NP-MRD: Showing NP-Card for Tabulalide A (NP0074562)

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Record Information

Version

2.0

Created at

2022-04-28 19:51:37 UTC

Updated at

2022-04-28 19:51:37 UTC

NP-MRD ID

NP0074562

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tabulalide A

Description

(1R,2S,7S,8R,9R,10R,11R,12R,16R,17R,18S,19R,20R,22S)-9,10,18-tris(acetyloxy)-12-(furan-3-yl)-8,17,19,20-tetrahydroxy-1,11-dimethyl-4,14-dioxo-5,13-dioxahexacyclo[17.2.1.0²,⁷.0⁷,²⁰.0⁸,¹⁷.0¹¹,¹⁶]Docosan-22-yl acetate belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. Tabulalide A is found in Chukrasia tabularis . Based on a literature review very few articles have been published on (1R,2S,7S,8R,9R,10R,11R,12R,16R,17R,18S,19R,20R,22S)-9,10,18-tris(acetyloxy)-12-(furan-3-yl)-8,17,19,20-tetrahydroxy-1,11-dimethyl-4,14-dioxo-5,13-dioxahexacyclo[17.2.1.0²,⁷.0⁷,²⁰.0⁸,¹⁷.0¹¹,¹⁶]Docosan-22-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282221512D          

 51 57  0  0  1  0            999 V2000
    2.4202   -0.8198    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0980   -0.0603    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5946    0.5985    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4134    0.4978    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7356   -0.2617    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2390   -0.9205    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1235   -1.8711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7235   -2.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7654   -2.9118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6433   -3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5545   -0.3623    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0511    0.2965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7288    1.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4067    1.6007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9100    1.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8767   -1.1218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4517   -1.8289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9928   -2.4516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7523   -2.1294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6805   -1.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1286   -0.9415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2088    1.3451    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3353    1.3925    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9838    0.6697    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2051   -0.0684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3136   -0.0700    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0585    1.0132    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5629    1.7415    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0922    2.3680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8471    2.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6602    2.5882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0638    3.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0224    0.4411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8015    1.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0414   -0.8321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3891   -1.5448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6048   -0.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8748    0.6251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5312    2.2995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4950    2.2157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2680    3.0474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3077    2.9446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7350    3.8071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0417    1.3347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0649   -1.1068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4553   -1.9143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3526   -2.9977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2071   -3.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8232   -3.7682    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
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  4 15  1  6  0  0  0
 11 16  1  1  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 16 20  1  0  0  0  0
  5 21  1  1  0  0  0
  3 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  2 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 27 33  1  0  0  0  0
 24 33  1  0  0  0  0
 27 34  1  6  0  0  0
 26 35  1  1  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 25 39  1  1  0  0  0
 24 40  1  1  0  0  0
 23 41  1  6  0  0  0
 22 42  1  1  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 43 45  1  0  0  0  0
  3 46  1  1  0  0  0
  2 47  1  1  0  0  0
  1 48  1  1  0  0  0
 48 49  1  0  0  0  0
 49 50  2  0  0  0  0
 49 51  1  0  0  0  0
M  END

     RDKit          3D

 91 97  0  0  0  0  0  0  0  0999 V2000
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    1.7810   -3.7248   -1.6760 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0282   -0.3431   -0.6582 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7348   -0.3494   -1.8913 O   0  0  0  0  0  0  0  0  0  0  0  0
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 41 83  1  0
 41 84  1  0
 32 79  1  1
 37 82  1  0
 35 81  1  0
 34 80  1  0
 31 76  1  0
 31 77  1  0
 31 78  1  0
 25 72  1  1
 28 73  1  0
 28 74  1  0
 28 75  1  0
 20 68  1  1
 23 69  1  0
 23 70  1  0
 23 71  1  0
 19 67  1  0
 12 62  1  0
 12 63  1  0
 16 64  1  0
 16 65  1  0
 17 66  1  1
M  END


