NP-MRD: Showing NP-Card for (+)-Leandreanin B (NP0079978)

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Record Information

Version

2.0

Created at

2022-04-29 01:02:15 UTC

Updated at

2022-04-29 01:02:15 UTC

NP-MRD ID

NP0079978

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Leandreanin B

Description

Methyl 2-[(1R,2S,3S,4S,5R,6S,7R,8S,10R,12R,13R,15R,16R)-2,3,4,13-tetrakis(acetyloxy)-15-(furan-3-carbonyl)-16-(2-methoxy-2-oxoethyl)-5,7,10,15-tetramethyl-9,11,17-trioxahexacyclo[8.6.1.1⁵,⁸.0¹,¹².0³,⁸.0⁷,¹²]Octadecan-6-yl]acetate belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. (+)-Leandreanin B is found in Neobeguea leandreana. Based on a literature review very few articles have been published on methyl 2-[(1R,2S,3S,4S,5R,6S,7R,8S,10R,12R,13R,15R,16R)-2,3,4,13-tetrakis(acetyloxy)-15-(furan-3-carbonyl)-16-(2-methoxy-2-oxoethyl)-5,7,10,15-tetramethyl-9,11,17-trioxahexacyclo[8.6.1.1⁵,⁸.0¹,¹².0³,⁸.0⁷,¹²]Octadecan-6-yl]acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304292203022D          

 55 61  0  0  1  0            999 V2000
    5.1560    1.9462    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2604    1.5192    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4790    0.7710    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2710    0.3589    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9773    0.8178    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9323    1.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8022    0.8335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2282    0.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2010    1.5557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8512    2.3028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4537    2.8664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1759    2.4675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0197    1.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4512    0.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3107   -0.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0442   -0.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7380   -0.3963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0840   -1.6668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8175   -2.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7924    0.2622    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9925    0.6210    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9738    1.4842    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0705    1.9151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9098    1.3430    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1776    0.5141    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7367   -0.1832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9123   -0.1499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4714   -0.8472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5290    0.5806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0901    1.4359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4643    2.2723    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3032    1.8917    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6233    2.6520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2178    3.0596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4127    3.2397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8542    2.6326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1662    4.0271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3612    4.2072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3559    2.4446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2679    2.1761    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7535    2.3597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7035    2.8767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9970    1.3850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8728   -0.1953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1060   -0.4997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9863   -1.3160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2817   -0.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8814   -0.5580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2156   -1.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3045   -1.8653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4608   -0.7121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1276    2.7707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8274    3.2076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7989    4.0321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5557    2.8200    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
  1  6  1  0  0  0  0
  5  7  1  1  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  2  0  0  0  0
  5 14  1  6  0  0  0
  4 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 24 30  1  1  0  0  0
 24 31  1  0  0  0  0
 31 32  1  0  0  0  0
  2 32  1  0  0  0  0
 22 32  1  0  0  0  0
 32 33  1  6  0  0  0
 31 34  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 22 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
  2 41  1  6  0  0  0
 40 42  1  6  0  0  0
 40 43  1  0  0  0  0
  3 43  1  6  0  0  0
 21 44  1  6  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 45 47  1  0  0  0  0
 20 48  1  6  0  0  0
 48 49  1  0  0  0  0
 49 50  2  0  0  0  0
 49 51  1  0  0  0  0
  1 52  1  6  0  0  0
 52 53  1  0  0  0  0
 53 54  2  0  0  0  0
 53 55  1  0  0  0  0
M  END


  Mrv1652304292203022D          

 55 61  0  0  1  0            999 V2000
    5.1560    1.9462    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2604    1.5192    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4790    0.7710    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2710    0.3589    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9773    0.8178    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9323    1.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8022    0.8335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2282    0.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2010    1.5557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8512    2.3028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4537    2.8664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1759    2.4675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0197    1.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4512    0.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3107   -0.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0442   -0.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7380   -0.3963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0840   -1.6668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8175   -2.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7924    0.2622    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9925    0.6210    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9738    1.4842    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0705    1.9151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9098    1.3430    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1776    0.5141    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7367   -0.1832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9123   -0.1499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4714   -0.8472    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5290    0.5806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0901    1.4359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4643    2.2723    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3032    1.8917    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6233    2.6520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2178    3.0596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4127    3.2397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8542    2.6326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1662    4.0271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3612    4.2072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3559    2.4446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2679    2.1761    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7535    2.3597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7035    2.8767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9970    1.3850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8728   -0.1953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1060   -0.4997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9863   -1.3160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2817   -0.4660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8814   -0.5580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2156   -1.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3045   -1.8653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4608   -0.7121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1276    2.7707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8274    3.2076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7989    4.0321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5557    2.8200    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
  1  6  1  0  0  0  0
  5  7  1  1  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 13  2  0  0  0  0
  5 14  1  6  0  0  0
  4 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 24 30  1  1  0  0  0
 24 31  1  0  0  0  0
 31 32  1  0  0  0  0
  2 32  1  0  0  0  0
 22 32  1  0  0  0  0
 32 33  1  6  0  0  0
 31 34  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 22 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
  2 41  1  6  0  0  0
 40 42  1  6  0  0  0
 40 43  1  0  0  0  0
  3 43  1  6  0  0  0
 21 44  1  6  0  0  0
 44 45  1  0  0  0  0
 45 46  2  0  0  0  0
 45 47  1  0  0  0  0
 20 48  1  6  0  0  0
 48 49  1  0  0  0  0
 49 50  2  0  0  0  0
 49 51  1  0  0  0  0
  1 52  1  6  0  0  0
 52 53  1  0  0  0  0
 53 54  2  0  0  0  0
 53 55  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0079978

