NP-MRD: Showing NP-Card for (-)-(1R,2R,3S,6R,10S)-2alpha,3alpha-diacetoxyamorpha-4,7(11)-dien-8-one (NP0024386)

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Record Information

Version

2.0

Created at

2021-06-19 16:46:55 UTC

Updated at

2021-06-29 23:48:41 UTC

NP-MRD ID

NP0024386

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-(1R,2R,3S,6R,10S)-2alpha,3alpha-diacetoxyamorpha-4,7(11)-dien-8-one

Provided By

JEOL Database JEOL Logo

Description

(4S)-1-Isopropylidene-4alpha,7-dimethyl-5beta,6beta-diacetoxy-1,2,3,4,4aalpha,5,6,8aalpha-octahydronaphthalene-2-one belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (-)-(1R,2R,3S,6R,10S)-2alpha,3alpha-diacetoxyamorpha-4,7(11)-dien-8-one is found in Marsupella emarginata var. aquatica and Marsupella emarginata. (-)-(1R,2R,3S,6R,10S)-2alpha,3alpha-diacetoxyamorpha-4,7(11)-dien-8-one was first documented in 2002 (Leong, Y.-W., et al.). Based on a literature review very few articles have been published on (4S)-1-Isopropylidene-4alpha,7-dimethyl-5beta,6beta-diacetoxy-1,2,3,4,4aalpha,5,6,8aalpha-octahydronaphthalene-2-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192118463D          

 50 51  0  0  0  0            999 V2000
    3.8115    1.1002    2.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2087    1.8675    1.5285 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2569    3.0834    1.4189 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6120    1.0106    0.6621 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9964    1.5811   -0.5105 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1837    0.5540   -1.6147 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5886    0.3925   -2.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1609   -0.1620   -2.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2749   -0.0508   -1.6515 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9992   -1.3779   -1.7594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7870   -1.7871   -2.7841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5669   -3.0828   -2.7883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9793   -1.0005   -4.0579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7881   -2.2718   -0.5789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4832   -3.4541   -0.7057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9957   -1.6349    0.7675 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0977   -0.4014    0.9112 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3026    0.1840    2.3108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3877    0.6088   -0.2402 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4917    1.8897   -0.2754 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2758    2.6800    0.9068 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4639    4.0225    0.7563 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2844    4.7165    2.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7115    4.5871   -0.2997 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0319    0.5474    3.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2802    1.7977    3.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5773    0.4184    2.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5129    2.5060   -0.7967 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9625    1.3450   -2.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2529    0.0594   -1.3215 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6509   -0.3438   -2.9334 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3509   -0.8550   -2.9431 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7647    4.6693    2.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
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  7 29  1  0  0  0  0
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  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
M  END

     RDKit          3D

 50 51  0  0  0  0  0  0  0  0999 V2000
    3.8115    1.1002    2.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2087    1.8675    1.5285 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2569    3.0834    1.4189 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6120    1.0106    0.6621 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9964    1.5811   -0.5105 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.9793   -1.0005   -4.0579 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4832   -3.4541   -0.7057 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2758    2.6800    0.9068 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4639    4.0225    0.7563 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2844    4.7165    2.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7115    4.5871   -0.2997 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306192118463D          

