NP-MRD: Showing NP-Card for Macrophyllic acid D (NP0025580)

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Record Information

Version

2.0

Created at

2021-06-19 17:39:54 UTC

Updated at

2021-06-29 23:50:37 UTC

NP-MRD ID

NP0025580

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Macrophyllic acid D

Provided By

JEOL Database JEOL Logo

Description

Macrophyllic acid d is also known as macrophyllate D. Macrophyllic acid D is found in Inula macrophylla. Macrophyllic acid D was first documented in 2001 (Su, B.-N., et al.). Based on a literature review very few articles have been published on Macrophyllic acid d.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119393D          

 40 42  0  0  0  0            999 V2000
    2.1876   -1.8716   -0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4515   -0.7881    0.7042 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6059   -1.2477    1.8635 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6905   -0.4630    1.9984 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4235    1.0377    1.9831 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1580    1.5429    0.6359 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7173    2.9612    0.8904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9789    1.6111   -0.4222 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4860    1.9418   -1.8351 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6089    0.9638   -2.2890 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1037    1.3345   -3.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0069    0.5279   -4.7335 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5135    0.9623   -6.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0409    2.0216   -6.3201 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3158   -0.0022   -6.9551 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7679    0.9477   -1.2816 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2559    0.6179    0.1029 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2963    0.3293    1.0430 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4609   -2.6856    0.6509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5529   -2.2863   -0.8184 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1182   -1.5162   -0.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3523   -2.3088    1.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1882   -1.1668    2.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3815   -0.7428    1.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1792   -0.7381    2.9405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3533    1.5737    2.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2716    1.2684    2.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1233    3.4238   -0.0136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5305    2.9370    1.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0627    3.6267    1.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4998    0.6479   -0.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7309    2.3516   -0.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1205    2.9754   -1.8713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3370    1.8934   -2.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1691   -0.0432   -2.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5630    2.3174   -3.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5606   -0.4574   -4.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6830    0.3805   -7.7789 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292    0.2349   -1.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2722    1.9221   -1.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0  0  0  0
 16 10  1  0  0  0  0
 10  9  1  0  0  0  0
  9  8  1  0  0  0  0
  6 17  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  4  3  1  0  0  0  0
 12 13  1  0  0  0  0
  4  5  1  0  0  0  0
 13 15  1  0  0  0  0
  3  2  1  0  0  0  0
 13 14  2  0  0  0  0
  2 17  1  0  0  0  0
  2  1  1  6  0  0  0
  6  5  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
 17 18  1  1  0  0  0
  2 18  1  0  0  0  0
  4 24  1  0  0  0  0
  4 25  1  0  0  0  0
  3 22  1  0  0  0  0
  3 23  1  0  0  0  0
  5 26  1  0  0  0  0
  5 27  1  0  0  0  0
 16 39  1  0  0  0  0
 16 40  1  0  0  0  0
 10 35  1  6  0  0  0
  9 33  1  0  0  0  0
  9 34  1  0  0  0  0
  8 31  1  0  0  0  0
  8 32  1  0  0  0  0
 11 36  1  0  0  0  0
 12 37  1  0  0  0  0
 15 38  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  7 28  1  0  0  0  0
  7 29  1  0  0  0  0
  7 30  1  0  0  0  0
M  END

