NP-MRD: Showing NP-Card for ansellone A (NP0039820)

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Record Information

Version

2.0

Created at

2021-06-20 22:08:31 UTC

Updated at

2021-06-30 00:13:21 UTC

NP-MRD ID

NP0039820

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ansellone A

Provided By

JEOL Database JEOL Logo

Description

Ansellone A belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. ansellone A is found in Nudibranch Cadlina luteromarginata and Sponge Phorbas sp.. ansellone A was first documented in 2010 (PMID: 20560657). Based on a literature review a small amount of articles have been published on Ansellone A (PMID: 33570413) (PMID: 28371092) (PMID: 27768313).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100083D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306212100083D          

 70 73  0  0  0  0            999 V2000
    3.2653    3.8051    0.9687 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1451    2.4217    1.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4809    1.4067    0.9372 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6054    2.4779    2.7782 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3710    1.2162    3.4109 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9517    0.7840    3.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6602   -0.2143    2.2946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7457   -0.6864    1.9913 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0081   -0.9962    0.4808 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1038    0.2077   -0.5709 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4025    1.0286   -0.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1063    1.1662   -0.4440 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2522    2.1578   -1.5978 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3363    1.4559   -2.9459 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8349    0.4836   -3.2322 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4233   -0.3444   -4.4816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0987    1.2704   -3.6302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0268   -0.4739   -1.9997 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1042   -1.5253   -2.1623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6112   -2.2092   -1.1260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1884   -2.0245    0.3117 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4300   -1.7701    1.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6899   -3.3081    0.7323 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7094    0.2408    2.4971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4502    0.6116    3.8501 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6707    1.3325    4.3338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7603    2.6589    4.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9794    3.3495    5.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5974    3.5196    4.1535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6208    4.7261    4.3922 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4327    2.8864    3.4256 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1657    1.4654    3.9272 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2742    4.2590    0.8895 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9169    4.4093    1.6049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054    3.7528   -0.0313 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1011    0.4610    3.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5266    1.3515    4.4871 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4668   -0.7309    1.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8629   -1.6256    2.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1056   -1.5562    0.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2932    0.5005   -0.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3825    1.9810   -0.9088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5668    1.3052    0.6622 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0314    0.5786   -0.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0368    1.7434    0.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1680    2.7424   -1.4456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5660    2.8842   -1.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2835    0.8994   -2.9742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4061    2.2109   -3.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2380   -0.9806   -4.8413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1401    0.3132   -5.3122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4372   -0.9884   -4.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9568    1.7639   -4.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9710    0.6167   -3.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3493    2.0650   -2.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0924   -1.0613   -1.9888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4636   -1.7639   -3.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3739   -2.9620   -1.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8746   -0.7865    1.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2086   -1.8814    2.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2063   -2.5190    0.9721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1164   -3.6389    0.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3324   -0.2950    4.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5309    0.7024    4.5473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7906    2.6429    5.2479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3507    4.0775    4.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7525    3.8743    5.9764 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4435    3.5186    3.6067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6532    2.9118    2.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1243    1.5207    4.9863 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 32 31  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 29  1  0  0  0  0
 29 31  1  0  0  0  0
 20 21  1  0  0  0  0
 27 28  1  0  0  0  0
 21  9  1  0  0  0  0
 29 30  2  0  0  0  0
  8 24  1  0  0  0  0
  6  5  1  0  0  0  0
 10 18  1  0  0  0  0
  5  4  1  0  0  0  0
 15 16  1  6  0  0  0
 13 14  1  0  0  0  0
 10 11  1  6  0  0  0
 13 12  1  0  0  0  0
 21 22  1  0  0  0  0
  8  7  1  0  0  0  0
 15 17  1  0  0  0  0
 24 25  1  0  0  0  0
 21 23  1  1  0  0  0
 32  6  1  0  0  0  0
  9 40  1  6  0  0  0
  6  7  2  0  0  0  0
  8 39  1  1  0  0  0
  9  8  1  0  0  0  0
 32 70  1  1  0  0  0
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 18 56  1  1  0  0  0
 14 15  1  0  0  0  0
 25 63  1  1  0  0  0
 15 18  1  0  0  0  0
  4  2  1  0  0  0  0
 10 12  1  0  0  0  0
  2  1  1  0  0  0  0
 10  9  1  0  0  0  0
  2  3  2  0  0  0  0
 13 46  1  0  0  0  0
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 14 48  1  0  0  0  0
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 12 44  1  0  0  0  0
 12 45  1  0  0  0  0
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  7 38  1  0  0  0  0
 26 64  1  0  0  0  0
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 31 69  1  0  0  0  0
 28 65  1  0  0  0  0
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 16 50  1  0  0  0  0
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 16 52  1  0  0  0  0
 11 41  1  0  0  0  0
 11 42  1  0  0  0  0
 11 43  1  0  0  0  0
 22 59  1  0  0  0  0
 22 60  1  0  0  0  0
 22 61  1  0  0  0  0
 17 53  1  0  0  0  0
 17 54  1  0  0  0  0
 17 55  1  0  0  0  0
 23 62  1  0  0  0  0
  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>
NP0039820

