NP-MRD: Showing NP-Card for 10'R-acetoxy-11'-hydroxyumbelliprenin (NP0034720)

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Record Information

Version

2.0

Created at

2021-06-20 18:22:08 UTC

Updated at

2021-06-30 00:05:18 UTC

NP-MRD ID

NP0034720

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10'R-acetoxy-11'-hydroxyumbelliprenin

Provided By

JEOL Database JEOL Logo

Description

10R'-acetyl-karatavacinol belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. 10'R-acetoxy-11'-hydroxyumbelliprenin is found in Ferula assa-foetida. 10'R-acetoxy-11'-hydroxyumbelliprenin was first documented in 2009 (Lee, C. -L., et al.). Based on a literature review very few articles have been published on 10R'-acetyl-karatavacinol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202120223D          

 66 67  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306202120223D          

 66 67  0  0  0  0            999 V2000
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   -3.8598    3.7690    0.3030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9633    3.6785    2.8327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4009    5.0330    3.1616 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2989    4.9007    4.0695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1195    4.4121    3.5766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2637    3.8543    4.5339 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9636    3.2917    4.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3491    3.2929    2.8229 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5974    2.7018    2.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9023    2.7219    1.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0165    3.3300    0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3005    3.2996   -1.1318 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8421    3.9072    0.5192 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5009    3.8751    1.8852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7220    4.4412    2.2433 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3804    0.6967   -3.1113 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8777    0.7348   -3.4488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6470   -0.0771   -4.2123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8900    2.0432   -3.1499 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3627   -3.5242   -0.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4449   -3.1519   -1.9253 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8095   -1.5507    0.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8113   -1.5141   -0.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3314   -2.5118    0.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7231    1.2966    1.8279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6314    0.8018    3.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2959   -0.3534    2.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6568    1.6460    2.0004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8527    1.4327    0.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5702    4.8174    0.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0519    3.2427   -0.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7529    3.7419   -0.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2230    3.1006    3.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1383    5.6541    2.3024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1757    5.5905    3.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5648    3.8427    5.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5990    2.8519    4.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2581    2.2365    3.0940 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8115    2.2695    0.6907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3287    4.8876    1.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0511    1.2761   -4.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4399    1.2708   -2.6762 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3016   -0.2693   -3.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4394   -0.0106   -4.0920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9354   -1.1327   -4.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8628    0.3545   -5.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4505    2.5841   -2.5500 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  2  0  0  0  0
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 19 18  2  0  0  0  0
 21 27  1  0  0  0  0
 11 12  1  0  0  0  0
  6  7  1  0  0  0  0
 12 13  1  0  0  0  0
 29  5  1  0  0  0  0
 13 15  2  0  0  0  0
  7  8  1  0  0  0  0
 21 22  1  0  0  0  0
 27 26  1  0  0  0  0
 26 24  1  0  0  0  0
 24 23  1  0  0  0  0
 23 22  2  0  0  0  0
 15 16  1  0  0  0  0
 24 25  2  0  0  0  0
 13 14  1  0  0  0  0
 30 29  1  0  0  0  0
 16 17  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 29 31  1  0  0  0  0
 17 18  1  0  0  0  0
 29 32  1  1  0  0  0
  5  6  1  0  0  0  0
  5  4  1  0  0  0  0
 18 28  1  0  0  0  0
  4  2  1  0  0  0  0
 28 27  2  0  0  0  0
  2  3  2  0  0  0  0
 10 11  1  0  0  0  0
  2  1  1  0  0  0  0
 30 60  1  0  0  0  0
 30 61  1  0  0  0  0
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  5 36  1  1  0  0  0
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  7 39  1  0  0  0  0
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  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0034720

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(C([H])([H])[H])(C([H])([H])[H])[C@]([H])(OC(=O)C([H])([H])[H])C([H])([H])C([H])([H])C(=C(/[H])C([H])([H])C([H])([H])C(=C(/[H])C([H])([H])OC1=C([H])C([H])=C2C([H])=C([H])C(=O)OC2=C1[H])\C([H])([H])[H])\C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O6/c1-18(9-13-24(26(4,5)29)31-20(3)27)7-6-8-19(2)15-16-30-22-12-10-21-11-14-25(28)32-23(21)17-22/h7,10-12,14-15,17,24,29H,6,8-9,13,16H2,1-5H3/b18-7+,19-15+/t24-/m1/s1

