NP-MRD: Showing NP-Card for 2alpha,4beta-dihydroxy-1alphaH,10alphaH-pseudoguai-11(13)-en-12,8alpha-ol+ (NP0039951)

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Record Information

Version

2.0

Created at

2021-06-20 22:14:22 UTC

Updated at

2021-06-30 00:13:34 UTC

NP-MRD ID

NP0039951

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2alpha,4beta-dihydroxy-1alphaH,10alphaH-pseudoguai-11(13)-en-12,8alpha-ol+

Provided By

JEOL Database JEOL Logo

Description

(3Aalpha,7aalpha,9abeta)-3-Methylene-4abeta,8beta-dimethyl-5beta,7alpha-dihydroxydodecahydroazuleno[6,5-b]furan-2-one belongs to the class of organic compounds known as ambrosanolides and secoambrosanolides. These are sesquiterpene lactones from the Ambrosia family, with a backbone derivative of azuleno[6,5-b]furan-2-one (ambrosanolides) or azuleno[4,5-b]furan-2-one (secoambrosanolides). 2alpha,4beta-dihydroxy-1alphaH,10alphaH-pseudoguai-11(13)-en-12,8alpha-ol+ is found in Gaillardia pulchella, Inula japonica and Inula japonica Thunb.. 2alpha,4beta-dihydroxy-1alphaH,10alphaH-pseudoguai-11(13)-en-12,8alpha-ol+ was first documented in 2010 (Qin, J.-J., et al.). Based on a literature review very few articles have been published on (3aalpha,7aalpha,9abeta)-3-Methylene-4abeta,8beta-dimethyl-5beta,7alpha-dihydroxydodecahydroazuleno[6,5-b]furan-2-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100143D          

 41 43  0  0  0  0            999 V2000
   -0.8806    2.1005   -3.8690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1633    1.0754   -3.3921 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6140    0.1881   -4.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8475    0.3685   -5.4650 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0422   -0.8644   -3.5406 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4042   -0.8577   -2.2492 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4214   -1.3900   -1.2414 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8923   -1.6543    0.1771 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1589   -2.9983    0.2243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1715   -0.4312    0.7970 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0227   -0.5654    2.3292 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1859   -0.2177    2.9900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1437    0.4012    2.7097 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5350    1.0823    1.4022 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8908    1.4879    1.4085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2151    0.0446    0.2827 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3020   -1.0539    0.2612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2264    0.7604   -1.0969 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0054    0.5879   -1.9896 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9024    2.3194   -4.9342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4556    2.7502   -3.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4613   -1.5268   -2.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2626   -0.6851   -1.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711   -2.3100   -1.6399 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7910   -1.8081    0.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6017   -3.0912   -0.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8724   -3.8133    0.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3054   -3.1882    1.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8736    0.4076    0.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2891   -1.5814    2.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0515   -0.3584    3.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8427    1.1375    3.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9974   -0.1475    3.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9168    1.9806    1.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0067    2.1197    2.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3046   -0.6213    0.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1825   -1.7175   -0.5985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3015   -1.6661    1.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1200    0.4537   -1.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3667    1.8394   -0.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8475    1.1456   -1.5582 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0  0  0  0
  7  8  1  0  0  0  0
  8 10  1  0  0  0  0
 16 10  1  0  0  0  0
 19  2  1  0  0  0  0
  2  1  2  3  0  0  0
  2  3  1  0  0  0  0
  3  5  1  0  0  0  0
  6 19  1  0  0  0  0
 10 11  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 16  1  0  0  0  0
  6  5  1  0  0  0  0
  8  9  1  0  0  0  0
 19 18  1  0  0  0  0
 16 17  1  6  0  0  0
 14 15  1  0  0  0  0
  6  7  1  0  0  0  0
 11 12  1  0  0  0  0
 18 16  1  0  0  0  0
 10 29  1  1  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  6 22  1  6  0  0  0
 19 41  1  1  0  0  0
 18 39  1  0  0  0  0
 18 40  1  0  0  0  0
  7 23  1  0  0  0  0
  7 24  1  0  0  0  0
  8 25  1  1  0  0  0
 11 30  1  6  0  0  0
 13 32  1  0  0  0  0
 13 33  1  0  0  0  0
 14 34  1  6  0  0  0
  9 26  1  0  0  0  0
  9 27  1  0  0  0  0
  9 28  1  0  0  0  0
 17 36  1  0  0  0  0
 17 37  1  0  0  0  0
 17 38  1  0  0  0  0
 15 35  1  0  0  0  0
 12 31  1  0  0  0  0
M  END

