NP-MRD: Showing NP-Card for (1s,2r,3r,5r,7r,10s,11r,14r,15s)-15-[(2r,3s,5r)-5-[(1s,2s)-1,3-dihydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl 3-methylbut-2-enoate (NP0316422)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-11 15:36:46 UTC

Updated at

2022-09-11 15:36:46 UTC

NP-MRD ID

NP0316422

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,3r,5r,7r,10s,11r,14r,15s)-15-[(2r,3s,5r)-5-[(1s,2s)-1,3-dihydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl 3-methylbut-2-enoate

Description

(1S,2R,3R,5R,7R,10S,11R,14R,15S)-15-[(2R,3S,5R)-5-[(1S,2S)-1,3-dihydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]Octadecan-7-yl 3-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. (1s,2r,3r,5r,7r,10s,11r,14r,15s)-15-[(2r,3s,5r)-5-[(1s,2s)-1,3-dihydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl 3-methylbut-2-enoate is found in Toona sinensis. Based on a literature review very few articles have been published on (1S,2R,3R,5R,7R,10S,11R,14R,15S)-15-[(2R,3S,5R)-5-[(1S,2S)-1,3-dihydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]Octadecan-7-yl 3-methylbut-2-enoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309112217362D          

 45 50  0  0  1  0            999 V2000
    0.7811   -2.6778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6359   -1.8657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1400   -1.5854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8229   -2.0484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4742   -1.5420    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2667   -1.7713    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8615   -1.1996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4643   -2.5723    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2653   -2.3746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6620   -3.3733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4545   -3.6026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6634   -2.7699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4341   -3.5624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1939   -0.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3693   -0.7929    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1370   -0.1416    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0923    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5906    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2419    0.6076    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7737   -0.0231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9616   -0.1684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4934   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3055   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5858    0.1221    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3979    0.2673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1176   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7419   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0222    0.5577    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8343    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3661    0.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0858   -0.7037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1782    0.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7101   -0.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5222   -0.2681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4298   -1.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4904    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2038    1.6026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2063    1.9630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6782    1.0432    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1464    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3343    1.5287    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8025    2.1594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0540    0.7528    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5222    1.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  8 12  1  6  0  0  0
 12 13  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
  3 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 21 20  1  6  0  0  0
 16 21  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 23  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 29 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 37 40  1  0  0  0  0
 25 40  1  0  0  0  0
 40 41  1  1  0  0  0
 41 42  1  0  0  0  0
 42 43  1  6  0  0  0
 42 44  1  0  0  0  0
 24 44  1  0  0  0  0
 19 44  1  0  0  0  0
 44 45  1  1  0  0  0
M  END


  Mrv1652309112217362D          

 45 50  0  0  1  0            999 V2000
    0.7811   -2.6778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6359   -1.8657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1400   -1.5854    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8229   -2.0484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4742   -1.5420    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2667   -1.7713    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8615   -1.1996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4643   -2.5723    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2653   -2.3746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6620   -3.3733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4545   -3.6026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6634   -2.7699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4341   -3.5624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1939   -0.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3693   -0.7929    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1370   -0.1416    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0923    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5906    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2419    0.6076    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7737   -0.0231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9616   -0.1684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4934   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3055   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5858    0.1221    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3979    0.2673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1176   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7419   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0222    0.5577    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8343    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3661    0.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0858   -0.7037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1782    0.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7101   -0.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5222   -0.2681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4298   -1.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4904    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2038    1.6026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2063    1.9630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6782    1.0432    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1464    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3343    1.5287    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8025    2.1594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0540    0.7528    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5222    1.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  8 12  1  6  0  0  0
 12 13  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
  3 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 21 20  1  6  0  0  0
 16 21  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 24 23  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 29 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 37 40  1  0  0  0  0
 25 40  1  0  0  0  0
 40 41  1  1  0  0  0
 41 42  1  0  0  0  0
 42 43  1  6  0  0  0
 42 44  1  0  0  0  0
 24 44  1  0  0  0  0
 19 44  1  0  0  0  0
 44 45  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0316422

