NP-MRD: Showing NP-Card for 11beta,13-dihydrourospermal A (NP0029741)

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Record Information

Version

2.0

Created at

2021-06-19 21:17:12 UTC

Updated at

2021-06-29 23:57:18 UTC

NP-MRD ID

NP0029741

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11beta,13-dihydrourospermal A

Provided By

JEOL Database JEOL Logo

Description

11beta,13-dihydrourospermal A is found in Sonchus asper. 11beta,13-dihydrourospermal A was first documented in 2000 (Helal, A. M., et al.). Based on a literature review very few articles have been published on 11beta,13-Dihydrourospermal A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123173D          

 40 41  0  0  0  0            999 V2000
   -0.6706    2.9159    2.8358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6535    3.4706    1.4184 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0255    3.4462    0.8176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0369    3.8868    1.3407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0076    2.8873   -0.4164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7104    2.3746   -0.7398 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9220    0.9146   -1.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4234    0.1868   -2.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8369   -1.2528   -2.2543 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2897   -2.0930   -2.0662 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5256    0.7364   -3.1159 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9970    0.3156   -2.9583 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5071    0.1791   -1.5464 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7090    1.1585   -0.6453 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2357    0.7146    0.6753 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4081    1.4940    1.6059 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4829    2.6336   -0.8649 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4994    3.3619    0.0835 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1758    3.7723    1.2750 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1959    2.6239    0.4642 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3391    2.8822    3.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2884    3.5413    3.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0893    1.9036    2.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3290    4.5178    1.4275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3800    2.9330   -1.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5912    0.4119   -0.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6097   -1.5513   -1.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2339   -1.4088   -3.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0314   -3.0063   -2.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4812    1.8289   -3.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1762    0.4316   -4.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6376    1.0107   -3.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1359   -0.6540   -3.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6989   -0.8586   -1.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4520   -0.3620    0.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1378    2.8025   -1.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4612    3.1292   -0.8013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2273    4.3022   -0.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6756    3.0017    1.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4639    1.6827    0.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0  0  0  0
  6  5  1  0  0  0  0
  5  3  1  0  0  0  0
  3  2  1  0  0  0  0
 20  2  1  0  0  0  0
 18 20  1  0  0  0  0
 14 17  1  0  0  0  0
 18 19  1  0  0  0  0
  7  6  1  0  0  0  0
  2  1  1  0  0  0  0
 12 13  1  0  0  0  0
  3  4  2  0  0  0  0
 17 18  1  0  0  0  0
 14 15  1  0  0  0  0
 20  6  1  0  0  0  0
 15 35  1  0  0  0  0
 11  8  1  0  0  0  0
 15 16  2  0  0  0  0
  8  7  2  0  0  0  0
  8  9  1  0  0  0  0
 14 13  2  0  0  0  0
  9 10  1  0  0  0  0
 12 32  1  0  0  0  0
 12 33  1  0  0  0  0
 11 30  1  0  0  0  0
 11 31  1  0  0  0  0
 13 34  1  0  0  0  0
  7 26  1  0  0  0  0
 17 36  1  0  0  0  0
 17 37  1  0  0  0  0
 18 38  1  6  0  0  0
 20 40  1  1  0  0  0
  6 25  1  6  0  0  0
  2 24  1  1  0  0  0
 19 39  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  9 27  1  0  0  0  0
  9 28  1  0  0  0  0
 10 29  1  0  0  0  0
M  END

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
   -0.6706    2.9159    2.8358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6535    3.4706    1.4184 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0255    3.4462    0.8176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0369    3.8868    1.3407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0076    2.8873   -0.4164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7104    2.3746   -0.7398 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9220    0.9146   -1.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4234    0.1868   -2.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8369   -1.2528   -2.2543 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2897   -2.0930   -2.0662 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5256    0.7364   -3.1159 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9970    0.3156   -2.9583 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5071    0.1791   -1.5464 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7090    1.1585   -0.6453 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2357    0.7146    0.6753 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4081    1.4940    1.6059 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4829    2.6336   -0.8649 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4994    3.3619    0.0835 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1758    3.7723    1.2750 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1959    2.6239    0.4642 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3391    2.8822    3.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2884    3.5413    3.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0893    1.9036    2.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3290    4.5178    1.4275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3800    2.9330   -1.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5912    0.4119   -0.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6097   -1.5513   -1.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2339   -1.4088   -3.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0314   -3.0063   -2.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4812    1.8289   -3.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1762    0.4316   -4.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6376    1.0107   -3.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1359   -0.6540   -3.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6989   -0.8586   -1.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4520   -0.3620    0.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1378    2.8025   -1.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4612    3.1292   -0.8013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2273    4.3022   -0.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6756    3.0017    1.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4639    1.6827    0.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
  6  5  1  0
  5  3  1  0
  3  2  1  0
 20  2  1  0
 18 20  1  0
 14 17  1  0
 18 19  1  0
  7  6  1  0
  2  1  1  0
 12 13  1  0
  3  4  2  0
 17 18  1  0
 14 15  1  0
 20  6  1  0
 15 35  1  0
 11  8  1  0
 15 16  2  0
  8  7  2  0
  8  9  1  0
 14 13  2  0
  9 10  1  0
 12 32  1  0
 12 33  1  0
 11 30  1  0
 11 31  1  0
 13 34  1  0
  7 26  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  6
 20 40  1  1
  6 25  1  6
  2 24  1  1
 19 39  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
M  END


