NP-MRD: Showing NP-Card for [2-(acetyloxy)-8-(2,4-dihydroxy-5-oxo-2h-furan-3-yl)-1-{[(5-methoxy-6-methyloxan-2-yl)oxy]methyl}-4a,7,8a-trimethyl-3,4,4b,5,8,9,10,10a-octahydro-2h-phenanthren-1-yl]methyl 5-methyl-1h-pyrrole-2-carboxylate (NP0222582)

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Record Information

Version

2.0

Created at

2022-09-06 00:27:15 UTC

Updated at

2022-09-06 00:27:15 UTC

NP-MRD ID

NP0222582

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[2-(acetyloxy)-8-(2,4-dihydroxy-5-oxo-2h-furan-3-yl)-1-{[(5-methoxy-6-methyloxan-2-yl)oxy]methyl}-4a,7,8a-trimethyl-3,4,4b,5,8,9,10,10a-octahydro-2h-phenanthren-1-yl]methyl 5-methyl-1h-pyrrole-2-carboxylate

Description

[2-(Acetyloxy)-8-(2,4-dihydroxy-5-oxo-2,5-dihydrofuran-3-yl)-1-{[(5-methoxy-6-methyloxan-2-yl)oxy]methyl}-4a,7,8a-trimethyl-1,2,3,4,4a,4b,5,8,8a,9,10,10a-dodecahydrophenanthren-1-yl]methyl 5-methyl-1H-pyrrole-2-carboxylate belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. Based on a literature review very few articles have been published on [2-(acetyloxy)-8-(2,4-dihydroxy-5-oxo-2,5-dihydrofuran-3-yl)-1-{[(5-methoxy-6-methyloxan-2-yl)oxy]methyl}-4a,7,8a-trimethyl-1,2,3,4,4a,4b,5,8,8a,9,10,10a-dodecahydrophenanthren-1-yl]methyl 5-methyl-1H-pyrrole-2-carboxylate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062202272D          

 50 55  0  0  0  0            999 V2000
   -3.8608   -5.8127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7175   -5.0003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9423   -4.7181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7990   -3.9056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0238   -3.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3918   -4.1538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6165   -3.8716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4733   -3.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4452   -3.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2205   -3.8716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3637   -4.6841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1390   -4.9662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7318   -5.2144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7893   -6.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0244   -6.3464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5059   -5.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3289   -5.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0687   -5.0148    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730   -2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8350   -3.5777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3870   -2.9646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0065   -4.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7602   -4.7202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2920   -4.7971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6789   -4.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8719   -4.4166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5350   -4.9662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3103   -5.2484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4535   -6.0609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
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  6  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
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 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 36 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
 35 41  1  0  0  0  0
 41 42  1  0  0  0  0
 34 43  1  0  0  0  0
 29 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 27 47  1  0  0  0  0
  9 47  1  0  0  0  0
  6 48  1  0  0  0  0
 48 49  1  0  0  0  0
  3 49  1  0  0  0  0
 49 50  1  0  0  0  0
M  END


  Mrv1652309062202272D          

 50 55  0  0  0  0            999 V2000
   -3.8608   -5.8127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7175   -5.0003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9423   -4.7181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7990   -3.9056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0238   -3.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3918   -4.1538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6165   -3.8716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4733   -3.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4452   -3.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2205   -3.8716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3637   -4.6841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1390   -4.9662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7318   -5.2144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7893   -6.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0244   -6.3464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5059   -5.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3289   -5.7720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0687   -5.0148    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730   -2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8350   -3.5777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3870   -2.9646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0065   -4.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7602   -4.7202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2920   -4.7971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6789   -4.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8719   -4.4166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3645   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5350   -4.9662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3103   -5.2484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4535   -6.0609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  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
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 14 19  1  0  0  0  0
  9 20  1  0  0  0  0
 20 21  1  0  0  0  0
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 43 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 27 47  1  0  0  0  0
  9 47  1  0  0  0  0
  6 48  1  0  0  0  0
 48 49  1  0  0  0  0
  3 49  1  0  0  0  0
 49 50  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0222582

