NP-MRD: Showing NP-Card for 15-[5-(1,2-dihydroxy-2-methylpropyl)-2-hydroxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl 2-methylbut-2-enoate (NP0256593)

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Record Information

Version

2.0

Created at

2022-09-07 21:28:38 UTC

Updated at

2022-09-07 21:28:38 UTC

NP-MRD ID

NP0256593

Secondary Accession Numbers

None

Natural Product Identification

Common Name

15-[5-(1,2-dihydroxy-2-methylpropyl)-2-hydroxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl 2-methylbut-2-enoate

Description

15-[5-(1,2-Dihydroxy-2-methylpropyl)-2-hydroxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]Octadecan-7-yl 2-methylbut-2-enoate belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. 15-[5-(1,2-dihydroxy-2-methylpropyl)-2-hydroxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl 2-methylbut-2-enoate is found in Aglaia crassinervia. 15-[5-(1,2-Dihydroxy-2-methylpropyl)-2-hydroxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]Octadecan-7-yl 2-methylbut-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171517252D          

 42 47  0  0  0  0            999 V2000
    8.0191   -1.7202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2070   -1.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9267   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4585   -0.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1146   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5828   -1.2846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8343    0.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0222    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7419    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3979    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1176    1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5858    0.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3055    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4934    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9616    0.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7737    0.8481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2419    0.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6359    2.6907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6782   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4904   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3736   -1.1801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1021   -0.9169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  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
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 21 22  1  0  0  0  0
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 25 26  1  0  0  0  0
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 26 27  1  0  0  0  0
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 28 29  1  0  0  0  0
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 34 35  1  0  0  0  0
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 11 39  1  0  0  0  0
 39 40  1  0  0  0  0
  8 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
M  END

     RDKit          3D

 98103  0  0  0  0  0  0  0  0999 V2000
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    6.9093    0.8292    0.1234 C   0  0  0  0  0  0  0  0  0  0  0  0
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 35 89  1  0
 36 90  1  0
 18 63  1  0
 18 64  1  0
 18 65  1  0
 15 61  1  6
 16 62  1  0
 14 59  1  0
 14 60  1  0
 13 58  1  1
 41 93  1  0
 41 94  1  0
 41 95  1  0
 42 96  1  0
 42 97  1  0
 42 98  1  0
M  END


  Mrv1533004171517252D          

 42 47  0  0  0  0            999 V2000
    8.0191   -1.7202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2070   -1.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9267   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4585   -0.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1146   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5828   -1.2846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8343    0.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0222    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7419    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3979    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1176    1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5858    0.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3055    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4934    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9616    0.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7737    0.8481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2419    0.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5906   -0.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0923    0.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1370    0.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3693    1.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1939    1.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4742    2.3670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8229    2.8734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1400    2.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6359    2.6907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2667    2.5963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4643    3.3973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8615    2.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4563    1.4530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4332    2.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2899    1.4298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0540    0.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5222   -0.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3343   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8025   -1.3344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1464   -0.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6782   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4904   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3736   -1.1801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1021   -0.9169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  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
 16 17  1  0  0  0  0
 17 18  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
 22 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
 22 26  1  0  0  0  0
 26 27  1  0  0  0  0
 24 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 18 34  1  0  0  0  0
 13 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 11 39  1  0  0  0  0
 39 40  1  0  0  0  0
  8 40  1  0  0  0  0
 40 41  1  0  0  0  0
 40 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0256593

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC=C(C)C(=O)OC1CCC2(C)C3CCC45CC4(CCC5C4CC(OC4O)C(O)C(C)(C)O)C3(C)C(O)CC2C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C35H56O7/c1-9-19(2)28(38)42-26-12-13-32(7)23-11-14-34-18-35(34,33(23,8)25(36)17-24(32)30(26,3)4)15-10-21(34)20-16-22(41-29(20)39)27(37)31(5,6)40/h9,20-27,29,36-37,39-40H,10-18H2,1-8H3

> <INCHI_KEY>
QOYIHGQDAPZLBL-UHFFFAOYSA-N

> <FORMULA>
C35H56O7

> <MOLECULAR_WEIGHT>
588.826

> <EXACT_MASS>
588.402604143

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
98

> <JCHEM_AVERAGE_POLARIZABILITY>
68.60015904951791

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
15-[5-(1,2-dihydroxy-2-methylpropyl)-2-hydroxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl 2-methylbut-2-enoate

> <ALOGPS_LOGP>
4.20

> <JCHEM_LOGP>
4.638850140333333

> <ALOGPS_LOGS>
-5.14

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.11134151048293

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.112085874600098

> <JCHEM_PKA_STRONGEST_BASIC>
-0.21550744672199718

> <JCHEM_POLAR_SURFACE_AREA>
116.45000000000002

> <JCHEM_REFRACTIVITY>
160.51430000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.25e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-[5-(1,2-dihydroxy-2-methylpropyl)-2-hydroxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl 2-methylbut-2-enoate