 50 51  0  0  0  0            999 V2000
    3.8115    1.1002    2.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2087    1.8675    1.5285 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2569    3.0834    1.4189 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6120    1.0106    0.6621 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9964    1.5811   -0.5105 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1837    0.5540   -1.6147 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5886    0.3925   -2.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1609   -0.1620   -2.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2749   -0.0508   -1.6515 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9992   -1.3779   -1.7594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7870   -1.7871   -2.7841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5669   -3.0828   -2.7883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9793   -1.0005   -4.0579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7881   -2.2718   -0.5789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4832   -3.4541   -0.7057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9957   -1.6349    0.7675 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.4297    0.9377   -0.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1311    2.4670   -1.1403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7647    4.6693    2.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5802    5.7646    1.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9220    4.2529    2.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 13  1  0  0  0  0
  5  6  1  0  0  0  0
 17 18  1  0  0  0  0
 19 46  1  1  0  0  0
 19  9  1  0  0  0  0
  9 33  1  6  0  0  0
 19 17  1  0  0  0  0
 20 47  1  6  0  0  0
  9 10  1  0  0  0  0
 20 21  1  0  0  0  0
  5 20  1  0  0  0  0
 21 22  1  0  0  0  0
  6  8  2  0  0  0  0
 22 23  1  0  0  0  0
  8  9  1  0  0  0  0
 22 24  2  0  0  0  0
 19 20  1  0  0  0  0
  6  7  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 11  2  3  0  0  0
  5  4  1  0  0  0  0
 14 16  1  0  0  0  0
  4  2  1  0  0  0  0
 11 12  1  0  0  0  0
  2  1  1  0  0  0  0
 16 17  1  0  0  0  0
  2  3  2  0  0  0  0
 16 40  1  0  0  0  0
 16 41  1  0  0  0  0
 17 42  1  1  0  0  0
  5 28  1  6  0  0  0
  8 32  1  0  0  0  0
 12 34  1  0  0  0  0
 12 35  1  0  0  0  0
 12 36  1  0  0  0  0
 13 37  1  0  0  0  0
 13 38  1  0  0  0  0
 13 39  1  0  0  0  0
 18 43  1  0  0  0  0
 18 44  1  0  0  0  0
 18 45  1  0  0  0  0
 23 48  1  0  0  0  0
 23 49  1  0  0  0  0
 23 50  1  0  0  0  0
  7 29  1  0  0  0  0
  7 30  1  0  0  0  0
  7 31  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0024386

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C(C([H])([H])[H])[C@]([H])(OC(=O)C([H])([H])[H])[C@]([H])(OC(=O)C([H])([H])[H])[C@@]2([H])[C@]1([H])C(=C(C([H])([H])[H])C([H])([H])[H])C(=O)C([H])([H])[C@]2([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O5/c1-9(2)16-14-7-11(4)18(23-12(5)20)19(24-13(6)21)17(14)10(3)8-15(16)22/h7,10,14,17-19H,8H2,1-6H3/t10-,14-,17+,18-,19+/m0/s1

> <INCHI_KEY>
GIHHWTGPMYARCT-RBVNUJLISA-N

> <FORMULA>
C19H26O5

> <MOLECULAR_WEIGHT>
334.412

> <EXACT_MASS>
334.178023937

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
36.42716204954089

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,4aR,8S,8aR)-2-(acetyloxy)-3,8-dimethyl-6-oxo-5-(propan-2-ylidene)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl acetate

> <ALOGPS_LOGP>
2.95

> <JCHEM_LOGP>
2.3918963883333335

> <ALOGPS_LOGS>
-3.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.779862051434204