> <INCHI_KEY>
XSNVYFAOCSBLDV-PKPWYKSASA-N

> <FORMULA>
C26H34O6

> <MOLECULAR_WEIGHT>
442.552

> <EXACT_MASS>
442.235538815

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
48.00837897000787

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,6E,10E)-2-hydroxy-2,6,10-trimethyl-12-[(2-oxo-2H-chromen-7-yl)oxy]dodeca-6,10-dien-3-yl acetate

> <ALOGPS_LOGP>
5.26

> <JCHEM_LOGP>
4.607049589000001

> <ALOGPS_LOGS>
-5.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.302280942190606

> <JCHEM_PKA_STRONGEST_BASIC>
-3.103982315885829

> <JCHEM_POLAR_SURFACE_AREA>
82.06

> <JCHEM_REFRACTIVITY>
126.23429999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.11e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,6E,10E)-2-hydroxy-2,6,10-trimethyl-12-[(2-oxochromen-7-yl)oxy]dodeca-6,10-dien-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 66 67  0  0  0  0  0  0  0  0999 V2000
    3.1747   -2.8880   -0.8997 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7587   -1.4502   -0.8384 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4086    0.5132    1.5023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7715    0.6062    2.1377 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.1448    3.1079    1.6238 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.9633    3.6785    2.8327 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2637    3.8543    4.5339 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9636    3.2917    4.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3491    3.2929    2.8229 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5974    2.7018    2.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9023    2.7219    1.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0165    3.3300    0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3005    3.2996   -1.1318 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8421    3.9072    0.5192 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5009    3.8751    1.8852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7220    4.4412    2.2433 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3804    0.6967   -3.1113 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8777    0.7348   -3.4488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6470   -0.0771   -4.2123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8900    2.0432   -3.1499 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4449   -3.1519   -1.9253 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0739    0.3021    0.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0716   -1.3780    0.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8095   -1.5507    0.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8113   -1.5141   -0.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3314   -2.5118    0.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7231    1.2966    1.8279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6314    0.8018    3.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2959   -0.3534    2.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6568    1.6460    2.0004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8527    1.4327    0.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5702    4.8174    0.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0519    3.2427   -0.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7529    3.7419   -0.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2230    3.1006    3.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1383    5.6541    2.3024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1757    5.5905    3.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5648    3.8427    5.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5990    2.8519    4.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2581    2.2365    3.0940 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8115    2.2695    0.6907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3287    4.8876    1.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0511    1.2761   -4.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4399    1.2708   -2.6762 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3016   -0.2693   -3.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4394   -0.0106   -4.0920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9354   -1.1327   -4.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8628    0.3545   -5.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4505    2.5841   -2.5500 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  2  0
 20 19  1  0
 19 18  2  0
 21 27  1  0
 11 12  1  0
  6  7  1  0
 12 13  1  0
 29  5  1  0
 13 15  2  0
  7  8  1  0
 21 22  1  0
 27 26  1  0
 26 24  1  0
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 23 22  2  0
 15 16  1  0
 24 25  2  0
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 30 29  1  0
 16 17  1  0
  8  9  1  0
  8 10  2  0
 29 31  1  0
 17 18  1  0
 29 32  1  1
  5  6  1  0
  5  4  1  0
 18 28  1  0
  4  2  1  0
 28 27  2  0
  2  3  2  0
 10 11  1  0
  2  1  1  0
 30 60  1  0
 30 61  1  0
 30 62  1  0
  5 36  1  1
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 28 59  1  0
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 14 49  1  0
 14 50  1  0
 14 51  1  0
  9 41  1  0
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 31 63  1  0
 31 64  1  0
 31 65  1  0
 32 66  1  0
  1 33  1  0
  1 34  1  0
  1 35  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       3.175  -2.888  -0.900  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.759  -1.450  -0.838  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.321  -0.598  -0.165  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.674  -1.251  -1.636  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.143   0.092  -1.696  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.343   0.035  -1.290  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.507  -0.384   0.179  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.954  -0.416   0.637  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.774  -1.555   0.093  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.409   0.513   1.502  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.772   0.606   2.138  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.672   1.686   1.516  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.145   3.108   1.624  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.860   3.769   0.303  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.963   3.679   2.833  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.401   5.033   3.162  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.299   4.901   4.069  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.119   4.412   3.577  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.264   3.854   4.534  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.964   3.292   4.162  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.349   3.293   2.823  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.597   2.702   2.371  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.902   2.722   1.069  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.017   3.330   0.062  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.301   3.300  -1.132  0.00  0.00           O+0
HETATM   26  O   UNK     0       0.842   3.907   0.519  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.501   3.875   1.885  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.722   4.441   2.243  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.380   0.697  -3.111  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.878   0.735  -3.449  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.647  -0.077  -4.212  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.890   2.043  -3.150  0.00  0.00           O+0