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C[C@H]1[C@@]2(C)C[C@]34O[C@]5(C)O[C@]6([C@H](CC(=O)OC)[C@@](C)(C[C@@H](OC(C)=O)[C@]6(O5)[C@]13C)C(=O)C1=COC=C1)[C@H](OC(C)=O)[C@@]4(OC(C)=O)[C@H]2OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C38H46O17/c1-18(39)49-25-15-31(5,28(45)22-11-12-48-16-22)24(14-27(44)47-10)36-30(51-20(3)41)37(52-21(4)42)29(50-19(2)40)32(6)17-35(37)33(7,23(32)13-26(43)46-9)38(25,36)55-34(8,53-35)54-36/h11-12,16,23-25,29-30H,13-15,17H2,1-10H3/t23-,24+,25+,29-,30-,31+,32+,33+,34+,35-,36+,37-,38-/m0/s1

> <INCHI_KEY>
WDSUDLNQRNVFBV-GKEVUJFVSA-N

> <FORMULA>
C38H46O17

> <MOLECULAR_WEIGHT>
774.769

> <EXACT_MASS>
774.273500021

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
101

> <JCHEM_AVERAGE_POLARIZABILITY>
70.93346943620173

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-[(1R,2S,3S,4S,5R,6S,7R,8S,10R,12R,13R,15R,16R)-2,3,4,13-tetrakis(acetyloxy)-15-(furan-3-carbonyl)-6-(2-methoxy-2-oxoethyl)-5,7,10,15-tetramethyl-9,11,17-trioxahexacyclo[8.6.1.1^{5,8}.0^{1,12}.0^{3,8}.0^{7,12}]octadecan-16-yl]acetate

> <ALOGPS_LOGP>
2.24

> <JCHEM_LOGP>
1.585210780666667

> <ALOGPS_LOGS>
-3.13

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.98966398537362

> <JCHEM_POLAR_SURFACE_AREA>
215.69999999999996

> <JCHEM_REFRACTIVITY>
177.24320000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.74e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl [(1R,2S,3S,4S,5R,6S,7R,8S,10R,12R,13R,15R,16R)-2,3,4,13-tetrakis(acetyloxy)-15-(furan-3-carbonyl)-6-(2-methoxy-2-oxoethyl)-5,7,10,15-tetramethyl-9,11,17-trioxahexacyclo[8.6.1.1^{5,8}.0^{1,12}.0^{3,8}.0^{7,12}]octadecan-16-yl]acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       9.625   3.633   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.953   2.836   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.361   1.439   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.839   0.670   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.158   1.527   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.074   3.061   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.697   1.556   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      13.493   0.237   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      13.442   2.904   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.789   4.299   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.914   5.351   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      15.262   4.606   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      14.970   3.094   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.042   0.266   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.913  -0.868   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.283  -1.573   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.578  -0.740   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      11.357  -3.111   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      12.726  -3.816   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.079   0.489   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.586   1.159   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.551   2.771   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.865   3.575   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.565   2.507   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.065   0.960   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.242  -0.342   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.703  -0.280   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.880  -1.581   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.987   1.084   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.035   2.680   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.600   4.242   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.166   3.531   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.763   4.950   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.140   5.711   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.637   6.048   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       1.594   4.914   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       2.177   7.517   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       0.674   7.854   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       6.264   4.563   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       7.967   4.062   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       8.873   4.405   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       8.780   5.370   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       9.328   2.585   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       5.363  -0.364   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       3.931  -0.933   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       3.708  -2.457   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0       2.393  -0.870   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       7.245  -1.042   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       6.002  -1.951   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       6.168  -3.482   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       4.593  -1.329   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0       9.571   5.172   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      10.878   5.988   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      10.825   7.527   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      12.237   5.264   0.000  0.00  0.00           C+0
CONECT    1    2    6   52                                                  
CONECT    2    1    3   32   41                                             
CONECT    3    2    4   20   43                                             
CONECT    4    3    5   15                                                  
CONECT    5    4    6    7   14                                             
CONECT    6    5    1                                                       
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    9                                                       
CONECT   14    5                                                            
CONECT   15    4   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20    3   21   48                                                  
CONECT   21   20   22   25   44                                             
CONECT   22   21   23   32   39                                             
CONECT   23   22   24                                                       
CONECT   24   23   25   30   31                                             
CONECT   25   24   21   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   24                                                            
CONECT   31   24   32   34                                                  
CONECT   32   31    2   22   33                                             
CONECT   33   32                                                            
CONECT   34   31   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37                                                            
CONECT   39   22   40                                                       
CONECT   40   39   41   42   43                                             
CONECT   41   40    2                                                       
CONECT   42   40                                                            
CONECT   43   40    3                                                       
CONECT   44   21   45                                                       
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45                                                            
CONECT   48   20   49                                                       
CONECT   49   48   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49                                                            
CONECT   52    1   53                                                       
CONECT   53   52   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  122    0
END

