NP-MRD: Showing NP-Card for 3a,6,7a-trihydroxy-2-(2-hydroxypropan-2-yl)-7-methyl-7-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)-2,3-dihydro-1-benzofuran-4-one (NP0303815)

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Record Information

Version

2.0

Created at

2022-09-10 18:29:02 UTC

Updated at

2022-09-10 18:29:03 UTC

NP-MRD ID

NP0303815

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3a,6,7a-trihydroxy-2-(2-hydroxypropan-2-yl)-7-methyl-7-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)-2,3-dihydro-1-benzofuran-4-one

Description

3A,6,7a-trihydroxy-2-(2-hydroxypropan-2-yl)-7-methyl-7-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)-2,3,3a,4,7,7a-hexahydro-1-benzofuran-4-one belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. 3a,6,7a-trihydroxy-2-(2-hydroxypropan-2-yl)-7-methyl-7-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)-2,3-dihydro-1-benzofuran-4-one is found in Hypericum papuanum. 3A,6,7a-trihydroxy-2-(2-hydroxypropan-2-yl)-7-methyl-7-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)-2,3,3a,4,7,7a-hexahydro-1-benzofuran-4-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231515062D          

 28 29  0  0  0  0            999 V2000
    4.7812    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1075    0.0660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1681    0.0660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8859   -0.7093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0735   -0.8526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7913   -1.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5432   -0.2206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8371    0.2900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8371    2.7559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9962    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
  6 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
M  END

     RDKit          3D

 60 61  0  0  0  0  0  0  0  0999 V2000
   -1.2606    3.3486   -1.8877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0919    3.8589   -0.5042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8929    5.0302   -0.0621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2531    3.2940    0.3231 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5907    2.1022   -0.0608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2498    0.9870    0.8640 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4245    1.4312    2.3248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2023    0.6389    0.7462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1206    1.4240    1.4003 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6493   -0.3970    0.0393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0950   -0.6734   -0.0222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9168    0.0835    0.5777 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6336   -1.8229   -0.7666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1662   -1.7174   -0.7368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2955   -3.0712    0.0237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7035   -1.2197   -0.6863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0945   -2.1924   -1.3915 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7264   -0.9468   -0.6244 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1916   -0.2077   -1.7119 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6127   -2.1616   -0.4417 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6592   -1.6147    0.5025 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0579   -1.8072   -0.0196 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1022   -1.3549    0.9697 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2506   -1.0488   -1.3066 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2381   -3.1812   -0.1877 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3587   -0.2481    0.7094 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0034   -0.2713    0.7025 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5866   -1.1747    1.6879 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8782    4.0627   -2.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2833    3.2841   -2.4354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7987    2.3745   -1.9255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3054    4.8916    0.9682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7384    5.2283   -0.7245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2053    5.9158   -0.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1260    3.6552    1.3198 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3248    1.8588   -1.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6515    2.4094    0.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4115    1.8827    2.4831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4145    2.0648    2.6477 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3879    0.4984    2.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7721    2.0650    1.0191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3569   -1.8700   -1.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5189   -1.5968    0.3056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5262   -2.7049   -1.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5278   -0.9375   -1.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5121   -2.9200    0.7867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0883   -3.9014   -0.6740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2102   -3.3391    0.6303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3459   -0.8243   -2.4717 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0999   -2.5013   -1.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0430   -3.0097    0.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5583   -2.1064    1.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0799   -1.7378    0.6146 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9448   -1.7703    1.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2040   -0.2341    0.9883 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7199   -1.5502   -2.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3573   -1.0246   -1.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8680   -0.0080   -1.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6486   -3.4109   -1.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0597   -1.8314    1.3606 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 15  1  0
 13 11  1  0
 11 12  2  0
 11 10  1  0
 10  8  2  0
  8  9  1  0
  8  6  1  0
  6  7  1  1
  6  5  1  0
  5  4  1  0
  4  2  2  3
  2  1  1  0
  2  3  1  0
  6 27  1  0
 27 28  1  1
 27 26  1  0
 26 21  1  0
 21 20  1  0
 20 18  1  0
 18 19  1  6
 18 16  1  0
 16 17  2  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  1  0
 16 10  1  0
 18 27  1  0
 14 43  1  0
 14 44  1  0
 14 45  1  0
 13 42  1  0
 15 46  1  0
 15 47  1  0
 15 48  1  0
  9 41  1  0
  7 38  1  0
  7 39  1  0
  7 40  1  0
  5 36  1  0
  5 37  1  0
  4 35  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  3 34  1  0
 28 60  1  0
 21 52  1  1
 20 50  1  0
 20 51  1  0
 19 49  1  0
 23 53  1  0
 23 54  1  0
 23 55  1  0
 24 56  1  0
 24 57  1  0
 24 58  1  0
 25 59  1  0
M  END


  Mrv1533004231515062D          

 28 29  0  0  0  0            999 V2000
    4.7812    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1075    0.0660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1681    0.0660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8859   -0.7093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0735   -0.8526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7913   -1.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5432   -0.2206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8371    0.2900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8371    2.7559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9962    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
  6 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0303815

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)C1=C(O)C(C)(CC=C(C)C)C2(O)OC(CC2(O)C1=O)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O7/c1-11(2)8-9-19(7)16(23)14(15(22)12(3)4)17(24)20(26)10-13(18(5,6)25)28-21(19,20)27/h8,12-13,23,25-27H,9-10H2,1-7H3