> <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      14.969  -3.211   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.453  -2.940   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.930  -1.492   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.923  -0.314   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.414  -1.221   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      10.421  -2.398   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      10.891   0.228   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.375   0.499   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.852   1.947   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.336   2.218   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.343   1.041   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.820   2.489   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.827   1.312   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.304   2.761   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.788   3.032   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.795   1.854   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.311   1.583   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.318   0.406   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.102  -0.539   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.172   0.325   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.256   1.804   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.689   3.020   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.229   2.970   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.752   4.418   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.536   5.364   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.261   4.499   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.187   5.023   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -4.231   4.846   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.600   6.342   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -5.341   3.779   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -6.452   2.712   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -6.409   4.890   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -4.274   2.669   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       3.834   0.135   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.841  -1.043   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.357  -1.314   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       3.365  -2.491   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       5.873  -1.585   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.866  -0.407   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       8.382  -0.678   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       8.164  -2.203   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       9.524  -1.712   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   40                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   39                                             
CONECT   12   11                                                            
CONECT   13   11   14   34                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   21                                             
CONECT   17   16   18                                                       
CONECT   18   17   16   19   34                                             
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16   22                                                  
CONECT   22   21   23   26                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   22   27                                                  
CONECT   27   26                                                            
CONECT   28   24   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30                                                            
CONECT   34   18   13   35   36                                             
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   11   40                                                  
CONECT   40   39    8   41   42                                             
CONECT   41   40                                                            
CONECT   42   40                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   94    0
END

View in JSmol

Synonyms

Value	Source
15-[5-(1,2-Dihydroxy-2-methylpropyl)-2-hydroxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0,.0,.0,]octadecan-7-yl 2-methylbut-2-enoic acid	Generator
15-[5-(1,2-Dihydroxy-2-methylpropyl)-2-hydroxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl 2-methylbut-2-enoic acid	Generator

Chemical Formula

C₃₅H₅₆O₇

Average Mass

588.8260 Da

Monoisotopic Mass

588.40260 Da

IUPAC Name

15-[5-(1,2-dihydroxy-2-methylpropyl)-2-hydroxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl 2-methylbut-2-enoate

Traditional Name

15-[5-(1,2-dihydroxy-2-methylpropyl)-2-hydroxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl 2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

CC=C(C)C(=O)OC1CCC2(C)C3CCC45CC4(CCC5C4CC(OC4O)C(O)C(C)(C)O)C3(C)C(O)CC2C1(C)C

InChI Identifier

InChI=1S/C35H56O7/c1-9-19(2)28(38)42-26-12-13-32(7)23-11-14-34-18-35(34,33(23,8)25(36)17-24(32)30(26,3)4)15-10-21(34)20-16-22(41-29(20)39)27(37)31(5,6)40/h9,20-27,29,36-37,39-40H,10-18H2,1-8H3

InChI Key

QOYIHGQDAPZLBL-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
Aglaia crassinervia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Limonoid skeleton
24-hydroxysteroid
Hydroxy bile acid, alcohol, or derivatives
Monohydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
Steroid ester
Steroid
Fatty acid ester
Fatty acyl
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Hemiacetal
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Alcohol
Organooxygen compound
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	4.2	ALOGPS
logP	4.64	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	12.11	ChemAxon
pKa (Strongest Basic)	-0.22	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.45 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	160.51 m³·mol⁻¹	ChemAxon
Polarizability	68.6 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	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

73150603

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 15-[5-(1,2-dihydroxy-2-methylpropyl)-2-hydroxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl 2-methylbut-2-enoate (NP0256593)

MOL for NP0256593 (15-[5-(1,2-dihydroxy-2-methylpropyl)-2-hydroxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl 2-methylbut-2-enoate)

3D MOL for NP0256593 (15-[5-(1,2-dihydroxy-2-methylpropyl)-2-hydroxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl 2-methylbut-2-enoate)

3D SDF for NP0256593 (15-[5-(1,2-dihydroxy-2-methylpropyl)-2-hydroxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl 2-methylbut-2-enoate)

3D-SDF for NP0256593 (15-[5-(1,2-dihydroxy-2-methylpropyl)-2-hydroxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl 2-methylbut-2-enoate)

PDB for NP0256593 (15-[5-(1,2-dihydroxy-2-methylpropyl)-2-hydroxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl 2-methylbut-2-enoate)

3D PDB for NP0256593 (15-[5-(1,2-dihydroxy-2-methylpropyl)-2-hydroxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl 2-methylbut-2-enoate)

SMILES for NP0256593 (15-[5-(1,2-dihydroxy-2-methylpropyl)-2-hydroxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl 2-methylbut-2-enoate)

INCHI for NP0256593 (15-[5-(1,2-dihydroxy-2-methylpropyl)-2-hydroxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl 2-methylbut-2-enoate)

Structure for NP0256593 (15-[5-(1,2-dihydroxy-2-methylpropyl)-2-hydroxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl 2-methylbut-2-enoate)

3D Structure for NP0256593 (15-[5-(1,2-dihydroxy-2-methylpropyl)-2-hydroxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl 2-methylbut-2-enoate)