NP-MRD: Showing NP-Card for 22-ethyl-7,11,14,15-tetrahydroxy-6'-(2-hydroxypropyl)-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione (NP0222794)

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Record Information

Version

2.0

Created at

2022-09-06 00:43:20 UTC

Updated at

2022-09-06 00:43:20 UTC

NP-MRD ID

NP0222794

Secondary Accession Numbers

None

Natural Product Identification

Common Name

22-ethyl-7,11,14,15-tetrahydroxy-6'-(2-hydroxypropyl)-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione

Description

Oligomycin A 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. 22-ethyl-7,11,14,15-tetrahydroxy-6'-(2-hydroxypropyl)-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione is found in Streptomyces libani. Oligomycin A is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004251506282D          

 56 58  0  0  0  0            999 V2000
    5.0359    3.8314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7076    3.3523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6285    2.5311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3792    2.8733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0509    2.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9719    1.5730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6436    1.0940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5645    0.2728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3152    0.6150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9869    0.1359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9079   -0.6853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5796   -1.1643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1572   -1.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0782   -1.8487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7499   -2.3277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6708   -3.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5005   -1.9855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4855   -0.5484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8138   -0.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7348   -0.8906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1422    0.4097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3915    0.0675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3125   -0.7537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9841   -1.2328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5618   -1.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4827   -1.9171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7320   -2.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0604   -1.7802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6530   -3.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3247   -3.5595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9023   -3.4226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8233   -4.2439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2306   -2.9436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3097   -2.1224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4799   -3.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4009   -4.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8083   -2.8067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0576   -3.1489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8873   -1.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2156   -1.5065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6380   -1.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9663   -1.1643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7170   -0.8222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8946   -0.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5104   -0.0234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4677   -0.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1394   -0.9590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5467    0.3412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8751    0.8203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2974    0.6834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3764    1.5046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1271    1.8468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2062    2.6680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9569    3.0101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2212    1.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5495    1.7099    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
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 13 18  1  0  0  0  0
  8 18  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  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
 23 24  2  0  0  0  0
 25 23  1  4  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 43 46  1  0  0  0  0
 46 47  1  0  0  0  0
 46 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 51 50  1  4  0  0  0
 51 52  2  0  0  0  0
 53 52  1  4  0  0  0
 53 54  2  0  0  0  0
  3 54  1  0  0  0  0
 21 55  1  0  0  0  0
  6 55  1  0  0  0  0
 55 56  1  0  0  0  0
M  END


  Mrv1533004251506282D          

 56 58  0  0  0  0            999 V2000
    5.0359    3.8314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7076    3.3523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6285    2.5311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3792    2.8733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0509    2.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9719    1.5730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6436    1.0940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5645    0.2728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3152    0.6150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9869    0.1359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9079   -0.6853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5796   -1.1643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1572   -1.0275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0782   -1.8487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7499   -2.3277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6708   -3.1489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5005   -1.9855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4855   -0.5484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8138   -0.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7348   -0.8906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1422    0.4097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3915    0.0675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3125   -0.7537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9841   -1.2328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5618   -1.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4827   -1.9171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7320   -2.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0604   -1.7802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6530   -3.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3247   -3.5595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9023   -3.4226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8233   -4.2439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2306   -2.9436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3097   -2.1224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4799   -3.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4009   -4.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8083   -2.8067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0576   -3.1489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8873   -1.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2156   -1.5065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6380   -1.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9663   -1.1643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7170   -0.8222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8946   -0.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5104   -0.0234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4677   -0.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1394   -0.9590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5467    0.3412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8751    0.8203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2974    0.6834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3764    1.5046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1271    1.8468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2062    2.6680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9569    3.0101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2212    1.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5495    1.7099    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
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 13 18  1  0  0  0  0
  8 18  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  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
 23 24  2  0  0  0  0
 25 23  1  4  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  1  0  0  0  0
 43 46  1  0  0  0  0
 46 47  1  0  0  0  0
 46 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 51 50  1  4  0  0  0
 51 52  2  0  0  0  0
 53 52  1  4  0  0  0
 53 54  2  0  0  0  0
  3 54  1  0  0  0  0
 21 55  1  0  0  0  0
  6 55  1  0  0  0  0
 55 56  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0222794

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1CCC2OC3(CCC(C)C(CC(C)O)O3)C(C)C(OC(=O)C=CC(C)C(O)C(C)C(=O)C(C)C(O)C(C)C(=O)C(C)(O)C(O)C(C)CC=CC=C1)C2C

> <INCHI_IDENTIFIER>
InChI=1S/C45H74O11/c1-12-34-17-15-13-14-16-27(4)42(51)44(11,53)43(52)32(9)40(50)31(8)39(49)30(7)38(48)26(3)18-21-37(47)54-41-29(6)35(20-19-34)55-45(33(41)10)23-22-25(2)36(56-45)24-28(5)46/h13-15,17-18,21,25-36,38,40-42,46,48,50-51,53H,12,16,19-20,22-24H2,1-11H3

> <INCHI_KEY>
MNULEGDCPYONBU-UHFFFAOYSA-N

> <FORMULA>
C45H74O11

> <MOLECULAR_WEIGHT>
791.076

> <EXACT_MASS>
790.523113203

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
130

> <JCHEM_AVERAGE_POLARIZABILITY>
89.09357368408371

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
22-ethyl-7,11,14,15-tetrahydroxy-6'-(2-hydroxypropyl)-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione

