NP-MRD: Showing NP-Card for 4alpha,13-dihydroxy-5,7(11)-eudesmadien-12,8-olide (NP0041616)

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Record Information

Version

1.0

Created at

2021-06-20 23:29:10 UTC

Updated at

2021-06-30 00:16:14 UTC

NP-MRD ID

NP0041616

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4alpha,13-dihydroxy-5,7(11)-eudesmadien-12,8-olide

Provided By

JEOL Database JEOL Logo

Description

4alpha,13-dihydroxy-5,7(11)-eudesmadien-12,8-olide is found in Inula racemosa. It was first documented in 2012 (Zhang, T., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212101293D          

 39 41  0  0  0  0            999 V2000
   -0.2616   -1.9686    2.5994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5866   -0.4810    2.4284 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0221   -0.4140    2.4353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1237    0.3439    3.6416 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3716    0.6268    3.6527 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7900    1.3368    2.3682 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4303    0.5588    1.0785 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3770   -0.6554    0.9217 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6914    1.5212   -0.1283 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0764    0.9628   -1.4023 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1862    1.8515   -2.5050 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0464    1.9727   -3.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2831    2.5613   -4.1147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0610    1.3330   -2.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4892    1.5061   -2.5757 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3510    1.0122   -1.5597 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3792    0.7992   -1.2066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8430    0.2083    0.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0465    0.0829    1.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8238   -2.3914    3.4411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5654   -2.5399    1.7141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7962   -2.1618    2.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2688    0.5097    2.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6633    1.3014    3.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4112   -0.1622    4.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6115    1.2656    4.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9381   -0.2995    3.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3015    2.3209    2.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8695    1.5322    2.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3972   -0.3290    0.6872 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0518   -1.3257    0.1186 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4520   -1.2545    1.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7653    1.6944   -0.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2682    2.5166    0.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5512    0.0169   -1.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7208    2.5661   -2.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7118    0.9663   -3.5019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2602    1.1307   -1.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8843   -0.1049    0.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 17  1  0  0  0  0
  2 19  1  0  0  0  0
  7  6  1  0  0  0  0
  7 19  1  0  0  0  0
  5  4  1  0  0  0  0
 17 14  2  0  0  0  0
 14 12  1  0  0  0  0
 12 11  1  0  0  0  0
 10 11  1  0  0  0  0
  5  6  1  0  0  0  0
 12 13  2  0  0  0  0
  4  2  1  0  0  0  0
 14 15  1  0  0  0  0
  7  9  1  0  0  0  0
  7  8  1  6  0  0  0
 19 18  2  0  0  0  0
  2  1  1  0  0  0  0
 18 17  1  0  0  0  0
 15 16  1  0  0  0  0
 10  9  1  0  0  0  0
  2  3  1  6  0  0  0
  5 26  1  0  0  0  0
  5 27  1  0  0  0  0
  4 24  1  0  0  0  0
  4 25  1  0  0  0  0
  6 28  1  0  0  0  0
  6 29  1  0  0  0  0
 18 39  1  0  0  0  0
  9 33  1  0  0  0  0
  9 34  1  0  0  0  0
 10 35  1  6  0  0  0
 15 36  1  0  0  0  0
 15 37  1  0  0  0  0
  8 30  1  0  0  0  0
  8 31  1  0  0  0  0
  8 32  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
 16 38  1  0  0  0  0
  3 23  1  0  0  0  0
M  END

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
   -0.2616   -1.9686    2.5994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5866   -0.4810    2.4284 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0221   -0.4140    2.4353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1237    0.3439    3.6416 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3716    0.6268    3.6527 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7900    1.3368    2.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4303    0.5588    1.0785 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3770   -0.6554    0.9217 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6914    1.5212   -0.1283 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0764    0.9628   -1.4023 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1862    1.8515   -2.5050 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0464    1.9727   -3.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2831    2.5613   -4.1147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0610    1.3330   -2.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4892    1.5061   -2.5757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3510    1.0122   -1.5597 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3792    0.7992   -1.2066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8430    0.2083    0.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0465    0.0829    1.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8238   -2.3914    3.4411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5654   -2.5399    1.7141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7962   -2.1618    2.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2688    0.5097    2.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6633    1.3014    3.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4112   -0.1622    4.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6115    1.2656    4.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9381   -0.2995    3.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3015    2.3209    2.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8695    1.5322    2.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3972   -0.3290    0.6872 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0518   -1.3257    0.1186 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4520   -1.2545    1.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7653    1.6944   -0.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2682    2.5166    0.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5512    0.0169   -1.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7208    2.5661   -2.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7118    0.9663   -3.5019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2602    1.1307   -1.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8843   -0.1049    0.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 17  1  0
  2 19  1  0
  7  6  1  0
  7 19  1  0
  5  4  1  0
 17 14  2  0
 14 12  1  0
 12 11  1  0
 10 11  1  0
  5  6  1  0
 12 13  2  0
  4  2  1  0
 14 15  1  0
  7  9  1  0
  7  8  1  6
 19 18  2  0
  2  1  1  0
 18 17  1  0
 15 16  1  0
 10  9  1  0
  2  3  1  6
  5 26  1  0
  5 27  1  0
  4 24  1  0
  4 25  1  0
  6 28  1  0
  6 29  1  0
 18 39  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  6
 15 36  1  0
 15 37  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
 16 38  1  0
  3 23  1  0
M  END