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
   -0.8806    2.1005   -3.8690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1633    1.0754   -3.3921 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6140    0.1881   -4.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8475    0.3685   -5.4650 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0422   -0.8644   -3.5406 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4042   -0.8577   -2.2492 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4214   -1.3900   -1.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8923   -1.6543    0.1771 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1589   -2.9983    0.2243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1715   -0.4312    0.7970 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0227   -0.5654    2.3292 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1859   -0.2177    2.9900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1437    0.4012    2.7097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5350    1.0823    1.4022 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8908    1.4879    1.4085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2151    0.0446    0.2827 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3020   -1.0539    0.2612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2264    0.7604   -1.0969 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0054    0.5879   -1.9896 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9024    2.3194   -4.9342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4556    2.7502   -3.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4613   -1.5268   -2.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2626   -0.6851   -1.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711   -2.3100   -1.6399 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7910   -1.8081    0.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6017   -3.0912   -0.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8724   -3.8133    0.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3054   -3.1882    1.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8736    0.4076    0.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2891   -1.5814    2.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0515   -0.3584    3.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8427    1.1375    3.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9974   -0.1475    3.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9168    1.9806    1.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0067    2.1197    2.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3046   -0.6213    0.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1825   -1.7175   -0.5985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3015   -1.6661    1.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1200    0.4537   -1.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3667    1.8394   -0.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8475    1.1456   -1.5582 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0
  7  8  1  0
  8 10  1  0
 16 10  1  0
 19  2  1  0
  2  1  2  3
  2  3  1  0
  3  5  1  0
  6 19  1  0
 10 11  1  0
 11 13  1  0
 13 14  1  0
 14 16  1  0
  6  5  1  0
  8  9  1  0
 19 18  1  0
 16 17  1  6
 14 15  1  0
  6  7  1  0
 11 12  1  0
 18 16  1  0
 10 29  1  1
  1 20  1  0
  1 21  1  0
  6 22  1  6
 19 41  1  1
 18 39  1  0
 18 40  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  1
 11 30  1  6
 13 32  1  0
 13 33  1  0
 14 34  1  6
  9 26  1  0
  9 27  1  0
  9 28  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 15 35  1  0
 12 31  1  0
M  END