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O5/c1-16-12-21-19(14-20(16)29)18(15-31-17(2)28)13-22(32-21)24-26(5)10-7-9-25(3,4)23(26)8-11-27(24,6)30/h8,11-13,19,21-24,30H,7,9-10,14-15H2,1-6H3/t19-,21-,22-,23+,24-,26+,27-/m1/s1

> <INCHI_KEY>
WQWLFFAOBHUZOZ-RTEGDMPBSA-N

> <FORMULA>
C27H38O5

> <MOLECULAR_WEIGHT>
442.596

> <EXACT_MASS>
442.271924324

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
49.25562350880645

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(2R,4aR,8aR)-2-[(1S,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-7-methyl-6-oxo-4a,5,6,8a-tetrahydro-2H-chromen-4-yl]methyl acetate

> <ALOGPS_LOGP>
4.17

> <JCHEM_LOGP>
3.6176075836666675

> <ALOGPS_LOGS>
-4.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.754541398894393

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.308267744693644

> <JCHEM_PKA_STRONGEST_BASIC>
-3.101356879705678

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
126.0588

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.57e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,4aR,8aR)-2-[(1S,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyl-4a,6,7,8-tetrahydro-1H-naphthalen-1-yl]-7-methyl-6-oxo-2,4a,5,8a-tetrahydrochromen-4-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 70 73  0  0  0  0  0  0  0  0999 V2000
    3.2653    3.8051    0.9687 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1451    2.4217    1.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4809    1.4067    0.9372 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6054    2.4779    2.7782 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3710    1.2162    3.4109 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9517    0.7840    3.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6602   -0.2143    2.2946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7457   -0.6864    1.9913 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0081   -0.9962    0.4808 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1038    0.2077   -0.5709 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4025    1.0286   -0.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1063    1.1662   -0.4440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2522    2.1578   -1.5978 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3363    1.4559   -2.9459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8349    0.4836   -3.2322 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4233   -0.3444   -4.4816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0987    1.2704   -3.6302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0268   -0.4739   -1.9997 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1042   -1.5253   -2.1623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6112   -2.2092   -1.1260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1884   -2.0245    0.3117 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4300   -1.7701    1.1766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6899   -3.3081    0.7323 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7094    0.2408    2.4971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4502    0.6116    3.8501 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6707    1.3325    4.3338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7603    2.6589    4.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9794    3.3495    5.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5974    3.5196    4.1535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6208    4.7261    4.3922 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4327    2.8864    3.4256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1657    1.4654    3.9272 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2742    4.2590    0.8895 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9169    4.4093    1.6049 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054    3.7528   -0.0313 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1011    0.4610    3.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5266    1.3515    4.4871 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4668   -0.7309    1.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8629   -1.6256    2.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1056   -1.5562    0.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2932    0.5005   -0.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3825    1.9810   -0.9088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5668    1.3052    0.6622 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0314    0.5786   -0.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0368    1.7434    0.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1680    2.7424   -1.4456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5660    2.8842   -1.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2835    0.8994   -2.9742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4061    2.2109   -3.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2380   -0.9806   -4.8413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1401    0.3132   -5.3122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4372   -0.9884   -4.2678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9568    1.7639   -4.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9710    0.6167   -3.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3493    2.0650   -2.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0924   -1.0613   -1.9888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4636   -1.7639   -3.1593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3739   -2.9620   -1.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8746   -0.7865    1.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2086   -1.8814    2.2436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2063   -2.5190    0.9721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1164   -3.6389    0.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3324   -0.2950    4.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5309    0.7024    4.5473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7906    2.6429    5.2479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3507    4.0775    4.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7525    3.8743    5.9764 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4435    3.5186    3.6067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6532    2.9118    2.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1243    1.5207    4.9863 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 19  1  0
 19 20  2  0
 32 31  1  0
 25 26  1  0
 26 27  2  0
 27 29  1  0
 29 31  1  0
 20 21  1  0
 27 28  1  0
 21  9  1  0
 29 30  2  0
  8 24  1  0
  6  5  1  0
 10 18  1  0
  5  4  1  0
 15 16  1  6
 13 14  1  0
 10 11  1  6
 13 12  1  0
 21 22  1  0
  8  7  1  0
 15 17  1  0
 24 25  1  0
 21 23  1  1
 32  6  1  0
  9 40  1  6
  6  7  2  0
  8 39  1  1
  9  8  1  0
 32 70  1  1
 32 25  1  0
 18 56  1  1
 14 15  1  0
 25 63  1  1
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 10  9  1  0
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  7 38  1  0
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 17 55  1  0
 23 62  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       3.265   3.805   0.969  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.145   2.422   1.531  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.481   1.407   0.937  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.605   2.478   2.778  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.371   1.216   3.411  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.952   0.784   3.152  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.660  -0.214   2.295  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.746  -0.686   1.991  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.008  -0.996   0.481  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.104   0.208  -0.571  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.402   1.029  -0.380  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.106   1.166  -0.444  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.252   2.158  -1.598  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.336   1.456  -2.946  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.835   0.484  -3.232  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.423  -0.344  -4.482  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.099   1.270  -3.630  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.027  -0.474  -2.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.104  -1.525  -2.162  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.611  -2.209  -1.126  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.188  -2.025   0.312  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.430  -1.770   1.177  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.690  -3.308   0.732  0.00  0.00           O+0
