0  0
 17 18  1  0  0  0  0
 15 25  1  1  0  0  0
 25 24  1  0  0  0  0
 10 12  1  0  0  0  0
 25 26  2  0  0  0  0
 17 43  1  0  0  0  0
 17 44  1  0  0  0  0
 18 45  1  0  0  0  0
 18 46  1  0  0  0  0
 16 41  1  0  0  0  0
 16 42  1  0  0  0  0
 23 54  1  1  0  0  0
  5 31  1  0  0  0  0
 13 40  1  0  0  0  0
  7 32  1  6  0  0  0
  8 33  1  0  0  0  0
  8 34  1  0  0  0  0
  8 35  1  0  0  0  0
  9 36  1  0  0  0  0
  9 37  1  0  0  0  0
  9 38  1  0  0  0  0
 20 47  1  0  0  0  0
 20 48  1  0  0  0  0
 20 49  1  0  0  0  0
 21 50  1  0  0  0  0
 21 51  1  0  0  0  0
 21 52  1  0  0  0  0
 11 39  1  0  0  0  0
  3 30  1  1  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0031793

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(C([H])=C2C(=C1O[H])[C@]13C(=O)O[C@@]([H])([C@@]1([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])C3([H])[H])[C@@]2([H])OC([H])([H])[H])C([H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O5/c1-10(2)11-9-12-13(15(23)14(11)22)21-8-6-7-20(3,4)18(21)17(16(12)25-5)26-19(21)24/h9-10,16-18,22-23H,6-8H2,1-5H3/t16-,17+,18-,21-/m0/s1

> <INCHI_KEY>
XNPVHIQPSAZTLC-NYUBLWNDSA-N

> <FORMULA>
C21H28O5

> <MOLECULAR_WEIGHT>
360.45

> <EXACT_MASS>
360.193674002

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
39.37295209100411

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,8S,9S,10S)-3,4-dihydroxy-8-methoxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[7.5.2.0^{1,10}.0^{2,7}]hexadeca-2,4,6-trien-15-one

> <ALOGPS_LOGP>
3.84

> <JCHEM_LOGP>
4.221470768999998

> <ALOGPS_LOGS>
-3.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.849976639893882