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
    2.1876   -1.8716   -0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4515   -0.7881    0.7042 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6059   -1.2477    1.8635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6905   -0.4630    1.9984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4235    1.0377    1.9831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1580    1.5429    0.6359 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7173    2.9612    0.8904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9789    1.6111   -0.4222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4860    1.9418   -1.8351 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6089    0.9638   -2.2890 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1037    1.3345   -3.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0069    0.5279   -4.7335 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5135    0.9623   -6.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0409    2.0216   -6.3201 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3158   -0.0022   -6.9551 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7679    0.9477   -1.2816 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2559    0.6179    0.1029 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2963    0.3293    1.0430 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4609   -2.6856    0.6509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5529   -2.2863   -0.8184 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1182   -1.5162   -0.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3523   -2.3088    1.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1882   -1.1668    2.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3815   -0.7428    1.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1792   -0.7381    2.9405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3533    1.5737    2.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2716    1.2684    2.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1233    3.4238   -0.0136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5305    2.9370    1.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0627    3.6267    1.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4998    0.6479   -0.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7309    2.3516   -0.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1205    2.9754   -1.8713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3370    1.8934   -2.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1691   -0.0432   -2.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5630    2.3174   -3.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5606   -0.4574   -4.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6830    0.3805   -7.7789 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292    0.2349   -1.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2722    1.9221   -1.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 10  1  0
 10  9  1  0
  9  8  1  0
  6 17  1  0
 10 11  1  0
 11 12  2  0
  4  3  1  0
 12 13  1  0
  4  5  1  0
 13 15  1  0
  3  2  1  0
 13 14  2  0
  2 17  1  0
  2  1  1  6
  6  5  1  0
  6  7  1  1
  6  8  1  0
 17 18  1  1
  2 18  1  0
  4 24  1  0
  4 25  1  0
  3 22  1  0
  3 23  1  0
  5 26  1  0
  5 27  1  0
 16 39  1  0
 16 40  1  0
 10 35  1  6
  9 33  1  0
  9 34  1  0
  8 31  1  0
  8 32  1  0
 11 36  1  0
 12 37  1  0
 15 38  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
M  END


  Mrv1652306192119393D          

 40 42  0  0  0  0            999 V2000
    2.1876   -1.8716   -0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4515   -0.7881    0.7042 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6059   -1.2477    1.8635 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6905   -0.4630    1.9984 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4235    1.0377    1.9831 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1580    1.5429    0.6359 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7173    2.9612    0.8904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9789    1.6111   -0.4222 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4860    1.9418   -1.8351 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6089    0.9638   -2.2890 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1037    1.3345   -3.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0069    0.5279   -4.7335 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5135    0.9623   -6.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0409    2.0216   -6.3201 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3158   -0.0022   -6.9551 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7679    0.9477   -1.2816 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2559    0.6179    0.1029 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2963    0.3293    1.0430 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4609   -2.6856    0.6509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5529   -2.2863   -0.8184 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1182   -1.5162   -0.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3523   -2.3088    1.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1882   -1.1668    2.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3815   -0.7428    1.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1792   -0.7381    2.9405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3533    1.5737    2.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2716    1.2684    2.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1233    3.4238   -0.0136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5305    2.9370    1.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0627    3.6267    1.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4998    0.6479   -0.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7309    2.3516   -0.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1205    2.9754   -1.8713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3370    1.8934   -2.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1691   -0.0432   -2.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5630    2.3174   -3.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5606   -0.4574   -4.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6830    0.3805   -7.7789 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292    0.2349   -1.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2722    1.9221   -1.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0  0  0  0
 16 10  1  0  0  0  0
 10  9  1  0  0  0  0
  9  8  1  0  0  0  0
  6 17  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  4  3  1  0  0  0  0
 12 13  1  0  0  0  0
  4  5  1  0  0  0  0
 13 15  1  0  0  0  0
  3  2  1  0  0  0  0
 13 14  2  0  0  0  0
  2 17  1  0  0  0  0
  2  1  1  6  0  0  0
  6  5  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
 17 18  1  1  0  0  0
  2 18  1  0  0  0  0
  4 24  1  0  0  0  0
  4 25  1  0  0  0  0
  3 22  1  0  0  0  0
  3 23  1  0  0  0  0
  5 26  1  0  0  0  0
  5 27  1  0  0  0  0
 16 39  1  0  0  0  0
 16 40  1  0  0  0  0
 10 35  1  6  0  0  0
  9 33  1  0  0  0  0
  9 34  1  0  0  0  0
  8 31  1  0  0  0  0
  8 32  1  0  0  0  0
 11 36  1  0  0  0  0
 12 37  1  0  0  0  0
 15 38  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  7 28  1  0  0  0  0
  7 29  1  0  0  0  0
  7 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025580

