NP-MRD: Showing NP-Card for Manoalide 25-acetate (NP0079170)

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Record Information

Version

2.0

Created at

2022-04-29 00:12:50 UTC

Updated at

2022-04-29 00:12:50 UTC

NP-MRD ID

NP0079170

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Manoalide 25-acetate

Description

(2S)-3-[(2R,6R)-6-hydroxy-5-[(3E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2H-pyran-2-yl]-5-oxo-2,5-dihydrofuran-2-yl acetate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Manoalide 25-acetate is found in Brachiaster sp. and Luffariella variabilis. Based on a literature review very few articles have been published on (2S)-3-[(2R,6R)-6-hydroxy-5-[(3E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2H-pyran-2-yl]-5-oxo-2,5-dihydrofuran-2-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292202122D          

 33 35  0  0  1  0            999 V2000
    1.4289   10.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   10.8911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   11.7161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   12.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   11.7161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   10.8911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9679   10.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5806   10.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   10.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    9.6536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    9.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    8.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    8.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    7.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    5.9411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.2911    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    4.7036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    5.5286    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    5.9411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819    2.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.1965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6119    1.5291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    2.1965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470    2.9812    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7376    3.2361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3507    2.6841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1792    1.8771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1353    2.9390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    8.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  2  9  1  0  0  0  0
  1 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  1  0  0  0
 19 23  1  6  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 12 33  1  0  0  0  0
M  END

     RDKit          3D

 71 73  0  0  0  0  0  0  0  0999 V2000
    6.6788    1.7456    2.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1289    1.4323    1.1769 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1150    2.3678    0.3180 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5639    0.1974    0.7623 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9952   -0.0698   -0.5803 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2780   -0.6147   -0.6263 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1676   -1.8917   -1.1552 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1493   -2.6788   -1.3393 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7579   -2.1291   -1.4414 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0488   -1.0836   -1.1164 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5916   -0.8315   -1.2122 C   0  0  1  0  0  0  0  0  0  0  0  0
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    3.4123   -2.0025   -1.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9507   -1.0680   -0.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5198   -1.1185    0.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8817    0.0909   -0.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4544    0.5158   -0.1602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4579   -0.0497    0.4656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2262   -1.3496    1.0757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8067    0.6287    0.5485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8203   -0.2699   -0.1070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1701    0.3309   -0.0637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8037    0.6211   -1.2088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1019    0.3166   -2.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1368    1.2232   -1.1549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0210    0.7323   -0.0572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2802    0.1191    1.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8422    0.6138    1.2018 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8531    2.1095    1.5001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2308   -0.0573    2.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1438   -0.5575    0.1001 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7039    2.8345    2.7248 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6564    1.3882    2.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4614    0.1138   -1.7774 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7253   -1.8257   -2.8761 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3080   -2.9557   -1.6409 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7937   -2.8253   -1.5854 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1784   -2.0900   -0.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7199   -1.0742    1.1893 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0684    0.1587   -1.4971 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5535    0.9480   -0.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7005    1.5074   -0.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5100   -1.3788    1.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1909   -1.6300    1.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1192   -2.1951    0.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0405    0.9218    1.5694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7818    1.5684   -0.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7669   -1.2682    0.3691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5003   -0.4628   -1.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9280   -0.7807   -2.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.0750    2.3489   -1.1721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7593   -0.0305   -0.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6607    1.5937    0.2747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8485    0.3267    2.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
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  9 10  2  0
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 18 20  1  0
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 22 23  2  0
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 27 28  1  0
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 14 31  1  0
 31 32  1  0
 31 33  1  0
 10  5  1  0
 33 11  1  0
 28 22  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  5 37  1  6
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 30 69  1  0
 31 70  1  1
 32 71  1  0
M  END


  Mrv1652304292202122D          

 33 35  0  0  1  0            999 V2000
    1.4289   10.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   10.8911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   11.7161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   12.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   11.7161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   10.8911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9679   10.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5806   10.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   10.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    9.6536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    9.2411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    8.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    8.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    7.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    5.9411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.2911    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    4.7036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    5.5286    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    5.9411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819    2.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.1965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6119    1.5291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    2.1965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7376    3.2361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1792    1.8771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1353    2.9390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    8.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  2  9  1  0  0  0  0
  1 10  1  0  0  0  0
 10 11  1  0  0  0  0
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 12 13  2  0  0  0  0
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 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
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 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  1  0  0  0
 19 23  1  6  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 12 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0079170