> <JCHEM_POLAR_SURFACE_AREA>
69.67000000000002

> <JCHEM_REFRACTIVITY>
90.128

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.70e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4aR,8S,8aR)-2-(acetyloxy)-3,8-dimethyl-6-oxo-5-(propan-2-ylidene)-1,2,4a,7,8,8a-hexahydronaphthalen-1-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 50 51  0  0  0  0  0  0  0  0999 V2000
    3.8115    1.1002    2.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2087    1.8675    1.5285 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2569    3.0834    1.4189 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6120    1.0106    0.6621 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9964    1.5811   -0.5105 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1837    0.5540   -1.6147 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5886    0.3925   -2.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1609   -0.1620   -2.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2749   -0.0508   -1.6515 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9992   -1.3779   -1.7594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7870   -1.7871   -2.7841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5669   -3.0828   -2.7883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9793   -1.0005   -4.0579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7881   -2.2718   -0.5789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4832   -3.4541   -0.7057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9957   -1.6349    0.7675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0977   -0.4014    0.9112 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3026    0.1840    2.3108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3877    0.6088   -0.2402 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4917    1.8897   -0.2754 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2758    2.6800    0.9068 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4639    4.0225    0.7563 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2844    4.7165    2.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7115    4.5871   -0.2997 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0319    0.5474    3.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2802    1.7977    3.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5773    0.4184    2.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5129    2.5060   -0.7967 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9625    1.3450   -2.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2529    0.0594   -1.3215 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6509   -0.3438   -2.9334 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3509   -0.8550   -2.9431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7592    0.6548   -2.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5691   -2.9166   -3.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0599   -3.8262   -3.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7185   -3.5039   -1.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9800   -0.5572   -4.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2464   -0.2022   -4.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8769   -1.6615   -4.9260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7514   -2.3757    1.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0572   -1.3833    0.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9376   -0.7532    0.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4668    0.9186    2.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2832    0.6629    2.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2400   -0.5997    3.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4297    0.9377   -0.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1311    2.4670   -1.1403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7647    4.6693    2.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5802    5.7646    1.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9220    4.2529    2.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 13  1  0
  5  6  1  0
 17 18  1  0
 19 46  1  1
 19  9  1  0
  9 33  1  6
 19 17  1  0
 20 47  1  6
  9 10  1  0
 20 21  1  0
  5 20  1  0
 21 22  1  0
  6  8  2  0
 22 23  1  0
  8  9  1  0
 22 24  2  0
 19 20  1  0
  6  7  1  0
 10 14  1  0
 14 15  2  0
 10 11  2  3
  5  4  1  0
 14 16  1  0
  4  2  1  0
 11 12  1  0
  2  1  1  0
 16 17  1  0
  2  3  2  0
 16 40  1  0
 16 41  1  0
 17 42  1  1
  5 28  1  6
  8 32  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 13 39  1  0
 18 43  1  0
 18 44  1  0
 18 45  1  0
 23 48  1  0
 23 49  1  0
 23 50  1  0
  7 29  1  0
  7 30  1  0
  7 31  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       3.812   1.100   2.665  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.209   1.867   1.529  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.257   3.083   1.419  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.612   1.011   0.662  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.996   1.581  -0.510  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.184   0.554  -1.615  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.589   0.393  -2.125  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.161  -0.162  -2.123  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.275  -0.051  -1.652  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.999  -1.378  -1.759  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.787  -1.787  -2.784  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.567  -3.083  -2.788  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.979  -1.000  -4.058  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.788  -2.272  -0.579  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.483  -3.454  -0.706  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.996  -1.635   0.768  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.098  -0.401   0.911  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.303   0.184   2.311  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.388   0.609  -0.240  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.492   1.890  -0.275  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.276   2.680   0.907  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.464   4.022   0.756  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.284   4.716   2.071  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.712   4.587  -0.300  0.00  0.00           O+0
HETATM   25  H   UNK     0       3.032   0.547   3.195  0.00  0.00           H+0
HETATM   26  H   UNK     0       4.280   1.798   3.365  0.00  0.00           H+0
HETATM   27  H   UNK     0       4.577   0.418   2.287  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.513   2.506  -0.797  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.962   1.345  -2.514  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.253   0.059  -1.321  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.651  -0.344  -2.933  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.351  -0.855  -2.943  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.759   0.655  -2.339  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.569  -2.917  -3.200  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.060  -3.826  -3.412  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.719  -3.504  -1.791  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.980  -0.557  -4.079  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.246  -0.202  -4.195  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.877  -1.662  -4.926  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.751  -2.376   1.538  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.057  -1.383   0.877  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.938  -0.753   0.840  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.467   0.919   2.559  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.283   0.663   2.402  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.240  -0.600   3.074  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.430   0.938  -0.106  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.131   2.467  -1.140  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.765   4.669   2.373  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.580   5.765   1.971  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.922   4.253   2.828  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2    4    1    3                                                  
CONECT    3    2                                                            
CONECT    4    5    2                                                       
CONECT    5    6   20    4   28                                             
CONECT    6    5    8    7                                                  
CONECT    7    6   29   30   31                                             
CONECT    8    6    9   32                                                  
CONECT    9   19   33   10    8                                             
CONECT   10    9   14   11                                                  
CONECT   11   13   10   12                                                  
CONECT   12   11   34   35   36                                             
CONECT   13   11   37   38   39                                             
CONECT   14   10   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   40   41                                             
CONECT   17   18   19   16   42                                             
CONECT   18   17   43   44   45                                             
CONECT   19   46    9   17   20                                             
CONECT   20   47   21    5   19                                             
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22   48   49   50                                             
CONECT   24   22                                                            
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    5                                                            
CONECT   29    7                                                            
CONECT   30    7                                                            
CONECT   31    7                                                            
CONECT   32    8                                                            
CONECT   33    9                                                            
CONECT   34   12                                                            
CONECT   35   12                                                            
CONECT   36   12                                                            
CONECT   37   13                                                            
CONECT   38   13                                                            
CONECT   39   13                                                            
CONECT   40   16                                                            
CONECT   41   16                                                            
CONECT   42   17                                                            
CONECT   43   18                                                            
CONECT   44   18                                                            
CONECT   45   18                                                            
CONECT   46   19                                                            
CONECT   47   20                                                            
CONECT   48   23                                                            
CONECT   49   23                                                            
CONECT   50   23                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  102    0
END

