NP-MRD: Showing NP-Card for Kihadalactone A (NP0076751)

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Record Information

Version

2.0

Created at

2022-04-28 21:56:35 UTC

Updated at

2022-04-28 21:56:35 UTC

NP-MRD ID

NP0076751

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Kihadalactone A

Description

(1R,2R,3S,8R,10R,11R,15R,16S)-3-(acetyloxy)-15-(furan-3-yl)-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]Octadec-12-en-10-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. Kihadalactone A is found in Aphanamixis polystacha, Aphanamixis polystachya, Carapa grandiflora and Phellodendron amurense . Based on a literature review very few articles have been published on (1R,2R,3S,8R,10R,11R,15R,16S)-3-(acetyloxy)-15-(furan-3-yl)-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]Octadec-12-en-10-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282223562D          

 37 41  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282223562D          

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    2.1289   -0.4536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4205    2.1751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1502    2.9545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3400    3.1101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6900    3.5784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6909    1.3956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  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
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  1  9  1  0  0  0  0
  8 10  1  1  0  0  0
  7 11  1  1  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 11 15  1  0  0  0  0
  3 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 20 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 19 32  1  6  0  0  0
 16 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
  3 37  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0076751

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1C[C@@H]2[C@@](C)([C@H]3CC[C@@]4(C)[C@@H](CC=C4[C@]13C)C1=COC=C1)[C@H](CC(=O)OC2(C)C)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H40O7/c1-17(31)35-24-14-23-27(3,4)37-26(33)15-25(36-18(2)32)30(23,7)22-10-12-28(5)20(19-11-13-34-16-19)8-9-21(28)29(22,24)6/h9,11,13,16,20,22-25H,8,10,12,14-15H2,1-7H3/t20-,22-,23-,24+,25-,28-,29-,30+/m0/s1

> <INCHI_KEY>
ONWYJKOVGIGNQN-IFRITVQJSA-N

> <FORMULA>
C30H40O7

> <MOLECULAR_WEIGHT>
512.643

> <EXACT_MASS>
512.277403628

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
55.12322035747964

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,3S,8R,10R,11R,15R,16S)-3-(acetyloxy)-15-(furan-3-yl)-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0^{2,8}.0^{12,16}]octadec-12-en-10-yl acetate

> <ALOGPS_LOGP>
6.08

> <JCHEM_LOGP>
3.9997408683333333

> <ALOGPS_LOGS>
-4.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8044389351036663

> <JCHEM_POLAR_SURFACE_AREA>
92.04000000000002

> <JCHEM_REFRACTIVITY>
135.99239999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.33e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,3S,8R,10R,11R,15R,16S)-3-(acetyloxy)-15-(furan-3-yl)-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0^{2,8}.0^{12,16}]octadec-12-en-10-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       5.379  -1.179   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.874   0.276   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.882   1.441   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.394   1.150   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.622   2.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.886   1.199   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.439  -0.274   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.899  -0.305   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.891  -1.469   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.553  -1.699   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.368  -1.502   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.921  -2.976   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      11.185  -3.856   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      12.413  -2.927   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.908  -1.472   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.377   2.896   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.865   3.186   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.857   2.021   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.362   0.566   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.539  -0.735   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.008  -0.903   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.078   0.188   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.533  -0.316   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.099   1.718   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.405   2.534   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.560   3.822   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.950   3.974   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.355  -2.041   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.631  -3.401   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.447  -4.707   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.092  -3.454   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.974  -0.847   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       6.385   4.060   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       5.880   5.515   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       4.368   5.805   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       6.888   6.680   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.890   2.605   0.000  0.00  0.00           C+0
CONECT    1    2    9                                                       
CONECT    2    1    3   19                                                  
CONECT    3    2    4   16   37                                             
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    4    9   10                                             
CONECT    9    8    1                                                       
CONECT   10    8                                                            
CONECT   11    7   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   11                                                       
CONECT   16    3   17   33                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   25                                                  
CONECT   19   18    2   20   32                                             
CONECT   20   19   21   28                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   18   26   27                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   20   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   19                                                            
CONECT   33   16   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37    3                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Value	Source
(1R,2R,3S,8R,10R,11R,15R,16S)-3-(Acetyloxy)-15-(furan-3-yl)-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0,.0,]octadec-12-en-10-yl acetic acid	Generator

Chemical Formula

C₃₀H₄₀O₇

Average Mass

512.6430 Da

Monoisotopic Mass

512.27740 Da

IUPAC Name

(1R,2R,3S,8R,10R,11R,15R,16S)-3-(acetyloxy)-15-(furan-3-yl)-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0^{2,8}.0^{12,16}]octadec-12-en-10-yl acetate

Traditional Name

(1R,2R,3S,8R,10R,11R,15R,16S)-3-(acetyloxy)-15-(furan-3-yl)-2,7,7,11,16-pentamethyl-5-oxo-6-oxatetracyclo[9.7.0.0^{2,8}.0^{12,16}]octadec-12-en-10-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1C[C@@H]2[C@@](C)([C@H]3CC[C@@]4(C)[C@@H](CC=C4[C@]13C)C1=COC=C1)[C@H](CC(=O)OC2(C)C)OC(C)=O

InChI Identifier

InChI=1S/C30H40O7/c1-17(31)35-24-14-23-27(3,4)37-26(33)15-25(36-18(2)32)30(23,7)22-10-12-28(5)20(19-11-13-34-16-19)8-9-21(28)29(22,24)6/h9,11,13,16,20,22-25H,8,10,12,14-15H2,1-7H3/t20-,22-,23-,24+,25-,28-,29-,30+/m0/s1

InChI Key

ONWYJKOVGIGNQN-IFRITVQJSA-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
Aphanamixis polystacha	Plant	KNApSAcK
Aphanamixis polystachya	LOTUS Database	35616633
Carapa grandiflora	LOTUS Database	35616633
Phellodendron amurense	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

Limonoid skeleton
Tricarboxylic acid or derivatives
Caprolactone
Oxepane
Furan
Heteroaromatic compound
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen 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	6.08	ALOGPS
logP	4	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	92.04 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	135.99 m³·mol⁻¹	ChemAxon
Polarizability	55.12 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

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

162965991

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Kihadalactone A (NP0076751)

MOL for NP0076751 (Kihadalactone A)

3D MOL for NP0076751 (Kihadalactone A)

3D SDF for NP0076751 (Kihadalactone A)

3D-SDF for NP0076751 (Kihadalactone A)

PDB for NP0076751 (Kihadalactone A)

3D PDB for NP0076751 (Kihadalactone A)

SMILES for NP0076751 (Kihadalactone A)

INCHI for NP0076751 (Kihadalactone A)

Structure for NP0076751 (Kihadalactone A)

3D Structure for NP0076751 (Kihadalactone A)