NP-MRD: Showing NP-Card for Tabulalide D (NP0074564)

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Record Information

Version

2.0

Created at

2022-04-28 19:51:49 UTC

Updated at

2022-04-28 19:51:50 UTC

NP-MRD ID

NP0074564

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tabulalide D

Description

[(1R,2R,6R,7R,8R,9R,10R,12S,14R,15S,16S,17R,18S,19R,20R)-8,18-bis(acetyloxy)-6-(furan-3-yl)-9,19,20-trihydroxy-16-(2-methoxy-2-oxoethyl)-7,12,17-trimethyl-4-oxo-5,11,13,21-tetraoxaheptacyclo[10.8.1.1¹⁴,¹⁷.0¹,¹⁰.0²,⁷.0¹⁰,¹⁵.0¹⁴,¹⁹]Docosan-15-yl]methyl 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 D is found in Chukrasia tabularis . Based on a literature review very few articles have been published on [(1R,2R,6R,7R,8R,9R,10R,12S,14R,15S,16S,17R,18S,19R,20R)-8,18-bis(acetyloxy)-6-(furan-3-yl)-9,19,20-trihydroxy-16-(2-methoxy-2-oxoethyl)-7,12,17-trimethyl-4-oxo-5,11,13,21-tetraoxaheptacyclo[10.8.1.1¹⁴,¹⁷.0¹,¹⁰.0²,⁷.0¹⁰,¹⁵.0¹⁴,¹⁹]Docosan-15-yl]methyl acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282221512D          

 52 59  0  0  1  0            999 V2000
    3.7904    2.0948    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5826    1.4271    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0592    0.8848    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9442    0.9211    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2652    1.6811    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7369    2.3895    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9917    3.1742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4397    3.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6327    3.6156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6945    4.5719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0838    1.7832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5816    1.1253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2606    0.3652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7583   -0.2927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4420    0.2632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4048    2.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2083    2.7303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2786    3.5523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5186    3.8732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9785    3.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5887    2.4401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5389    1.6508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8218    2.5510    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2791    2.1020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8447    2.4278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4548    1.3818    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6879    1.8818    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9121    2.2942    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3649    1.6020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5884    0.5436    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4830    0.5328    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3685    0.3122    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5518   -0.4922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3775   -0.2855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0649   -0.0940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2509    0.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2726   -0.5971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0395    0.8128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4823    1.0558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5617    1.7904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7429    3.1017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9590    3.3588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3443    2.8085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7897    4.1663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0058    4.4234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0685    2.6138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6248    3.3093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0054    4.0413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5617    4.7369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8296    4.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1327    3.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4158    2.8299    0.0000 O   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  6  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  1  0  0  0
 11 16  1  6  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  6  0  0  0
  3 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  2 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  2 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 26 31  1  0  0  0  0
 31 32  1  0  0  0  0
  3 32  1  0  0  0  0
 32 33  1  6  0  0  0
 31 34  1  6  0  0  0
 30 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
 29 39  1  0  0  0  0
 26 39  1  6  0  0  0
 29 40  1  1  0  0  0
 28 41  1  6  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
 44 45  1  0  0  0  0
 27 46  1  6  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  2  0  0  0  0
 48 50  1  0  0  0  0
 23 51  1  1  0  0  0
  1 52  1  6  0  0  0
M  END


  Mrv1652304282221512D          

 52 59  0  0  1  0            999 V2000
    3.7904    2.0948    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5826    1.4271    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0592    0.8848    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9442    0.9211    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2652    1.6811    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7369    2.3895    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9917    3.1742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4397    3.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6327    3.6156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6945    4.5719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0838    1.7832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5816    1.1253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2606    0.3652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7583   -0.2927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4420    0.2632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4048    2.5432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2083    2.7303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2786    3.5523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5186    3.8732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9785    3.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5887    2.4401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5389    1.6508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8218    2.5510    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2791    2.1020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8447    2.4278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4548    1.3818    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6879    1.8818    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9121    2.2942    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3649    1.6020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5884    0.5436    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4830    0.5328    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3685    0.3122    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5518   -0.4922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3775   -0.2855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0649   -0.0940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2509    0.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2726   -0.5971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0395    0.8128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4823    1.0558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5617    1.7904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7429    3.1017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9590    3.3588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3443    2.8085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7897    4.1663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0058    4.4234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0685    2.6138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6248    3.3093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0054    4.0413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5617    4.7369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8296    4.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1327    3.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4158    2.8299    0.0000 O   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  6  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  1  0  0  0
 11 16  1  6  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  6  0  0  0
  3 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  2 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  2 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 26 31  1  0  0  0  0
 31 32  1  0  0  0  0
  3 32  1  0  0  0  0
 32 33  1  6  0  0  0
 31 34  1  6  0  0  0
 30 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
 29 39  1  0  0  0  0
 26 39  1  6  0  0  0
 29 40  1  1  0  0  0
 28 41  1  6  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
 44 45  1  0  0  0  0
 27 46  1  6  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  2  0  0  0  0
 48 50  1  0  0  0  0
 23 51  1  1  0  0  0
  1 52  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0074564