  Mrv1652306212100143D          

 41 43  0  0  0  0            999 V2000
   -0.8806    2.1005   -3.8690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1633    1.0754   -3.3921 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6140    0.1881   -4.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8475    0.3685   -5.4650 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0422   -0.8644   -3.5406 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4042   -0.8577   -2.2492 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4214   -1.3900   -1.2414 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8923   -1.6543    0.1771 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1589   -2.9983    0.2243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1715   -0.4312    0.7970 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0227   -0.5654    2.3292 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1859   -0.2177    2.9900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1437    0.4012    2.7097 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5350    1.0823    1.4022 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8908    1.4879    1.4085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2151    0.0446    0.2827 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3020   -1.0539    0.2612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2264    0.7604   -1.0969 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0054    0.5879   -1.9896 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9024    2.3194   -4.9342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4556    2.7502   -3.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4613   -1.5268   -2.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2626   -0.6851   -1.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711   -2.3100   -1.6399 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7910   -1.8081    0.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6017   -3.0912   -0.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8724   -3.8133    0.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3054   -3.1882    1.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8736    0.4076    0.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2891   -1.5814    2.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0515   -0.3584    3.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8427    1.1375    3.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9974   -0.1475    3.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9168    1.9806    1.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0067    2.1197    2.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3046   -0.6213    0.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1825   -1.7175   -0.5985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3015   -1.6661    1.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1200    0.4537   -1.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3667    1.8394   -0.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8475    1.1456   -1.5582 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0  0  0  0
  7  8  1  0  0  0  0
  8 10  1  0  0  0  0
 16 10  1  0  0  0  0
 19  2  1  0  0  0  0
  2  1  2  3  0  0  0
  2  3  1  0  0  0  0
  3  5  1  0  0  0  0
  6 19  1  0  0  0  0
 10 11  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 16  1  0  0  0  0
  6  5  1  0  0  0  0
  8  9  1  0  0  0  0
 19 18  1  0  0  0  0
 16 17  1  6  0  0  0
 14 15  1  0  0  0  0
  6  7  1  0  0  0  0
 11 12  1  0  0  0  0
 18 16  1  0  0  0  0
 10 29  1  1  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  6 22  1  6  0  0  0
 19 41  1  1  0  0  0
 18 39  1  0  0  0  0
 18 40  1  0  0  0  0
  7 23  1  0  0  0  0
  7 24  1  0  0  0  0
  8 25  1  1  0  0  0
 11 30  1  6  0  0  0
 13 32  1  0  0  0  0
 13 33  1  0  0  0  0
 14 34  1  6  0  0  0
  9 26  1  0  0  0  0
  9 27  1  0  0  0  0
  9 28  1  0  0  0  0
 17 36  1  0  0  0  0
 17 37  1  0  0  0  0
 17 38  1  0  0  0  0
 15 35  1  0  0  0  0
 12 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0039951

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O4/c1-7-4-11-9(8(2)14(18)19-11)6-15(3)12(17)5-10(16)13(7)15/h7,9-13,16-17H,2,4-6H2,1,3H3/t7-,9+,10-,11-,12-,13+,15+/m0/s1

> <INCHI_KEY>
BPUNWVGCTMEMKQ-UOIIZJLGSA-N

> <FORMULA>
C15H22O4

> <MOLECULAR_WEIGHT>
266.337

> <EXACT_MASS>
266.151809188

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
28.73421033335875

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4aS,5S,7S,7aS,8S,9aS)-5,7-dihydroxy-4a,8-dimethyl-3-methylidene-dodecahydroazuleno[6,5-b]furan-2-one

> <ALOGPS_LOGP>
0.70

> <JCHEM_LOGP>
1.093251262999999

> <ALOGPS_LOGS>
-1.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.146669843365896