HETATM   24  O   UNK     0      -1.709   0.241   2.497  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.450   0.612   3.850  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.671   1.333   4.334  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.760   2.659   4.521  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.979   3.349   5.043  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.597   3.520   4.154  0.00  0.00           C+0
HETATM   30  O   UNK     0      -1.621   4.726   4.392  0.00  0.00           O+0
HETATM   31  C   UNK     0      -0.433   2.886   3.426  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.166   1.465   3.927  0.00  0.00           C+0
HETATM   33  H   UNK     0       2.274   4.259   0.890  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.917   4.409   1.605  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.705   3.753  -0.031  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.101   0.461   3.095  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.527   1.351   4.487  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.467  -0.731   1.777  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.863  -1.626   2.549  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.106  -1.556   0.181  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.293   0.500  -0.729  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.382   1.981  -0.909  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.567   1.305   0.662  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.031   0.579  -0.392  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.037   1.743   0.482  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.168   2.742  -1.446  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.566   2.884  -1.597  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.284   0.899  -2.974  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.406   2.211  -3.740  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.238  -0.981  -4.841  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.140   0.313  -5.312  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.437  -0.988  -4.268  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.957   1.764  -4.600  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.971   0.617  -3.729  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.349   2.065  -2.929  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.092  -1.061  -1.989  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.464  -1.764  -3.159  0.00  0.00           H+0
HETATM   58  H   UNK     0      -3.374  -2.962  -1.318  0.00  0.00           H+0
HETATM   59  H   UNK     0      -3.875  -0.787   1.013  0.00  0.00           H+0
HETATM   60  H   UNK     0      -3.209  -1.881   2.244  0.00  0.00           H+0
HETATM   61  H   UNK     0      -4.206  -2.519   0.972  0.00  0.00           H+0
HETATM   62  H   UNK     0      -1.116  -3.639   0.019  0.00  0.00           H+0
HETATM   63  H   UNK     0      -1.332  -0.295   4.460  0.00  0.00           H+0
HETATM   64  H   UNK     0      -3.531   0.702   4.547  0.00  0.00           H+0
HETATM   65  H   UNK     0      -4.791   2.643   5.248  0.00  0.00           H+0
HETATM   66  H   UNK     0      -4.351   4.077   4.314  0.00  0.00           H+0
HETATM   67  H   UNK     0      -3.753   3.874   5.976  0.00  0.00           H+0
HETATM   68  H   UNK     0       0.444   3.519   3.607  0.00  0.00           H+0
HETATM   69  H   UNK     0      -0.653   2.912   2.353  0.00  0.00           H+0
HETATM   70  H   UNK     0       0.124   1.521   4.986  0.00  0.00           H+0
CONECT    1    2   33   34   35                                             
CONECT    2    4    1    3                                                  
CONECT    3    2                                                            
CONECT    4    5    2                                                       
CONECT    5    6    4   36   37                                             
CONECT    6    5   32    7                                                  
CONECT    7    8    6   38                                                  
CONECT    8   24    7   39    9                                             
CONECT    9   21   40    8   10                                             
CONECT   10   18   11   12    9                                             
CONECT   11   10   41   42   43                                             
CONECT   12   13   10   44   45                                             
CONECT   13   14   12   46   47                                             
CONECT   14   13   15   48   49                                             
CONECT   15   16   17   14   18                                             
CONECT   16   15   50   51   52                                             
CONECT   17   15   53   54   55                                             
CONECT   18   19   10   56   15                                             
CONECT   19   18   20   57                                                  
CONECT   20   19   21   58                                                  
CONECT   21   20    9   22   23                                             
CONECT   22   21   59   60   61                                             
CONECT   23   21   62                                                       
CONECT   24    8   25                                                       
CONECT   25   26   24   32   63                                             
CONECT   26   25   27   64                                                  
CONECT   27   26   29   28                                                  
CONECT   28   27   65   66   67                                             
CONECT   29   27   31   30                                                  
CONECT   30   29                                                            
CONECT   31   32   29   68   69                                             
CONECT   32   31    6   70   25                                             
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    5                                                            
CONECT   37    5                                                            
CONECT   38    7                                                            
CONECT   39    8                                                            
CONECT   40    9                                                            
CONECT   41   11                                                            
CONECT   42   11                                                            
CONECT   43   11                                                            
CONECT   44   12                                                            
CONECT   45   12                                                            
CONECT   46   13                                                            
CONECT   47   13                                                            
CONECT   48   14                                                            
CONECT   49   14                                                            
CONECT   50   16                                                            
CONECT   51   16                                                            
CONECT   52   16                                                            
CONECT   53   17                                                            
CONECT   54   17                                                            
CONECT   55   17                                                            
CONECT   56   18                                                            
CONECT   57   19                                                            
CONECT   58   20                                                            
CONECT   59   22                                                            
CONECT   60   22                                                            
CONECT   61   22                                                            
CONECT   62   23                                                            
CONECT   63   25                                                            
CONECT   64   26                                                            
CONECT   65   28                                                            
CONECT   66   28                                                            
CONECT   67   28                                                            
CONECT   68   31                                                            
CONECT   69   31                                                            
CONECT   70   32                                                            
MASTER        0    0    0    0    0    0    0    0   70    0  146    0
END