View in JSmol

Synonyms

Value	Source
Methyl 2-[(1R,2S,3S,4S,5R,6S,7R,8S,10R,12R,13R,15R,16R)-2,3,4,13-tetrakis(acetyloxy)-15-(furan-3-carbonyl)-16-(2-methoxy-2-oxoethyl)-5,7,10,15-tetramethyl-9,11,17-trioxahexacyclo[8.6.1.1,.0,.0,.0,]octadecan-6-yl]acetic acid	Generator

Chemical Formula

C₃₈H₄₆O₁₇

Average Mass

774.7690 Da

Monoisotopic Mass

774.27350 Da

IUPAC Name

methyl 2-[(1R,2S,3S,4S,5R,6S,7R,8S,10R,12R,13R,15R,16R)-2,3,4,13-tetrakis(acetyloxy)-15-(furan-3-carbonyl)-6-(2-methoxy-2-oxoethyl)-5,7,10,15-tetramethyl-9,11,17-trioxahexacyclo[8.6.1.1^{5,8}.0^{1,12}.0^{3,8}.0^{7,12}]octadecan-16-yl]acetate

Traditional Name

methyl [(1R,2S,3S,4S,5R,6S,7R,8S,10R,12R,13R,15R,16R)-2,3,4,13-tetrakis(acetyloxy)-15-(furan-3-carbonyl)-6-(2-methoxy-2-oxoethyl)-5,7,10,15-tetramethyl-9,11,17-trioxahexacyclo[8.6.1.1^{5,8}.0^{1,12}.0^{3,8}.0^{7,12}]octadecan-16-yl]acetate

CAS Registry Number

Not Available

SMILES

COC(=O)C[C@H]1[C@@]2(C)C[C@]34O[C@]5(C)O[C@]6([C@H](CC(=O)OC)[C@@](C)(C[C@@H](OC(C)=O)[C@]6(O5)[C@]13C)C(=O)C1=COC=C1)[C@H](OC(C)=O)[C@@]4(OC(C)=O)[C@H]2OC(C)=O

InChI Identifier

InChI=1S/C38H46O17/c1-18(39)49-25-15-31(5,28(45)22-11-12-48-16-22)24(14-27(44)47-10)36-30(51-20(3)41)37(52-21(4)42)29(50-19(2)40)32(6)17-35(37)33(7,23(32)13-26(43)46-9)38(25,36)55-34(8,53-35)54-36/h11-12,16,23-25,29-30H,13-15,17H2,1-10H3/t23-,24+,25+,29-,30-,31+,32+,33+,34+,35-,36+,37-,38-/m0/s1

InChI Key

WDSUDLNQRNVFBV-GKEVUJFVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Neobeguea leandreana	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins and related compounds

Alternative Parents

Substituents

Prostaglandin skeleton
Hexacarboxylic acid or derivatives
Diterpenoid
Aryl alkyl ketone
Aryl ketone
Ortho ester
Dioxepane
Carboxylic acid orthoester
1,3-dioxepane
Meta-dioxane
Heteroaromatic compound
Methyl ester
Furan
Meta-dioxolane
Orthocarboxylic acid derivative
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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	2.24	ALOGPS
logP	1.59	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	215.7 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	177.24 m³·mol⁻¹	ChemAxon
Polarizability	70.93 Å³	ChemAxon
Number of Rings	7	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

162909374

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Leandreanin B (NP0079978)

MOL for NP0079978 ((+)-Leandreanin B)

3D MOL for NP0079978 ((+)-Leandreanin B)

3D SDF for NP0079978 ((+)-Leandreanin B)

3D-SDF for NP0079978 ((+)-Leandreanin B)

PDB for NP0079978 ((+)-Leandreanin B)

3D PDB for NP0079978 ((+)-Leandreanin B)

SMILES for NP0079978 ((+)-Leandreanin B)

INCHI for NP0079978 ((+)-Leandreanin B)

Structure for NP0079978 ((+)-Leandreanin B)

3D Structure for NP0079978 ((+)-Leandreanin B)