NP-MRD: Showing NP-Card for (2r,3s,4s,5r)-6-({2-[(1ar,2r,4ar,7r,8ar)-2,7-dihydroxy-4a-methyl-8-methylidene-hexahydronaphtho[1,8a-b]oxiren-2-yl]propan-2-yl}oxy)-2-methyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-4-[(2-methylpropanoyl)oxy]oxan-3-yl (2z)-2-methylbut-2-enoate (NP0224898)

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Record Information

Version

2.0

Created at

2022-09-06 03:27:42 UTC

Updated at

2022-09-06 03:27:42 UTC

NP-MRD ID

NP0224898

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3s,4s,5r)-6-({2-[(1ar,2r,4ar,7r,8ar)-2,7-dihydroxy-4a-methyl-8-methylidene-hexahydronaphtho[1,8a-b]oxiren-2-yl]propan-2-yl}oxy)-2-methyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-4-[(2-methylpropanoyl)oxy]oxan-3-yl (2z)-2-methylbut-2-enoate

Description

(3R,4S,5S,6R)-2-({2-[(R,1bR,4R,5aR,5bR)-4-dihydroxy-1b-methyl-5-methylidene-octahydro-H-naphtho[1,8a-b]oxiren--yl]propan-2-yl}oxy)-6-methyl-5-{[(2Z)-2-methylbut-2-enoyl]oxy}-4-[(2-methylpropanoyl)oxy]oxan-3-yl (2Z)-2-methylbut-2-enoate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (2r,3s,4s,5r)-6-({2-[(1ar,2r,4ar,7r,8ar)-2,7-dihydroxy-4a-methyl-8-methylidene-hexahydronaphtho[1,8a-b]oxiren-2-yl]propan-2-yl}oxy)-2-methyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-4-[(2-methylpropanoyl)oxy]oxan-3-yl (2z)-2-methylbut-2-enoate is found in Calendula arvensis. Based on a literature review very few articles have been published on (3R,4S,5S,6R)-2-({2-[(R,1bR,4R,5aR,5bR)-4-dihydroxy-1b-methyl-5-methylidene-octahydro-H-naphtho[1,8a-b]oxiren--yl]propan-2-yl}oxy)-6-methyl-5-{[(2Z)-2-methylbut-2-enoyl]oxy}-4-[(2-methylpropanoyl)oxy]oxan-3-yl (2Z)-2-methylbut-2-enoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062205272D          

 46 49  0  0  1  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3848   -1.0942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8545   -2.0127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0793   -2.2949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6298   -1.7306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1367   -2.7880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6064   -3.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7939   -3.2767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2636   -3.9087    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4512   -3.7654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5458   -4.6840    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0155   -5.3159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2030   -5.1727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9209   -4.3974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6727   -5.8047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9549   -6.5799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1397   -5.6614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4219   -4.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3583   -4.8272    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6404   -5.6025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4529   -5.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9832   -5.1137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7351   -6.5210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2048   -7.1530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5475   -6.6642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8886   -4.1952    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7010   -4.3385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2313   -3.7065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9492   -2.9313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0438   -3.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5741   -3.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3260   -4.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7957   -5.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
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 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 29 36  1  0  0  0  0
 17 36  1  0  0  0  0
 36 37  1  6  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  1  0  0  0  0
 40 42  2  0  0  0  0
 42 43  1  0  0  0  0
 11 44  1  0  0  0  0
 44 45  1  1  0  0  0
 46 45  1  1  0  0  0
  2 46  1  0  0  0  0
 44 46  1  0  0  0  0
  7 46  1  0  0  0  0
M  END