RDKit          3D

70 73  0  0  0  0  0  0  0  0999 V2000
    3.2653    3.8051    0.9687 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1451    2.4217    1.5309 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4809    1.4067    0.9372 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6054    2.4779    2.7782 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3710    1.2162    3.4109 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9517    0.7840    3.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6602   -0.2143    2.2946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7457   -0.6864    1.9913 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0081   -0.9962    0.4808 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1038    0.2077   -0.5709 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4025    1.0286   -0.3797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1063    1.1662   -0.4440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2522    2.1578   -1.5978 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3363    1.4559   -2.9459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8349    0.4836   -3.2322 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4233   -0.3444   -4.4816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0987    1.2704   -3.6302 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.7603    2.6589    4.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9794    3.3495    5.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1657    1.4654    3.9272 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2742    4.2590    0.8895 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1011    0.4610    3.0948 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5266    1.3515    4.4871 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2932    0.5005   -0.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0368    1.7434    0.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1680    2.7424   -1.4456 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2835    0.8994   -2.9742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4061    2.2109   -3.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5309    0.7024    4.5473 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4435    3.5186    3.6067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6532    2.9118    2.3532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1243    1.5207    4.9863 H   0  0  0  0  0  0  0  0  0  0  0  0
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  6  5  1  0
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 26 64  1  0
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  1 33  1  0
  1 34  1  0
  1 35  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₈O₅