  Mrv1652306192123173D          

 40 41  0  0  0  0            999 V2000
   -0.6706    2.9159    2.8358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6535    3.4706    1.4184 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0255    3.4462    0.8176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0369    3.8868    1.3407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0076    2.8873   -0.4164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7104    2.3746   -0.7398 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9220    0.9146   -1.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4234    0.1868   -2.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8369   -1.2528   -2.2543 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2897   -2.0930   -2.0662 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5256    0.7364   -3.1159 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9970    0.3156   -2.9583 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5071    0.1791   -1.5464 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7090    1.1585   -0.6453 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2357    0.7146    0.6753 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4081    1.4940    1.6059 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4829    2.6336   -0.8649 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4994    3.3619    0.0835 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1758    3.7723    1.2750 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1959    2.6239    0.4642 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3391    2.8822    3.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2884    3.5413    3.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0893    1.9036    2.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3290    4.5178    1.4275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3800    2.9330   -1.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5912    0.4119   -0.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6097   -1.5513   -1.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2339   -1.4088   -3.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0314   -3.0063   -2.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4812    1.8289   -3.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1762    0.4316   -4.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6376    1.0107   -3.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1359   -0.6540   -3.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6989   -0.8586   -1.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4520   -0.3620    0.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1378    2.8025   -1.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4612    3.1292   -0.8013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2273    4.3022   -0.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6756    3.0017    1.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4639    1.6827    0.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0  0  0  0
  6  5  1  0  0  0  0
  5  3  1  0  0  0  0
  3  2  1  0  0  0  0
 20  2  1  0  0  0  0
 18 20  1  0  0  0  0
 14 17  1  0  0  0  0
 18 19  1  0  0  0  0
  7  6  1  0  0  0  0
  2  1  1  0  0  0  0
 12 13  1  0  0  0  0
  3  4  2  0  0  0  0
 17 18  1  0  0  0  0
 14 15  1  0  0  0  0
 20  6  1  0  0  0  0
 15 35  1  0  0  0  0
 11  8  1  0  0  0  0
 15 16  2  0  0  0  0
  8  7  2  0  0  0  0
  8  9  1  0  0  0  0
 14 13  2  0  0  0  0
  9 10  1  0  0  0  0
 12 32  1  0  0  0  0
 12 33  1  0  0  0  0
 11 30  1  0  0  0  0
 11 31  1  0  0  0  0
 13 34  1  0  0  0  0
  7 26  1  0  0  0  0
 17 36  1  0  0  0  0
 17 37  1  0  0  0  0
 18 38  1  6  0  0  0
 20 40  1  1  0  0  0
  6 25  1  6  0  0  0
  2 24  1  1  0  0  0
 19 39  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  9 27  1  0  0  0  0
  9 28  1  0  0  0  0
 10 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0029741

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O5/c1-9-14-12(18)5-10(7-16)3-2-4-11(8-17)6-13(14)20-15(9)19/h3,6-7,9,12-14,17-18H,2,4-5,8H2,1H3/b10-3+,11-6+/t9-,12-,13+,14+/m0/s1

> <INCHI_KEY>
HOSMFPQDFZLVEZ-ODVDRCMSSA-N

> <FORMULA>
C15H20O5

> <MOLECULAR_WEIGHT>
280.32

> <EXACT_MASS>
280.131073744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
28.587323172600993

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,3aR,4S,11aR)-4-hydroxy-10-(hydroxymethyl)-3-methyl-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carbaldehyde

> <ALOGPS_LOGP>
0.33

> <JCHEM_LOGP>
0.08165533233333411

> <ALOGPS_LOGS>
-2.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.291055090199166

