NP-MRD: Showing NP-Card for oleandolide (NP0312803)

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Record Information

Version

2.0

Created at

2022-09-11 09:54:12 UTC

Updated at

2022-09-11 09:54:12 UTC

NP-MRD ID

NP0312803

Secondary Accession Numbers

None

Natural Product Identification

Common Name

oleandolide

Description

Oleandolide belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. Thus, oleandolide is considered to be a macrolide. Oleandolide is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. oleandolide is found in Apis cerana. oleandolide was first documented in 2002 (PMID: 12392427). Based on a literature review a small amount of articles have been published on oleandolide (PMID: 30277648) (PMID: 17924640).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309112211542D          

 27 28  0  0  1  0            999 V2000
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9520    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6020    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270   -0.3020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1895    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.0164    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6020   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9520   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  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
  4  6  1  6  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
  2 26  1  0  0  0  0
 26 27  1  1  0  0  0
M  END

     RDKit          3D

 61 62  0  0  0  0  0  0  0  0999 V2000
   -2.8533   -2.2026    1.3831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9326   -1.2439    0.6410 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2260   -1.9871   -0.4212 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1402   -2.5082    0.0431 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2080   -3.6010    0.9926 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5543   -2.2204    1.3181 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1139   -2.5344   -1.0904 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6632   -3.0341   -2.1340 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4967   -2.0130   -0.9887 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3020   -2.6388    0.1042 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5550   -0.5014   -0.9886 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4054   -0.0356   -1.6237 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6732    0.0832    0.3923 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8781    1.0299    0.4871 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4651    0.9212    0.7652 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4477    0.9813    2.2974 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6575    2.2090    0.2183 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7115    3.1530   -0.0317 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8842    4.3410    0.3148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5437    2.8006   -0.7184 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2194    4.0157   -1.3322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5506    2.1169    0.1497 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6799    2.9410    0.3687 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0889    0.9205   -0.6415 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1195    1.4908   -1.6069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7564   -0.0883    0.1952 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9222   -0.6162   -0.4079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8926   -3.1978    0.8544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5605   -2.3281    2.4441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9047   -1.8477    1.3947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1671   -0.8995    1.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8049   -2.9236   -0.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0560   -1.4723   -1.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0441   -4.2988    0.9400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6104   -3.9184    1.6579 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0118   -2.3194   -1.9501 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2824   -2.1475    0.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5077   -3.7022   -0.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8266   -2.6976    1.0749 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4155   -0.1319   -1.5836 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2007   -0.6636   -2.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8135   -0.6607    1.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6978    0.6086   -0.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2467    1.0791    1.5406 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5799    2.0252    0.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5837    0.4011    0.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6179    1.5721    2.6855 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3902    1.5175    2.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5361   -0.0374    2.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2468    2.1604   -1.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6935    3.8125   -2.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4526    4.8098   -1.5116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9772    4.4334   -0.6461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1969    1.8265    1.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1097    2.7305    1.2434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2555    0.5543   -1.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6861    1.6520   -2.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9492    0.7469   -1.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6002    2.3998   -1.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1381    0.4215    1.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7159   -1.2842   -1.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  4  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26  2  1  0
  4  6  1  1
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  1
  3 32  1  0
  3 33  1  0
  5 34  1  0
  5 35  1  0
  9 36  1  6
 10 37  1  0
 10 38  1  0
 10 39  1  0
 11 40  1  6
 12 41  1  0
 13 42  1  1
 14 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  6
 16 47  1  0
 16 48  1  0
 16 49  1  0
 20 50  1  6
 21 51  1  0
 21 52  1  0
 21 53  1  0
 22 54  1  1
 23 55  1  0
 24 56  1  6
 25 57  1  0
 25 58  1  0
 25 59  1  0
 26 60  1  1
 27 61  1  0
M  END

  Mrv1652309112211542D          

 27 28  0  0  1  0            999 V2000
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9520    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6020    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270   -0.3020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1895    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895   -1.0164    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6020   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9520   -1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  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
  4  6  1  6  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
  2 26  1  0  0  0  0
 26 27  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0312803

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C[C@@]2(CO2)C(=O)[C@H](C)[C@@H](O)[C@@H](C)[C@@H](C)OC(=O)[C@H](C)[C@@H](O)[C@H](C)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O7/c1-9-7-20(8-26-20)18(24)12(4)16(22)10(2)14(6)27-19(25)13(5)17(23)11(3)15(9)21/h9-17,21-23H,7-8H2,1-6H3/t9-,10-,11+,12+,13+,14+,15-,16-,17-,20+/m0/s1

