NP-MRD: Showing NP-Card for (2r,11r)-3-(acetyloxy)-2,7,7,11,16-pentamethyl-5-oxo-15-[(3s)-5-oxooxolan-3-yl]-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-10-yl acetate (NP0218113)

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Record Information

Version

2.0

Created at

2022-09-05 18:40:29 UTC

Updated at

2022-09-05 18:40:29 UTC

NP-MRD ID

NP0218113

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,11r)-3-(acetyloxy)-2,7,7,11,16-pentamethyl-5-oxo-15-[(3s)-5-oxooxolan-3-yl]-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-10-yl acetate

Description

Kihadalactone B 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. (2r,11r)-3-(acetyloxy)-2,7,7,11,16-pentamethyl-5-oxo-15-[(3s)-5-oxooxolan-3-yl]-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-10-yl acetate is found in Phellodendron amurense and Raulinoa echinata. (2r,11r)-3-(acetyloxy)-2,7,7,11,16-pentamethyl-5-oxo-15-[(3s)-5-oxooxolan-3-yl]-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-10-yl acetate was first documented in 2001 (PMID: 11531091). Based on a literature review very few articles have been published on Kihadalactone B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052220402D          

 38 42  0  0  1  0            999 V2000
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 37 38  1  1  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309052220402D          

 38 42  0  0  1  0            999 V2000
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    3.6918    1.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2316    0.9883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5819    1.7352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9612    0.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6190   -0.2892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2959    0.1825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0564    0.9720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5544    1.6298    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3150    2.4193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9919    2.8909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6496    2.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4391    2.6324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3793    1.6135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1510    0.0532    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6909   -0.5706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 15 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 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
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 25 30  1  0  0  0  0
 31 30  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 31 36  1  0  0  0  0
 27 37  1  0  0  0  0
  5 37  1  0  0  0  0
 22 37  1  0  0  0  0
 37 38  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0218113

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1CC2[C@@](C)(C3CCC4(C)C(CC=C4[C@]13C)[C@H]1COC(=O)C1)C(CC(=O)OC2(C)C)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H42O8/c1-16(31)36-23-13-22-27(3,4)38-26(34)14-24(37-17(2)32)30(22,7)21-10-11-28(5)19(18-12-25(33)35-15-18)8-9-20(28)29(21,23)6/h9,18-19,21-24H,8,10-15H2,1-7H3/t18-,19?,21?,22?,23?,24?,28?,29+,30-/m1/s1

> <INCHI_KEY>
HJPHEKIKOJMFTJ-YPZQBJONSA-N

> <FORMULA>
C30H42O8

> <MOLECULAR_WEIGHT>
530.658

> <EXACT_MASS>
530.287968312

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
57.14082615341548

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,11R)-3-(acetyloxy)-2,7,7,11,16-pentamethyl-5-oxo-15-[(3S)-5-oxooxolan-3-yl]-6-oxatetracyclo[9.7.0.0^{2,8}.0^{12,16}]octadec-12-en-10-yl acetate

> <JCHEM_LOGP>
2.8873522746666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.428350674604788

> <JCHEM_POLAR_SURFACE_AREA>
105.20000000000002

> <JCHEM_REFRACTIVITY>
137.1595

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,11R)-3-(acetyloxy)-2,7,7,11,16-pentamethyl-5-oxo-15-[(3S)-5-oxooxolan-3-yl]-6-oxatetracyclo[9.7.0.0^{2,8}.0^{12,16}]octadec-12-en-10-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       4.368  -4.265   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.880  -3.975   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.888  -5.140   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.385  -2.520   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.377  -1.356   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.865  -1.646   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.857  -0.481   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.405  -0.994   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.228  -2.296   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.319  -2.086   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.099  -0.178   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.078   1.352   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.533   1.856   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.008   2.443   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.539   2.275   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.355   3.581   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.631   4.941   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.447   6.247   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.092   4.994   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.362   0.974   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.974   2.387   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.874   1.264   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.379   2.719   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.891   3.009   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.899   1.845   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.553   3.239   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.394   0.390   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.622  -0.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.886   0.341   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.439   1.814   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.368   3.042   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.921   4.516   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      11.185   5.396   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      12.413   4.467   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      13.886   4.914   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      11.908   3.012   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.882   0.099   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.890  -1.065   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   37                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   20                                                  
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   15    7   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   23   37                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27   30                                             
CONECT   26   25                                                            
CONECT   27   25   28   37                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   25   31                                                  
CONECT   31   30   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   31                                                       
CONECT   37   27    5   22   38                                             
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₂O₈

