NP-MRD: Showing NP-Card for squadiolin B (NP0033729)

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Record Information

Version

2.0

Created at

2021-06-20 17:39:56 UTC

Updated at

2021-06-30 00:03:41 UTC

NP-MRD ID

NP0033729

Secondary Accession Numbers

None

Natural Product Identification

Common Name

squadiolin B

Provided By

JEOL Database JEOL Logo

Description

Squadiolin B belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. squadiolin B is found in Annona squamosa. squadiolin B was first documented in 2008 (Liaw, C. -C., et al.). Based on a literature review very few articles have been published on squadiolin B.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202119393D          

113114  0  0  0  0            999 V2000
   -2.4986    7.7968   -4.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2777    7.2467   -4.8906 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7898    5.9454   -4.2523 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4411    5.3996   -4.9795 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9035    4.0371   -4.4551 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4260    4.0839   -3.0176 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9715    2.7219   -2.5828 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4861    2.7626   -1.1422 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0086    1.3938   -0.7059 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5642    1.3720    0.7161 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6483    1.8164    1.8634 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4720    1.7912    3.0496 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4177    0.9214    2.1447 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0299    1.1569    3.5126 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2198    1.1931    1.2303 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0703    0.5100    1.7053 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1133    0.3975    0.5917 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2578    1.6583   -0.0741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5127   -0.0572    1.0643 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3007   -0.2524   -0.1208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5036   -1.3210    1.9294 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8896   -1.8561    2.3238 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7540   -2.5491    1.2526 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4898   -1.5829    0.5034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0017   -3.5236    0.3284 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9072   -4.3474   -0.5725 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9201   -4.8338   -1.6051 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0421   -3.6071   -1.8091 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5854   -3.9558   -2.1138 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7924   -2.7219   -2.5633 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2806   -2.9662   -2.5975 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3552   -2.8524   -1.2079 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8589   -3.1386   -1.2489 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5805   -2.7677    0.0510 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0977   -3.5532    1.2725 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8383   -3.1128    2.5403 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4005   -3.8555    3.8088 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9356   -3.8533    4.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1039   -4.8879    4.1843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2823   -4.4355    4.4194 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2359   -4.8705    3.3192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1812   -3.0097    4.4244 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1179   -2.6439    4.2343 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5189   -1.4941    4.1892 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0994   -2.8483   -0.5795 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8307    8.7263   -4.6435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2717    8.0117   -3.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3281    7.0833   -4.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5294    7.0742   -5.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4778    7.9959   -4.8664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5936    5.1998   -4.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5527    6.1311   -3.1988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2081    5.2929   -6.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2646    6.1205   -4.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0796    3.3167   -4.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7010    3.6708   -5.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6220    4.3808   -2.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2173    4.8389   -2.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1804    1.9667   -2.6684 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7834    2.4182   -3.2547 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6750    3.0893   -0.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2888    3.5050   -1.0582 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8171    1.0943   -1.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2350    0.6297   -0.8220 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4660    1.9997    0.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9307    0.3589    0.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3412    2.8602    1.7400 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8209    1.7970    3.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7132   -0.1292    2.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7279    0.2870    3.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4450    0.8589    0.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0328    2.2731    1.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8390   -0.4950    2.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4832    1.0856    2.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7444   -0.3002   -0.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0785    1.5856   -0.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9934    0.7600    1.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9732   -1.0844   -0.5358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9755   -1.0911    2.8635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9207   -2.1125    1.4474 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.4643   -1.0371    2.7748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5130   -3.1282    1.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8438   -0.9329    0.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3909   -4.1984    0.9424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4097   -5.1603   -0.0413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6677   -3.7229   -1.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3407   -5.6720   -1.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3933   -5.1708   -2.5317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4627   -2.9734   -2.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1259   -4.3840   -1.2157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5378   -4.7139   -2.9047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1266   -2.4506   -3.5726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0122   -1.8621   -1.9218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0652   -3.9465   -3.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1769   -2.2136   -3.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1854   -1.8419   -0.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1316   -3.5515   -0.5204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0252   -4.1987   -1.4751 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3159   -2.5646   -2.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4548   -1.6944    0.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6551   -2.9394   -0.0866 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0236   -3.3911    1.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2503   -4.6262    1.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7044   -2.0365    2.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9158   -3.2688    2.4034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7562   -4.8918    3.7416 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9144   -3.4134    4.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3942   -5.9268    4.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6448   -4.7665    5.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9287   -4.4772    2.3430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2991   -5.9613    3.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2391   -4.4776    3.5128 H   0  0  0  0  0  0  0  0  0  0  0  0
 39 38  2  0  0  0  0
 28 45  1  0  0  0  0
 43 44  2  0  0  0  0
 10  9  1  0  0  0  0
 40 41  1  0  0  0  0
  5  4  1  0  0  0  0
 36 35  1  0  0  0  0
  8  7  1  0  0  0  0
 35 34  1  0  0  0  0
  4  3  1  0  0  0  0
 34 33  1  0  0  0  0
 45 25  1  0  0  0  0
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 30 31  1  0  0  0  0
 26 27  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 27 28  1  0  0  0  0
 30 29  1  0  0  0  0
 28 29  1  0  0  0  0
 25 23  1  0  0  0  0
  3  2  1  0  0  0  0
 23 22  1  0  0  0  0
 36 37  1  0  0  0  0
 22 21  1  0  0  0  0
  7  6  1  0  0  0  0
 21 19  1  0  0  0  0
 37 38  1  0  0  0  0
 19 17  1  0  0  0  0
 38 43  1  0  0  0  0
 17 16  1  0  0  0  0
  2  1  1  0  0  0  0
 23 24  1  0  0  0  0
  9  8  1  0  0  0  0
 19 20  1  0  0  0  0
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  6  5  1  0  0  0  0
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M  END