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.178559332771945

> <JCHEM_PKA_STRONGEST_BASIC>
-4.172452713471289

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
97.4648

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.32e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,8S,9S,10S)-3,4-dihydroxy-5-isopropyl-8-methoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0^{1,10}.0^{2,7}]hexadeca-2,4,6-trien-15-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
   -2.1073   -0.3972    4.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0352   -0.0434    2.7086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9236   -0.6515    2.0394 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3535   -0.9225    0.6023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4371   -1.8025    0.3830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8752   -2.1415   -0.9054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0637   -3.0674   -1.1068 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6096   -4.5282   -1.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2077   -2.8430   -0.1092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1469   -1.6082   -1.9717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4015   -1.9186   -3.2869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0766   -0.7174   -1.7675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4335   -0.2695   -2.8893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6689   -0.3290   -0.4891 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5119    0.6300   -0.1812 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9393    1.5437   -1.3424 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8452    2.7100   -0.9695 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2542    3.5231    0.1703 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0686    2.6749    1.4429 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3188    3.5393    2.4857 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4556    2.3613    2.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1792    1.4254    1.1063 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3033    0.2817    2.1087 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4817   -0.4323    1.6907 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6521   -0.2429    0.3362 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5689   -0.7332   -0.3008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2689   -1.4741    4.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1988   -0.0978    4.6135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9579    0.1267    4.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6736   -1.6216    2.4913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9360   -2.2207    1.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5018   -2.8638   -2.0916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8422   -4.7209   -1.8336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4511   -5.2005   -1.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1873   -4.7967   -0.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5043   -1.7887   -0.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0863   -3.4295   -0.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9390   -3.1489    0.9072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9206   -2.7383   -3.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9071   -0.6936   -3.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4629    0.9666   -2.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0431    1.9736   -1.8100 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9713    3.3577   -1.8456 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8458    2.3451   -0.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2878    3.9349   -0.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9028    4.3845    0.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8824    4.4484    2.7252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1600    2.9912    3.4205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6632    3.8524    2.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3729    1.8623    3.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0198    3.2861    2.2225 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0722    1.7331    1.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8576    1.7893    1.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4501    0.6382    3.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 14  2  0
 17 16  1  0
 12 13  1  0
 15 14  1  0
  6  7  1  0
 22 23  1  0
  7  8  1  0
 18 19  1  0
  7  9  1  0
 19 22  1  0
 19 20  1  1
 14  4  1  0
 22 53  1  6
 15 16  1  0
 19 21  1  0
  4  5  2  0
 10 11  1  0
 15 22  1  0
  4  3  1  0
  3 23  1  0
  5  6  1  0
  3  2  1  0
  2  1  1  0
  6 10  2  0
 23 24  1  0
 17 18  1  0
 15 25  1  1
 25 24  1  0
 10 12  1  0
 25 26  2  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 16 41  1  0
 16 42  1  0
 23 54  1  1
  5 31  1  0
 13 40  1  0
  7 32  1  6
  8 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
  9 38  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
 11 39  1  0
  3 30  1  1
  1 27  1  0
  1 28  1  0
  1 29  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.107  -0.397   4.083  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.035  -0.043   2.709  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.924  -0.652   2.039  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.353  -0.923   0.602  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.437  -1.803   0.383  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.875  -2.142  -0.905  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.064  -3.067  -1.107  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.610  -4.528  -1.076  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.208  -2.843  -0.109  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.147  -1.608  -1.972  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.401  -1.919  -3.287  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.077  -0.717  -1.768  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.434  -0.270  -2.889  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.669  -0.329  -0.489  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.512   0.630  -0.181  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.939   1.544  -1.342  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.845   2.710  -0.970  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.254   3.523   0.170  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.069   2.675   1.443  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.319   3.539   2.486  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.456   2.361   2.050  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.179   1.425   1.106  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.303   0.282   2.109  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.482  -0.432   1.691  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.652  -0.243   0.336  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.569  -0.733  -0.301  0.00  0.00           O+0
HETATM   27  H   UNK     0      -2.269  -1.474   4.191  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.199  -0.098   4.614  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.958   0.127   4.528  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.674  -1.622   2.491  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.936  -2.221   1.256  0.00  0.00           H+0
HETATM   32  H   UNK     0      -4.502  -2.864  -2.092  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.842  -4.721  -1.834  0.00  0.00           H+0
HETATM   34  H   UNK     0      -4.451  -5.200  -1.275  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.187  -4.797  -0.101  0.00  0.00           H+0
HETATM   36  H   UNK     0      -5.504  -1.789  -0.081  0.00  0.00           H+0
HETATM   37  H   UNK     0      -6.086  -3.430  -0.401  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.939  -3.149   0.907  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.921  -2.738  -3.317  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.907  -0.694  -3.634  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.463   0.967  -2.114  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.043   1.974  -1.810  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.971   3.358  -1.846  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.846   2.345  -0.716  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.288   3.935  -0.150  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.903   4.385   0.374  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.882   4.448   2.725  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.160   2.991   3.421  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.663   3.852   2.113  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.373   1.862   3.022  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.020   3.286   2.223  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.072   1.733   1.404  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.858   1.789   1.053  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.450   0.638   3.132  0.00  0.00           H+0
CONECT    1    2   27   28   29                                             
CONECT    2    3    1                                                       
CONECT    3    4   23    2   30                                             
CONECT    4   14    5    3                                                  
CONECT    5    4    6   31                                                  
CONECT    6    7    5   10                                                  
CONECT    7    6    8    9   32                                             
CONECT    8    7   33   34   35                                             
CONECT    9    7   36   37   38                                             
CONECT   10   11    6   12                                                  
CONECT   11   10   39                                                       
CONECT   12   14   13   10                                                  
CONECT   13   12   40                                                       
CONECT   14   12   15    4                                                  
CONECT   15   14   16   22   25                                             
CONECT   16   17   15   41   42                                             
CONECT   17   16   18   43   44                                             
CONECT   18   19   17   45   46                                             
CONECT   19   18   22   20   21                                             
CONECT   20   19   47   48   49                                             
CONECT   21   19   50   51   52                                             
CONECT   22   23   19   53   15                                             
CONECT   23   22    3   24   54                                             
CONECT   24   23   25                                                       
CONECT   25   15   24   26                                                  
CONECT   26   25                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    3                                                            
CONECT   31    5                                                            
CONECT   32    7                                                            
CONECT   33    8                                                            
CONECT   34    8                                                            
CONECT   35    8                                                            
CONECT   36    9                                                            
CONECT   37    9                                                            
CONECT   38    9                                                            
CONECT   39   11                                                            
CONECT   40   13                                                            
CONECT   41   16                                                            
CONECT   42   16                                                            
CONECT   43   17                                                            
CONECT   44   17                                                            
CONECT   45   18                                                            
CONECT   46   18                                                            
CONECT   47   20                                                            
CONECT   48   20                                                            
CONECT   49   20                                                            
CONECT   50   21                                                            
CONECT   51   21                                                            
CONECT   52   21                                                            
CONECT   53   22                                                            
CONECT   54   23                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  114    0
END