Average Mass

530.6580 Da

Monoisotopic Mass

530.28797 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CC2[C@@](C)(C3CCC4(C)C(CC=C4[C@]13C)[C@H]1COC(=O)C1)C(CC(=O)OC2(C)C)OC(C)=O

InChI Identifier

InChI=1S/C30H42O8/c1-16(31)36-23-13-22-27(3,4)38-26(34)14-24(37-17(2)32)30(22,7)21-10-11-28(5)19(18-12-25(33)35-15-18)8-9-20(28)29(21,23)6/h9,18-19,21-24H,8,10-15H2,1-7H3/t18-,19?,21?,22?,23?,24?,28?,29+,30-/m1/s1

InChI Key

HJPHEKIKOJMFTJ-YPZQBJONSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Phellodendron amurense	LOTUS Database	35616633
Raulinoa echinata	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
Tetracarboxylic acid or derivatives
Caprolactone
Oxepane
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00058563

Chemspider ID

332518

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

374818

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Biavatti MW, Vieira PC, da Silva MF, Fernandes JB, Albuquerque S: Limonoids from the endemic Brazilian species Raulinoa echinata. Z Naturforsch C J Biosci. 2001 Jul-Aug;56(7-8):570-4. doi: 10.1515/znc-2001-7-815. [PubMed:11531091 ]
LOTUS database [Link]

Showing NP-Card for (2r,11r)-3-(acetyloxy)-2,7,7,11,16-pentamethyl-5-oxo-15-[(3s)-5-oxooxolan-3-yl]-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-10-yl acetate (NP0218113)

MOL for NP0218113 ((2r,11r)-3-(acetyloxy)-2,7,7,11,16-pentamethyl-5-oxo-15-[(3s)-5-oxooxolan-3-yl]-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-10-yl acetate)

3D MOL for NP0218113 ((2r,11r)-3-(acetyloxy)-2,7,7,11,16-pentamethyl-5-oxo-15-[(3s)-5-oxooxolan-3-yl]-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-10-yl acetate)

3D SDF for NP0218113 ((2r,11r)-3-(acetyloxy)-2,7,7,11,16-pentamethyl-5-oxo-15-[(3s)-5-oxooxolan-3-yl]-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-10-yl acetate)

3D-SDF for NP0218113 ((2r,11r)-3-(acetyloxy)-2,7,7,11,16-pentamethyl-5-oxo-15-[(3s)-5-oxooxolan-3-yl]-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-10-yl acetate)

PDB for NP0218113 ((2r,11r)-3-(acetyloxy)-2,7,7,11,16-pentamethyl-5-oxo-15-[(3s)-5-oxooxolan-3-yl]-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-10-yl acetate)

3D PDB for NP0218113 ((2r,11r)-3-(acetyloxy)-2,7,7,11,16-pentamethyl-5-oxo-15-[(3s)-5-oxooxolan-3-yl]-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-10-yl acetate)

SMILES for NP0218113 ((2r,11r)-3-(acetyloxy)-2,7,7,11,16-pentamethyl-5-oxo-15-[(3s)-5-oxooxolan-3-yl]-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-10-yl acetate)

INCHI for NP0218113 ((2r,11r)-3-(acetyloxy)-2,7,7,11,16-pentamethyl-5-oxo-15-[(3s)-5-oxooxolan-3-yl]-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-10-yl acetate)

Structure for NP0218113 ((2r,11r)-3-(acetyloxy)-2,7,7,11,16-pentamethyl-5-oxo-15-[(3s)-5-oxooxolan-3-yl]-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-10-yl acetate)

3D Structure for NP0218113 ((2r,11r)-3-(acetyloxy)-2,7,7,11,16-pentamethyl-5-oxo-15-[(3s)-5-oxooxolan-3-yl]-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadec-12-en-10-yl acetate)