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1O[C@H](C[C@H]1[C@@H]1CC[C@]23C[C@]12CC[C@@H]1[C@@]2(C)CC[C@@H](OC(=O)C=C(C)C)C(C)(C)[C@@H]2C[C@@H](O)[C@@]31C)[C@H](O)[C@](C)(CO)OC

> <INCHI_IDENTIFIER>
InChI=1S/C37H60O8/c1-21(2)16-29(40)45-28-12-13-33(5)25-11-14-36-19-37(36,35(25,7)27(39)18-26(33)32(28,3)4)15-10-23(36)22-17-24(44-31(22)42-8)30(41)34(6,20-38)43-9/h16,22-28,30-31,38-39,41H,10-15,17-20H2,1-9H3/t22-,23-,24+,25+,26-,27+,28+,30-,31+,33+,34-,35-,36+,37+/m0/s1

> <INCHI_KEY>
CPTHHUMNHVBJMW-JWZLIDDHSA-N

> <FORMULA>
C37H60O8

> <MOLECULAR_WEIGHT>
632.879

> <EXACT_MASS>
632.428818892

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
105

> <JCHEM_AVERAGE_POLARIZABILITY>
72.0785445798365

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,3R,5R,7R,10S,11R,14R,15S)-15-[(2R,3S,5R)-5-[(1S,2S)-1,3-dihydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0^{1,14}.0^{2,11}.0^{5,10}]octadecan-7-yl 3-methylbut-2-enoate

> <JCHEM_LOGP>
4.7260039633333335

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.40862113609711

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.969491698203676

> <JCHEM_PKA_STRONGEST_BASIC>
-0.21542416669093034

> <JCHEM_POLAR_SURFACE_AREA>
114.68000000000002

> <JCHEM_REFRACTIVITY>
171.48530000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3R,5R,7R,10S,11R,14R,15S)-15-[(2R,3S,5R)-5-[(1S,2S)-1,3-dihydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0^{1,14}.0^{2,11}.0^{5,10}]octadecan-7-yl 3-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       1.458  -4.999   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.187  -3.483   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.261  -2.959   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.536  -3.824   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.752  -2.878   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.231  -3.306   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -5.341  -2.239   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -4.600  -4.802   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.095  -4.433   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.969  -6.297   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -6.448  -6.725   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -3.105  -5.171   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.677  -6.650   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.229  -1.430   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.689  -1.480   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.256  -0.264   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.172   1.215   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.102   2.079   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.318   1.134   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.311  -0.043   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.795  -0.314   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.788  -1.492   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.304  -1.221   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.827   0.228   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.343   0.499   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.820  -0.949   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.336  -0.678   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.852  -0.407   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.375   1.041   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      10.891   1.312   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      11.883   0.135   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      11.360  -1.314   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      13.399   0.406   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      14.392  -0.771   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      15.908  -0.500   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      13.869  -2.220   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.382   2.218   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.714   2.992   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       7.852   3.664   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       6.866   1.947   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       5.873   3.125   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       4.357   2.854   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       3.365   4.031   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       3.834   1.405   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       2.841   2.583   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   12                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10                                                            
CONECT   12    8   13                                                       
CONECT   13   12                                                            
CONECT   14    5   15                                                       
CONECT   15   14    3   16                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21   44                                             
CONECT   20   19   21                                                       
CONECT   21   20   16   19   22                                             
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   44                                                  
CONECT   25   24   26   27   40                                             
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   37                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   29   38   39   40                                             
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   37   25   41                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   24   19   45                                             
CONECT   45   44                                                            
MASTER        0    0    0    0    0    0    0    0   45    0  100    0
END

View in JSmol

Synonyms

Value	Source
(1S,2R,3R,5R,7R,10S,11R,14R,15S)-15-[(2R,3S,5R)-5-[(1S,2S)-1,3-Dihydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0,.0,.0,]octadecan-7-yl 3-methylbut-2-enoic acid	Generator