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1CCC(OCC2(COC(=O)C3=CC=C(C)N3)C(CCC3(C)C2CCC2(C)C3CC=C(C)C2C2=C(O)C(=O)OC2O)OC(C)=O)OC1C

> <INCHI_IDENTIFIER>
InChI=1S/C38H53NO11/c1-20-8-12-26-36(5)17-15-28(49-23(4)40)38(19-47-33(42)24-10-9-21(2)39-24,18-46-29-13-11-25(45-7)22(3)48-29)27(36)14-16-37(26,6)31(20)30-32(41)35(44)50-34(30)43/h8-10,22,25-29,31,34,39,41,43H,11-19H2,1-7H3

> <INCHI_KEY>
ZIOIITMDKMWZOA-UHFFFAOYSA-N

> <FORMULA>
C38H53NO11

> <MOLECULAR_WEIGHT>
699.838

> <EXACT_MASS>
699.361861531

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
103

> <JCHEM_AVERAGE_POLARIZABILITY>
75.9958986320802

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[2-(acetyloxy)-8-(2,4-dihydroxy-5-oxo-2,5-dihydrofuran-3-yl)-1-{[(5-methoxy-6-methyloxan-2-yl)oxy]methyl}-4a,7,8a-trimethyl-1,2,3,4,4a,4b,5,8,8a,9,10,10a-dodecahydrophenanthren-1-yl]methyl 5-methyl-1H-pyrrole-2-carboxylate

> <JCHEM_LOGP>
4.438172492999998

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.996645596644013

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.56010976295724

> <JCHEM_PKA_STRONGEST_BASIC>
-3.364906943818246

> <JCHEM_POLAR_SURFACE_AREA>
162.83999999999997

> <JCHEM_REFRACTIVITY>
183.18420000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[2-(acetyloxy)-8-(2,4-dihydroxy-5-oxo-2H-furan-3-yl)-1-{[(5-methoxy-6-methyloxan-2-yl)oxy]methyl}-4a,7,8a-trimethyl-3,4,4b,5,8,9,10,10a-octahydro-2H-phenanthren-1-yl]methyl 5-methyl-1H-pyrrole-2-carboxylate

> <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      -7.207 -10.850   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -6.939  -9.334   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -5.492  -8.807   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.225  -7.291   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.778  -6.764   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.598  -7.754   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.151  -7.227   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.883  -5.710   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.564  -5.184   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.831  -6.700   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.278  -7.227   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.546  -8.744   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.993  -9.270   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.366  -9.733   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.473 -11.270   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.045 -11.847   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.944 -10.667   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.481 -10.774   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      -0.128  -9.361   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      -0.206  -3.850   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.746  -3.850   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.516  -5.184   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.746  -6.517   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.056  -5.184   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.564  -2.516   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.104  -2.516   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.874  -3.850   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.644  -2.516   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.414  -3.850   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.184  -2.516   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.724  -2.516   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.494  -3.850   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.034  -3.850   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.724  -5.184   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.494  -6.517   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.025  -6.678   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      10.056  -5.534   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       9.345  -8.185   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      10.752  -8.811   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       8.012  -8.955   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       6.867  -7.924   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       5.361  -8.244   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       5.184  -5.184   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       5.954  -6.517   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       4.414  -6.517   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       2.874  -6.517   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       2.104  -5.184   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      -2.865  -9.270   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      -4.313  -9.797   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -4.580 -11.314   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   49                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   48                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   20   47                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   14                                                       
CONECT   20    9   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   20   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29   47                                             
CONECT   28   27                                                            
CONECT   29   27   30   43                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   43                                                  
CONECT   35   34   36   41                                                  
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   35   42                                                  
CONECT   42   41                                                            
CONECT   43   34   29   44   45                                             
CONECT   44   43                                                            
CONECT   45   43   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   27    9                                                  
CONECT   48    6   49                                                       
CONECT   49   48    3   50                                                  
CONECT   50   49                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  110    0
END

