NP-MRD: Showing NP-Card for 1-({4,5-dihydroxy-3-[(8-hydroxy-2,6-dimethylocta-2,6-dienoyl)oxy]-6-(hydroxymethyl)oxan-2-yl}oxy)-4-formyl-4a-hydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-7-yl 8-hydroxy-2,6-dimethylocta-2,6-dienoate (NP0221987)

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Record Information

Version

2.0

Created at

2022-09-05 23:42:24 UTC

Updated at

2022-09-05 23:42:24 UTC

NP-MRD ID

NP0221987

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-({4,5-dihydroxy-3-[(8-hydroxy-2,6-dimethylocta-2,6-dienoyl)oxy]-6-(hydroxymethyl)oxan-2-yl}oxy)-4-formyl-4a-hydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-7-yl 8-hydroxy-2,6-dimethylocta-2,6-dienoate

Description

1-({4,5-Dihydroxy-3-[(8-hydroxy-2,6-dimethylocta-2,6-dienoyl)oxy]-6-(hydroxymethyl)oxan-2-yl}oxy)-4-formyl-4a-hydroxy-7-methyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-7-yl 8-hydroxy-2,6-dimethylocta-2,6-dienoate belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. 1-({4,5-dihydroxy-3-[(8-hydroxy-2,6-dimethylocta-2,6-dienoyl)oxy]-6-(hydroxymethyl)oxan-2-yl}oxy)-4-formyl-4a-hydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-7-yl 8-hydroxy-2,6-dimethylocta-2,6-dienoate is found in Rotheca incisa. 1-({4,5-Dihydroxy-3-[(8-hydroxy-2,6-dimethylocta-2,6-dienoyl)oxy]-6-(hydroxymethyl)oxan-2-yl}oxy)-4-formyl-4a-hydroxy-7-methyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-7-yl 8-hydroxy-2,6-dimethylocta-2,6-dienoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004171501242D          

 50 52  0  0  0  0            999 V2000
    0.4210    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4210    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4210    9.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4782   -0.8205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1154    1.8336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0654    1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3636    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0780    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0780    0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7925   -0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7925   -0.9826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5070   -1.3951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5070   -2.2201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2215   -2.6326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0780   -1.3951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3636    2.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  4  0  0  0
  4  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  4  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  4  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  4  0  0  0
 46 47  1  0  0  0  0
 44 48  1  0  0  0  0
 40 49  1  0  0  0  0
 35 50  1  0  0  0  0
 25 50  1  0  0  0  0
 31 50  1  0  0  0  0
M  END


  Mrv1533004171501242D          

 50 52  0  0  0  0            999 V2000
    0.4210    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4210    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4210    9.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4782   -0.8205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1154    1.8336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0654    1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3636    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0780    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0780    0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7925   -0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7925   -0.9826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5070   -1.3951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5070   -2.2201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2215   -2.6326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0780   -1.3951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3636    2.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  4  0  0  0
  4  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  4  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  4  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  4  0  0  0
 46 47  1  0  0  0  0
 44 48  1  0  0  0  0
 40 49  1  0  0  0  0
 35 50  1  0  0  0  0
 25 50  1  0  0  0  0
 31 50  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0221987

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC=C(C)C(=O)OC1C(OC2OC=C(C=O)C3(O)CCC(C)(OC(=O)C(C)=CCCC(C)=CCO)C23)OC(CO)C(O)C1O)=CCO

> <INCHI_IDENTIFIER>
InChI=1S/C36H52O14/c1-21(12-16-37)8-6-10-23(3)31(43)48-29-28(42)27(41)26(19-40)47-33(29)49-34-30-35(5,14-15-36(30,45)25(18-39)20-46-34)50-32(44)24(4)11-7-9-22(2)13-17-38/h10-13,18,20,26-30,33-34,37-38,40-42,45H,6-9,14-17,19H2,1-5H3

> <INCHI_KEY>
OGOIOIQOMMXKKU-UHFFFAOYSA-N

> <FORMULA>
C36H52O14

> <MOLECULAR_WEIGHT>
708.798

> <EXACT_MASS>
708.335706354

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
102

> <JCHEM_AVERAGE_POLARIZABILITY>
75.3899998149645

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-({4,5-dihydroxy-3-[(8-hydroxy-2,6-dimethylocta-2,6-dienoyl)oxy]-6-(hydroxymethyl)oxan-2-yl}oxy)-4-formyl-4a-hydroxy-7-methyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-7-yl 8-hydroxy-2,6-dimethylocta-2,6-dienoate

