NP-MRD: Showing NP-Card for 1-benzoylnimbolinin C (NP0040686)

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Record Information

Version

2.0

Created at

2021-06-20 22:46:54 UTC

Updated at

2021-06-30 00:14:44 UTC

NP-MRD ID

NP0040686

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-benzoylnimbolinin C

Provided By

JEOL Database JEOL Logo

Description

CHEMBL3581419 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. 1-benzoylnimbolinin C is found in Melia azedarach and Munronia pinnata. 1-benzoylnimbolinin C was first documented in 2011 (Liu, H.-B., et al.). Based on a literature review very few articles have been published on CHEMBL3581419.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100463D          

 89 95  0  0  0  0            999 V2000
    0.9935   -2.1770    2.2789 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4403   -0.9903    1.7252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8402   -1.2180    1.1377 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5479    0.1242    0.9089 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8721    1.0682   -0.1213 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2267    0.7030   -1.6597 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7563    0.7740   -1.9017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7803   -0.7293   -2.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0065   -1.4531   -3.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7231   -1.1094   -4.4186 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3938   -3.9311   -2.9570 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5825    5.1105   -2.0474 C   0  0  2  0  0  0  0  0  0  0  0  0
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 32 27  1  0  0  0  0
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M  END

     RDKit          3D

 89 95  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306212100463D          

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M  END
> <DATABASE_ID>
NP0040686

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])[C@]2([H])OC([H])([H])[C@@]3(C([H])([H])[H])[C@@]2([H])[C@](C([H])([H])[H])([C@@]([H])(OC(=O)C2=C([H])C([H])=C([H])C([H])=C2[H])C([H])([H])[C@@]3([H])OC(=O)C([H])([H])[H])[C@@]2([H])C([H])([H])[C@]([H])(OC([H])([H])[H])O[C@]3([H])C(=C(C([H])([H])[H])[C@]([H])(C4=C([H])OC([H])=C4[H])C3([H])[H])[C@]12C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C36H44O9/c1-19-23(22-12-13-41-17-22)14-24-29(19)36(5)25(15-28(40-6)44-24)35(4)27(45-33(39)21-10-8-7-9-11-21)16-26(43-20(2)37)34(3)18-42-30(31(34)35)32(36)38/h7-13,17,23-28,30-32,38H,14-16,18H2,1-6H3/t23-,24+,25-,26-,27+,28-,30-,31+,32-,34-,35+,36-/m1/s1

> <INCHI_KEY>
QCDUZQJTCDFJLU-AZOYZBKUSA-N

> <FORMULA>
C36H44O9

> <MOLECULAR_WEIGHT>
620.739

> <EXACT_MASS>
620.298532997

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
89

> <JCHEM_AVERAGE_POLARIZABILITY>
65.90056184429773

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,4R,6S,8R,11R,12S,13R,16R,17R,19S,20R)-17-(acetyloxy)-8-(furan-3-yl)-12-hydroxy-4-methoxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0^{2,11}.0^{6,10}.0^{16,20}]icos-9-en-19-yl benzoate