Chemical Formula

C₃₇H₆₀O₈

Average Mass

632.8790 Da

Monoisotopic Mass

632.42882 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CO[C@@H]1O[C@H](C[C@H]1[C@@H]1CC[C@]23C[C@]12CC[C@@H]1[C@@]2(C)CC[C@@H](OC(=O)C=C(C)C)C(C)(C)[C@@H]2C[C@@H](O)[C@@]31C)[C@H](O)[C@](C)(CO)OC

InChI Identifier

InChI=1S/C37H60O8/c1-21(2)16-29(40)45-28-12-13-33(5)25-11-14-36-19-37(36,35(25,7)27(39)18-26(33)32(28,3)4)15-10-23(36)22-17-24(44-31(22)42-8)30(41)34(6,20-38)43-9/h16,22-28,30-31,38-39,41H,10-15,17-20H2,1-9H3/t22-,23-,24+,25+,26-,27+,28+,30-,31+,33+,34-,35-,36+,37+/m0/s1

InChI Key

CPTHHUMNHVBJMW-JWZLIDDHSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Toona sinensis	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
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Acetal
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organooxygen compound
Primary alcohol
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
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	4.73	ChemAxon
pKa (Strongest Acidic)	12.97	ChemAxon
pKa (Strongest Basic)	-0.22	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	114.68 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	171.49 m³·mol⁻¹	ChemAxon
Polarizability	72.08 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

162850151

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,3r,5r,7r,10s,11r,14r,15s)-15-[(2r,3s,5r)-5-[(1s,2s)-1,3-dihydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl 3-methylbut-2-enoate (NP0316422)

MOL for NP0316422 ((1s,2r,3r,5r,7r,10s,11r,14r,15s)-15-[(2r,3s,5r)-5-[(1s,2s)-1,3-dihydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl 3-methylbut-2-enoate)

3D MOL for NP0316422 ((1s,2r,3r,5r,7r,10s,11r,14r,15s)-15-[(2r,3s,5r)-5-[(1s,2s)-1,3-dihydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl 3-methylbut-2-enoate)

3D SDF for NP0316422 ((1s,2r,3r,5r,7r,10s,11r,14r,15s)-15-[(2r,3s,5r)-5-[(1s,2s)-1,3-dihydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl 3-methylbut-2-enoate)

3D-SDF for NP0316422 ((1s,2r,3r,5r,7r,10s,11r,14r,15s)-15-[(2r,3s,5r)-5-[(1s,2s)-1,3-dihydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl 3-methylbut-2-enoate)

PDB for NP0316422 ((1s,2r,3r,5r,7r,10s,11r,14r,15s)-15-[(2r,3s,5r)-5-[(1s,2s)-1,3-dihydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl 3-methylbut-2-enoate)

3D PDB for NP0316422 ((1s,2r,3r,5r,7r,10s,11r,14r,15s)-15-[(2r,3s,5r)-5-[(1s,2s)-1,3-dihydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl 3-methylbut-2-enoate)

SMILES for NP0316422 ((1s,2r,3r,5r,7r,10s,11r,14r,15s)-15-[(2r,3s,5r)-5-[(1s,2s)-1,3-dihydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl 3-methylbut-2-enoate)

INCHI for NP0316422 ((1s,2r,3r,5r,7r,10s,11r,14r,15s)-15-[(2r,3s,5r)-5-[(1s,2s)-1,3-dihydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl 3-methylbut-2-enoate)

Structure for NP0316422 ((1s,2r,3r,5r,7r,10s,11r,14r,15s)-15-[(2r,3s,5r)-5-[(1s,2s)-1,3-dihydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl 3-methylbut-2-enoate)

3D Structure for NP0316422 ((1s,2r,3r,5r,7r,10s,11r,14r,15s)-15-[(2r,3s,5r)-5-[(1s,2s)-1,3-dihydroxy-2-methoxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-3-hydroxy-2,6,6,10-tetramethylpentacyclo[12.3.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]octadecan-7-yl 3-methylbut-2-enoate)