NP-MRD: Showing NP-Card for Neosarcodonin O (NP0005382)

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Record Information

Version

2.0

Created at

2020-12-09 02:38:28 UTC

Updated at

2021-07-15 16:51:50 UTC

NP-MRD ID

NP0005382

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Neosarcodonin O

Provided By

NPAtlas

Description

(3AR,5aR,6R,7S)-6-hydroxy-7-methoxy-3a,5a-dimethyl-1-(propan-2-yl)-2H,3H,3aH,4H,5H,5aH,6H,7H,10H,10aH-cyclohepta[e]indene-8-carbaldehyde belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Neosarcodonin O is found in Sarcodon scabrosus. Neosarcodonin O was first documented in 2004 (PMID: 15215604). Based on a literature review very few articles have been published on (3aR,5aR,6R,7S)-6-hydroxy-7-methoxy-3a,5a-dimethyl-1-(propan-2-yl)-2H,3H,3aH,4H,5H,5aH,6H,7H,10H,10aH-cyclohepta[e]indene-8-carbaldehyde.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118183D          

 56 58  0  0  0  0            999 V2000
    4.9595    0.4244    1.6155 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4395    0.2178    0.3505 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0696    0.4845    0.3205 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7418    1.4945   -0.7221 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8366    1.9337   -1.5489 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5969    2.7890   -2.4448 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5420    1.9848   -0.9157 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3371    1.5837   -0.0996 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0134    0.1543   -0.3131 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4229   -0.2290   -0.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5694    0.1573    0.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8478    1.2935    1.1266 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8551    1.7790    2.1108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7757    2.3348    0.5494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7289   -0.7129   -0.2288 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0829   -1.9508   -0.6299 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.5962   -1.3666   -2.4765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7958   -2.6012   -0.4373 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5971   -2.1904   -0.5773 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9061   -0.8763    0.2023 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7279   -1.0988    1.6659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3711   -0.7722   -0.0828 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7024   -1.1569   -1.3807 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4192   -0.2701    2.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0417    0.1801    1.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4664    2.6980   -1.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4661    2.2069   -0.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6323    0.8173    1.8796 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3790    2.7343    1.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2812    1.9628    3.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5192   -1.6916   -3.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4098   -0.3247   -2.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1001   -2.8216    0.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3099   -0.5834   -2.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  2  0  0  0  0
  4  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
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 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23  3  1  0  0  0  0
 21  9  1  0  0  0  0
 17 10  1  0  0  0  0
  1 25  1  0  0  0  0
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  1 27  1  0  0  0  0
  3 28  1  1  0  0  0
  5 29  1  0  0  0  0
  7 30  1  0  0  0  0
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  8 32  1  0  0  0  0
  9 33  1  6  0  0  0
 12 34  1  1  0  0  0
 13 35  1  0  0  0  0
 13 36  1  0  0  0  0
 13 37  1  0  0  0  0
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 23 55  1  1  0  0  0
 24 56  1  0  0  0  0
M  END

     RDKit          3D

 56 58  0  0  0  0  0  0  0  0999 V2000
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   -0.0134    0.1543   -0.3131 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306242118183D          

 56 58  0  0  0  0            999 V2000
    4.9595    0.4244    1.6155 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4395    0.2178    0.3505 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0696    0.4845    0.3205 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7418    1.4945   -0.7221 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8366    1.9337   -1.5489 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6674    1.8390    0.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1885    0.0874   -1.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6323    0.8173    1.8796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0914    1.0048    2.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3790    2.7343    1.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2812    1.9628    3.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3474    2.8929    1.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4472    1.8050   -0.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1447    3.0081   -0.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5092   -0.7929    0.5543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1824   -0.1994   -1.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6396   -2.3927   -1.4998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0690   -2.7070    0.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5192   -1.6916   -3.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7953   -2.0657   -2.8465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4098   -0.3247   -2.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1001   -2.8216    0.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9751   -3.5080   -1.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8356   -1.9621   -1.6255 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3149   -2.9344   -0.1339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3473   -1.2426    1.9044 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3370   -1.9836    1.9898 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0558   -0.1835    2.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8363   -1.5842    0.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3099   -0.5834   -2.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  2  0  0  0  0
  4  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23  3  1  0  0  0  0
 21  9  1  0  0  0  0
 17 10  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
  3 28  1  1  0  0  0
  5 29  1  0  0  0  0
  7 30  1  0  0  0  0
  8 31  1  0  0  0  0
  8 32  1  0  0  0  0
  9 33  1  6  0  0  0
 12 34  1  1  0  0  0
 13 35  1  0  0  0  0
 13 36  1  0  0  0  0
 13 37  1  0  0  0  0
 14 38  1  0  0  0  0
 14 39  1  0  0  0  0
 14 40  1  0  0  0  0
 15 41  1  0  0  0  0
 15 42  1  0  0  0  0
 16 43  1  0  0  0  0
 16 44  1  0  0  0  0
 18 45  1  0  0  0  0
 18 46  1  0  0  0  0
 18 47  1  0  0  0  0
 19 48  1  0  0  0  0
 19 49  1  0  0  0  0
 20 50  1  0  0  0  0
 20 51  1  0  0  0  0
 22 52  1  0  0  0  0
 22 53  1  0  0  0  0
 22 54  1  0  0  0  0
 23 55  1  1  0  0  0
 24 56  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0005382