RDKit          3D

50 51  0  0  0  0  0  0  0  0999 V2000
    3.8115    1.1002    2.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2087    1.8675    1.5285 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2569    3.0834    1.4189 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6120    1.0106    0.6621 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9964    1.5811   -0.5105 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1837    0.5540   -1.6147 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5886    0.3925   -2.1252 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1609   -0.1620   -2.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2749   -0.0508   -1.6515 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9992   -1.3779   -1.7594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7870   -1.7871   -2.7841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5669   -3.0828   -2.7883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9793   -1.0005   -4.0579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7881   -2.2718   -0.5789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4832   -3.4541   -0.7057 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9957   -1.6349    0.7675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0977   -0.4014    0.9112 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3026    0.1840    2.3108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3877    0.6088   -0.2402 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4917    1.8897   -0.2754 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2758    2.6800    0.9068 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4639    4.0225    0.7563 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2844    4.7165    2.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7115    4.5871   -0.2997 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0319    0.5474    3.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2802    1.7977    3.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5773    0.4184    2.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5129    2.5060   -0.7967 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9625    1.3450   -2.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2529    0.0594   -1.3215 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6509   -0.3438   -2.9334 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3509   -0.8550   -2.9431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7592    0.6548   -2.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5691   -2.9166   -3.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0599   -3.8262   -3.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7185   -3.5039   -1.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9800   -0.5572   -4.0794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2464   -0.2022   -4.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8769   -1.6615   -4.9260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7514   -2.3757    1.5382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0572   -1.3833    0.8766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9376   -0.7532    0.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4668    0.9186    2.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2832    0.6629    2.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2400   -0.5997    3.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4297    0.9377   -0.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1311    2.4670   -1.1403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7647    4.6693    2.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5802    5.7646    1.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9220    4.2529    2.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 13  1  0
  5  6  1  0
 17 18  1  0
 19 46  1  1
 19  9  1  0
  9 33  1  6
 19 17  1  0
 20 47  1  6
  9 10  1  0
 20 21  1  0
  5 20  1  0
 21 22  1  0
  6  8  2  0
 22 23  1  0
  8  9  1  0
 22 24  2  0
 19 20  1  0
  6  7  1  0
 10 14  1  0
 14 15  2  0
 10 11  2  3
  5  4  1  0
 14 16  1  0
  4  2  1  0
 11 12  1  0
  2  1  1  0
 16 17  1  0
  2  3  2  0
 16 40  1  0
 16 41  1  0
 17 42  1  1
  5 28  1  6
  8 32  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 13 39  1  0
 18 43  1  0
 18 44  1  0
 18 45  1  0
 23 48  1  0
 23 49  1  0
 23 50  1  0
  7 29  1  0
  7 30  1  0
  7 31  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
(4S)-1-Isopropylidene-4a,7-dimethyl-5b,6b-diacetoxy-1,2,3,4,4aalpha,5,6,8aalpha-octahydronaphthalene-2-one	Generator
(4S)-1-Isopropylidene-4α,7-dimethyl-5β,6β-diacetoxy-1,2,3,4,4aalpha,5,6,8aalpha-octahydronaphthalene-2-one	Generator
(1R,2S,4AR,8S,8ar)-2-(acetyloxy)-3,8-dimethyl-6-oxo-5-(propan-2-ylidene)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl acetic acid	Generator