> <ALOGPS_LOGP>
4.94

> <JCHEM_LOGP>
4.028074067666667

> <ALOGPS_LOGS>
-4.44

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.673097592644076

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8289080896670233

> <JCHEM_POLAR_SURFACE_AREA>
113.66000000000003

> <JCHEM_REFRACTIVITY>
163.46459999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.25e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4R,6S,8R,11R,12S,13R,16R,17R,19S,20R)-17-(acetyloxy)-8-(furan-3-yl)-12-hydroxy-4-methoxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0^{2,11}.0^{6,10}.0^{16,20}]icos-9-en-19-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 89 95  0  0  0  0  0  0  0  0999 V2000
    0.9935   -2.1770    2.2789 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4403   -0.9903    1.7252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8402   -1.2180    1.1377 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5479    0.1242    0.9089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8721    1.0682   -0.1213 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2267    0.7030   -1.6597 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7563    0.7740   -1.9017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7803   -0.7293   -2.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0065   -1.4531   -3.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7231   -1.1094   -4.4186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3836   -2.8302   -3.0776 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3938   -3.9311   -2.9570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5087   -5.0775   -3.7976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5693   -5.8112   -3.3220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1210   -5.2006   -2.2445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4078   -4.0670   -2.0275 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5590   -2.7134   -1.8825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0499   -1.5284   -1.0589 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7825   -2.0290   -0.0230 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4925    1.7134   -2.6214 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9300    1.4769   -2.6029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7489    3.1702   -2.2158 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0473    4.1142   -2.9745 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5825    5.1105   -2.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1421    4.9045   -0.7023 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4395    5.7389   -0.7384 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6432    5.2265    0.5888 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0108    4.7859    0.4502 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9391    5.4443    1.1966 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2930    4.8390    0.9872 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7117    6.3817    1.9475 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0002    4.5099    1.8102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2483    2.9802    1.6283 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0360    2.3225    1.6129 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5520    1.9395    2.8047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0511    2.1355    3.9002 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8663    1.2738    2.5989 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6551    1.0034    3.7249 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8978    0.3835    3.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3568    0.0280    2.3124 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5756    0.2889    1.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3328    0.9103    1.3271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0252    2.6183    0.2938 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5014    3.0285    0.4869 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2975    3.3970   -0.8003 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1442   -2.9355    1.5053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3488   -2.5684    3.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9656   -1.9317    2.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4526   -1.7659    1.8652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5857    0.6206    1.8844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5847   -0.0696    0.6188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2060    0.8878   -0.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2802   -0.0775   -1.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0086    0.7744   -2.9650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2140    1.6766   -1.5092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8907   -0.0410   -4.5473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6926   -1.6154   -4.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1344   -1.4314   -5.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2235   -3.0078   -3.9756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8916   -5.3340   -4.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0338   -6.7399   -3.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7327   -3.4654   -1.1895 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6318   -3.6373   -1.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5663   -2.4781   -2.2533 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9237   -0.9904   -0.6782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7997    1.5828   -3.6629 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3156    2.2236   -3.1020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7999    3.4243   -2.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4324    6.1045   -2.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6605    4.9293   -1.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0300    5.6519    0.1747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1968    6.8036   -0.8441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0868    5.4789   -1.5812 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6321    6.3123    0.7487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3770    3.9155    1.5629 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4575    4.6430   -0.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0591    5.5446    1.3209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9466    5.0019    2.0547 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6553    4.6506    2.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8324    2.6183    2.4837 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3030    1.2754    4.7182 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5059    0.1768    4.4576 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3236   -0.4571    2.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9302    0.0047    0.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7330    1.0937    0.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1100    2.2068    0.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6184    3.8347    1.2162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9678    3.3820   -0.4345 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7385    3.0163   -0.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