> <ALOGPS_LOGP>
1.81

> <JCHEM_LOGP>
1.4536101359999984

> <ALOGPS_LOGS>
-3.61

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.422817469306516

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.626417046968822

> <JCHEM_PKA_STRONGEST_BASIC>
-2.217047406800316

> <JCHEM_POLAR_SURFACE_AREA>
218.73999999999998

> <JCHEM_REFRACTIVITY>
181.77400000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.73e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-({4,5-dihydroxy-3-[(8-hydroxy-2,6-dimethylocta-2,6-dienoyl)oxy]-6-(hydroxymethyl)oxan-2-yl}oxy)-4-formyl-4a-hydroxy-7-methyl-1H,5H,6H,7aH-cyclopenta[c]pyran-7-yl 8-hydroxy-2,6-dimethylocta-2,6-dienoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       0.786  13.090   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.120  13.860   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.120  15.400   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.786  16.170   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.786  17.710   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.453  13.090   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.453  11.550   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.787  10.780   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.787   9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.453   8.470   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.121   8.470   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.454   9.240   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       6.121   6.930   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       7.454   6.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.788   6.930   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.788   8.470   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      10.122   6.160   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      11.455   6.930   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      10.122   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.455   3.850   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      11.455   2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.788   3.850   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.454   4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.121   3.850   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.454   1.540   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.121  -2.310   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       7.454  -3.080   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.626  -1.532   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.949   3.423   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       1.989   2.786   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       0.655   2.016   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       0.655   0.476   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -0.679   2.786   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -2.012   2.016   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -2.012   0.476   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -3.346  -0.294   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -3.346  -1.834   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -4.680  -2.604   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -4.680  -4.144   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      -6.013  -4.914   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      -2.012  -2.604   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -0.679   4.326   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    2    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   23                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   23                                                       
CONECT   23   22   14   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   50                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28   32   33   50                                             
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37   50                                             
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   49                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45   48                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46                                                            
CONECT   48   44                                                            
CONECT   49   40                                                            
CONECT   50   35   25   31                                                  
MASTER        0    0    0    0    0    0    0    0   50    0  104    0
END

View in JSmol

Synonyms

Value	Source
1-({4,5-dihydroxy-3-[(8-hydroxy-2,6-dimethylocta-2,6-dienoyl)oxy]-6-(hydroxymethyl)oxan-2-yl}oxy)-4-formyl-4a-hydroxy-7-methyl-1H,4ah,5H,6H,7H,7ah-cyclopenta[c]pyran-7-yl 8-hydroxy-2,6-dimethylocta-2,6-dienoic acid	Generator

Chemical Formula

C₃₆H₅₂O₁₄

Average Mass

708.7980 Da

Monoisotopic Mass

708.33571 Da

IUPAC Name

1-({4,5-dihydroxy-3-[(8-hydroxy-2,6-dimethylocta-2,6-dienoyl)oxy]-6-(hydroxymethyl)oxan-2-yl}oxy)-4-formyl-4a-hydroxy-7-methyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-7-yl 8-hydroxy-2,6-dimethylocta-2,6-dienoate

Traditional Name

1-({4,5-dihydroxy-3-[(8-hydroxy-2,6-dimethylocta-2,6-dienoyl)oxy]-6-(hydroxymethyl)oxan-2-yl}oxy)-4-formyl-4a-hydroxy-7-methyl-1H,5H,6H,7aH-cyclopenta[c]pyran-7-yl 8-hydroxy-2,6-dimethylocta-2,6-dienoate

CAS Registry Number

Not Available

SMILES

CC(CCC=C(C)C(=O)OC1C(OC2OC=C(C=O)C3(O)CCC(C)(OC(=O)C(C)=CCCC(C)=CCO)C23)OC(CO)C(O)C1O)=CCO

InChI Identifier

InChI=1S/C36H52O14/c1-21(12-16-37)8-6-10-23(3)31(43)48-29-28(42)27(41)26(19-40)47-33(29)49-34-30-35(5,14-15-36(30,45)25(18-39)20-46-34)50-32(44)24(4)11-7-9-22(2)13-17-38/h10-13,18,20,26-30,33-34,37-38,40-42,45H,6-9,14-17,19H2,1-5H3

InChI Key

OGOIOIQOMMXKKU-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
Rotheca incisa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Stigmastanes and derivatives