> <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](O)[C@@]3(O)[C@H]2OC(C)=O)[C@@H]2CC(=O)O[C@@H](C3=COC=C3)[C@]2(C)[C@@H](OC(C)=O)[C@@H](O)[C@]6(O5)[C@]14COC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C35H42O17/c1-15(36)46-14-31-19(10-21(39)44-7)28(4)13-32(31)33(43,27(28)48-17(3)38)26(42)34-20-11-22(40)49-24(18-8-9-45-12-18)29(20,5)25(47-16(2)37)23(41)35(31,34)52-30(6,50-32)51-34/h8-9,12,19-20,23-27,41-43H,10-11,13-14H2,1-7H3/t19-,20+,23+,24-,25-,26+,27-,28+,29+,30-,31+,32+,33+,34+,35-/m0/s1

> <INCHI_KEY>
XQYBLSBUGMZEFP-MKSOBYFMSA-N

> <FORMULA>
C35H42O17

> <MOLECULAR_WEIGHT>
734.704

> <EXACT_MASS>
734.242199892

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
94

> <JCHEM_AVERAGE_POLARIZABILITY>
69.00974426793798

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1R,2R,6R,7R,8R,9R,10R,12S,14R,15S,16S,17R,18S,19R,20R)-8,18-bis(acetyloxy)-6-(furan-3-yl)-9,19,20-trihydroxy-16-(2-methoxy-2-oxoethyl)-7,12,17-trimethyl-4-oxo-5,11,13,21-tetraoxaheptacyclo[10.8.1.1^{14,17}.0^{1,10}.0^{2,7}.0^{10,15}.0^{14,19}]docosan-15-yl]methyl acetate

> <ALOGPS_LOGP>
0.88

> <JCHEM_LOGP>
-0.9795674819999998

> <ALOGPS_LOGS>
-2.24

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.806751019231513

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.682281325361135

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8624925496100664

> <JCHEM_POLAR_SURFACE_AREA>
233.01999999999995

> <JCHEM_REFRACTIVITY>
163.3358

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.26e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,2R,6R,7R,8R,9R,10R,12S,14R,15S,16S,17R,18S,19R,20R)-8,18-bis(acetyloxy)-6-(furan-3-yl)-9,19,20-trihydroxy-16-(2-methoxy-2-oxoethyl)-7,12,17-trimethyl-4-oxo-5,11,13,21-tetraoxaheptacyclo[10.8.1.1^{14,17}.0^{1,10}.0^{2,7}.0^{10,15}.0^{14,19}]docosan-15-yl]methyl 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       7.075   3.910   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.687   2.664   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.577   1.652   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.229   1.719   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.828   3.138   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.842   4.460   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.318   5.925   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.287   7.069   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.781   6.749   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.763   8.534   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.356   3.329   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.286   2.100   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      11.686   0.682   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      12.616  -0.546   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      10.158   0.491   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.956   4.747   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.455   5.097   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      13.587   6.631   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      12.168   7.230   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.160   6.066   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.432   4.555   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.473   3.082   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.134   4.762   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.988   3.924   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       5.310   4.532   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.582   2.579   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.018   3.513   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.569   4.283   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.548   2.990   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.965   1.015   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.635   0.994   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.288   0.583   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       6.630  -0.919   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       4.438  -0.533   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       1.988  -0.175   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       0.468   0.076   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -0.509  -1.115   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -0.074   1.517   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.767   1.971   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       1.049   3.342   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       3.253   5.790   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       1.790   6.270   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       0.643   5.243   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       1.474   7.777   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       0.011   8.257   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       5.728   4.879   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       4.900   6.177   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0       5.610   7.544   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0       4.782   8.842   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0       7.149   7.612   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       7.714   6.188   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0       6.376   5.282   0.000  0.00  0.00           O+0
CONECT    1    2    6   52                                                  
CONECT    2    1    3   24   27                                             
CONECT    3    2    4   22   32                                             
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                                                       
CONECT   23   22   24   25   51                                             
CONECT   24   23    2                                                       
CONECT   25   23   26                                                       
CONECT   26   25   27   31   39                                             
CONECT   27   26    2   28   46                                             
CONECT   28   27   29   41                                                  
CONECT   29   28   30   39   40                                             
CONECT   30   29   31   35                                                  
CONECT   31   30   26   32   34                                             
CONECT   32   31    3   33                                                  
CONECT   33   32                                                            
CONECT   34   31                                                            
CONECT   35   30   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   29   26                                                       
CONECT   40   29                                                            
CONECT   41   28   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45                                                       
CONECT   45   44                                                            
CONECT   46   27   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48                                                            
CONECT   51   23                                                            
CONECT   52    1                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  118    0
END