  Mrv1652309062205272D          

 46 49  0  0  1  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3848   -1.0942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8545   -2.0127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0793   -2.2949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6298   -1.7306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1367   -2.7880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6064   -3.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7939   -3.2767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2636   -3.9087    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4512   -3.7654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5458   -4.6840    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0155   -5.3159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2030   -5.1727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9209   -4.3974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6727   -5.8047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9549   -6.5799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1397   -5.6614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4219   -4.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3583   -4.8272    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6404   -5.6025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4529   -5.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9832   -5.1137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7351   -6.5210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2048   -7.1530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5475   -6.6642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8886   -4.1952    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7010   -4.3385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2313   -3.7065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9492   -2.9313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0438   -3.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5741   -3.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3260   -4.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7957   -5.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  6  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
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 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
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 29 30  1  1  0  0  0
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 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 29 36  1  0  0  0  0
 17 36  1  0  0  0  0
 36 37  1  6  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  1  0  0  0  0
 40 42  2  0  0  0  0
 42 43  1  0  0  0  0
 11 44  1  0  0  0  0
 44 45  1  1  0  0  0
 46 45  1  1  0  0  0
  2 46  1  0  0  0  0
 44 46  1  0  0  0  0
  7 46  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0224898

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(\C)C(=O)O[C@H]1[C@@H](C)OC(OC(C)(C)[C@@]2(O)CC[C@@]3(C)CC[C@@H](O)C(=C)[C@]33O[C@H]23)[C@H](OC(=O)C(\C)=C/C)[C@H]1OC(=O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C35H52O11/c1-12-19(5)28(38)42-24-22(8)41-30(26(44-29(39)20(6)13-2)25(24)43-27(37)18(3)4)45-32(9,10)34(40)17-16-33(11)15-14-23(36)21(7)35(33)31(34)46-35/h12-13,18,22-26,30-31,36,40H,7,14-17H2,1-6,8-11H3/b19-12-,20-13-/t22-,23-,24+,25+,26-,30?,31-,33-,34-,35-/m1/s1

> <INCHI_KEY>
WMACAWYSWIYFLP-KFWXLWKSSA-N

> <FORMULA>
C35H52O11

> <MOLECULAR_WEIGHT>
648.79

> <EXACT_MASS>
648.350962494

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
98

> <JCHEM_AVERAGE_POLARIZABILITY>
68.66370136403478

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S,4S,5R)-6-({2-[(R,1bR,4R,5aR,5bR)-4-dihydroxy-1b-methyl-5-methylidene-octahydro-H-naphtho[1,8a-b]oxiren--yl]propan-2-yl}oxy)-2-methyl-5-{[(2Z)-2-methylbut-2-enoyl]oxy}-4-[(2-methylpropanoyl)oxy]oxan-3-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_LOGP>
6.001389722333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.553983628974088

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.68658565628606

> <JCHEM_PKA_STRONGEST_BASIC>
-2.996585997397861

> <JCHEM_POLAR_SURFACE_AREA>
150.35000000000002

> <JCHEM_REFRACTIVITY>
167.1277

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,4S,5R)-6-({2-[(R,1bR,4R,5aR,5bR)-4-dihydroxy-1b-methyl-5-methylidene-hexahydronaphtho[1,8a-b]oxiren--yl]propan-2-yl}oxy)-2-methyl-5-{[(2Z)-2-methylbut-2-enoyl]oxy}-4-[(2-methylpropanoyl)oxy]oxan-3-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.185  -2.043   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.195  -3.757   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.748  -4.284   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.642  -3.230   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.722  -5.204   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.732  -6.384   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.215  -6.117   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.225  -7.296   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.709  -7.029   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.752  -8.743   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.762  -9.923   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.246  -9.656   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.719  -8.209   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.256 -10.835   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.782 -12.283   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.261 -10.568   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.788  -9.121   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.269  -9.011   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.795 -10.458   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       8.312 -10.725   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.302  -9.546   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       8.839 -12.172   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.849 -13.352   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.355 -12.440   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.259  -7.831   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       8.775  -8.099   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       9.765  -6.919   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       9.238  -5.472   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      11.282  -7.186   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      12.272  -6.007   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      11.808  -8.633   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      10.819  -9.813   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       4.001  -3.850   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   46                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   46                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   44                                             
CONECT   12   11                                                            
CONECT   13   11   14   15   16                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18   36                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   29                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27                                                            
CONECT   29   21   30   36                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   29   17   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43                                                       
CONECT   43   42                                                            
CONECT   44   11   45   46                                                  
CONECT   45   44   46                                                       
CONECT   46   45    2   44    7                                             
MASTER        0    0    0    0    0    0    0    0   46    0   98    0
END