     RDKit          3D

113114  0  0  0  0  0  0  0  0999 V2000
   -2.4986    7.7968   -4.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2777    7.2467   -4.8906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7898    5.9454   -4.2523 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4411    5.3996   -4.9795 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9035    4.0371   -4.4551 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4260    4.0839   -3.0176 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9715    2.7219   -2.5828 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4861    2.7626   -1.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0086    1.3938   -0.7059 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5642    1.3720    0.7161 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6483    1.8164    1.8634 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4720    1.7912    3.0496 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4177    0.9214    2.1447 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0299    1.1569    3.5126 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2198    1.1931    1.2303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0703    0.5100    1.7053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1133    0.3975    0.5917 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2578    1.6583   -0.0741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5127   -0.0572    1.0643 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3007   -0.2524   -0.1208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5036   -1.3210    1.9294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8896   -1.8561    2.3238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7540   -2.5491    1.2526 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.4898   -1.5829    0.5034 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0017   -3.5236    0.3284 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306202119393D          

113114  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0033729

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]([H])(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])[C@@]([H])(O[H])C([H])([H])C([H])([H])[C@]([H])(O[H])[C@@]([H])(O[H])C([H])([H])C([H])([H])[C@@]([H])(O[H])[C@]1([H])O[C@@]([H])(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C2=C([H])[C@@]([H])(OC2=O)C([H])([H])[H])C([H])([H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C37H68O8/c1-3-4-5-6-7-11-14-17-20-31(38)32(39)22-23-33(40)34(41)24-25-35(42)36-26-21-30(45-36)19-16-13-10-8-9-12-15-18-29-27-28(2)44-37(29)43/h27-28,30-36,38-42H,3-26H2,1-2H3/t28-,30-,31-,32-,33-,34-,35+,36+/m0/s1

> <INCHI_KEY>
OICKTCBVAYOJGE-CRYMFWFMSA-N

> <FORMULA>
C37H68O8

> <MOLECULAR_WEIGHT>
640.943

> <EXACT_MASS>
640.49141915

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
113

> <JCHEM_AVERAGE_POLARIZABILITY>
74.99587463396594

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S)-5-methyl-3-{9-[(2S,5R)-5-[(1R,4S,5S,8S,9S)-1,4,5,8,9-pentahydroxynonadecyl]oxolan-2-yl]nonyl}-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
5.91

> <JCHEM_LOGP>
7.520488360999999

> <ALOGPS_LOGS>
-5.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.673869734734268