RDKit          3D

54 57  0  0  0  0  0  0  0  0999 V2000
   -2.1073   -0.3972    4.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0352   -0.0434    2.7086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9236   -0.6515    2.0394 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3535   -0.9225    0.6023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4371   -1.8025    0.3830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8752   -2.1415   -0.9054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0637   -3.0674   -1.1068 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6096   -4.5282   -1.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2077   -2.8430   -0.1092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1469   -1.6082   -1.9717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4015   -1.9186   -3.2869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0766   -0.7174   -1.7675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4335   -0.2695   -2.8893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6689   -0.3290   -0.4891 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5119    0.6300   -0.1812 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9393    1.5437   -1.3424 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8452    2.7100   -0.9695 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2542    3.5231    0.1703 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0686    2.6749    1.4429 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3188    3.5393    2.4857 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4556    2.3613    2.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1792    1.4254    1.1063 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3033    0.2817    2.1087 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4817   -0.4323    1.6907 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6521   -0.2429    0.3362 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5689   -0.7332   -0.3008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2689   -1.4741    4.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1988   -0.0978    4.6135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9579    0.1267    4.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6736   -1.6216    2.4913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9360   -2.2207    1.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5018   -2.8638   -2.0916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8422   -4.7209   -1.8336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4511   -5.2005   -1.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1873   -4.7967   -0.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5043   -1.7887   -0.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0863   -3.4295   -0.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9390   -3.1489    0.9072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9206   -2.7383   -3.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9071   -0.6936   -3.6335 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4629    0.9666   -2.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0431    1.9736   -1.8100 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9713    3.3577   -1.8456 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8458    2.3451   -0.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2878    3.9349   -0.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9028    4.3845    0.3738 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8824    4.4484    2.7252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1600    2.9912    3.4205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6632    3.8524    2.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3729    1.8623    3.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0198    3.2861    2.2225 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0722    1.7331    1.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8576    1.7893    1.0534 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4501    0.6382    3.1319 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 14  2  0
 17 16  1  0
 12 13  1  0
 15 14  1  0
  6  7  1  0
 22 23  1  0
  7  8  1  0
 18 19  1  0
  7  9  1  0
 19 22  1  0
 19 20  1  1
 14  4  1  0
 22 53  1  6
 15 16  1  0
 19 21  1  0
  4  5  2  0
 10 11  1  0
 15 22  1  0
  4  3  1  0
  3 23  1  0
  5  6  1  0
  3  2  1  0
  2  1  1  0
  6 10  2  0
 23 24  1  0
 17 18  1  0
 15 25  1  1
 25 24  1  0
 10 12  1  0
 25 26  2  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 16 41  1  0
 16 42  1  0
 23 54  1  1
  5 31  1  0
 13 40  1  0
  7 32  1  6
  8 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
  9 38  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
 11 39  1  0
  3 30  1  1
  1 27  1  0
  1 28  1  0
  1 29  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
7-beta-Methoxyrosmanol	MeSH
7alpha-Methoxyrosmanol	MeSH

Chemical Formula

C₂₁H₂₈O₅

Average Mass

360.4500 Da

Monoisotopic Mass

360.19367 Da

IUPAC Name

(1R,8S,9S,10S)-3,4-dihydroxy-8-methoxy-11,11-dimethyl-5-(propan-2-yl)-16-oxatetracyclo[7.5.2.0^{1,10}.0^{2,7}]hexadeca-2,4,6-trien-15-one