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.598384906414825

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7347321803182636

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
74.28020000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.66e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,3aR,4S,11aR)-4-hydroxy-10-(hydroxymethyl)-3-methyl-2-oxo-3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
   -0.6706    2.9159    2.8358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6535    3.4706    1.4184 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0255    3.4462    0.8176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0369    3.8868    1.3407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0076    2.8873   -0.4164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7104    2.3746   -0.7398 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9220    0.9146   -1.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4234    0.1868   -2.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8369   -1.2528   -2.2543 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2897   -2.0930   -2.0662 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5256    0.7364   -3.1159 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9970    0.3156   -2.9583 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5071    0.1791   -1.5464 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7090    1.1585   -0.6453 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2357    0.7146    0.6753 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4081    1.4940    1.6059 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4829    2.6336   -0.8649 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4994    3.3619    0.0835 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1758    3.7723    1.2750 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1959    2.6239    0.4642 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3391    2.8822    3.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2884    3.5413    3.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0893    1.9036    2.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3290    4.5178    1.4275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3800    2.9330   -1.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5912    0.4119   -0.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6097   -1.5513   -1.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2339   -1.4088   -3.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0314   -3.0063   -2.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4812    1.8289   -3.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1762    0.4316   -4.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6376    1.0107   -3.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1359   -0.6540   -3.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6989   -0.8586   -1.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4520   -0.3620    0.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1378    2.8025   -1.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4612    3.1292   -0.8013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2273    4.3022   -0.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6756    3.0017    1.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4639    1.6827    0.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
  6  5  1  0
  5  3  1  0
  3  2  1  0
 20  2  1  0
 18 20  1  0
 14 17  1  0
 18 19  1  0
  7  6  1  0
  2  1  1  0
 12 13  1  0
  3  4  2  0
 17 18  1  0
 14 15  1  0
 20  6  1  0
 15 35  1  0
 11  8  1  0
 15 16  2  0
  8  7  2  0
  8  9  1  0
 14 13  2  0
  9 10  1  0
 12 32  1  0
 12 33  1  0
 11 30  1  0
 11 31  1  0
 13 34  1  0
  7 26  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  6
 20 40  1  1
  6 25  1  6
  2 24  1  1
 19 39  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  9 27  1  0
  9 28  1  0
 10 29  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      -0.671   2.916   2.836  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.654   3.471   1.418  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.026   3.446   0.818  0.00  0.00           C+0
HETATM    4  O   UNK     0      -3.037   3.887   1.341  0.00  0.00           O+0
HETATM    5  O   UNK     0      -2.008   2.887  -0.416  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.710   2.375  -0.740  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.922   0.915  -1.048  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.423   0.187  -2.071  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.837  -1.253  -2.254  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.290  -2.093  -2.066  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.526   0.736  -3.116  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.997   0.316  -2.958  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.507   0.179  -1.546  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.709   1.159  -0.645  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.236   0.715   0.675  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.408   1.494   1.606  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.483   2.634  -0.865  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.499   3.362   0.084  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.176   3.772   1.275  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.196   2.624   0.464  0.00  0.00           C+0
HETATM   21  H   UNK     0       0.339   2.882   3.257  0.00  0.00           H+0
HETATM   22  H   UNK     0      -1.288   3.541   3.489  0.00  0.00           H+0
HETATM   23  H   UNK     0      -1.089   1.904   2.864  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.329   4.518   1.428  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.380   2.933  -1.619  0.00  0.00           H+0
HETATM   26  H   UNK     0      -1.591   0.412  -0.348  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.610  -1.551  -1.538  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.234  -1.409  -3.263  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.031  -3.006  -2.157  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.481   1.829  -3.146  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.176   0.432  -4.111  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.638   1.011  -3.515  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.136  -0.654  -3.455  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.699  -0.859  -1.269  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.452  -0.362   0.781  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.138   2.803  -1.890  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.461   3.129  -0.801  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.227   4.302  -0.414  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.676   3.002   1.628  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.464   1.683   0.961  0.00  0.00           H+0
CONECT    1    2   21   22   23                                             
CONECT    2    3   20    1   24                                             
CONECT    3    5    2    4                                                  
CONECT    4    3                                                            
CONECT    5    6    3                                                       
CONECT    6    5    7   20   25                                             
CONECT    7    6    8   26                                                  
CONECT    8   11    7    9                                                  
CONECT    9    8   10   27   28                                             
CONECT   10    9   29                                                       
CONECT   11   12    8   30   31                                             
CONECT   12   11   13   32   33                                             
CONECT   13   12   14   34                                                  
CONECT   14   17   15   13                                                  
CONECT   15   14   35   16                                                  
CONECT   16   15                                                            
CONECT   17   14   18   36   37                                             
CONECT   18   20   19   17   38                                             
CONECT   19   18   39                                                       
CONECT   20    2   18    6   40                                             
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    2                                                            
CONECT   25    6                                                            
CONECT   26    7                                                            
CONECT   27    9                                                            
CONECT   28    9                                                            
CONECT   29   10                                                            
CONECT   30   11                                                            
CONECT   31   11                                                            
CONECT   32   12                                                            
CONECT   33   12                                                            
CONECT   34   13                                                            
CONECT   35   15                                                            
CONECT   36   17                                                            
CONECT   37   17                                                            
CONECT   38   18                                                            
CONECT   39   19                                                            
CONECT   40   20                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   82    0
END