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])[C@@]([H])(OC([H])([H])[H])C(C([H])=O)=C([H])C([H])([H])[C@]2([H])C3=C(C([H])([H])C([H])([H])[C@]3(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]12C([H])([H])[H])C([H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O3/c1-13(2)15-8-9-20(3)10-11-21(4)16(17(15)20)7-6-14(12-22)18(24-5)19(21)23/h6,12-13,16,18-19,23H,7-11H2,1-5H3/t16-,18+,19+,20-,21-/m1/s1

> <INCHI_KEY>
CSMSQWRDDWOVOS-BNWQVIHTSA-N

> <FORMULA>
C21H32O3

> <MOLECULAR_WEIGHT>
332.484

> <EXACT_MASS>
332.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
38.503287910487366

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,5aR,6R,7S)-6-hydroxy-7-methoxy-3a,5a-dimethyl-1-(propan-2-yl)-2H,3H,3aH,4H,5H,5aH,6H,7H,10H,10aH-cyclohepta[e]indene-8-carbaldehyde

> <ALOGPS_LOGP>
4.33

> <JCHEM_LOGP>
3.243610273000001

> <ALOGPS_LOGS>
-4.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.655287955423365

> <JCHEM_PKA_STRONGEST_BASIC>
-3.38697704829782

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
97.49640000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.90e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,5aR,6R,7S)-6-hydroxy-1-isopropyl-7-methoxy-3a,5a-dimethyl-2H,3H,4H,5H,6H,7H,10H,10aH-cyclohepta[e]indene-8-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 56 58  0  0  0  0  0  0  0  0999 V2000
    4.9595    0.4244    1.6155 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4395    0.2178    0.3505 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0696    0.4845    0.3205 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7418    1.4945   -0.7221 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8366    1.9337   -1.5489 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5969    2.7890   -2.4448 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5420    1.9848   -0.9157 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3371    1.5837   -0.0996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0134    0.1543   -0.3131 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4229   -0.2290   -0.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5694    0.1573    0.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8478    1.2935    1.1266 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8551    1.7790    2.1108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7757    2.3348    0.5494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7289   -0.7129   -0.2288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0829   -1.9508   -0.6299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7029   -1.5259   -1.0082 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5962   -1.3666   -2.4765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7958   -2.6012   -0.4373 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5971   -2.1904   -0.5773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9061   -0.8763    0.2023 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7279   -1.0988    1.6659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3711   -0.7722   -0.0828 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7024   -1.1569   -1.3807 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4192   -0.2701    2.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8262    1.4852    1.8769 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0417    0.1801    1.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7588    0.7929    1.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8420    1.5826   -1.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4664    2.6980   -1.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4661    2.2069   -0.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6674    1.8390    0.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1885    0.0874   -1.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6323    0.8173    1.8796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0914    1.0048    2.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3790    2.7343    1.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2812    1.9628    3.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3474    2.8929    1.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4472    1.8050   -0.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1447    3.0081   -0.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5092   -0.7929    0.5543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1824   -0.1994   -1.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6396   -2.3927   -1.4998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0690   -2.7070    0.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5192   -1.6916   -3.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7953   -2.0657   -2.8465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4098   -0.3247   -2.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1001   -2.8216    0.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9751   -3.5080   -1.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8356   -1.9621   -1.6255 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3149   -2.9344   -0.1339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3473   -1.2426    1.9044 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3370   -1.9836    1.9898 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0558   -0.1835    2.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8363   -1.5842    0.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3099   -0.5834   -2.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  4  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 11 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  1  0
 23  3  1  0
 21  9  1  0
 17 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  1
  5 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  6
 12 34  1  1
 13 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 22 52  1  0
 22 53  1  0
 22 54  1  0
 23 55  1  1
 24 56  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       4.960   0.424   1.615  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.439   0.218   0.351  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.070   0.485   0.321  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.742   1.494  -0.722  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.837   1.934  -1.549  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.597   2.789  -2.445  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.542   1.985  -0.916  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.337   1.584  -0.100  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.013   0.154  -0.313  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.423  -0.229  -0.261  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.569   0.157   0.263  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.848   1.294   1.127  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.855   1.779   2.111  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.776   2.335   0.549  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.729  -0.713  -0.229  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.083  -1.951  -0.630  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.703  -1.526  -1.008  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.596  -1.367  -2.477  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.796  -2.601  -0.437  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.597  -2.190  -0.577  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.906  -0.876   0.202  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.728  -1.099   1.666  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.371  -0.772  -0.083  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.702  -1.157  -1.381  0.00  0.00           O+0