  Mrv1652306212101293D          

 39 41  0  0  0  0            999 V2000
   -0.2616   -1.9686    2.5994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5866   -0.4810    2.4284 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0221   -0.4140    2.4353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1237    0.3439    3.6416 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3716    0.6268    3.6527 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7900    1.3368    2.3682 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4303    0.5588    1.0785 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3770   -0.6554    0.9217 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6914    1.5212   -0.1283 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0764    0.9628   -1.4023 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1862    1.8515   -2.5050 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0464    1.9727   -3.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2831    2.5613   -4.1147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0610    1.3330   -2.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4892    1.5061   -2.5757 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3510    1.0122   -1.5597 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3792    0.7992   -1.2066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8430    0.2083    0.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0465    0.0829    1.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8238   -2.3914    3.4411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5654   -2.5399    1.7141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7962   -2.1618    2.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2688    0.5097    2.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6633    1.3014    3.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4112   -0.1622    4.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6115    1.2656    4.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9381   -0.2995    3.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3015    2.3209    2.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8695    1.5322    2.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3972   -0.3290    0.6872 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0518   -1.3257    0.1186 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4520   -1.2545    1.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7653    1.6944   -0.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2682    2.5166    0.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5512    0.0169   -1.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7208    2.5661   -2.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7118    0.9663   -3.5019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2602    1.1307   -1.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8843   -0.1049    0.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 17  1  0  0  0  0
  2 19  1  0  0  0  0
  7  6  1  0  0  0  0
  7 19  1  0  0  0  0
  5  4  1  0  0  0  0
 17 14  2  0  0  0  0
 14 12  1  0  0  0  0
 12 11  1  0  0  0  0
 10 11  1  0  0  0  0
  5  6  1  0  0  0  0
 12 13  2  0  0  0  0
  4  2  1  0  0  0  0
 14 15  1  0  0  0  0
  7  9  1  0  0  0  0
  7  8  1  6  0  0  0
 19 18  2  0  0  0  0
  2  1  1  0  0  0  0
 18 17  1  0  0  0  0
 15 16  1  0  0  0  0
 10  9  1  0  0  0  0
  2  3  1  6  0  0  0
  5 26  1  0  0  0  0
  5 27  1  0  0  0  0
  4 24  1  0  0  0  0
  4 25  1  0  0  0  0
  6 28  1  0  0  0  0
  6 29  1  0  0  0  0
 18 39  1  0  0  0  0
  9 33  1  0  0  0  0
  9 34  1  0  0  0  0
 10 35  1  6  0  0  0
 15 36  1  0  0  0  0
 15 37  1  0  0  0  0
  8 30  1  0  0  0  0
  8 31  1  0  0  0  0
  8 32  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
 16 38  1  0  0  0  0
  3 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0041616

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C1=C2C([H])=C3[C@@](O[H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@]3(C([H])([H])[H])C([H])([H])[C@]2([H])OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-14-4-3-5-15(2,18)12(14)6-9-10(8-16)13(17)19-11(9)7-14/h6,11,16,18H,3-5,7-8H2,1-2H3/t11-,14+,15+/m0/s1

> <INCHI_KEY>
CXRZREVFSVBXDP-NILFDRSVSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.321

> <EXACT_MASS>
264.136159124

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
28.23758492836373

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5R,8aR,9aS)-5-hydroxy-3-(hydroxymethyl)-5,8a-dimethyl-2H,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one

> <ALOGPS_LOGP>
1.58

> <JCHEM_LOGP>
0.7583792349999996

> <ALOGPS_LOGS>
-2.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.95333947321324