HETATM   33  H   UNK     0       4.048  -3.040  -0.259  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.363  -3.524  -0.539  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.445  -3.152  -1.925  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.640   0.741  -0.968  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.814   1.014  -1.441  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.866  -0.691  -1.923  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.074   0.302   0.809  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.072  -1.378   0.341  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.809  -1.551   0.441  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.811  -1.514  -1.000  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.331  -2.512   0.388  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.723   1.297   1.828  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.631   0.802   3.208  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.296  -0.353   2.094  0.00  0.00           H+0
HETATM   47  H   UNK     0      -5.657   1.646   2.000  0.00  0.00           H+0
HETATM   48  H   UNK     0      -4.853   1.433   0.463  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.570   4.817   0.396  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.052   3.243  -0.216  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.753   3.742  -0.331  0.00  0.00           H+0
HETATM   52  H   UNK     0      -4.223   3.101   3.719  0.00  0.00           H+0
HETATM   53  H   UNK     0      -3.138   5.654   2.302  0.00  0.00           H+0
HETATM   54  H   UNK     0      -4.176   5.590   3.701  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.565   3.843   5.579  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.599   2.852   4.927  0.00  0.00           H+0
HETATM   57  H   UNK     0       3.258   2.236   3.094  0.00  0.00           H+0
HETATM   58  H   UNK     0       3.812   2.269   0.691  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.329   4.888   1.466  0.00  0.00           H+0
HETATM   60  H   UNK     0       3.051   1.276  -4.386  0.00  0.00           H+0
HETATM   61  H   UNK     0       3.440   1.271  -2.676  0.00  0.00           H+0
HETATM   62  H   UNK     0       3.302  -0.269  -3.549  0.00  0.00           H+0
HETATM   63  H   UNK     0      -0.439  -0.011  -4.092  0.00  0.00           H+0
HETATM   64  H   UNK     0       0.935  -1.133  -4.232  0.00  0.00           H+0
HETATM   65  H   UNK     0       0.863   0.355  -5.197  0.00  0.00           H+0
HETATM   66  H   UNK     0       1.450   2.584  -2.550  0.00  0.00           H+0
CONECT    1    2   33   34   35                                             
CONECT    2    4    3    1                                                  
CONECT    3    2                                                            
CONECT    4    5    2                                                       
CONECT    5   29    6    4   36                                             
CONECT    6    7    5   37   38                                             
CONECT    7    6    8   39   40                                             
CONECT    8    7    9   10                                                  
CONECT    9    8   41   42   43                                             
CONECT   10    8   11   44                                                  
CONECT   11   12   10   45   46                                             
CONECT   12   11   13   47   48                                             
CONECT   13   12   15   14                                                  
CONECT   14   13   49   50   51                                             
CONECT   15   13   16   52                                                  
CONECT   16   15   17   53   54                                             
CONECT   17   16   18                                                       
CONECT   18   19   17   28                                                  
CONECT   19   20   18   55                                                  
CONECT   20   21   19   56                                                  
CONECT   21   20   27   22                                                  
CONECT   22   21   23   57                                                  
CONECT   23   24   22   58                                                  
CONECT   24   26   23   25                                                  
CONECT   25   24                                                            
CONECT   26   27   24                                                       
CONECT   27   21   26   28                                                  
CONECT   28   18   27   59                                                  
CONECT   29    5   30   31   32                                             
CONECT   30   29   60   61   62                                             
CONECT   31   29   63   64   65                                             
CONECT   32   29   66                                                       
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    5                                                            
CONECT   37    6                                                            
CONECT   38    6                                                            
CONECT   39    7                                                            
CONECT   40    7                                                            
CONECT   41    9                                                            
CONECT   42    9                                                            
CONECT   43    9                                                            
CONECT   44   10                                                            
CONECT   45   11                                                            
CONECT   46   11                                                            
CONECT   47   12                                                            
CONECT   48   12                                                            
CONECT   49   14                                                            
CONECT   50   14                                                            
CONECT   51   14                                                            
CONECT   52   15                                                            
CONECT   53   16                                                            
CONECT   54   16                                                            
CONECT   55   19                                                            
CONECT   56   20                                                            
CONECT   57   22                                                            
CONECT   58   23                                                            
CONECT   59   28                                                            
CONECT   60   30                                                            
CONECT   61   30                                                            
CONECT   62   30                                                            
CONECT   63   31                                                            
CONECT   64   31                                                            
CONECT   65   31                                                            
CONECT   66   32                                                            
MASTER        0    0    0    0    0    0    0    0   66    0  134    0
END