Traditional Name

(1R,8S,9S,10S)-3,4-dihydroxy-5-isopropyl-8-methoxy-11,11-dimethyl-16-oxatetracyclo[7.5.2.0^{1,10}.0^{2,7}]hexadeca-2,4,6-trien-15-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C(C([H])=C2C(=C1O[H])[C@]13C(=O)O[C@@]([H])([C@@]1([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])C3([H])[H])[C@@]2([H])OC([H])([H])[H])C([H])(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C21H28O5/c1-10(2)11-9-12-13(15(23)14(11)22)21-8-6-7-20(3,4)18(21)17(16(12)25-5)26-19(21)24/h9-10,16-18,22-23H,6-8H2,1-5H3/t16-,17+,18-,21-/m0/s1

InChI Key

XNPVHIQPSAZTLC-NYUBLWNDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Lepechinia urbanii	LOTUS Database	35616633
Salvia africana-lutea	LOTUS Database	35616633
Salvia canariensis	LOTUS Database	35616633
Salvia columbariae	LOTUS Database	35616633
Salvia dorrii	JEOL database	Ahmed A. A., et al, Phytochemistry 67, 424 (2006)
Salvia mellifera	LOTUS Database	35616633
Salvia munzii	LOTUS Database	35616633
Salvia officinalis	Plant	KNApSAcK
Salvia pachyphylla	Plant	KNApSAcK
Salvia rosmarinus	Plant	KNApSAcK
Salvinia molesta	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Phenanthrene
Benzoxepine
Tetralin
Cumene
1-hydroxy-4-unsubstituted benzenoid
Phenol
Benzenoid
Gamma butyrolactone
Oxolane
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Dialkyl ether
Oxacycle
Organoheterocyclic compound
Ether
Monocarboxylic acid or derivatives
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	3.84	ALOGPS
logP	4.22	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	9.18	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	97.46 m³·mol⁻¹	ChemAxon
Polarizability	39.37 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

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

10347062

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23243692

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Etsassala NGER, Badmus JA, Marnewick JL, Iwuoha EI, Nchu F, Hussein AA: Alpha-Glucosidase and Alpha-Amylase Inhibitory Activities, Molecular Docking, and Antioxidant Capacities of Salvia aurita Constituents. Antioxidants (Basel). 2020 Nov 19;9(11). pii: antiox9111149. doi: 10.3390/antiox9111149. [PubMed:33228164 ]
Zhang Y, Adelakun TA, Qu L, Li X, Li J, Han L, Wang T: New terpenoid glycosides obtained from Rosmarinus officinalis L. aerial parts. Fitoterapia. 2014 Dec;99:78-85. doi: 10.1016/j.fitote.2014.09.004. Epub 2014 Sep 6. [PubMed:25200369 ]
Guerrero IC, Andres LS, Leon LG, Machin RP, Padron JM, Luis JG, Delgadillo J: Abietane diterpenoids from Salvia pachyphylla and S. clevelandii with cytotoxic activity against human cancer cell lines. J Nat Prod. 2006 Dec;69(12):1803-5. doi: 10.1021/np060279i. [PubMed:17190465 ]
Ninomiya K, Matsuda H, Shimoda H, Nishida N, Kasajima N, Yoshino T, Morikawa T, Yoshikawa M: Carnosic acid, a new class of lipid absorption inhibitor from sage. Bioorg Med Chem Lett. 2004 Apr 19;14(8):1943-6. doi: 10.1016/j.bmcl.2004.01.091. [PubMed:15050633 ]
Kavvadias D, Monschein V, Sand P, Riederer P, Schreier P: Constituents of sage (Salvia officinalis) with in vitro affinity to human brain benzodiazepine receptor. Planta Med. 2003 Feb;69(2):113-7. doi: 10.1055/s-2003-37712. [PubMed:12624814 ]
Ahmed A. A., et al. (2006). Ahmed A. A., et al, Phytochemistry 67, 424 (2006) . Phytochem..

Showing NP-Card for 7alpha-methoxyrosmanol (NP0031793)

MOL for NP0031793 (7alpha-methoxyrosmanol)

3D MOL for NP0031793 (7alpha-methoxyrosmanol)

3D SDF for NP0031793 (7alpha-methoxyrosmanol)

3D-SDF for NP0031793 (7alpha-methoxyrosmanol)

PDB for NP0031793 (7alpha-methoxyrosmanol)

3D PDB for NP0031793 (7alpha-methoxyrosmanol)

SMILES for NP0031793 (7alpha-methoxyrosmanol)

INCHI for NP0031793 (7alpha-methoxyrosmanol)

Structure for NP0031793 (7alpha-methoxyrosmanol)

3D Structure for NP0031793 (7alpha-methoxyrosmanol)