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.186916540353472

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1440776478873698

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
179.9067

> <JCHEM_ROTATABLE_BOND_COUNT>
28

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.83e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
squadiolin B

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

113114  0  0  0  0  0  0  0  0999 V2000
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   -5.3933   -5.1708   -2.5317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4627   -2.9734   -2.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1259   -4.3840   -1.2157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5378   -4.7139   -2.9047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1266   -2.4506   -3.5726 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0652   -3.9465   -3.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1769   -2.2136   -3.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1854   -1.8419   -0.8170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1316   -3.5515   -0.5204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0252   -4.1987   -1.4751 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3159   -2.5646   -2.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4548   -1.6944    0.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6551   -2.9394   -0.0866 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0236   -3.3911    1.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2503   -4.6262    1.1073 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7044   -2.0365    2.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9158   -3.2688    2.4034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7562   -4.8918    3.7416 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9144   -3.4134    4.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3942   -5.9268    4.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6448   -4.7665    5.3982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9287   -4.4772    2.3430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2991   -5.9613    3.2521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2391   -4.4776    3.5128 H   0  0  0  0  0  0  0  0  0  0  0  0
 39 38  2  0
 28 45  1  0
 43 44  2  0
 10  9  1  0
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M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.499   7.797  -4.170  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.278   7.247  -4.891  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.790   5.945  -4.252  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.441   5.400  -4.979  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.904   4.037  -4.455  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.426   4.084  -3.018  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.972   2.722  -2.583  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.486   2.763  -1.142  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.009   1.394  -0.706  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.564   1.372   0.716  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.648   1.816   1.863  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.472   1.791   3.050  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.418   0.921   2.145  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.030   1.157   3.513  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.220   1.193   1.230  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.070   0.510   1.705  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.113   0.398   0.592  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.258   1.658  -0.074  0.00  0.00           O+0
HETATM   19  C   UNK     0      -3.513  -0.057   1.064  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.301  -0.252  -0.121  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.504  -1.321   1.929  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.890  -1.856   2.324  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.754  -2.549   1.253  0.00  0.00           C+0
HETATM   24  O   UNK     0      -6.490  -1.583   0.503  0.00  0.00           O+0
HETATM   25  C   UNK     0      -5.002  -3.524   0.328  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.907  -4.347  -0.573  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.920  -4.834  -1.605  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.042  -3.607  -1.809  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.585  -3.956  -2.114  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.792  -2.722  -2.563  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.281  -2.966  -2.598  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.355  -2.852  -1.208  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.859  -3.139  -1.249  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.580  -2.768   0.051  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.098  -3.553   1.272  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.838  -3.113   2.540  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.401  -3.856   3.809  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.936  -3.853   4.067  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.104  -4.888   4.184  0.00  0.00           C+0
HETATM   40  C   UNK     0      -1.282  -4.436   4.419  0.00  0.00           C+0
HETATM   41  C   UNK     0      -2.236  -4.870   3.319  0.00  0.00           C+0
HETATM   42  O   UNK     0      -1.181  -3.010   4.424  0.00  0.00           O+0
HETATM   43  C   UNK     0       0.118  -2.644   4.234  0.00  0.00           C+0
HETATM   44  O   UNK     0       0.519  -1.494   4.189  0.00  0.00           O+0
HETATM   45  O   UNK     0      -4.099  -2.848  -0.580  0.00  0.00           O+0
HETATM   46  H   UNK     0      -2.831   8.726  -4.644  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.272   8.012  -3.121  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.328   7.083  -4.204  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.529   7.074  -5.944  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.478   7.996  -4.866  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.594   5.200  -4.279  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.553   6.131  -3.199  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.208   5.293  -6.046  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.265   6.120  -4.907  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.080   3.317  -4.527  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.701   3.671  -5.114  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.622   4.381  -2.335  0.00  0.00           H+0