View in JSmol

Synonyms

Value	Source
[2-(Acetyloxy)-8-(2,4-dihydroxy-5-oxo-2,5-dihydrofuran-3-yl)-1-{[(5-methoxy-6-methyloxan-2-yl)oxy]methyl}-4a,7,8a-trimethyl-1,2,3,4,4a,4b,5,8,8a,9,10,10a-dodecahydrophenanthren-1-yl]methyl 5-methyl-1H-pyrrole-2-carboxylic acid	Generator

Chemical Formula

C₃₈H₅₃NO₁₁

Average Mass

699.8380 Da

Monoisotopic Mass

699.36186 Da

IUPAC Name

[2-(acetyloxy)-8-(2,4-dihydroxy-5-oxo-2,5-dihydrofuran-3-yl)-1-{[(5-methoxy-6-methyloxan-2-yl)oxy]methyl}-4a,7,8a-trimethyl-1,2,3,4,4a,4b,5,8,8a,9,10,10a-dodecahydrophenanthren-1-yl]methyl 5-methyl-1H-pyrrole-2-carboxylate

Traditional Name

[2-(acetyloxy)-8-(2,4-dihydroxy-5-oxo-2H-furan-3-yl)-1-{[(5-methoxy-6-methyloxan-2-yl)oxy]methyl}-4a,7,8a-trimethyl-3,4,4b,5,8,9,10,10a-octahydro-2H-phenanthren-1-yl]methyl 5-methyl-1H-pyrrole-2-carboxylate

CAS Registry Number

Not Available

SMILES

COC1CCC(OCC2(COC(=O)C3=CC=C(C)N3)C(CCC3(C)C2CCC2(C)C3CC=C(C)C2C2=C(O)C(=O)OC2O)OC(C)=O)OC1C

InChI Identifier

InChI=1S/C38H53NO11/c1-20-8-12-26-36(5)17-15-28(49-23(4)40)38(19-47-33(42)24-10-9-21(2)39-24,18-46-29-13-11-25(45-7)22(3)48-29)27(36)14-16-37(26,6)31(20)30-32(41)35(44)50-34(30)43/h8-10,22,25-29,31,34,39,41,43H,11-19H2,1-7H3

InChI Key

ZIOIITMDKMWZOA-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Diterpene glycosides

Alternative Parents

Substituents

Diterpene glycoside
Diterpene lactone
Diterpenoid
Isocopalane diterpenoid
Steroid
Hydrophenanthrene
Phenanthrene
Tricarboxylic acid or derivatives
Pyrrole-2-carboxylic acid or derivatives
2-furanone
Oxane
Substituted pyrrole
Dihydrofuran
Heteroaromatic compound
Pyrrole
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Carboxylic acid ester
Hemiacetal
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Azacycle
Ether
Enol
Dialkyl ether
Acetal
Organooxygen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	4.44	ChemAxon
pKa (Strongest Acidic)	8.56	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	162.84 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	183.18 m³·mol⁻¹	ChemAxon
Polarizability	76 Å³	ChemAxon
Number of Rings	6	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

75972086

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [2-(acetyloxy)-8-(2,4-dihydroxy-5-oxo-2h-furan-3-yl)-1-{[(5-methoxy-6-methyloxan-2-yl)oxy]methyl}-4a,7,8a-trimethyl-3,4,4b,5,8,9,10,10a-octahydro-2h-phenanthren-1-yl]methyl 5-methyl-1h-pyrrole-2-carboxylate (NP0222582)

MOL for NP0222582 ([2-(acetyloxy)-8-(2,4-dihydroxy-5-oxo-2h-furan-3-yl)-1-{[(5-methoxy-6-methyloxan-2-yl)oxy]methyl}-4a,7,8a-trimethyl-3,4,4b,5,8,9,10,10a-octahydro-2h-phenanthren-1-yl]methyl 5-methyl-1h-pyrrole-2-carboxylate)