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.409439954587558

> <JCHEM_PKA_STRONGEST_BASIC>
-2.870452030089698

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
69.4843

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.00e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,4aS,5S,7S,7aS,8S,9aS)-5,7-dihydroxy-4a,8-dimethyl-3-methylidene-octahydro-3aH-azuleno[6,5-b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
   -0.8806    2.1005   -3.8690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1633    1.0754   -3.3921 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6140    0.1881   -4.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8475    0.3685   -5.4650 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0422   -0.8644   -3.5406 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4042   -0.8577   -2.2492 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4214   -1.3900   -1.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8923   -1.6543    0.1771 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1589   -2.9983    0.2243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1715   -0.4312    0.7970 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0227   -0.5654    2.3292 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1859   -0.2177    2.9900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1437    0.4012    2.7097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5350    1.0823    1.4022 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8908    1.4879    1.4085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2151    0.0446    0.2827 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3020   -1.0539    0.2612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2264    0.7604   -1.0969 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0054    0.5879   -1.9896 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9024    2.3194   -4.9342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4556    2.7502   -3.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4613   -1.5268   -2.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2626   -0.6851   -1.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711   -2.3100   -1.6399 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7910   -1.8081    0.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6017   -3.0912   -0.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8724   -3.8133    0.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3054   -3.1882    1.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8736    0.4076    0.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2891   -1.5814    2.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0515   -0.3584    3.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8427    1.1375    3.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9974   -0.1475    3.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9168    1.9806    1.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0067    2.1197    2.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3046   -0.6213    0.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1825   -1.7175   -0.5985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3015   -1.6661    1.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1200    0.4537   -1.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3667    1.8394   -0.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8475    1.1456   -1.5582 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0
  7  8  1  0
  8 10  1  0
 16 10  1  0
 19  2  1  0
  2  1  2  3
  2  3  1  0
  3  5  1  0
  6 19  1  0
 10 11  1  0
 11 13  1  0
 13 14  1  0
 14 16  1  0
  6  5  1  0
  8  9  1  0
 19 18  1  0
 16 17  1  6
 14 15  1  0
  6  7  1  0
 11 12  1  0
 18 16  1  0
 10 29  1  1
  1 20  1  0
  1 21  1  0
  6 22  1  6
 19 41  1  1
 18 39  1  0
 18 40  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  1
 11 30  1  6
 13 32  1  0
 13 33  1  0
 14 34  1  6
  9 26  1  0
  9 27  1  0
  9 28  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 15 35  1  0
 12 31  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      -0.881   2.100  -3.869  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.163   1.075  -3.392  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.614   0.188  -4.285  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.848   0.369  -5.465  0.00  0.00           O+0
HETATM    5  O   UNK     0       1.042  -0.864  -3.541  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.404  -0.858  -2.249  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.421  -1.390  -1.241  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.892  -1.654   0.177  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.159  -2.998   0.224  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.172  -0.431   0.797  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.023  -0.565   2.329  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.186  -0.218   2.990  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.144   0.401   2.710  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.535   1.082   1.402  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.891   1.488   1.409  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.215   0.045   0.283  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.302  -1.054   0.261  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.226   0.760  -1.097  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.005   0.588  -1.990  0.00  0.00           C+0
HETATM   20  H   UNK     0      -0.902   2.319  -4.934  0.00  0.00           H+0
HETATM   21  H   UNK     0      -1.456   2.750  -3.219  0.00  0.00           H+0
HETATM   22  H   UNK     0      -0.461  -1.527  -2.318  0.00  0.00           H+0
HETATM   23  H   UNK     0       2.263  -0.685  -1.181  0.00  0.00           H+0
HETATM   24  H   UNK     0       1.871  -2.310  -1.640  0.00  0.00           H+0
HETATM   25  H   UNK     0       1.791  -1.808   0.794  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.602  -3.091  -0.553  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.872  -3.813   0.052  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.305  -3.188   1.194  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.874   0.408   0.659  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.289  -1.581   2.633  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.052  -0.358   3.944  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.843   1.137   3.463  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.997  -0.148   3.125  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.917   1.981   1.270  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.007   2.120   2.139  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.305  -0.621   0.166  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.183  -1.718  -0.599  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.301  -1.666   1.168  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.120   0.454  -1.659  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.367   1.839  -0.944  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.848   1.146  -1.558  0.00  0.00           H+0
CONECT    1    2   20   21                                                  
CONECT    2   19    1    3                                                  
CONECT    3    4    2    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6   19    5    7   22                                             
CONECT    7    8    6   23   24                                             
CONECT    8    7   10    9   25                                             
CONECT    9    8   26   27   28                                             
CONECT   10    8   16   11   29                                             
CONECT   11   10   13   12   30                                             
CONECT   12   11   31                                                       
CONECT   13   11   14   32   33                                             
CONECT   14   13   16   15   34                                             
CONECT   15   14   35                                                       
CONECT   16   10   14   17   18                                             
CONECT   17   16   36   37   38                                             
CONECT   18   19   16   39   40                                             
CONECT   19    2    6   18   41                                             
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    6                                                            
CONECT   23    7                                                            
CONECT   24    7                                                            
CONECT   25    8                                                            
CONECT   26    9                                                            
CONECT   27    9                                                            
CONECT   28    9                                                            
CONECT   29   10                                                            
CONECT   30   11                                                            
CONECT   31   12                                                            
CONECT   32   13                                                            
CONECT   33   13                                                            
CONECT   34   14                                                            
CONECT   35   15                                                            
CONECT   36   17                                                            
CONECT   37   17                                                            
CONECT   38   17                                                            
CONECT   39   18                                                            
CONECT   40   18                                                            
CONECT   41   19                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   86    0
END