View in JSmol

Synonyms

Value	Source
[(1R,2R,6R,7R,8R,9R,10R,12S,14R,15S,16S,17R,18S,19R,20R)-8,18-Bis(acetyloxy)-6-(furan-3-yl)-9,19,20-trihydroxy-16-(2-methoxy-2-oxoethyl)-7,12,17-trimethyl-4-oxo-5,11,13,21-tetraoxaheptacyclo[10.8.1.1,.0,.0,.0,.0,]docosan-15-yl]methyl acetic acid	Generator

Chemical Formula

C₃₅H₄₂O₁₇

Average Mass

734.7040 Da

Monoisotopic Mass

734.24220 Da

IUPAC Name

[(1R,2R,6R,7R,8R,9R,10R,12S,14R,15S,16S,17R,18S,19R,20R)-8,18-bis(acetyloxy)-6-(furan-3-yl)-9,19,20-trihydroxy-16-(2-methoxy-2-oxoethyl)-7,12,17-trimethyl-4-oxo-5,11,13,21-tetraoxaheptacyclo[10.8.1.1^{14,17}.0^{1,10}.0^{2,7}.0^{10,15}.0^{14,19}]docosan-15-yl]methyl acetate

Traditional Name

[(1R,2R,6R,7R,8R,9R,10R,12S,14R,15S,16S,17R,18S,19R,20R)-8,18-bis(acetyloxy)-6-(furan-3-yl)-9,19,20-trihydroxy-16-(2-methoxy-2-oxoethyl)-7,12,17-trimethyl-4-oxo-5,11,13,21-tetraoxaheptacyclo[10.8.1.1^{14,17}.0^{1,10}.0^{2,7}.0^{10,15}.0^{14,19}]docosan-15-yl]methyl 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](O)[C@@]3(O)[C@H]2OC(C)=O)[C@@H]2CC(=O)O[C@@H](C3=COC=C3)[C@]2(C)[C@@H](OC(C)=O)[C@@H](O)[C@]6(O5)[C@]14COC(C)=O

InChI Identifier

InChI=1S/C35H42O17/c1-15(36)46-14-31-19(10-21(39)44-7)28(4)13-32(31)33(43,27(28)48-17(3)38)26(42)34-20-11-22(40)49-24(18-8-9-45-12-18)29(20,5)25(47-16(2)37)23(41)35(31,34)52-30(6,50-32)51-34/h8-9,12,19-20,23-27,41-43H,10-11,13-14H2,1-7H3/t19-,20+,23+,24-,25-,26+,27-,28+,29+,30-,31+,32+,33+,34+,35-/m0/s1

InChI Key

XQYBLSBUGMZEFP-MKSOBYFMSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

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
Eicosanoid
Pentacarboxylic acid or derivatives
Naphthopyran
Naphthalene
Ortho ester
Delta_valerolactone
Dioxepane
Delta valerolactone
Carboxylic acid orthoester
1,3-dioxepane
Fatty acyl
Pyran
Oxane
Meta-dioxane
Heteroaromatic compound
Methyl ester
Tertiary alcohol
Furan
Cyclic alcohol
Meta-dioxolane
Secondary alcohol
Orthocarboxylic acid derivative
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	0.88	ALOGPS
logP	-0.98	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	11.68	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	233.02 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	163.34 m³·mol⁻¹	ChemAxon
Polarizability	69.01 Å³	ChemAxon
Number of Rings	8	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

154497548

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Tabulalide D (NP0074564)

MOL for NP0074564 (Tabulalide D)

3D MOL for NP0074564 (Tabulalide D)

3D SDF for NP0074564 (Tabulalide D)

3D-SDF for NP0074564 (Tabulalide D)

PDB for NP0074564 (Tabulalide D)

3D PDB for NP0074564 (Tabulalide D)

SMILES for NP0074564 (Tabulalide D)

INCHI for NP0074564 (Tabulalide D)

Structure for NP0074564 (Tabulalide D)

3D Structure for NP0074564 (Tabulalide D)