HETATM   58  H   UNK     0       2.217   4.839  -2.938  0.00  0.00           H+0
HETATM   59  H   UNK     0       1.180   1.967  -2.668  0.00  0.00           H+0
HETATM   60  H   UNK     0       2.783   2.418  -3.255  0.00  0.00           H+0
HETATM   61  H   UNK     0       1.675   3.089  -0.484  0.00  0.00           H+0
HETATM   62  H   UNK     0       3.289   3.505  -1.058  0.00  0.00           H+0
HETATM   63  H   UNK     0       3.817   1.094  -1.386  0.00  0.00           H+0
HETATM   64  H   UNK     0       2.235   0.630  -0.822  0.00  0.00           H+0
HETATM   65  H   UNK     0       4.466   2.000   0.740  0.00  0.00           H+0
HETATM   66  H   UNK     0       3.931   0.359   0.930  0.00  0.00           H+0
HETATM   67  H   UNK     0       2.341   2.860   1.740  0.00  0.00           H+0
HETATM   68  H   UNK     0       2.821   1.797   3.784  0.00  0.00           H+0
HETATM   69  H   UNK     0       1.713  -0.129   2.074  0.00  0.00           H+0
HETATM   70  H   UNK     0       0.728   0.287   3.861  0.00  0.00           H+0
HETATM   71  H   UNK     0       0.445   0.859   0.216  0.00  0.00           H+0
HETATM   72  H   UNK     0       0.033   2.273   1.185  0.00  0.00           H+0
HETATM   73  H   UNK     0      -0.839  -0.495   2.074  0.00  0.00           H+0
HETATM   74  H   UNK     0      -1.483   1.086   2.543  0.00  0.00           H+0
HETATM   75  H   UNK     0      -1.744  -0.300  -0.168  0.00  0.00           H+0
HETATM   76  H   UNK     0      -3.079   1.586  -0.601  0.00  0.00           H+0
HETATM   77  H   UNK     0      -3.993   0.760   1.615  0.00  0.00           H+0
HETATM   78  H   UNK     0      -3.973  -1.084  -0.536  0.00  0.00           H+0
HETATM   79  H   UNK     0      -2.975  -1.091   2.864  0.00  0.00           H+0
HETATM   80  H   UNK     0      -2.921  -2.112   1.447  0.00  0.00           H+0
HETATM   81  H   UNK     0      -4.721  -2.591   3.122  0.00  0.00           H+0
HETATM   82  H   UNK     0      -5.464  -1.037   2.775  0.00  0.00           H+0
HETATM   83  H   UNK     0      -6.513  -3.128   1.793  0.00  0.00           H+0
HETATM   84  H   UNK     0      -5.844  -0.933   0.153  0.00  0.00           H+0
HETATM   85  H   UNK     0      -4.391  -4.198   0.942  0.00  0.00           H+0
HETATM   86  H   UNK     0      -6.410  -5.160  -0.041  0.00  0.00           H+0
HETATM   87  H   UNK     0      -6.668  -3.723  -1.056  0.00  0.00           H+0
HETATM   88  H   UNK     0      -4.341  -5.672  -1.199  0.00  0.00           H+0
HETATM   89  H   UNK     0      -5.393  -5.171  -2.532  0.00  0.00           H+0
HETATM   90  H   UNK     0      -4.463  -2.973  -2.599  0.00  0.00           H+0
HETATM   91  H   UNK     0      -2.126  -4.384  -1.216  0.00  0.00           H+0
HETATM   92  H   UNK     0      -2.538  -4.714  -2.905  0.00  0.00           H+0
HETATM   93  H   UNK     0      -2.127  -2.451  -3.573  0.00  0.00           H+0
HETATM   94  H   UNK     0      -2.012  -1.862  -1.922  0.00  0.00           H+0
HETATM   95  H   UNK     0      -0.065  -3.946  -3.039  0.00  0.00           H+0
HETATM   96  H   UNK     0       0.177  -2.214  -3.252  0.00  0.00           H+0
HETATM   97  H   UNK     0       0.185  -1.842  -0.817  0.00  0.00           H+0
HETATM   98  H   UNK     0      -0.132  -3.551  -0.520  0.00  0.00           H+0
HETATM   99  H   UNK     0       2.025  -4.199  -1.475  0.00  0.00           H+0
HETATM  100  H   UNK     0       2.316  -2.565  -2.064  0.00  0.00           H+0
HETATM  101  H   UNK     0       2.455  -1.694   0.234  0.00  0.00           H+0
HETATM  102  H   UNK     0       3.655  -2.939  -0.087  0.00  0.00           H+0
HETATM  103  H   UNK     0       1.024  -3.391   1.405  0.00  0.00           H+0
HETATM  104  H   UNK     0       2.250  -4.626   1.107  0.00  0.00           H+0
HETATM  105  H   UNK     0       2.704  -2.037   2.689  0.00  0.00           H+0
HETATM  106  H   UNK     0       3.916  -3.269   2.403  0.00  0.00           H+0
HETATM  107  H   UNK     0       2.756  -4.892   3.742  0.00  0.00           H+0
HETATM  108  H   UNK     0       2.914  -3.413   4.671  0.00  0.00           H+0
HETATM  109  H   UNK     0       0.394  -5.927   4.115  0.00  0.00           H+0
HETATM  110  H   UNK     0      -1.645  -4.766   5.398  0.00  0.00           H+0
HETATM  111  H   UNK     0      -1.929  -4.477   2.343  0.00  0.00           H+0
HETATM  112  H   UNK     0      -2.299  -5.961   3.252  0.00  0.00           H+0
HETATM  113  H   UNK     0      -3.239  -4.478   3.513  0.00  0.00           H+0
CONECT    1    2   46   47   48                                             
CONECT    2    3    1   49   50                                             
CONECT    3    4    2   51   52                                             
CONECT    4    5    3   53   54                                             
CONECT    5    4    6   55   56                                             
CONECT    6    7    5   57   58                                             
CONECT    7    8    6   59   60                                             
CONECT    8    7    9   61   62                                             
CONECT    9   10    8   63   64                                             
CONECT   10    9   11   65   66                                             
CONECT   11   10   13   12   67                                             
CONECT   12   11   68                                                       
CONECT   13   15   11   14   69                                             
CONECT   14   13   70                                                       
CONECT   15   16   13   71   72                                             
CONECT   16   17   15   73   74                                             
CONECT   17   19   16   18   75                                             
CONECT   18   17   76                                                       
CONECT   19   21   17   20   77                                             
CONECT   20   19   78                                                       
CONECT   21   22   19   79   80                                             
CONECT   22   23   21   81   82                                             
CONECT   23   25   22   24   83                                             
CONECT   24   23   84                                                       
CONECT   25   45   26   23   85                                             
CONECT   26   25   27   86   87                                             
CONECT   27   26   28   88   89                                             