RDKit          3D

41 43  0  0  0  0  0  0  0  0999 V2000
   -0.8806    2.1005   -3.8690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1633    1.0754   -3.3921 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6140    0.1881   -4.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8475    0.3685   -5.4650 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0422   -0.8644   -3.5406 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4042   -0.8577   -2.2492 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4214   -1.3900   -1.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8923   -1.6543    0.1771 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1589   -2.9983    0.2243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1715   -0.4312    0.7970 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0227   -0.5654    2.3292 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1859   -0.2177    2.9900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1437    0.4012    2.7097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5350    1.0823    1.4022 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8908    1.4879    1.4085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2151    0.0446    0.2827 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3020   -1.0539    0.2612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2264    0.7604   -1.0969 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0054    0.5879   -1.9896 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9024    2.3194   -4.9342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4556    2.7502   -3.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4613   -1.5268   -2.3185 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2626   -0.6851   -1.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711   -2.3100   -1.6399 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7910   -1.8081    0.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6017   -3.0912   -0.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8724   -3.8133    0.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3054   -3.1882    1.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8736    0.4076    0.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2891   -1.5814    2.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0515   -0.3584    3.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8427    1.1375    3.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9974   -0.1475    3.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9168    1.9806    1.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0067    2.1197    2.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3046   -0.6213    0.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1825   -1.7175   -0.5985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3015   -1.6661    1.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1200    0.4537   -1.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3667    1.8394   -0.9437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8475    1.1456   -1.5582 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0
  7  8  1  0
  8 10  1  0
 16 10  1  0
 19  2  1  0
  2  1  2  3
  2  3  1  0
  3  5  1  0
  6 19  1  0
 10 11  1  0
 11 13  1  0
 13 14  1  0
 14 16  1  0
  6  5  1  0
  8  9  1  0
 19 18  1  0
 16 17  1  6
 14 15  1  0
  6  7  1  0
 11 12  1  0
 18 16  1  0
 10 29  1  1
  1 20  1  0
  1 21  1  0
  6 22  1  6
 19 41  1  1
 18 39  1  0
 18 40  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  1
 11 30  1  6
 13 32  1  0
 13 33  1  0
 14 34  1  6
  9 26  1  0
  9 27  1  0
  9 28  1  0
 17 36  1  0
 17 37  1  0
 17 38  1  0
 15 35  1  0
 12 31  1  0
M  END

View in JSmol

Synonyms

Value	Source
(3Aalpha,7aalpha,9abeta)-3-methylene-4abeta,8b-dimethyl-5b,7a-dihydroxydodecahydroazuleno[6,5-b]furan-2-one	Generator
(3Aalpha,7aalpha,9abeta)-3-methylene-4abeta,8β-dimethyl-5β,7α-dihydroxydodecahydroazuleno[6,5-b]furan-2-one	Generator

Chemical Formula

C₁₅H₂₂O₄

Average Mass

266.3370 Da

Monoisotopic Mass

266.15181 Da

IUPAC Name

(3aR,4aS,5S,7S,7aS,8S,9aS)-5,7-dihydroxy-4a,8-dimethyl-3-methylidene-dodecahydroazuleno[6,5-b]furan-2-one