Chemical Formula

C₁₉H₂₆O₅

Average Mass

334.4120 Da

Monoisotopic Mass

334.17802 Da

IUPAC Name

(1R,2S,4aR,8S,8aR)-2-(acetyloxy)-3,8-dimethyl-6-oxo-5-(propan-2-ylidene)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl acetate

Traditional Name

(1R,2S,4aR,8S,8aR)-2-(acetyloxy)-3,8-dimethyl-6-oxo-5-(propan-2-ylidene)-1,2,4a,7,8,8a-hexahydronaphthalen-1-yl acetate

CAS Registry Number

Not Available

SMILES

[H]C1=C(C([H])([H])[H])[C@]([H])(OC(=O)C([H])([H])[H])[C@]([H])(OC(=O)C([H])([H])[H])[C@@]2([H])[C@]1([H])C(=C(C([H])([H])[H])C([H])([H])[H])C(=O)C([H])([H])[C@]2([H])C([H])([H])[H]

InChI Identifier

InChI=1S/C19H26O5/c1-9(2)16-14-7-11(4)18(23-12(5)20)19(24-13(6)21)17(14)10(3)8-15(16)22/h7,10,14,17-19H,8H2,1-6H3/t10-,14-,17+,18-,19+/m0/s1

InChI Key

GIHHWTGPMYARCT-RBVNUJLISA-N

Experimental Spectra

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

Predicted Spectra

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
Marsupella aquatica	JEOL database	Leong, Y.-W., et al, Tetrahedron 58, 4335 (2002)
Marsupella emarginata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Cadinane sesquiterpenoid
Dicarboxylic acid or derivatives
Cyclic ketone
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	2.95	ALOGPS
logP	2.39	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	69.67 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	90.13 m³·mol⁻¹	ChemAxon
Polarizability	36.43 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

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

15923268

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Leong, Y.-W., et al. (2002). Leong, Y.-W., et al, Tetrahedron 58, 4335 (2002). Tetrahedron.

Showing NP-Card for (-)-(1R,2R,3S,6R,10S)-2alpha,3alpha-diacetoxyamorpha-4,7(11)-dien-8-one (NP0024386)

MOL for NP0024386 ((-)-(1R,2R,3S,6R,10S)-2alpha,3alpha-diacetoxyamorpha-4,7(11)-dien-8-one)

3D MOL for NP0024386 ((-)-(1R,2R,3S,6R,10S)-2alpha,3alpha-diacetoxyamorpha-4,7(11)-dien-8-one)

3D SDF for NP0024386 ((-)-(1R,2R,3S,6R,10S)-2alpha,3alpha-diacetoxyamorpha-4,7(11)-dien-8-one)

3D-SDF for NP0024386 ((-)-(1R,2R,3S,6R,10S)-2alpha,3alpha-diacetoxyamorpha-4,7(11)-dien-8-one)

PDB for NP0024386 ((-)-(1R,2R,3S,6R,10S)-2alpha,3alpha-diacetoxyamorpha-4,7(11)-dien-8-one)

3D PDB for NP0024386 ((-)-(1R,2R,3S,6R,10S)-2alpha,3alpha-diacetoxyamorpha-4,7(11)-dien-8-one)

SMILES for NP0024386 ((-)-(1R,2R,3S,6R,10S)-2alpha,3alpha-diacetoxyamorpha-4,7(11)-dien-8-one)

INCHI for NP0024386 ((-)-(1R,2R,3S,6R,10S)-2alpha,3alpha-diacetoxyamorpha-4,7(11)-dien-8-one)

Structure for NP0024386 ((-)-(1R,2R,3S,6R,10S)-2alpha,3alpha-diacetoxyamorpha-4,7(11)-dien-8-one)

3D Structure for NP0024386 ((-)-(1R,2R,3S,6R,10S)-2alpha,3alpha-diacetoxyamorpha-4,7(11)-dien-8-one)