CONECT   28   45   27   29   90                                             
CONECT   29   30   28   91   92                                             
CONECT   30   31   29   93   94                                             
CONECT   31   30   32   95   96                                             
CONECT   32   31   33   97   98                                             
CONECT   33   34   32   99  100                                             
CONECT   34   35   33  101  102                                             
CONECT   35   36   34  103  104                                             
CONECT   36   35   37  105  106                                             
CONECT   37   36   38  107  108                                             
CONECT   38   39   37   43                                                  
CONECT   39   38   40  109                                                  
CONECT   40   41   42   39  110                                             
CONECT   41   40  111  112  113                                             
CONECT   42   43   40                                                       
CONECT   43   44   38   42                                                  
CONECT   44   43                                                            
CONECT   45   28   25                                                       
CONECT   46    1                                                            
CONECT   47    1                                                            
CONECT   48    1                                                            
CONECT   49    2                                                            
CONECT   50    2                                                            
CONECT   51    3                                                            
CONECT   52    3                                                            
CONECT   53    4                                                            
CONECT   54    4                                                            
CONECT   55    5                                                            
CONECT   56    5                                                            
CONECT   57    6                                                            
CONECT   58    6                                                            
CONECT   59    7                                                            
CONECT   60    7                                                            
CONECT   61    8                                                            
CONECT   62    8                                                            
CONECT   63    9                                                            
CONECT   64    9                                                            
CONECT   65   10                                                            
CONECT   66   10                                                            
CONECT   67   11                                                            
CONECT   68   12                                                            
CONECT   69   13                                                            
CONECT   70   14                                                            
CONECT   71   15                                                            
CONECT   72   15                                                            
CONECT   73   16                                                            
CONECT   74   16                                                            
CONECT   75   17                                                            
CONECT   76   18                                                            
CONECT   77   19                                                            
CONECT   78   20                                                            
CONECT   79   21                                                            
CONECT   80   21                                                            
CONECT   81   22                                                            
CONECT   82   22                                                            
CONECT   83   23                                                            
CONECT   84   24                                                            
CONECT   85   25                                                            
CONECT   86   26                                                            
CONECT   87   26                                                            
CONECT   88   27                                                            
CONECT   89   27                                                            
CONECT   90   28                                                            
CONECT   91   29                                                            
CONECT   92   29                                                            
CONECT   93   30                                                            
CONECT   94   30                                                            
CONECT   95   31                                                            
CONECT   96   31                                                            
CONECT   97   32                                                            
CONECT   98   32                                                            
CONECT   99   33                                                            
CONECT  100   33                                                            
CONECT  101   34                                                            
CONECT  102   34                                                            
CONECT  103   35                                                            
CONECT  104   35                                                            
CONECT  105   36                                                            
CONECT  106   36                                                            
CONECT  107   37                                                            
CONECT  108   37                                                            
CONECT  109   39                                                            
CONECT  110   40                                                            
CONECT  111   41                                                            
CONECT  112   41                                                            
CONECT  113   41                                                            
MASTER        0    0    0    0    0    0    0    0  113    0  228    0
END