RDKit          3D

40 41  0  0  0  0  0  0  0  0999 V2000
   -0.6706    2.9159    2.8358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6535    3.4706    1.4184 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0255    3.4462    0.8176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0369    3.8868    1.3407 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0076    2.8873   -0.4164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7104    2.3746   -0.7398 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9220    0.9146   -1.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4234    0.1868   -2.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8369   -1.2528   -2.2543 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2897   -2.0930   -2.0662 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5256    0.7364   -3.1159 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9970    0.3156   -2.9583 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5071    0.1791   -1.5464 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7090    1.1585   -0.6453 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2357    0.7146    0.6753 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4081    1.4940    1.6059 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4829    2.6336   -0.8649 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4994    3.3619    0.0835 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1758    3.7723    1.2750 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1959    2.6239    0.4642 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3391    2.8822    3.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2884    3.5413    3.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0893    1.9036    2.8642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3290    4.5178    1.4275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3800    2.9330   -1.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5912    0.4119   -0.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6097   -1.5513   -1.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2339   -1.4088   -3.2629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0314   -3.0063   -2.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4812    1.8289   -3.1455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1762    0.4316   -4.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6376    1.0107   -3.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1359   -0.6540   -3.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6989   -0.8586   -1.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4520   -0.3620    0.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1378    2.8025   -1.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4612    3.1292   -0.8013 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2273    4.3022   -0.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6756    3.0017    1.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4639    1.6827    0.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
  6  5  1  0
  5  3  1  0
  3  2  1  0
 20  2  1  0
 18 20  1  0
 14 17  1  0
 18 19  1  0
  7  6  1  0
  2  1  1  0
 12 13  1  0
  3  4  2  0
 17 18  1  0
 14 15  1  0
 20  6  1  0
 15 35  1  0
 11  8  1  0
 15 16  2  0
  8  7  2  0
  8  9  1  0
 14 13  2  0
  9 10  1  0
 12 32  1  0
 12 33  1  0
 11 30  1  0
 11 31  1  0
 13 34  1  0
  7 26  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  6
 20 40  1  1
  6 25  1  6
  2 24  1  1
 19 39  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
M  END

View in JSmol

Synonyms

Value	Source
11b,13-Dihydrourospermal a	Generator
11Β,13-dihydrourospermal a	Generator

Chemical Formula

C₁₅H₂₀O₅

Average Mass

280.3200 Da

Monoisotopic Mass

280.13107 Da

IUPAC Name

(3S,3aR,4S,11aR)-4-hydroxy-10-(hydroxymethyl)-3-methyl-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carbaldehyde

Traditional Name

(3S,3aR,4S,11aR)-4-hydroxy-10-(hydroxymethyl)-3-methyl-2-oxo-3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carbaldehyde

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H20O5/c1-9-14-12(18)5-10(7-16)3-2-4-11(8-17)6-13(14)20-15(9)19/h3,6-7,9,12-14,17-18H,2,4-5,8H2,1H3/b10-3+,11-6+/t9-,12-,13+,14+/m0/s1

InChI Key

HOSMFPQDFZLVEZ-ODVDRCMSSA-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
Sonchus asper	JEOL database	Helal, A. M., et al, Phytochemistry 53, 473 (2000)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Germacrane sesquiterpenoid
Sesquiterpenoid
Gamma butyrolactone
Oxolane
Carboxylic acid ester
Lactone
Secondary alcohol
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Aldehyde
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Primary alcohol
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	0.33	ALOGPS
logP	0.082	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	14.6	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	74.28 m³·mol⁻¹	ChemAxon
Polarizability	28.59 Å³	ChemAxon
Number of Rings	2	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

101665849

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Helal, A. M., et al. (2000). Helal, A. M., et al, Phytochemistry 53, 473 (2000). Phytochem..

Showing NP-Card for 11beta,13-dihydrourospermal A (NP0029741)

MOL for NP0029741 (11beta,13-dihydrourospermal A)

3D MOL for NP0029741 (11beta,13-dihydrourospermal A)

3D SDF for NP0029741 (11beta,13-dihydrourospermal A)

3D-SDF for NP0029741 (11beta,13-dihydrourospermal A)

PDB for NP0029741 (11beta,13-dihydrourospermal A)

3D PDB for NP0029741 (11beta,13-dihydrourospermal A)

SMILES for NP0029741 (11beta,13-dihydrourospermal A)

INCHI for NP0029741 (11beta,13-dihydrourospermal A)

Structure for NP0029741 (11beta,13-dihydrourospermal A)

3D Structure for NP0029741 (11beta,13-dihydrourospermal A)