HETATM   25  H   UNK     0       4.419  -0.270   2.304  0.00  0.00           H+0
HETATM   26  H   UNK     0       4.826   1.485   1.877  0.00  0.00           H+0
HETATM   27  H   UNK     0       6.042   0.180   1.589  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.759   0.793   1.323  0.00  0.00           H+0
HETATM   29  H   UNK     0       4.842   1.583  -1.454  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.466   2.698  -1.700  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.466   2.207  -0.514  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.667   1.839   0.926  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.189   0.087  -1.468  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.632   0.817   1.880  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.091   1.005   2.295  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.379   2.734   1.794  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.281   1.963   3.140  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.347   2.893   1.280  0.00  0.00           H+0
HETATM   39  H   UNK     0      -4.447   1.805  -0.157  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.145   3.008  -0.076  0.00  0.00           H+0
HETATM   41  H   UNK     0      -4.509  -0.793   0.554  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.182  -0.199  -1.106  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.640  -2.393  -1.500  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.069  -2.707   0.217  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.519  -1.692  -3.020  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.795  -2.066  -2.846  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.410  -0.325  -2.814  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.100  -2.822   0.603  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.975  -3.508  -1.021  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.836  -1.962  -1.626  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.315  -2.934  -0.134  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.347  -1.243   1.904  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.337  -1.984   1.990  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.056  -0.184   2.193  0.00  0.00           H+0
HETATM   55  H   UNK     0       2.836  -1.584   0.562  0.00  0.00           H+0
HETATM   56  H   UNK     0       2.310  -0.583  -2.074  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   23   28                                             
CONECT    4    3    5    7                                                  
CONECT    5    4    6   29                                                  
CONECT    6    5                                                            
CONECT    7    4    8   30                                                  
CONECT    8    7    9   31   32                                             
CONECT    9    8   10   21   33                                             
CONECT   10    9   11   17                                                  
CONECT   11   10   12   15                                                  
CONECT   12   11   13   14   34                                             
CONECT   13   12   35   36   37                                             
CONECT   14   12   38   39   40                                             
CONECT   15   11   16   41   42                                             
CONECT   16   15   17   43   44                                             
CONECT   17   16   18   19   10                                             
CONECT   18   17   45   46   47                                             
CONECT   19   17   20   48   49                                             
CONECT   20   19   21   50   51                                             
CONECT   21   20   22   23    9                                             
CONECT   22   21   52   53   54                                             
CONECT   23   21   24    3   55                                             
CONECT   24   23   56                                                       
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    3                                                            
CONECT   29    5                                                            
CONECT   30    7                                                            
CONECT   31    8                                                            
CONECT   32    8                                                            
CONECT   33    9                                                            
CONECT   34   12                                                            
CONECT   35   13                                                            
CONECT   36   13                                                            
CONECT   37   13                                                            
CONECT   38   14                                                            
CONECT   39   14                                                            
CONECT   40   14                                                            
CONECT   41   15                                                            
CONECT   42   15                                                            
CONECT   43   16                                                            
CONECT   44   16                                                            
CONECT   45   18                                                            
CONECT   46   18                                                            
CONECT   47   18                                                            
CONECT   48   19                                                            
CONECT   49   19                                                            
CONECT   50   20                                                            
CONECT   51   20                                                            
CONECT   52   22                                                            
CONECT   53   22                                                            
CONECT   54   22                                                            
CONECT   55   23                                                            
CONECT   56   24                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  116    0
END