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C(\[H])=C(/[H])[C@]1([H])C([H])([H])C([H])([H])[C@@]2(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@@]3(O[C@]23C1([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O3/c1-13-7-3-8-14(2)15(13,18-14)10-11(6-9-13)4-5-12(16)17/h4-5,11H,3,6-10H2,1-2H3,(H,16,17)/b5-4+/t11-,13-,14+,15-/m1/s1

> <INCHI_KEY>
CZFYTAOSDOKUHD-OHSMQCEASA-N

> <FORMULA>
C15H22O3

> <MOLECULAR_WEIGHT>
250.338

> <EXACT_MASS>
250.156894568

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
28.1352921900769

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-[(4aR,7R,8aR,8bS)-4a,8b-dimethyl-octahydro-2H-naphtho[4,4a-b]oxiren-7-yl]prop-2-enoic acid

> <ALOGPS_LOGP>
3.64

> <JCHEM_LOGP>
3.028723749666667

> <ALOGPS_LOGS>
-3.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.851759561433552

> <JCHEM_PKA_STRONGEST_BASIC>
-4.252370370128845

> <JCHEM_POLAR_SURFACE_AREA>
49.83

> <JCHEM_REFRACTIVITY>
69.1051

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.61e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-[(4aR,7R,8aR,8bS)-4a,8b-dimethyl-hexahydro-2H-naphtho[4,4a-b]oxiren-7-yl]prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
    2.1876   -1.8716   -0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4515   -0.7881    0.7042 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6059   -1.2477    1.8635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6905   -0.4630    1.9984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4235    1.0377    1.9831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1580    1.5429    0.6359 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7173    2.9612    0.8904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9789    1.6111   -0.4222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4860    1.9418   -1.8351 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6089    0.9638   -2.2890 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1037    1.3345   -3.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0069    0.5279   -4.7335 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5135    0.9623   -6.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0409    2.0216   -6.3201 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3158   -0.0022   -6.9551 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7679    0.9477   -1.2816 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2559    0.6179    0.1029 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2963    0.3293    1.0430 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4609   -2.6856    0.6509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5529   -2.2863   -0.8184 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1182   -1.5162   -0.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3523   -2.3088    1.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1882   -1.1668    2.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3815   -0.7428    1.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1792   -0.7381    2.9405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3533    1.5737    2.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2716    1.2684    2.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1233    3.4238   -0.0136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5305    2.9370    1.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0627    3.6267    1.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4998    0.6479   -0.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7309    2.3516   -0.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1205    2.9754   -1.8713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3370    1.8934   -2.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1691   -0.0432   -2.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5630    2.3174   -3.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5606   -0.4574   -4.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6830    0.3805   -7.7789 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292    0.2349   -1.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2722    1.9221   -1.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 10  1  0
 10  9  1  0
  9  8  1  0
  6 17  1  0
 10 11  1  0
 11 12  2  0
  4  3  1  0
 12 13  1  0
  4  5  1  0
 13 15  1  0
  3  2  1  0
 13 14  2  0
  2 17  1  0
  2  1  1  6
  6  5  1  0
  6  7  1  1
  6  8  1  0
 17 18  1  1
  2 18  1  0
  4 24  1  0
  4 25  1  0
  3 22  1  0
  3 23  1  0
  5 26  1  0
  5 27  1  0
 16 39  1  0
 16 40  1  0
 10 35  1  6
  9 33  1  0
  9 34  1  0
  8 31  1  0
  8 32  1  0
 11 36  1  0
 12 37  1  0
 15 38  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  7 28  1  0
  7 29  1  0