 32 27  1  0
 32 33  1  0
 25 45  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
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 11 12  1  0
  6  5  1  0
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  7 55  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       0.994  -2.177   2.279  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.440  -0.990   1.725  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.840  -1.218   1.138  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.548   0.124   0.909  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.872   1.068  -0.121  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.227   0.703  -1.660  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.756   0.774  -1.902  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.780  -0.729  -2.031  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.006  -1.453  -3.153  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.723  -1.109  -4.419  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.384  -2.830  -3.078  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.394  -3.931  -2.957  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.509  -5.077  -3.798  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.569  -5.811  -3.322  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.121  -5.201  -2.244  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.408  -4.067  -2.027  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.559  -2.713  -1.883  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.050  -1.528  -1.059  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.783  -2.029  -0.023  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.493   1.713  -2.621  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.930   1.477  -2.603  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.749   3.170  -2.216  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.047   4.114  -2.974  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.583   5.111  -2.047  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.142   4.904  -0.702  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.440   5.739  -0.738  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.643   5.226   0.589  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.011   4.786   0.450  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.939   5.444   1.197  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.293   4.839   0.987  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.712   6.382   1.948  0.00  0.00           O+0
HETATM   32  C   UNK     0       0.000   4.510   1.810  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.248   2.980   1.628  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.036   2.322   1.613  0.00  0.00           O+0
HETATM   35  C   UNK     0       1.552   1.940   2.805  0.00  0.00           C+0
HETATM   36  O   UNK     0       1.051   2.135   3.900  0.00  0.00           O+0
HETATM   37  C   UNK     0       2.866   1.274   2.599  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.655   1.003   3.725  0.00  0.00           C+0
HETATM   39  C   UNK     0       4.898   0.384   3.580  0.00  0.00           C+0
HETATM   40  C   UNK     0       5.357   0.028   2.312  0.00  0.00           C+0
HETATM   41  C   UNK     0       4.576   0.289   1.187  0.00  0.00           C+0
HETATM   42  C   UNK     0       3.333   0.910   1.327  0.00  0.00           C+0
HETATM   43  C   UNK     0      -1.025   2.618   0.294  0.00  0.00           C+0
HETATM   44  C   UNK     0      -2.501   3.029   0.487  0.00  0.00           C+0
HETATM   45  C   UNK     0      -0.298   3.397  -0.800  0.00  0.00           C+0
HETATM   46  H   UNK     0       1.144  -2.936   1.505  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.349  -2.568   3.072  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.966  -1.932   2.715  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.453  -1.766   1.865  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.586   0.621   1.884  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.585  -0.070   0.619  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.206   0.888  -0.043  0.00  0.00           H+0
HETATM   53  H   UNK     0      -3.280  -0.078  -1.453  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.009   0.774  -2.965  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.214   1.677  -1.509  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.891  -0.041  -4.547  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.693  -1.615  -4.458  0.00  0.00           H+0
HETATM   58  H   UNK     0      -1.134  -1.431  -5.285  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.224  -3.008  -3.976  0.00  0.00           H+0
HETATM   60  H   UNK     0      -0.892  -5.334  -4.647  0.00  0.00           H+0
HETATM   61  H   UNK     0      -3.034  -6.740  -3.622  0.00  0.00           H+0
HETATM   62  H   UNK     0      -2.733  -3.465  -1.190  0.00  0.00           H+0
HETATM   63  H   UNK     0       0.632  -3.637  -1.297  0.00  0.00           H+0
HETATM   64  H   UNK     0       1.566  -2.478  -2.253  0.00  0.00           H+0
HETATM   65  H   UNK     0       0.924  -0.990  -0.678  0.00  0.00           H+0
HETATM   66  H   UNK     0      -0.800   1.583  -3.663  0.00  0.00           H+0
HETATM   67  H   UNK     0       1.316   2.224  -3.102  0.00  0.00           H+0
HETATM   68  H   UNK     0      -1.800   3.424  -2.381  0.00  0.00           H+0
HETATM   69  H   UNK     0       0.432   6.104  -2.480  0.00  0.00           H+0
HETATM   70  H   UNK     0       1.661   4.929  -1.987  0.00  0.00           H+0
HETATM   71  H   UNK     0      -2.030   5.652   0.175  0.00  0.00           H+0
HETATM   72  H   UNK     0      -1.197   6.804  -0.844  0.00  0.00           H+0
HETATM   73  H   UNK     0      -2.087   5.479  -1.581  0.00  0.00           H+0
HETATM   74  H   UNK     0       0.632   6.312   0.749  0.00  0.00           H+0
HETATM   75  H   UNK     0       4.377   3.916   1.563  0.00  0.00           H+0
HETATM   76  H   UNK     0       4.457   4.643  -0.076  0.00  0.00           H+0
HETATM   77  H   UNK     0       5.059   5.545   1.321  0.00  0.00           H+0
HETATM   78  H   UNK     0      -0.947   5.002   2.055  0.00  0.00           H+0
HETATM   79  H   UNK     0       0.655   4.651   2.678  0.00  0.00           H+0
HETATM   80  H   UNK     0      -0.832   2.618   2.484  0.00  0.00           H+0
HETATM   81  H   UNK     0       3.303   1.275   4.718  0.00  0.00           H+0
HETATM   82  H   UNK     0       5.506   0.177   4.458  0.00  0.00           H+0
HETATM   83  H   UNK     0       6.324  -0.457   2.201  0.00  0.00           H+0
HETATM   84  H   UNK     0       4.930   0.005   0.199  0.00  0.00           H+0
HETATM   85  H   UNK     0       2.733   1.094   0.438  0.00  0.00           H+0