> <INCHI_KEY>
MRMBKYJWDGDPQH-UHFFFAOYSA-N

> <FORMULA>
C21H32O7

> <MOLECULAR_WEIGHT>
396.48

> <EXACT_MASS>
396.21480337

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
42.59481758413951

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3a,6,7a-trihydroxy-2-(2-hydroxypropan-2-yl)-7-methyl-7-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)-2,3,3a,4,7,7a-hexahydro-1-benzofuran-4-one

> <ALOGPS_LOGP>
0.99

> <JCHEM_LOGP>
2.472363290333334

> <ALOGPS_LOGS>
-2.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.479903717842262

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.386510422994204

> <JCHEM_PKA_STRONGEST_BASIC>
-3.098854992151284

> <JCHEM_POLAR_SURFACE_AREA>
124.29

> <JCHEM_REFRACTIVITY>
105.08389999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.63e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3a,6,7a-trihydroxy-2-(2-hydroxypropan-2-yl)-7-methyl-7-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)-2,3-dihydro-1-benzofuran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       8.925   2.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.259   4.383   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       7.591   5.923   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.591   1.303   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.934   0.123   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.914   0.123   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.387  -1.324   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.870  -1.591   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.344  -3.039   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.881  -0.412   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.429   0.541   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.429   5.144   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.924   5.923   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.320   2.843   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.860   2.843   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.320   4.383   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.320   1.303   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   23                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11   16                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    9   17   18   21                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16   22   23                                             
CONECT   22   21                                                            
CONECT   23   21    6   24                                                  
CONECT   24   23                                                            
CONECT   25   19   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₂O₇

Average Mass

396.4800 Da

Monoisotopic Mass

396.21480 Da

IUPAC Name

3a,6,7a-trihydroxy-2-(2-hydroxypropan-2-yl)-7-methyl-7-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)-2,3,3a,4,7,7a-hexahydro-1-benzofuran-4-one

Traditional Name

3a,6,7a-trihydroxy-2-(2-hydroxypropan-2-yl)-7-methyl-7-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)-2,3-dihydro-1-benzofuran-4-one

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)C1=C(O)C(C)(CC=C(C)C)C2(O)OC(CC2(O)C1=O)C(C)(C)O

InChI Identifier

InChI=1S/C21H32O7/c1-11(2)8-9-19(7)16(23)14(15(22)12(3)4)17(24)20(26)10-13(18(5,6)25)28-21(19,20)27/h8,12-13,23,25-27H,9-10H2,1-7H3

InChI Key

MRMBKYJWDGDPQH-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Hypericum papuanum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

Alternative Parents

Substituents

Benzofuran
Cyclohexenone
Oxolane
Vinylogous acid
Tertiary alcohol
Hemiacetal
Ketone
Enol
Oxacycle
Polyol
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organooxygen compound
Organic oxygen compound
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	0.99	ALOGPS
logP	2.47	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.39	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.29 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	105.08 m³·mol⁻¹	ChemAxon
Polarizability	42.59 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

10430862

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3a,6,7a-trihydroxy-2-(2-hydroxypropan-2-yl)-7-methyl-7-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)-2,3-dihydro-1-benzofuran-4-one (NP0303815)

MOL for NP0303815 (3a,6,7a-trihydroxy-2-(2-hydroxypropan-2-yl)-7-methyl-7-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)-2,3-dihydro-1-benzofuran-4-one)

3D MOL for NP0303815 (3a,6,7a-trihydroxy-2-(2-hydroxypropan-2-yl)-7-methyl-7-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)-2,3-dihydro-1-benzofuran-4-one)

3D SDF for NP0303815 (3a,6,7a-trihydroxy-2-(2-hydroxypropan-2-yl)-7-methyl-7-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)-2,3-dihydro-1-benzofuran-4-one)

3D-SDF for NP0303815 (3a,6,7a-trihydroxy-2-(2-hydroxypropan-2-yl)-7-methyl-7-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)-2,3-dihydro-1-benzofuran-4-one)

PDB for NP0303815 (3a,6,7a-trihydroxy-2-(2-hydroxypropan-2-yl)-7-methyl-7-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)-2,3-dihydro-1-benzofuran-4-one)

3D PDB for NP0303815 (3a,6,7a-trihydroxy-2-(2-hydroxypropan-2-yl)-7-methyl-7-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)-2,3-dihydro-1-benzofuran-4-one)

SMILES for NP0303815 (3a,6,7a-trihydroxy-2-(2-hydroxypropan-2-yl)-7-methyl-7-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)-2,3-dihydro-1-benzofuran-4-one)

INCHI for NP0303815 (3a,6,7a-trihydroxy-2-(2-hydroxypropan-2-yl)-7-methyl-7-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)-2,3-dihydro-1-benzofuran-4-one)

Structure for NP0303815 (3a,6,7a-trihydroxy-2-(2-hydroxypropan-2-yl)-7-methyl-7-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)-2,3-dihydro-1-benzofuran-4-one)

3D Structure for NP0303815 (3a,6,7a-trihydroxy-2-(2-hydroxypropan-2-yl)-7-methyl-7-(3-methylbut-2-en-1-yl)-5-(2-methylpropanoyl)-2,3-dihydro-1-benzofuran-4-one)