> <INCHI_KEY>
PFDLUBNRHMFBGI-HRVFELILSA-N

> <FORMULA>
C20H34O7

> <MOLECULAR_WEIGHT>
386.485

> <EXACT_MASS>
386.230453435

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
41.416528052080636

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,5R,6S,7R,8R,11R,12S,13R,14S,15S)-6,12,14-trihydroxy-5,7,8,11,13,15-hexamethyl-1,9-dioxaspiro[2.13]hexadecane-4,10-dione

> <JCHEM_LOGP>
1.4801839896666664

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.48484631161547

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.972915869442012

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9628530746953032

> <JCHEM_POLAR_SURFACE_AREA>
116.59

> <JCHEM_REFRACTIVITY>
98.08309999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
oleandolide

> <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       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334   3.437   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.644   4.771   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.724   4.771   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.494   3.437   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.264   2.104   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.574   0.770   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.264  -0.564   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.034  -1.897   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.954   0.770   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.954  -1.897   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.724  -3.231   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.644  -3.231   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6    7                                             
CONECT    5    4    6                                                       
CONECT    6    5    4                                                       
CONECT    7    4    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24    2   27                                                  
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

View in JSmol

Synonyms

Value	Source
(-)-Oleandolide	ChEBI
Oleandomycin aglycone	ChEBI
Oleandonolide	ChEBI

Chemical Formula

C₂₀H₃₄O₇

Average Mass

386.4850 Da

Monoisotopic Mass

386.23045 Da

IUPAC Name

(3R,5R,6S,7R,8R,11R,12S,13R,14S,15S)-6,12,14-trihydroxy-5,7,8,11,13,15-hexamethyl-1,9-dioxaspiro[2.13]hexadecane-4,10-dione

Traditional Name

oleandolide

CAS Registry Number

Not Available

SMILES

C[C@H]1C[C@@]2(CO2)C(=O)[C@H](C)[C@@H](O)[C@@H](C)[C@@H](C)OC(=O)[C@H](C)[C@@H](O)[C@H](C)[C@H]1O

InChI Identifier

InChI=1S/C20H34O7/c1-9-7-20(8-26-20)18(24)12(4)16(22)10(2)14(6)27-19(25)13(5)17(23)11(3)15(9)21/h9-17,21-23H,7-8H2,1-6H3/t9-,10-,11+,12+,13+,14+,15-,16-,17-,20+/m0/s1

InChI Key

PFDLUBNRHMFBGI-HRVFELILSA-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
Apis cerana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Carboxylic acid ester
Ketone
Lactone
Secondary alcohol
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Monocarboxylic acid or derivatives
Polyol
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

macrolide (CHEBI:29658 )
Macrolides and lactone polyketides (C11990 )
Macrolides and lactone polyketides (LMPK04000031 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.48	ChemAxon
pKa (Strongest Acidic)	13.97	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	116.59 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	98.08 m³·mol⁻¹	ChemAxon
Polarizability	41.42 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

20016206

KEGG Compound ID

C11990

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

443564

PDB ID

Not Available

ChEBI ID

29658

Good Scents ID

Not Available

References

General References

Mu Y, Lin X, Wang Z, Hou Q, Wang Y, Hu Z: High-production dairy cattle exhibit different rumen and fecal bacterial community and rumen metabolite profile than low-production cattle. Microbiologyopen. 2019 Apr;8(4):e00673. doi: 10.1002/mbo3.673. Epub 2018 Sep 11. [PubMed:30277648 ]
Parker KA, Wang P: Deconstruction-reconstruction strategy for accessing valuable polyketides. Preparation of the C15-C24 stereopentad of discodermolide. Org Lett. 2007 Nov 8;9(23):4793-6. doi: 10.1021/ol702144u. Epub 2007 Oct 9. [PubMed:17924640 ]
Hu T, Takenaka N, Panek JS: Asymmetric crotylation reactions in synthesis of polypropionate-derived macrolides: application to total synthesis of oleandolide. J Am Chem Soc. 2002 Oct 30;124(43):12806-15. doi: 10.1021/ja020853m. [PubMed:12392427 ]
LOTUS database [Link]

Showing NP-Card for oleandolide (NP0312803)

MOL for NP0312803 (oleandolide)

3D MOL for NP0312803 (oleandolide)

3D SDF for NP0312803 (oleandolide)

3D-SDF for NP0312803 (oleandolide)

PDB for NP0312803 (oleandolide)

3D PDB for NP0312803 (oleandolide)

SMILES for NP0312803 (oleandolide)

INCHI for NP0312803 (oleandolide)

Structure for NP0312803 (oleandolide)

3D Structure for NP0312803 (oleandolide)