  7 30  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       2.188  -1.872  -0.029  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.452  -0.788   0.704  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.606  -1.248   1.863  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.691  -0.463   1.998  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.424   1.038   1.983  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.158   1.543   0.636  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.717   2.961   0.890  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.979   1.611  -0.422  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.486   1.942  -1.835  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.609   0.964  -2.289  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.104   1.335  -3.665  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.007   0.528  -4.734  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.514   0.962  -6.043  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.041   2.022  -6.320  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.316  -0.002  -6.955  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.768   0.948  -1.282  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.256   0.618   0.103  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.296   0.329   1.043  0.00  0.00           O+0
HETATM   19  H   UNK     0       2.461  -2.686   0.651  0.00  0.00           H+0
HETATM   20  H   UNK     0       1.553  -2.286  -0.818  0.00  0.00           H+0
HETATM   21  H   UNK     0       3.118  -1.516  -0.482  0.00  0.00           H+0
HETATM   22  H   UNK     0       0.352  -2.309   1.750  0.00  0.00           H+0
HETATM   23  H   UNK     0       1.188  -1.167   2.790  0.00  0.00           H+0
HETATM   24  H   UNK     0      -1.381  -0.743   1.197  0.00  0.00           H+0
HETATM   25  H   UNK     0      -1.179  -0.738   2.941  0.00  0.00           H+0
HETATM   26  H   UNK     0      -1.353   1.574   2.212  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.272   1.268   2.802  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.123   3.424  -0.014  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.531   2.937   1.625  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.063   3.627   1.278  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.500   0.648  -0.478  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.731   2.352  -0.122  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.121   2.975  -1.871  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.337   1.893  -2.527  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.169  -0.043  -2.318  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.563   2.317  -3.775  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.561  -0.457  -4.679  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.683   0.381  -7.779  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.529   0.235  -1.615  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.272   1.922  -1.261  0.00  0.00           H+0
CONECT    1    2   19   20   21                                             
CONECT    2    3   17    1   18                                             
CONECT    3    4    2   22   23                                             
CONECT    4    3    5   24   25                                             
CONECT    5    4    6   26   27                                             
CONECT    6   17    5    7    8                                             
CONECT    7    6   28   29   30                                             
CONECT    8    9    6   31   32                                             
CONECT    9   10    8   33   34                                             
CONECT   10   16    9   11   35                                             
CONECT   11   10   12   36                                                  
CONECT   12   11   13   37                                                  
CONECT   13   12   15   14                                                  
CONECT   14   13                                                            
CONECT   15   13   38                                                       
CONECT   16   17   10   39   40                                             
CONECT   17   16    6    2   18                                             
CONECT   18   17    2                                                       
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    3                                                            
CONECT   23    3                                                            
CONECT   24    4                                                            
CONECT   25    4                                                            
CONECT   26    5                                                            
CONECT   27    5                                                            
CONECT   28    7                                                            
CONECT   29    7                                                            
CONECT   30    7                                                            
CONECT   31    8                                                            
CONECT   32    8                                                            
CONECT   33    9                                                            
CONECT   34    9                                                            
CONECT   35   10                                                            
CONECT   36   11                                                            
CONECT   37   12                                                            
CONECT   38   15                                                            
CONECT   39   16                                                            
CONECT   40   16                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   84    0
END