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1OC(=O)C=C1[C@H]1CC=C(CC\C=C(/C)CCC2=C(C)CCCC2(C)C)[C@H](O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O6/c1-17(11-13-22-18(2)9-7-15-27(22,4)5)8-6-10-20-12-14-23(32-25(20)30)21-16-24(29)33-26(21)31-19(3)28/h8,12,16,23,25-26,30H,6-7,9-11,13-15H2,1-5H3/b17-8+/t23-,25-,26+/m1/s1

> <INCHI_KEY>
IBDCHSSSHBQBDQ-TUMCFDGYSA-N

> <FORMULA>
C27H38O6

> <MOLECULAR_WEIGHT>
458.595

> <EXACT_MASS>
458.266838944

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
51.75044323673583

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-3-[(2R,6R)-6-hydroxy-5-[(3E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2H-pyran-2-yl]-5-oxo-2,5-dihydrofuran-2-yl acetate

> <ALOGPS_LOGP>
5.11

> <JCHEM_LOGP>
5.377757476333333

> <ALOGPS_LOGS>
-5.29

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.841402053530727

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7695762081970772

> <JCHEM_PKA_STRONGEST_BASIC>
-4.1813791836745215

> <JCHEM_POLAR_SURFACE_AREA>
82.06

> <JCHEM_REFRACTIVITY>
128.63409999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.37e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-3-[(2R,6R)-6-hydroxy-5-[(3E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2H-pyran-2-yl]-5-oxo-2H-furan-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       2.667  19.560   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  20.330   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  21.870   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  22.640   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  21.870   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  20.330   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.540  20.276   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.817  19.024   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.000  19.560   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  18.020   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  17.250   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  15.710   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.000  14.940   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.000  13.400   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  12.630   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  11.090   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  10.320   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   8.780   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   8.010   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.000   8.780   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.000  10.320   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.334  11.090   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.334   6.470   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.580   5.565   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.104   4.100   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.009   2.854   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.564   4.100   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.088   5.565   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.377   6.041   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.521   5.010   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.201   3.504   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -3.986   5.486   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.667  14.940   0.000  0.00  0.00           C+0
CONECT    1    2    6   10                                                  
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7    8                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    2                                                            
CONECT   10    1   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   33                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   23                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16   22                                                  
CONECT   22   21                                                            
CONECT   23   19   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   23   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   12                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Value	Source
(2S)-3-[(2R,6R)-6-Hydroxy-5-[(3E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2H-pyran-2-yl]-5-oxo-2,5-dihydrofuran-2-yl acetic acid	Generator

Chemical Formula

C₂₇H₃₈O₆

Average Mass

458.5950 Da

Monoisotopic Mass

458.26684 Da

IUPAC Name

(2S)-3-[(2R,6R)-6-hydroxy-5-[(3E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2H-pyran-2-yl]-5-oxo-2,5-dihydrofuran-2-yl acetate

Traditional Name

(2S)-3-[(2R,6R)-6-hydroxy-5-[(3E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2H-pyran-2-yl]-5-oxo-2H-furan-2-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1OC(=O)C=C1[C@H]1CC=C(CC\C=C(/C)CCC2=C(C)CCCC2(C)C)[C@H](O)O1

InChI Identifier

InChI=1S/C27H38O6/c1-17(11-13-22-18(2)9-7-15-27(22,4)5)8-6-10-20-12-14-23(32-25(20)30)21-16-24(29)33-26(21)31-19(3)28/h8,12,16,23,25-26,30H,6-7,9-11,13-15H2,1-5H3/b17-8+/t23-,25-,26+/m1/s1

InChI Key

IBDCHSSSHBQBDQ-TUMCFDGYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Brachiaster sp.	-	KNApSAcK
Luffariella variabilis	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
Acylal
2-furanone
Dicarboxylic acid or derivatives
Pyran
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Hemiacetal
Lactone
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	5.11	ALOGPS
logP	5.38	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	1.77	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	128.63 m³·mol⁻¹	ChemAxon
Polarizability	51.75 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

162925909

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Manoalide 25-acetate (NP0079170)

MOL for NP0079170 (Manoalide 25-acetate)

3D MOL for NP0079170 (Manoalide 25-acetate)

3D SDF for NP0079170 (Manoalide 25-acetate)

3D-SDF for NP0079170 (Manoalide 25-acetate)

PDB for NP0079170 (Manoalide 25-acetate)

3D PDB for NP0079170 (Manoalide 25-acetate)

SMILES for NP0079170 (Manoalide 25-acetate)

INCHI for NP0079170 (Manoalide 25-acetate)

Structure for NP0079170 (Manoalide 25-acetate)

3D Structure for NP0079170 (Manoalide 25-acetate)