3D MOL for NP0222582 ([2-(acetyloxy)-8-(2,4-dihydroxy-5-oxo-2h-furan-3-yl)-1-{[(5-methoxy-6-methyloxan-2-yl)oxy]methyl}-4a,7,8a-trimethyl-3,4,4b,5,8,9,10,10a-octahydro-2h-phenanthren-1-yl]methyl 5-methyl-1h-pyrrole-2-carboxylate)

3D SDF for NP0222582 ([2-(acetyloxy)-8-(2,4-dihydroxy-5-oxo-2h-furan-3-yl)-1-{[(5-methoxy-6-methyloxan-2-yl)oxy]methyl}-4a,7,8a-trimethyl-3,4,4b,5,8,9,10,10a-octahydro-2h-phenanthren-1-yl]methyl 5-methyl-1h-pyrrole-2-carboxylate)

3D-SDF for NP0222582 ([2-(acetyloxy)-8-(2,4-dihydroxy-5-oxo-2h-furan-3-yl)-1-{[(5-methoxy-6-methyloxan-2-yl)oxy]methyl}-4a,7,8a-trimethyl-3,4,4b,5,8,9,10,10a-octahydro-2h-phenanthren-1-yl]methyl 5-methyl-1h-pyrrole-2-carboxylate)

PDB for NP0222582 ([2-(acetyloxy)-8-(2,4-dihydroxy-5-oxo-2h-furan-3-yl)-1-{[(5-methoxy-6-methyloxan-2-yl)oxy]methyl}-4a,7,8a-trimethyl-3,4,4b,5,8,9,10,10a-octahydro-2h-phenanthren-1-yl]methyl 5-methyl-1h-pyrrole-2-carboxylate)

3D PDB for NP0222582 ([2-(acetyloxy)-8-(2,4-dihydroxy-5-oxo-2h-furan-3-yl)-1-{[(5-methoxy-6-methyloxan-2-yl)oxy]methyl}-4a,7,8a-trimethyl-3,4,4b,5,8,9,10,10a-octahydro-2h-phenanthren-1-yl]methyl 5-methyl-1h-pyrrole-2-carboxylate)

SMILES for NP0222582 ([2-(acetyloxy)-8-(2,4-dihydroxy-5-oxo-2h-furan-3-yl)-1-{[(5-methoxy-6-methyloxan-2-yl)oxy]methyl}-4a,7,8a-trimethyl-3,4,4b,5,8,9,10,10a-octahydro-2h-phenanthren-1-yl]methyl 5-methyl-1h-pyrrole-2-carboxylate)

INCHI for NP0222582 ([2-(acetyloxy)-8-(2,4-dihydroxy-5-oxo-2h-furan-3-yl)-1-{[(5-methoxy-6-methyloxan-2-yl)oxy]methyl}-4a,7,8a-trimethyl-3,4,4b,5,8,9,10,10a-octahydro-2h-phenanthren-1-yl]methyl 5-methyl-1h-pyrrole-2-carboxylate)

Structure for NP0222582 ([2-(acetyloxy)-8-(2,4-dihydroxy-5-oxo-2h-furan-3-yl)-1-{[(5-methoxy-6-methyloxan-2-yl)oxy]methyl}-4a,7,8a-trimethyl-3,4,4b,5,8,9,10,10a-octahydro-2h-phenanthren-1-yl]methyl 5-methyl-1h-pyrrole-2-carboxylate)

3D Structure for NP0222582 ([2-(acetyloxy)-8-(2,4-dihydroxy-5-oxo-2h-furan-3-yl)-1-{[(5-methoxy-6-methyloxan-2-yl)oxy]methyl}-4a,7,8a-trimethyl-3,4,4b,5,8,9,10,10a-octahydro-2h-phenanthren-1-yl]methyl 5-methyl-1h-pyrrole-2-carboxylate)