  Mrv1652304282221512D          

 51 57  0  0  1  0            999 V2000
    2.4202   -0.8198    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0980   -0.0603    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5946    0.5985    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4134    0.4978    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7356   -0.2617    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2390   -0.9205    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1235   -1.8711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7235   -2.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7654   -2.9118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6433   -3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5545   -0.3623    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0511    0.2965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7288    1.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4067    1.6007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9100    1.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8767   -1.1218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4517   -1.8289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9928   -2.4516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7523   -2.1294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6805   -1.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1286   -0.9415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2088    1.3451    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3353    1.3925    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9838    0.6697    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2051   -0.0684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3136   -0.0700    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0585    1.0132    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5629    1.7415    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0922    2.3680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8471    2.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6602    2.5882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0638    3.6646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0224    0.4411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8015    1.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0414   -0.8321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3891   -1.5448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2672   -2.1233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2161   -1.5460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6048   -0.8267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8748    0.6251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5312    2.2995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4950    2.2157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2680    3.0474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3077    2.9446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7350    3.8071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0417    1.3347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0649   -1.1068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4553   -1.9143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3526   -2.9977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2071   -3.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8232   -3.7682    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
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  4 15  1  6  0  0  0
 11 16  1  1  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 16 20  1  0  0  0  0
  5 21  1  1  0  0  0
  3 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  2 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 27 33  1  0  0  0  0
 24 33  1  0  0  0  0
 27 34  1  6  0  0  0
 26 35  1  1  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 25 39  1  1  0  0  0
 24 40  1  1  0  0  0
 23 41  1  6  0  0  0
 22 42  1  1  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 43 45  1  0  0  0  0
  3 46  1  1  0  0  0
  2 47  1  1  0  0  0
  1 48  1  1  0  0  0
 48 49  1  0  0  0  0
 49 50  2  0  0  0  0
 49 51  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0074562

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1[C@]2(C)C[C@]3(O)[C@]1(O)[C@@H](OC(C)=O)[C@]1(O)[C@@H]4CC(=O)O[C@@H](C5=COC=C5)[C@]4(C)[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@]1(O)[C@@]31COC(=O)C[C@@H]21

> <INCHI_IDENTIFIER>
InChI=1S/C34H40O17/c1-14(35)47-24-25(48-15(2)36)34(44)30-13-46-21(39)9-19(30)28(5)12-31(30,41)33(43,26(28)49-16(3)37)27(50-17(4)38)32(34,42)20-10-22(40)51-23(29(20,24)6)18-7-8-45-11-18/h7-8,11,19-20,23-27,41-44H,9-10,12-13H2,1-6H3/t19-,20+,23-,24-,25+,26-,27-,28+,29+,30+,31+,32+,33+,34-/m0/s1

> <INCHI_KEY>
FLRDRVHXKFQNNT-DQMDLUEPSA-N

> <FORMULA>
C34H40O17

> <MOLECULAR_WEIGHT>
720.677

> <EXACT_MASS>
720.226549828

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
91

> <JCHEM_AVERAGE_POLARIZABILITY>
51.83000686669696

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,7S,8R,9R,10R,11R,12R,16R,17R,18S,19R,20R,22S)-9,10,18-tris(acetyloxy)-12-(furan-3-yl)-8,17,19,20-tetrahydroxy-1,11-dimethyl-4,14-dioxo-5,13-dioxahexacyclo[17.2.1.0^{2,7}.0^{7,20}.0^{8,17}.0^{11,16}]docosan-22-yl acetate