RDKit          3D

66 67  0  0  0  0  0  0  0  0999 V2000
    3.1747   -2.8880   -0.8997 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7587   -1.4502   -0.8384 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3214   -0.5984   -0.1652 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6743   -1.2512   -1.6364 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1428    0.0921   -1.6955 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3431    0.0349   -1.2898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5067   -0.3841    0.1786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9540   -0.4158    0.6372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7744   -1.5550    0.0932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4086    0.5132    1.5023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7715    0.6062    2.1377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6720    1.6856    1.5162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1448    3.1079    1.6238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8598    3.7690    0.3030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9633    3.6785    2.8327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4009    5.0330    3.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2989    4.9007    4.0695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1195    4.4121    3.5766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2637    3.8543    4.5339 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9636    3.2917    4.1622 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3491    3.2929    2.8229 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5974    2.7018    2.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9023    2.7219    1.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0165    3.3300    0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3005    3.2996   -1.1318 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8421    3.9072    0.5192 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5009    3.8751    1.8852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7220    4.4412    2.2433 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3804    0.6967   -3.1113 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8777    0.7348   -3.4488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6470   -0.0771   -4.2123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8900    2.0432   -3.1499 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0481   -3.0403   -0.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3627   -3.5242   -0.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4449   -3.1519   -1.9253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6395    0.7414   -0.9682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8137    1.0135   -1.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8655   -0.6910   -1.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0739    0.3021    0.8093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0716   -1.3780    0.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8095   -1.5507    0.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8113   -1.5141   -0.9997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3314   -2.5118    0.3882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7231    1.2966    1.8279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6314    0.8018    3.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2959   -0.3534    2.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6568    1.6460    2.0004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8527    1.4327    0.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5702    4.8174    0.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0519    3.2427   -0.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7529    3.7419   -0.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2230    3.1006    3.7193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1383    5.6541    2.3024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1757    5.5905    3.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5648    3.8427    5.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5990    2.8519    4.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2581    2.2365    3.0940 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8115    2.2695    0.6907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3287    4.8876    1.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0511    1.2761   -4.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4399    1.2708   -2.6762 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3016   -0.2693   -3.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4394   -0.0106   -4.0920 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9354   -1.1327   -4.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8628    0.3545   -5.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4505    2.5841   -2.5500 H   0  0  0  0  0  0  0  0  0  0  0  0
 21 20  2  0
 20 19  1  0
 19 18  2  0
 21 27  1  0
 11 12  1  0
  6  7  1  0
 12 13  1  0
 29  5  1  0
 13 15  2  0
  7  8  1  0
 21 22  1  0
 27 26  1  0
 26 24  1  0
 24 23  1  0
 23 22  2  0
 15 16  1  0
 24 25  2  0
 13 14  1  0
 30 29  1  0
 16 17  1  0
  8  9  1  0
  8 10  2  0
 29 31  1  0
 17 18  1  0
 29 32  1  1
  5  6  1  0
  5  4  1  0
 18 28  1  0
  4  2  1  0
 28 27  2  0
  2  3  2  0
 10 11  1  0
  2  1  1  0
 30 60  1  0
 30 61  1  0
 30 62  1  0
  5 36  1  1
  6 37  1  0
  6 38  1  0
  7 39  1  0
  7 40  1  0
 10 44  1  0
 11 45  1  0
 11 46  1  0
 12 47  1  0
 12 48  1  0
 15 52  1  0
 16 53  1  0
 16 54  1  0
 28 59  1  0
 20 56  1  0
 19 55  1  0
 23 58  1  0
 22 57  1  0
 14 49  1  0
 14 50  1  0
 14 51  1  0
  9 41  1  0
  9 42  1  0
  9 43  1  0
 31 63  1  0
 31 64  1  0
 31 65  1  0
 32 66  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₄O₆