RDKit          3D

113114  0  0  0  0  0  0  0  0999 V2000
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M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₇H₆₈O₈

Average Mass

640.9430 Da

Monoisotopic Mass

640.49142 Da

IUPAC Name

(5S)-5-methyl-3-{9-[(2S,5R)-5-[(1R,4S,5S,8S,9S)-1,4,5,8,9-pentahydroxynonadecyl]oxolan-2-yl]nonyl}-2,5-dihydrofuran-2-one

Traditional Name

squadiolin B

CAS Registry Number

Not Available

SMILES

[H]O[C@@]([H])(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])[C@@]([H])(O[H])C([H])([H])C([H])([H])[C@]([H])(O[H])[C@@]([H])(O[H])C([H])([H])C([H])([H])[C@@]([H])(O[H])[C@]1([H])O[C@@]([H])(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C2=C([H])[C@@]([H])(OC2=O)C([H])([H])[H])C([H])([H])C1([H])[H]

InChI Identifier

InChI=1S/C37H68O8/c1-3-4-5-6-7-11-14-17-20-31(38)32(39)22-23-33(40)34(41)24-25-35(42)36-26-21-30(45-36)19-16-13-10-8-9-12-15-18-29-27-28(2)44-37(29)43/h27-28,30-36,38-42H,3-26H2,1-2H3/t28-,30-,31-,32-,33-,34-,35+,36+/m0/s1

InChI Key

OICKTCBVAYOJGE-CRYMFWFMSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Annona squamosa	JEOL database	Liaw, C. -C., et al, J. Nat. Prod. 71, 764 (2008)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Annonaceous acetogenins

Alternative Parents

Substituents

Annonaceae acetogenin skeleton
Long chain fatty alcohol
2-furanone
Dihydrofuran
Oxolane
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
1,2-diol
Lactone
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	5.91	ALOGPS
logP	7.52	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	13.19	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	28	ChemAxon
Refractivity	179.91 m³·mol⁻¹	ChemAxon
Polarizability	75 Å³	ChemAxon
Number of Rings	2	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

24711295

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44577075

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liaw, C. -C., et al. (2008). Liaw, C. -C., et al, J. Nat. Prod. 71, 764 (2008) . J. Nat. Prod..

Showing NP-Card for squadiolin B (NP0033729)

MOL for NP0033729 (squadiolin B)

3D MOL for NP0033729 (squadiolin B)

3D SDF for NP0033729 (squadiolin B)

3D-SDF for NP0033729 (squadiolin B)

PDB for NP0033729 (squadiolin B)

3D PDB for NP0033729 (squadiolin B)

SMILES for NP0033729 (squadiolin B)

INCHI for NP0033729 (squadiolin B)

Structure for NP0033729 (squadiolin B)

3D Structure for NP0033729 (squadiolin B)