Traditional Name

(3aR,4aS,5S,7S,7aS,8S,9aS)-5,7-dihydroxy-4a,8-dimethyl-3-methylidene-octahydro-3aH-azuleno[6,5-b]furan-2-one

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])C([H])([H])[C@]([H])(O[H])[C@@]2(C([H])([H])[H])C([H])([H])[C@]3([H])C(=C([H])[H])C(=O)O[C@@]3([H])C([H])([H])[C@]([H])(C([H])([H])[H])[C@]12[H]

InChI Identifier

InChI=1S/C15H22O4/c1-7-4-11-9(8(2)14(18)19-11)6-15(3)12(17)5-10(16)13(7)15/h7,9-13,16-17H,2,4-6H2,1,3H3/t7-,9+,10-,11-,12-,13+,15+/m0/s1

InChI Key

BPUNWVGCTMEMKQ-UOIIZJLGSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, 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
Gaillardia pulchella	Plant	KNApSAcK
Inula japonica	LOTUS Database	35616633
Inula japonica Thunb.	JEOL database	Qin, J.-J., et al, Tetrahedron 66, 9379 (2010).

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ambrosanolides and secoambrosanolides. These are sesquiterpene lactones from the Ambrosia family, with a backbone derivative of azuleno[6,5-b]furan-2-one (ambrosanolides) or azuleno[4,5-b]furan-2-one (secoambrosanolides).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Ambrosanolides and secoambrosanolides

Alternative Parents

Substituents

Ambrosanolide
Pseudoguaiane sesquiterpenoid
Sesquiterpenoid
Gamma butyrolactone
Cyclic alcohol
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	0.7	ALOGPS
logP	1.09	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	14.41	ChemAxon
pKa (Strongest Basic)	-2.9	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	0	ChemAxon
Refractivity	69.48 m³·mol⁻¹	ChemAxon
Polarizability	28.73 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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

50915273

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Qin, J.-J., et al. (2010). Qin, J.-J., et al, Tetrahedron 66, 9379 (2010).. Tetrahedron.

Showing NP-Card for 2alpha,4beta-dihydroxy-1alphaH,10alphaH-pseudoguai-11(13)-en-12,8alpha-ol+ (NP0039951)

MOL for NP0039951 (2alpha,4beta-dihydroxy-1alphaH,10alphaH-pseudoguai-11(13)-en-12,8alpha-ol+)

3D MOL for NP0039951 (2alpha,4beta-dihydroxy-1alphaH,10alphaH-pseudoguai-11(13)-en-12,8alpha-ol+)

3D SDF for NP0039951 (2alpha,4beta-dihydroxy-1alphaH,10alphaH-pseudoguai-11(13)-en-12,8alpha-ol+)

3D-SDF for NP0039951 (2alpha,4beta-dihydroxy-1alphaH,10alphaH-pseudoguai-11(13)-en-12,8alpha-ol+)

PDB for NP0039951 (2alpha,4beta-dihydroxy-1alphaH,10alphaH-pseudoguai-11(13)-en-12,8alpha-ol+)

3D PDB for NP0039951 (2alpha,4beta-dihydroxy-1alphaH,10alphaH-pseudoguai-11(13)-en-12,8alpha-ol+)

SMILES for NP0039951 (2alpha,4beta-dihydroxy-1alphaH,10alphaH-pseudoguai-11(13)-en-12,8alpha-ol+)

INCHI for NP0039951 (2alpha,4beta-dihydroxy-1alphaH,10alphaH-pseudoguai-11(13)-en-12,8alpha-ol+)

Structure for NP0039951 (2alpha,4beta-dihydroxy-1alphaH,10alphaH-pseudoguai-11(13)-en-12,8alpha-ol+)

3D Structure for NP0039951 (2alpha,4beta-dihydroxy-1alphaH,10alphaH-pseudoguai-11(13)-en-12,8alpha-ol+)