View in JSmol

Synonyms

Value	Source
(3R,4S,5S,6R)-2-({2-[(R,1BR,4R,5ar,5BR)-4-dihydroxy-1b-methyl-5-methylidene-octahydro-H-naphtho[1,8a-b]oxiren--yl]propan-2-yl}oxy)-6-methyl-5-{[(2Z)-2-methylbut-2-enoyl]oxy}-4-[(2-methylpropanoyl)oxy]oxan-3-yl (2Z)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₃₅H₅₂O₁₁

Average Mass

648.7900 Da

Monoisotopic Mass

648.35096 Da

IUPAC Name

(2R,3S,4S,5R)-6-({2-[(R,1bR,4R,5aR,5bR)-4-dihydroxy-1b-methyl-5-methylidene-octahydro-H-naphtho[1,8a-b]oxiren--yl]propan-2-yl}oxy)-2-methyl-5-{[(2Z)-2-methylbut-2-enoyl]oxy}-4-[(2-methylpropanoyl)oxy]oxan-3-yl (2Z)-2-methylbut-2-enoate

Traditional Name

(2R,3S,4S,5R)-6-({2-[(R,1bR,4R,5aR,5bR)-4-dihydroxy-1b-methyl-5-methylidene-hexahydronaphtho[1,8a-b]oxiren--yl]propan-2-yl}oxy)-2-methyl-5-{[(2Z)-2-methylbut-2-enoyl]oxy}-4-[(2-methylpropanoyl)oxy]oxan-3-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

C\C=C(\C)C(=O)O[C@H]1[C@@H](C)OC(OC(C)(C)[C@@]2(O)CC[C@@]3(C)CC[C@@H](O)C(=C)[C@]33O[C@H]23)[C@H](OC(=O)C(\C)=C/C)[C@H]1OC(=O)C(C)C

InChI Identifier

InChI=1S/C35H52O11/c1-12-19(5)28(38)42-24-22(8)41-30(26(44-29(39)20(6)13-2)25(24)43-27(37)18(3)4)45-32(9,10)34(40)17-16-33(11)15-14-23(36)21(7)35(33)31(34)46-35/h12-13,18,22-26,30-31,36,40H,7,14-17H2,1-6,8-11H3/b19-12-,20-13-/t22-,23-,24+,25+,26-,30?,31-,33-,34-,35-/m1/s1

InChI Key

WMACAWYSWIYFLP-KFWXLWKSSA-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
Calendula arvensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
O-glycosyl compound
Glycosyl compound
Tricarboxylic acid or derivatives
Oxepane
Fatty acid ester
Fatty acyl
Oxane
Monosaccharide
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	6	ChemAxon
pKa (Strongest Acidic)	12.69	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	150.35 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	167.13 m³·mol⁻¹	ChemAxon
Polarizability	68.66 Å³	ChemAxon
Number of Rings	4	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

162837867

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3s,4s,5r)-6-({2-[(1ar,2r,4ar,7r,8ar)-2,7-dihydroxy-4a-methyl-8-methylidene-hexahydronaphtho[1,8a-b]oxiren-2-yl]propan-2-yl}oxy)-2-methyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-4-[(2-methylpropanoyl)oxy]oxan-3-yl (2z)-2-methylbut-2-enoate (NP0224898)

MOL for NP0224898 ((2r,3s,4s,5r)-6-({2-[(1ar,2r,4ar,7r,8ar)-2,7-dihydroxy-4a-methyl-8-methylidene-hexahydronaphtho[1,8a-b]oxiren-2-yl]propan-2-yl}oxy)-2-methyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-4-[(2-methylpropanoyl)oxy]oxan-3-yl (2z)-2-methylbut-2-enoate)