> <ALOGPS_LOGP>
0.67

> <JCHEM_LOGP>
-2.5696890739999985

> <ALOGPS_LOGS>
-1.99

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.169557046127336

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.518170368131203

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8887602389231644

> <JCHEM_POLAR_SURFACE_AREA>
251.85999999999996

> <JCHEM_REFRACTIVITY>
158.82150000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.34e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,7S,8R,9R,10R,11R,12R,16R,17R,18S,19R,20R,22S)-9,10,18-tris(acetyloxy)-12-(furan-3-yl)-8,17,19,20-tetrahydroxy-1,11-dimethyl-4,14-dioxo-5,13-dioxahexacyclo[17.2.1.0^{2,7}.0^{7,20}.0^{8,17}.0^{11,16}]docosan-22-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       4.518  -1.530   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.916  -0.113   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.843   1.117   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.372   0.929   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.973  -0.488   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.046  -1.718   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.831  -3.493   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.084  -5.069   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.295  -5.435   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.934  -6.875   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.502  -0.676   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.429   0.553   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.827   1.971   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      10.093   2.988   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.299   2.159   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.103  -2.094   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.310  -3.414   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.320  -4.576   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      10.738  -3.975   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.604  -2.441   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.707  -1.757   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.123   2.511   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.492   2.599   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.836   1.250   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.250  -0.128   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.585  -0.131   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.109   1.891   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.051   3.251   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.172   4.420   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.581   5.273   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -3.099   4.831   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -1.986   6.841   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.042   0.823   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.496   2.195   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.077  -1.553   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.726  -2.884   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -0.499  -3.963   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       2.270  -2.886   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       2.996  -1.543   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       3.500   1.167   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       2.858   4.292   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       4.657   4.136   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       4.234   5.688   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       2.441   5.496   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       5.105   7.107   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       5.678   2.491   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0       3.854  -2.066   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       4.583  -3.573   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       4.391  -5.596   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       5.987  -6.393   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       3.403  -7.034   0.000  0.00  0.00           C+0
CONECT    1    2    6   48                                                  
CONECT    2    1    3   25   47                                             
CONECT    3    2    4   22   46                                             
CONECT    4    3    5   15                                                  
CONECT    5    4    6   11   21                                             
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    5   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    4                                                       
CONECT   16   11   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   16                                                       
CONECT   21    5                                                            
CONECT   22    3   23   42                                                  
CONECT   23   22   24   28   41                                             
CONECT   24   23   25   33   40                                             
CONECT   25   24    2   26   39                                             
CONECT   26   25   27   35                                                  
CONECT   27   26   28   33   34                                             
CONECT   28   27   23   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   27   24                                                       
CONECT   34   27                                                            
CONECT   35   26   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   25                                                       
CONECT   40   24                                                            
CONECT   41   23                                                            
CONECT   42   22   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43                                                            
CONECT   46    3                                                            
CONECT   47    2                                                            
CONECT   48    1   49                                                       
CONECT   49   48   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  114    0
END

View in JSmol

Synonyms

Value	Source
(1R,2S,7S,8R,9R,10R,11R,12R,16R,17R,18S,19R,20R,22S)-9,10,18-Tris(acetyloxy)-12-(furan-3-yl)-8,17,19,20-tetrahydroxy-1,11-dimethyl-4,14-dioxo-5,13-dioxahexacyclo[17.2.1.0,.0,.0,.0,]docosan-22-yl acetic acid	Generator

Chemical Formula

C₃₄H₄₀O₁₇

Average Mass

720.6770 Da

Monoisotopic Mass

720.22655 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1[C@]2(C)C[C@]3(O)[C@]1(O)[C@@H](OC(C)=O)[C@]1(O)[C@@H]4CC(=O)O[C@@H](C5=COC=C5)[C@]4(C)[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@]1(O)[C@@]31COC(=O)C[C@@H]21

InChI Identifier

InChI=1S/C34H40O17/c1-14(35)47-24-25(48-15(2)36)34(44)30-13-46-21(39)9-19(30)28(5)12-31(30,41)33(43,26(28)49-16(3)37)27(50-17(4)38)32(34,42)20-10-22(40)51-23(29(20,24)6)18-7-8-45-11-18/h7-8,11,19-20,23-27,41-44H,9-10,12-13H2,1-6H3/t19-,20+,23-,24-,25+,26-,27-,28+,29+,30+,31+,32+,33+,34-/m0/s1

InChI Key

FLRDRVHXKFQNNT-DQMDLUEPSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Chukrasia tabularis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Mexicanolide
Limonoid skeleton
Prostaglandin skeleton
Steroid lactone
Eicosanoid
Hexacarboxylic acid or derivatives
2-oxosteroid
Oxosteroid
Steroid
Naphthopyran
Naphthalene
Delta_valerolactone
Delta valerolactone
Fatty acyl
Pyran
Oxane
Heteroaromatic compound
Tertiary alcohol
Furan
Cyclic alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	0.67	ALOGPS
logP	-2.6	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	11.52	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	251.86 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	158.82 m³·mol⁻¹	ChemAxon
Polarizability	51.83 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

162865849

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Tabulalide A (NP0074562)

MOL for NP0074562 (Tabulalide A)

3D MOL for NP0074562 (Tabulalide A)

3D SDF for NP0074562 (Tabulalide A)

3D-SDF for NP0074562 (Tabulalide A)

PDB for NP0074562 (Tabulalide A)

3D PDB for NP0074562 (Tabulalide A)

SMILES for NP0074562 (Tabulalide A)

INCHI for NP0074562 (Tabulalide A)

Structure for NP0074562 (Tabulalide A)

3D Structure for NP0074562 (Tabulalide A)