Average Mass

442.5960 Da

Monoisotopic Mass

442.27192 Da

IUPAC Name

[(2R,4aR,8aR)-2-[(1S,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-7-methyl-6-oxo-4a,5,6,8a-tetrahydro-2H-chromen-4-yl]methyl acetate

Traditional Name

[(2R,4aR,8aR)-2-[(1S,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyl-4a,6,7,8-tetrahydro-1H-naphthalen-1-yl]-7-methyl-6-oxo-2,4a,5,8a-tetrahydrochromen-4-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C27H38O5/c1-16-12-21-19(14-20(16)29)18(15-31-17(2)28)13-22(32-21)24-26(5)10-7-9-25(3,4)23(26)8-11-27(24,6)30/h8,11-13,19,21-24,30H,7,9-10,14-15H2,1-6H3/t19-,21-,22-,23+,24-,26+,27-/m1/s1

InChI Key

WQWLFFAOBHUZOZ-RTEGDMPBSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₆D₆, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₆D₆, 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
Cadlina luteomarginata	JEOL database	Daoust, J. et al, Org. Lett. 12, 3208 (2010).
Sponge Phorbas sp.	JEOL database	Daoust, J. et al, Org. Lett. 12, 3208 (2010).

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	4.17	ALOGPS
logP	3.62	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	14.31	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	126.06 m³·mol⁻¹	ChemAxon
Polarizability	49.26 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28287844

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46867460

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yanagihara M, Murai K, Kishimoto N, Abe T, Misumi S, Arisawa M: Total Synthesis and Biological Evaluation of the Potent HIV Latency-Reversing Agent Ansellone A and its Analogues. Org Lett. 2021 Mar 5;23(5):1720-1725. doi: 10.1021/acs.orglett.1c00151. Epub 2021 Feb 11. [PubMed:33570413 ]
Zhang W, Yao H, Yu J, Zhang Z, Tong R: Total Syntheses of Sesterterpenoid Ansellones A and B, and Phorbadione. Angew Chem Int Ed Engl. 2017 Apr 18;56(17):4787-4791. doi: 10.1002/anie.201701879. Epub 2017 Mar 28. [PubMed:28371092 ]
Wang M, Tietjen I, Chen M, Williams DE, Daoust J, Brockman MA, Andersen RJ: Sesterterpenoids Isolated from the Sponge Phorbas sp. Activate Latent HIV-1 Provirus Expression. J Org Chem. 2016 Nov 18;81(22):11324-11334. doi: 10.1021/acs.joc.6b02312. Epub 2016 Nov 4. [PubMed:27768313 ]
Daoust J, Fontana A, Merchant CE, de Voogd NJ, Patrick BO, Kieffer TJ, Andersen RJ: Ansellone A, a sesterterpenoid isolated from the nudibranch Cadlina luteromarginata and the sponge Phorbas sp., activates the cAMP signaling pathway. Org Lett. 2010 Jul 16;12(14):3208-11. doi: 10.1021/ol101151f. [PubMed:20560657 ]
Daoust, J. et al. (2010). Daoust, J. et al, Org. Lett. 12, 3208 (2010).. Org. Lett..

Showing NP-Card for ansellone A (NP0039820)

MOL for NP0039820 (ansellone A)

3D MOL for NP0039820 (ansellone A)

3D SDF for NP0039820 (ansellone A)

3D-SDF for NP0039820 (ansellone A)

PDB for NP0039820 (ansellone A)

3D PDB for NP0039820 (ansellone A)

SMILES for NP0039820 (ansellone A)

INCHI for NP0039820 (ansellone A)

Structure for NP0039820 (ansellone A)

3D Structure for NP0039820 (ansellone A)