HETATM   86  H   UNK     0      -3.110   2.207   0.875  0.00  0.00           H+0
HETATM   87  H   UNK     0      -2.618   3.835   1.216  0.00  0.00           H+0
HETATM   88  H   UNK     0      -2.968   3.382  -0.435  0.00  0.00           H+0
HETATM   89  H   UNK     0       0.739   3.016  -0.763  0.00  0.00           H+0
CONECT    1    2   46   47   48                                             
CONECT    2    3    1                                                       
CONECT    3    4   19    2   49                                             
CONECT    4    5    3   50   51                                             
CONECT    5    6   43    4   52                                             
CONECT    6    5    8   20    7                                             
CONECT    7    6   53   54   55                                             
CONECT    8    6   18    9                                                  
CONECT    9   10    8   11                                                  
CONECT   10    9   56   57   58                                             
CONECT   11   12    9   17   59                                             
CONECT   12   16   11   13                                                  
CONECT   13   14   12   60                                                  
CONECT   14   13   15   61                                                  
CONECT   15   14   16                                                       
CONECT   16   15   12   62                                                  
CONECT   17   11   18   63   64                                             
CONECT   18   19    8   17   65                                             
CONECT   19    3   18                                                       
CONECT   20   21   22    6   66                                             
CONECT   21   20   67                                                       
CONECT   22   23   45   20   68                                             
CONECT   23   22   24                                                       
CONECT   24   25   23   69   70                                             
CONECT   25   45   26   24   27                                             
CONECT   26   25   71   72   73                                             
CONECT   27   32   28   25   74                                             
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29   75   76   77                                             
CONECT   31   29                                                            
CONECT   32   27   33   78   79                                             
CONECT   33   32   34   43   80                                             
CONECT   34   33   35                                                       
CONECT   35   34   37   36                                                  
CONECT   36   35                                                            
CONECT   37   35   38   42                                                  
CONECT   38   37   39   81                                                  
CONECT   39   38   40   82                                                  
CONECT   40   39   41   83                                                  
CONECT   41   40   42   84                                                  
CONECT   42   41   37   85                                                  
CONECT   43    5   33   44   45                                             
CONECT   44   43   86   87   88                                             
CONECT   45   25   22   43   89                                             
CONECT   46    1                                                            
CONECT   47    1                                                            
CONECT   48    1                                                            
CONECT   49    3                                                            
CONECT   50    4                                                            
CONECT   51    4                                                            
CONECT   52    5                                                            
CONECT   53    7                                                            
CONECT   54    7                                                            
CONECT   55    7                                                            
CONECT   56   10                                                            
CONECT   57   10                                                            
CONECT   58   10                                                            
CONECT   59   11                                                            
CONECT   60   13                                                            
CONECT   61   14                                                            
CONECT   62   16                                                            
CONECT   63   17                                                            
CONECT   64   17                                                            
CONECT   65   18                                                            
CONECT   66   20                                                            
CONECT   67   21                                                            
CONECT   68   22                                                            
CONECT   69   24                                                            
CONECT   70   24                                                            
CONECT   71   26                                                            
CONECT   72   26                                                            
CONECT   73   26                                                            
CONECT   74   27                                                            
CONECT   75   30                                                            
CONECT   76   30                                                            
CONECT   77   30                                                            
CONECT   78   32                                                            
CONECT   79   32                                                            
CONECT   80   33                                                            
CONECT   81   38                                                            
CONECT   82   39                                                            
CONECT   83   40                                                            
CONECT   84   41                                                            
CONECT   85   42                                                            
CONECT   86   44                                                            
CONECT   87   44                                                            
CONECT   88   44                                                            
CONECT   89   45                                                            
MASTER        0    0    0    0    0    0    0    0   89    0  190    0
END