RDKit          3D

56 58  0  0  0  0  0  0  0  0999 V2000
    4.9595    0.4244    1.6155 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4395    0.2178    0.3505 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0696    0.4845    0.3205 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7418    1.4945   -0.7221 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8366    1.9337   -1.5489 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5969    2.7890   -2.4448 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5420    1.9848   -0.9157 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3371    1.5837   -0.0996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0134    0.1543   -0.3131 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4229   -0.2290   -0.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5694    0.1573    0.2632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8478    1.2935    1.1266 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8551    1.7790    2.1108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7757    2.3348    0.5494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7289   -0.7129   -0.2288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0829   -1.9508   -0.6299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7029   -1.5259   -1.0082 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5962   -1.3666   -2.4765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7958   -2.6012   -0.4373 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5971   -2.1904   -0.5773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9061   -0.8763    0.2023 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7279   -1.0988    1.6659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3711   -0.7722   -0.0828 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7024   -1.1569   -1.3807 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4192   -0.2701    2.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8262    1.4852    1.8769 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0417    0.1801    1.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7588    0.7929    1.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8420    1.5826   -1.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4664    2.6980   -1.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4661    2.2069   -0.5141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6674    1.8390    0.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1885    0.0874   -1.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6323    0.8173    1.8796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0914    1.0048    2.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3790    2.7343    1.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2812    1.9628    3.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3474    2.8929    1.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4472    1.8050   -0.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1447    3.0081   -0.0760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5092   -0.7929    0.5543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1824   -0.1994   -1.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6396   -2.3927   -1.4998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0690   -2.7070    0.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5192   -1.6916   -3.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7953   -2.0657   -2.8465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4098   -0.3247   -2.8144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1001   -2.8216    0.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9751   -3.5080   -1.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8356   -1.9621   -1.6255 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3149   -2.9344   -0.1339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3473   -1.2426    1.9044 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3370   -1.9836    1.9898 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0558   -0.1835    2.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8363   -1.5842    0.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3099   -0.5834   -2.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  4  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 11 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  1  0
 23  3  1  0
 21  9  1  0
 17 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  1
  5 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
  9 33  1  6
 12 34  1  1
 13 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  0
 20 51  1  0
 22 52  1  0
 22 53  1  0
 22 54  1  0
 23 55  1  1
 24 56  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₁H₃₂O₃

Average Mass

332.4840 Da

Monoisotopic Mass

332.23514 Da

IUPAC Name

(3aR,5aR,6R,7S)-6-hydroxy-7-methoxy-3a,5a-dimethyl-1-(propan-2-yl)-2H,3H,3aH,4H,5H,5aH,6H,7H,10H,10aH-cyclohepta[e]indene-8-carbaldehyde

Traditional Name

(3aR,5aR,6R,7S)-6-hydroxy-1-isopropyl-7-methoxy-3a,5a-dimethyl-2H,3H,4H,5H,6H,7H,10H,10aH-cyclohepta[e]indene-8-carbaldehyde

CAS Registry Number

Not Available

SMILES

CO[C@@H]1[C@H](O)[C@]2(C)CC[C@@]3(C)CCC(C(C)C)=C3C2CC=C1C=O

InChI Identifier

InChI=1S/C21H32O3/c1-13(2)15-8-9-20(3)10-11-21(4)16(17(15)20)7-6-14(12-22)18(24-5)19(21)23/h6,12-13,16,18-19,23H,7-11H2,1-5H3/t16?,18-,19-,20+,21+/m0/s1

InChI Key

CSMSQWRDDWOVOS-BNWQVIHTSA-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
Sarcodon scabrosus	NPAtlas	15215604

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Secondary alcohol
Ether
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Alcohol
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	4.33	ALOGPS
logP	3.24	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	13.66	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	97.5 m³·mol⁻¹	ChemAxon
Polarizability	38.5 Å³	ChemAxon
Number of Rings	3	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

NPAtlas ID

NPA009823

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78437424

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139585813

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kamo T, Imura Y, Hagio T, Makabe H, Shibata H, Hirota M: Anti-inflammatory cyathane diterpenoids from Sarcodon scabrosus. Biosci Biotechnol Biochem. 2004 Jun;68(6):1362-5. doi: 10.1271/bbb.68.1362. [PubMed:15215604 ]

Showing NP-Card for Neosarcodonin O (NP0005382)

MOL for NP0005382 (Neosarcodonin O)

3D MOL for NP0005382 (Neosarcodonin O)

3D SDF for NP0005382 (Neosarcodonin O)

3D-SDF for NP0005382 (Neosarcodonin O)

PDB for NP0005382 (Neosarcodonin O)

3D PDB for NP0005382 (Neosarcodonin O)

SMILES for NP0005382 (Neosarcodonin O)

INCHI for NP0005382 (Neosarcodonin O)

Structure for NP0005382 (Neosarcodonin O)

3D Structure for NP0005382 (Neosarcodonin O)