Direct Parent

Stigmastanes and derivatives

Alternative Parents

Substituents

C24-propyl-sterol-skeleton
Stigmastane-skeleton
Triterpenoid
Tetrahydroxy bile acid, alcohol, or derivatives
23-hydroxysteroid
Hydroxy bile acid, alcohol, or derivatives
22-hydroxysteroid
Bile acid, alcohol, or derivatives
Hydroxysteroid
2-hydroxysteroid
3-hydroxysteroid
Cyclic alcohol
Secondary alcohol
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	1.81	ALOGPS
logP	1.45	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	12.63	ChemAxon
pKa (Strongest Basic)	-2.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	218.74 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	181.77 m³·mol⁻¹	ChemAxon
Polarizability	75.39 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-({4,5-dihydroxy-3-[(8-hydroxy-2,6-dimethylocta-2,6-dienoyl)oxy]-6-(hydroxymethyl)oxan-2-yl}oxy)-4-formyl-4a-hydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-7-yl 8-hydroxy-2,6-dimethylocta-2,6-dienoate (NP0221987)

MOL for NP0221987 (1-({4,5-dihydroxy-3-[(8-hydroxy-2,6-dimethylocta-2,6-dienoyl)oxy]-6-(hydroxymethyl)oxan-2-yl}oxy)-4-formyl-4a-hydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-7-yl 8-hydroxy-2,6-dimethylocta-2,6-dienoate)

3D MOL for NP0221987 (1-({4,5-dihydroxy-3-[(8-hydroxy-2,6-dimethylocta-2,6-dienoyl)oxy]-6-(hydroxymethyl)oxan-2-yl}oxy)-4-formyl-4a-hydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-7-yl 8-hydroxy-2,6-dimethylocta-2,6-dienoate)

3D SDF for NP0221987 (1-({4,5-dihydroxy-3-[(8-hydroxy-2,6-dimethylocta-2,6-dienoyl)oxy]-6-(hydroxymethyl)oxan-2-yl}oxy)-4-formyl-4a-hydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-7-yl 8-hydroxy-2,6-dimethylocta-2,6-dienoate)

3D-SDF for NP0221987 (1-({4,5-dihydroxy-3-[(8-hydroxy-2,6-dimethylocta-2,6-dienoyl)oxy]-6-(hydroxymethyl)oxan-2-yl}oxy)-4-formyl-4a-hydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-7-yl 8-hydroxy-2,6-dimethylocta-2,6-dienoate)

PDB for NP0221987 (1-({4,5-dihydroxy-3-[(8-hydroxy-2,6-dimethylocta-2,6-dienoyl)oxy]-6-(hydroxymethyl)oxan-2-yl}oxy)-4-formyl-4a-hydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-7-yl 8-hydroxy-2,6-dimethylocta-2,6-dienoate)

3D PDB for NP0221987 (1-({4,5-dihydroxy-3-[(8-hydroxy-2,6-dimethylocta-2,6-dienoyl)oxy]-6-(hydroxymethyl)oxan-2-yl}oxy)-4-formyl-4a-hydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-7-yl 8-hydroxy-2,6-dimethylocta-2,6-dienoate)

SMILES for NP0221987 (1-({4,5-dihydroxy-3-[(8-hydroxy-2,6-dimethylocta-2,6-dienoyl)oxy]-6-(hydroxymethyl)oxan-2-yl}oxy)-4-formyl-4a-hydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-7-yl 8-hydroxy-2,6-dimethylocta-2,6-dienoate)

INCHI for NP0221987 (1-({4,5-dihydroxy-3-[(8-hydroxy-2,6-dimethylocta-2,6-dienoyl)oxy]-6-(hydroxymethyl)oxan-2-yl}oxy)-4-formyl-4a-hydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-7-yl 8-hydroxy-2,6-dimethylocta-2,6-dienoate)

Structure for NP0221987 (1-({4,5-dihydroxy-3-[(8-hydroxy-2,6-dimethylocta-2,6-dienoyl)oxy]-6-(hydroxymethyl)oxan-2-yl}oxy)-4-formyl-4a-hydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-7-yl 8-hydroxy-2,6-dimethylocta-2,6-dienoate)

3D Structure for NP0221987 (1-({4,5-dihydroxy-3-[(8-hydroxy-2,6-dimethylocta-2,6-dienoyl)oxy]-6-(hydroxymethyl)oxan-2-yl}oxy)-4-formyl-4a-hydroxy-7-methyl-1h,5h,6h,7ah-cyclopenta[c]pyran-7-yl 8-hydroxy-2,6-dimethylocta-2,6-dienoate)