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.986642512648185

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7991140229609398

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
71.3786

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.19e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5R,8aR,9aS)-5-hydroxy-3-(hydroxymethyl)-5,8a-dimethyl-6H,7H,8H,9H,9aH-naphtho[2,3-b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
   -0.2616   -1.9686    2.5994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5866   -0.4810    2.4284 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0221   -0.4140    2.4353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1237    0.3439    3.6416 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3716    0.6268    3.6527 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7900    1.3368    2.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4303    0.5588    1.0785 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3770   -0.6554    0.9217 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6914    1.5212   -0.1283 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0764    0.9628   -1.4023 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1862    1.8515   -2.5050 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0464    1.9727   -3.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2831    2.5613   -4.1147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0610    1.3330   -2.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4892    1.5061   -2.5757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3510    1.0122   -1.5597 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3792    0.7992   -1.2066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8430    0.2083    0.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0465    0.0829    1.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8238   -2.3914    3.4411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5654   -2.5399    1.7141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7962   -2.1618    2.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2688    0.5097    2.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6633    1.3014    3.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4112   -0.1622    4.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6115    1.2656    4.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9381   -0.2995    3.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3015    2.3209    2.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8695    1.5322    2.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3972   -0.3290    0.6872 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0518   -1.3257    0.1186 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4520   -1.2545    1.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7653    1.6944   -0.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2682    2.5166    0.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5512    0.0169   -1.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7208    2.5661   -2.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7118    0.9663   -3.5019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2602    1.1307   -1.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8843   -0.1049    0.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 17  1  0
  2 19  1  0
  7  6  1  0
  7 19  1  0
  5  4  1  0
 17 14  2  0
 14 12  1  0
 12 11  1  0
 10 11  1  0
  5  6  1  0
 12 13  2  0
  4  2  1  0
 14 15  1  0
  7  9  1  0
  7  8  1  6
 19 18  2  0
  2  1  1  0
 18 17  1  0
 15 16  1  0
 10  9  1  0
  2  3  1  6
  5 26  1  0
  5 27  1  0
  4 24  1  0
  4 25  1  0
  6 28  1  0
  6 29  1  0
 18 39  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  6
 15 36  1  0
 15 37  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
 16 38  1  0
  3 23  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      -0.262  -1.969   2.599  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.587  -0.481   2.428  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.022  -0.414   2.435  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.124   0.344   3.642  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.372   0.627   3.653  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.790   1.337   2.368  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.430   0.559   1.079  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.377  -0.655   0.922  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.691   1.521  -0.128  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.076   0.963  -1.402  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.186   1.851  -2.505  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.046   1.973  -3.074  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.283   2.561  -4.115  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.061   1.333  -2.221  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.489   1.506  -2.576  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.351   1.012  -1.560  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.379   0.799  -1.207  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.843   0.208   0.019  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.047   0.083   1.107  0.00  0.00           C+0
HETATM   20  H   UNK     0      -0.824  -2.391   3.441  0.00  0.00           H+0
HETATM   21  H   UNK     0      -0.565  -2.540   1.714  0.00  0.00           H+0
HETATM   22  H   UNK     0       0.796  -2.162   2.784  0.00  0.00           H+0
HETATM   23  H   UNK     0      -2.269   0.510   2.255  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.663   1.301   3.662  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.411  -0.162   4.572  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.611   1.266   4.511  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.938  -0.300   3.791  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.302   2.321   2.354  0.00  0.00           H+0
HETATM   29  H   UNK     0       2.869   1.532   2.401  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.397  -0.329   0.687  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.052  -1.326   0.119  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.452  -1.254   1.831  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.765   1.694  -0.275  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.268   2.517   0.072  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.551   0.017  -1.688  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.721   2.566  -2.723  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.712   0.966  -3.502  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.260   1.131  -1.884  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.884  -0.105   0.051  0.00  0.00           H+0
CONECT    1    2   20   21   22                                             
CONECT    2   19    4    1    3                                             
CONECT    3    2   23                                                       
CONECT    4    5    2   24   25                                             
CONECT    5    4    6   26   27                                             
CONECT    6    7    5   28   29                                             
CONECT    7    6   19    9    8                                             
CONECT    8    7   30   31   32                                             
CONECT    9    7   10   33   34                                             
CONECT   10   17   11    9   35                                             
CONECT   11   12   10                                                       
CONECT   12   14   11   13                                                  
CONECT   13   12                                                            
CONECT   14   17   12   15                                                  
CONECT   15   14   16   36   37                                             
CONECT   16   15   38                                                       
CONECT   17   10   14   18                                                  
CONECT   18   19   17   39                                                  
CONECT   19    2    7   18                                                  
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    3                                                            
CONECT   24    4                                                            
CONECT   25    4                                                            
CONECT   26    5                                                            
CONECT   27    5                                                            
CONECT   28    6                                                            
CONECT   29    6                                                            
CONECT   30    8                                                            
CONECT   31    8                                                            
CONECT   32    8                                                            
CONECT   33    9                                                            
CONECT   34    9                                                            
CONECT   35   10                                                            
CONECT   36   15                                                            
CONECT   37   15                                                            
CONECT   38   16                                                            
CONECT   39   18                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