3D MOL for NP0224898 ((2r,3s,4s,5r)-6-({2-[(1ar,2r,4ar,7r,8ar)-2,7-dihydroxy-4a-methyl-8-methylidene-hexahydronaphtho[1,8a-b]oxiren-2-yl]propan-2-yl}oxy)-2-methyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-4-[(2-methylpropanoyl)oxy]oxan-3-yl (2z)-2-methylbut-2-enoate)

3D SDF for NP0224898 ((2r,3s,4s,5r)-6-({2-[(1ar,2r,4ar,7r,8ar)-2,7-dihydroxy-4a-methyl-8-methylidene-hexahydronaphtho[1,8a-b]oxiren-2-yl]propan-2-yl}oxy)-2-methyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-4-[(2-methylpropanoyl)oxy]oxan-3-yl (2z)-2-methylbut-2-enoate)

3D-SDF for NP0224898 ((2r,3s,4s,5r)-6-({2-[(1ar,2r,4ar,7r,8ar)-2,7-dihydroxy-4a-methyl-8-methylidene-hexahydronaphtho[1,8a-b]oxiren-2-yl]propan-2-yl}oxy)-2-methyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-4-[(2-methylpropanoyl)oxy]oxan-3-yl (2z)-2-methylbut-2-enoate)

PDB for NP0224898 ((2r,3s,4s,5r)-6-({2-[(1ar,2r,4ar,7r,8ar)-2,7-dihydroxy-4a-methyl-8-methylidene-hexahydronaphtho[1,8a-b]oxiren-2-yl]propan-2-yl}oxy)-2-methyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-4-[(2-methylpropanoyl)oxy]oxan-3-yl (2z)-2-methylbut-2-enoate)

3D PDB for NP0224898 ((2r,3s,4s,5r)-6-({2-[(1ar,2r,4ar,7r,8ar)-2,7-dihydroxy-4a-methyl-8-methylidene-hexahydronaphtho[1,8a-b]oxiren-2-yl]propan-2-yl}oxy)-2-methyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-4-[(2-methylpropanoyl)oxy]oxan-3-yl (2z)-2-methylbut-2-enoate)

SMILES for NP0224898 ((2r,3s,4s,5r)-6-({2-[(1ar,2r,4ar,7r,8ar)-2,7-dihydroxy-4a-methyl-8-methylidene-hexahydronaphtho[1,8a-b]oxiren-2-yl]propan-2-yl}oxy)-2-methyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-4-[(2-methylpropanoyl)oxy]oxan-3-yl (2z)-2-methylbut-2-enoate)

INCHI for NP0224898 ((2r,3s,4s,5r)-6-({2-[(1ar,2r,4ar,7r,8ar)-2,7-dihydroxy-4a-methyl-8-methylidene-hexahydronaphtho[1,8a-b]oxiren-2-yl]propan-2-yl}oxy)-2-methyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-4-[(2-methylpropanoyl)oxy]oxan-3-yl (2z)-2-methylbut-2-enoate)

Structure for NP0224898 ((2r,3s,4s,5r)-6-({2-[(1ar,2r,4ar,7r,8ar)-2,7-dihydroxy-4a-methyl-8-methylidene-hexahydronaphtho[1,8a-b]oxiren-2-yl]propan-2-yl}oxy)-2-methyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-4-[(2-methylpropanoyl)oxy]oxan-3-yl (2z)-2-methylbut-2-enoate)

3D Structure for NP0224898 ((2r,3s,4s,5r)-6-({2-[(1ar,2r,4ar,7r,8ar)-2,7-dihydroxy-4a-methyl-8-methylidene-hexahydronaphtho[1,8a-b]oxiren-2-yl]propan-2-yl}oxy)-2-methyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-4-[(2-methylpropanoyl)oxy]oxan-3-yl (2z)-2-methylbut-2-enoate)