> <ALOGPS_LOGP>
4.88

> <JCHEM_LOGP>
7.447626754666667

> <ALOGPS_LOGS>
-5.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.70521012616219

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.264529805973504

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5454300947629065

> <JCHEM_POLAR_SURFACE_AREA>
180.05

> <JCHEM_REFRACTIVITY>
219.2278000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.52e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
22-ethyl-7,11,14,15-tetrahydroxy-6'-(2-hydroxypropyl)-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       9.400   7.152   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.654   6.258   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.507   4.725   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.908   5.363   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.162   4.469   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.014   2.936   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      14.268   2.042   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      14.120   0.509   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.522   1.148   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.776   0.254   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.628  -1.279   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.882  -2.173   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.227  -1.918   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.079  -3.451   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.333  -4.345   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.186  -5.878   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      17.734  -3.706   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      13.973  -1.024   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      12.719  -0.130   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.572  -1.662   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.465   0.765   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.064   0.126   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.917  -1.407   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      11.170  -2.301   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.515  -2.046   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.368  -3.579   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.966  -4.217   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.713  -3.323   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.819  -5.750   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.073  -6.644   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.418  -6.389   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.270  -7.922   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.164  -5.495   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.311  -3.962   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.763  -6.133   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.615  -7.666   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.509  -5.239   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       0.107  -5.878   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       1.656  -3.706   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       0.402  -2.812   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       3.058  -3.068   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       1.804  -2.173   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       3.205  -1.535   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       1.670  -1.656   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       2.819  -0.044   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       4.606  -0.896   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       5.860  -1.790   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0       4.754   0.637   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       3.500   1.531   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       6.155   1.276   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       6.303   2.809   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       7.704   3.447   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       7.852   4.980   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       9.253   5.619   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      11.613   2.298   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      10.359   3.192   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   54                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   55                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   18   19                                             
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13    8                                                       
CONECT   19    8   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   55                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44   45   46                                             
CONECT   44   43                                                            
CONECT   45   43                                                            
CONECT   46   43   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53    3                                                       
CONECT   55   21    6   56                                                  
CONECT   56   55                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  116    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₅H₇₄O₁₁

Average Mass

791.0760 Da

Monoisotopic Mass

790.52311 Da

IUPAC Name

22-ethyl-7,11,14,15-tetrahydroxy-6'-(2-hydroxypropyl)-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione

Traditional Name

22-ethyl-7,11,14,15-tetrahydroxy-6'-(2-hydroxypropyl)-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione

CAS Registry Number

Not Available

SMILES

CCC1CCC2OC3(CCC(C)C(CC(C)O)O3)C(C)C(OC(=O)C=CC(C)C(O)C(C)C(=O)C(C)C(O)C(C)C(=O)C(C)(O)C(O)C(C)CC=CC=C1)C2C

InChI Identifier

InChI=1S/C45H74O11/c1-12-34-17-15-13-14-16-27(4)42(51)44(11,53)43(52)32(9)40(50)31(8)39(49)30(7)38(48)26(3)18-21-37(47)54-41-29(6)35(20-19-34)55-45(33(41)10)23-22-25(2)36(56-45)24-28(5)46/h13-15,17-18,21,25-36,38,40-42,46,48,50-51,53H,12,16,19-20,22-24H2,1-11H3

InChI Key

MNULEGDCPYONBU-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces libani	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
Ketal
Acyloin
Oxane
Tertiary alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Cyclic ketone
Secondary alcohol
Carboxylic acid ester
Lactone
Ketone
Oxacycle
Acetal
Polyol
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Organooxygen compound
Carbonyl group
Alcohol
Hydrocarbon derivative
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	4.88	ALOGPS
logP	7.45	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	12.26	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	180.05 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	219.23 m³·mol⁻¹	ChemAxon
Polarizability	89.09 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

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

4591

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 22-ethyl-7,11,14,15-tetrahydroxy-6'-(2-hydroxypropyl)-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione (NP0222794)

MOL for NP0222794 (22-ethyl-7,11,14,15-tetrahydroxy-6'-(2-hydroxypropyl)-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione)

3D MOL for NP0222794 (22-ethyl-7,11,14,15-tetrahydroxy-6'-(2-hydroxypropyl)-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione)

3D SDF for NP0222794 (22-ethyl-7,11,14,15-tetrahydroxy-6'-(2-hydroxypropyl)-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione)

3D-SDF for NP0222794 (22-ethyl-7,11,14,15-tetrahydroxy-6'-(2-hydroxypropyl)-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione)

PDB for NP0222794 (22-ethyl-7,11,14,15-tetrahydroxy-6'-(2-hydroxypropyl)-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione)

3D PDB for NP0222794 (22-ethyl-7,11,14,15-tetrahydroxy-6'-(2-hydroxypropyl)-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione)

SMILES for NP0222794 (22-ethyl-7,11,14,15-tetrahydroxy-6'-(2-hydroxypropyl)-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione)

INCHI for NP0222794 (22-ethyl-7,11,14,15-tetrahydroxy-6'-(2-hydroxypropyl)-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione)

Structure for NP0222794 (22-ethyl-7,11,14,15-tetrahydroxy-6'-(2-hydroxypropyl)-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione)

3D Structure for NP0222794 (22-ethyl-7,11,14,15-tetrahydroxy-6'-(2-hydroxypropyl)-5',6,8,10,12,14,16,28,29-nonamethyl-2,26-dioxaspiro[bicyclo[23.3.1]nonacosane-27,2'-oxane]-4,18,20-triene-3,9,13-trione)