Average Mass

442.5520 Da

Monoisotopic Mass

442.23554 Da

IUPAC Name

(3R,6E,10E)-2-hydroxy-2,6,10-trimethyl-12-[(2-oxo-2H-chromen-7-yl)oxy]dodeca-6,10-dien-3-yl acetate

Traditional Name

(3R,6E,10E)-2-hydroxy-2,6,10-trimethyl-12-[(2-oxochromen-7-yl)oxy]dodeca-6,10-dien-3-yl acetate

CAS Registry Number

Not Available

SMILES

[H]OC(C([H])([H])[H])(C([H])([H])[H])[C@]([H])(OC(=O)C([H])([H])[H])C([H])([H])C([H])([H])C(=C(/[H])C([H])([H])C([H])([H])C(=C(/[H])C([H])([H])OC1=C([H])C([H])=C2C([H])=C([H])C(=O)OC2=C1[H])\C([H])([H])[H])\C([H])([H])[H]

InChI Identifier

InChI=1S/C26H34O6/c1-18(9-13-24(26(4,5)29)31-20(3)27)7-6-8-19(2)15-16-30-22-12-10-21-11-14-25(28)32-23(21)17-22/h7,10-12,14-15,17,24,29H,6,8-9,13,16H2,1-5H3/b18-7+,19-15+/t24-/m1/s1

InChI Key

XSNVYFAOCSBLDV-PKPWYKSASA-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

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ferula assa-foetida	JEOL database	Lee, C. -L., et al, J. Nat. Prod. 72, 1568 (2009)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Sesquiterpenoid
Farsesane sesquiterpenoid
Fatty alcohol ester
Coumarin
Benzopyran
1-benzopyran
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Tertiary alcohol
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Ether
Alcohol
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organooxygen compound
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	5.26	ALOGPS
logP	4.61	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	14.3	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	126.23 m³·mol⁻¹	ChemAxon
Polarizability	48.01 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

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

28637699

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44479215

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lee, C. -L., et al. (2009). Lee, C. -L., et al, J. Nat. Prod. 72, 1568 (2009). J. Nat. Prod..

Showing NP-Card for 10'R-acetoxy-11'-hydroxyumbelliprenin (NP0034720)

MOL for NP0034720 (10'R-acetoxy-11'-hydroxyumbelliprenin)

3D MOL for NP0034720 (10'R-acetoxy-11'-hydroxyumbelliprenin)

3D SDF for NP0034720 (10'R-acetoxy-11'-hydroxyumbelliprenin)

3D-SDF for NP0034720 (10'R-acetoxy-11'-hydroxyumbelliprenin)

PDB for NP0034720 (10'R-acetoxy-11'-hydroxyumbelliprenin)

3D PDB for NP0034720 (10'R-acetoxy-11'-hydroxyumbelliprenin)

SMILES for NP0034720 (10'R-acetoxy-11'-hydroxyumbelliprenin)

INCHI for NP0034720 (10'R-acetoxy-11'-hydroxyumbelliprenin)

Structure for NP0034720 (10'R-acetoxy-11'-hydroxyumbelliprenin)

3D Structure for NP0034720 (10'R-acetoxy-11'-hydroxyumbelliprenin)