RDKit          3D

39 41  0  0  0  0  0  0  0  0999 V2000
   -0.2616   -1.9686    2.5994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5866   -0.4810    2.4284 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0221   -0.4140    2.4353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1237    0.3439    3.6416 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3716    0.6268    3.6527 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7900    1.3368    2.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4303    0.5588    1.0785 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3770   -0.6554    0.9217 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6914    1.5212   -0.1283 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0764    0.9628   -1.4023 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1862    1.8515   -2.5050 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0464    1.9727   -3.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2831    2.5613   -4.1147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0610    1.3330   -2.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4892    1.5061   -2.5757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3510    1.0122   -1.5597 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3792    0.7992   -1.2066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8430    0.2083    0.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0465    0.0829    1.1067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8238   -2.3914    3.4411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5654   -2.5399    1.7141 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7962   -2.1618    2.7838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2688    0.5097    2.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6633    1.3014    3.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4112   -0.1622    4.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6115    1.2656    4.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9381   -0.2995    3.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3015    2.3209    2.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8695    1.5322    2.4013 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3972   -0.3290    0.6872 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0518   -1.3257    0.1186 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4520   -1.2545    1.8310 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7653    1.6944   -0.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2682    2.5166    0.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5512    0.0169   -1.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7208    2.5661   -2.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7118    0.9663   -3.5019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2602    1.1307   -1.8841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8843   -0.1049    0.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 17  1  0
  2 19  1  0
  7  6  1  0
  7 19  1  0
  5  4  1  0
 17 14  2  0
 14 12  1  0
 12 11  1  0
 10 11  1  0
  5  6  1  0
 12 13  2  0
  4  2  1  0
 14 15  1  0
  7  9  1  0
  7  8  1  6
 19 18  2  0
  2  1  1  0
 18 17  1  0
 15 16  1  0
 10  9  1  0
  2  3  1  6
  5 26  1  0
  5 27  1  0
  4 24  1  0
  4 25  1  0
  6 28  1  0
  6 29  1  0
 18 39  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  6
 15 36  1  0
 15 37  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
 16 38  1  0
  3 23  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₄

Average Mass

264.3210 Da

Monoisotopic Mass

264.13616 Da

IUPAC Name

(5R,8aR,9aS)-5-hydroxy-3-(hydroxymethyl)-5,8a-dimethyl-2H,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-2-one

Traditional Name

(5R,8aR,9aS)-5-hydroxy-3-(hydroxymethyl)-5,8a-dimethyl-6H,7H,8H,9H,9aH-naphtho[2,3-b]furan-2-one

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])C1=C2C([H])=C3[C@@](O[H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@]3(C([H])([H])[H])C([H])([H])[C@]2([H])OC1=O

InChI Identifier

InChI=1S/C15H20O4/c1-14-4-3-5-15(2,18)12(14)6-9-10(8-16)13(17)19-11(9)7-14/h6,11,16,18H,3-5,7-8H2,1-2H3/t11-,14+,15+/m0/s1

InChI Key

CXRZREVFSVBXDP-NILFDRSVSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Inula racemosa	JEOL database	Zhang, T., et al, Phytochem. Lett. 5, 229 (2012)

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	1.58	ALOGPS
logP	0.76	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	12.99	ChemAxon
pKa (Strongest Basic)	-0.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	71.38 m³·mol⁻¹	ChemAxon
Polarizability	28.24 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

Not Available

References

General References

Zhang, T., et al. (2012). Zhang, T., et al, Phytochem. Lett. 5, 229 (2012). Phytochem..

Showing NP-Card for 4alpha,13-dihydroxy-5,7(11)-eudesmadien-12,8-olide (NP0041616)

MOL for NP0041616 (4alpha,13-dihydroxy-5,7(11)-eudesmadien-12,8-olide)

3D MOL for NP0041616 (4alpha,13-dihydroxy-5,7(11)-eudesmadien-12,8-olide)

3D SDF for NP0041616 (4alpha,13-dihydroxy-5,7(11)-eudesmadien-12,8-olide)

3D-SDF for NP0041616 (4alpha,13-dihydroxy-5,7(11)-eudesmadien-12,8-olide)

PDB for NP0041616 (4alpha,13-dihydroxy-5,7(11)-eudesmadien-12,8-olide)

3D PDB for NP0041616 (4alpha,13-dihydroxy-5,7(11)-eudesmadien-12,8-olide)

SMILES for NP0041616 (4alpha,13-dihydroxy-5,7(11)-eudesmadien-12,8-olide)

INCHI for NP0041616 (4alpha,13-dihydroxy-5,7(11)-eudesmadien-12,8-olide)

Structure for NP0041616 (4alpha,13-dihydroxy-5,7(11)-eudesmadien-12,8-olide)

3D Structure for NP0041616 (4alpha,13-dihydroxy-5,7(11)-eudesmadien-12,8-olide)