RDKit          3D

40 42  0  0  0  0  0  0  0  0999 V2000
    2.1876   -1.8716   -0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4515   -0.7881    0.7042 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6059   -1.2477    1.8635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6905   -0.4630    1.9984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4235    1.0377    1.9831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1580    1.5429    0.6359 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7173    2.9612    0.8904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9789    1.6111   -0.4222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4860    1.9418   -1.8351 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6089    0.9638   -2.2890 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1037    1.3345   -3.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0069    0.5279   -4.7335 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5135    0.9623   -6.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0409    2.0216   -6.3201 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3158   -0.0022   -6.9551 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7679    0.9477   -1.2816 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2559    0.6179    0.1029 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2963    0.3293    1.0430 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4609   -2.6856    0.6509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5529   -2.2863   -0.8184 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1182   -1.5162   -0.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3523   -2.3088    1.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1882   -1.1668    2.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3815   -0.7428    1.1966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1792   -0.7381    2.9405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3533    1.5737    2.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2716    1.2684    2.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1233    3.4238   -0.0136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5305    2.9370    1.6250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0627    3.6267    1.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4998    0.6479   -0.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7309    2.3516   -0.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1205    2.9754   -1.8713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3370    1.8934   -2.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1691   -0.0432   -2.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5630    2.3174   -3.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5606   -0.4574   -4.6788 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6830    0.3805   -7.7789 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292    0.2349   -1.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2722    1.9221   -1.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 10  1  0
 10  9  1  0
  9  8  1  0
  6 17  1  0
 10 11  1  0
 11 12  2  0
  4  3  1  0
 12 13  1  0
  4  5  1  0
 13 15  1  0
  3  2  1  0
 13 14  2  0
  2 17  1  0
  2  1  1  6
  6  5  1  0
  6  7  1  1
  6  8  1  0
 17 18  1  1
  2 18  1  0
  4 24  1  0
  4 25  1  0
  3 22  1  0
  3 23  1  0
  5 26  1  0
  5 27  1  0
 16 39  1  0
 16 40  1  0
 10 35  1  6
  9 33  1  0
  9 34  1  0
  8 31  1  0
  8 32  1  0
 11 36  1  0
 12 37  1  0
 15 38  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
Macrophyllate D	Generator

Chemical Formula

C₁₅H₂₂O₃

Average Mass

250.3380 Da

Monoisotopic Mass

250.15689 Da

IUPAC Name

(2E)-3-[(4aR,7R,8aR,8bS)-4a,8b-dimethyl-octahydro-2H-naphtho[4,4a-b]oxiren-7-yl]prop-2-enoic acid

Traditional Name

(2E)-3-[(4aR,7R,8aR,8bS)-4a,8b-dimethyl-hexahydro-2H-naphtho[4,4a-b]oxiren-7-yl]prop-2-enoic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C(\[H])=C(/[H])[C@]1([H])C([H])([H])C([H])([H])[C@@]2(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@@]3(O[C@]23C1([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C15H22O3/c1-13-7-3-8-14(2)15(13,18-14)10-11(6-9-13)4-5-12(16)17/h4-5,11H,3,6-10H2,1-2H3,(H,16,17)/b5-4+/t11-,13-,14+,15-/m1/s1

InChI Key

CZFYTAOSDOKUHD-OHSMQCEASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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
Inula macrophylla	JEOL database	Su, B.-N., et al, J. Nat. Prod. 64, 466 (2001)

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	3.64	ALOGPS
logP	3.03	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	4.85	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	69.11 m³·mol⁻¹	ChemAxon
Polarizability	28.14 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00046105

Chemspider ID

10214218

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Su, B.-N., et al. (2001). Su, B.-N., et al, J. Nat. Prod. 64, 466 (2001). J. Nat. Prod..

Showing NP-Card for Macrophyllic acid D (NP0025580)

MOL for NP0025580 (Macrophyllic acid D)

3D MOL for NP0025580 (Macrophyllic acid D)

3D SDF for NP0025580 (Macrophyllic acid D)

3D-SDF for NP0025580 (Macrophyllic acid D)

PDB for NP0025580 (Macrophyllic acid D)

3D PDB for NP0025580 (Macrophyllic acid D)

SMILES for NP0025580 (Macrophyllic acid D)

INCHI for NP0025580 (Macrophyllic acid D)

Structure for NP0025580 (Macrophyllic acid D)

3D Structure for NP0025580 (Macrophyllic acid D)