RDKit          3D

89 95  0  0  0  0  0  0  0  0999 V2000
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  7 55  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₆H₄₄O₉

Average Mass

620.7390 Da

Monoisotopic Mass

620.29853 Da

IUPAC Name

(1R,2R,4R,6S,8R,11R,12S,13R,16R,17R,19S,20R)-17-(acetyloxy)-8-(furan-3-yl)-12-hydroxy-4-methoxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0^{2,11}.0^{6,10}.0^{16,20}]icos-9-en-19-yl benzoate

Traditional Name

(1R,2R,4R,6S,8R,11R,12S,13R,16R,17R,19S,20R)-17-(acetyloxy)-8-(furan-3-yl)-12-hydroxy-4-methoxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0^{2,11}.0^{6,10}.0^{16,20}]icos-9-en-19-yl benzoate

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])[C@]2([H])OC([H])([H])[C@@]3(C([H])([H])[H])[C@@]2([H])[C@](C([H])([H])[H])([C@@]([H])(OC(=O)C2=C([H])C([H])=C([H])C([H])=C2[H])C([H])([H])[C@@]3([H])OC(=O)C([H])([H])[H])[C@@]2([H])C([H])([H])[C@]([H])(OC([H])([H])[H])O[C@]3([H])C(=C(C([H])([H])[H])[C@]([H])(C4=C([H])OC([H])=C4[H])C3([H])[H])[C@]12C([H])([H])[H]

InChI Identifier

InChI=1S/C36H44O9/c1-19-23(22-12-13-41-17-22)14-24-29(19)36(5)25(15-28(40-6)44-24)35(4)27(45-33(39)21-10-8-7-9-11-21)16-26(43-20(2)37)34(3)18-42-30(31(34)35)32(36)38/h7-13,17,23-28,30-32,38H,14-16,18H2,1-6H3/t23-,24+,25-,26-,27+,28-,30-,31+,32-,34-,35+,36-/m1/s1

InChI Key

QCDUZQJTCDFJLU-AZOYZBKUSA-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
Melia azedarach	JEOL database	Liu, H.-B., et al, Chem. Pharm. Bull. 59, 1003 (2011)
Munronia pinnata	LOTUS Database	35616633

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

Limonoid skeleton
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Oxepane
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Heteroaromatic compound
Cyclic alcohol
Furan
Tetrahydrofuran
Carboxylic acid ester
Secondary alcohol
Ether
Oxacycle
Dialkyl ether
Carboxylic acid derivative
Acetal
Organoheterocyclic compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
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	4.94	ALOGPS
logP	4.03	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	13.67	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	113.66 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	163.46 m³·mol⁻¹	ChemAxon
Polarizability	65.9 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	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

59006448

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53493834

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liu, H.-B., et al. (2011). Liu, H.-B., et al, Chem. Pharm. Bull. 59, 1003 (2011). Chem. Pharm. Bull..

Showing NP-Card for 1-benzoylnimbolinin C (NP0040686)

MOL for NP0040686 (1-benzoylnimbolinin C)

3D MOL for NP0040686 (1-benzoylnimbolinin C)

3D SDF for NP0040686 (1-benzoylnimbolinin C)

3D-SDF for NP0040686 (1-benzoylnimbolinin C)

PDB for NP0040686 (1-benzoylnimbolinin C)

3D PDB for NP0040686 (1-benzoylnimbolinin C)

SMILES for NP0040686 (1-benzoylnimbolinin C)

INCHI for NP0040686 (1-benzoylnimbolinin C)

Structure for NP0040686 (1-benzoylnimbolinin C)

3D Structure for NP0040686 (1-benzoylnimbolinin C)