NP-MRD: Showing NP-Card for (+)-7-Deoxo-7beta-acetoxykihadanin A (NP0075048)

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Record Information

Version

2.0

Created at

2022-04-28 20:22:01 UTC

Updated at

2022-04-28 20:22:01 UTC

NP-MRD ID

NP0075048

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-7-Deoxo-7beta-acetoxykihadanin A

Description

(1S,2R,4S,7R,8S,11R,12R,18R,20S)-7-[(2R)-2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl]-1,8,12,17,17-pentamethyl-5,15-dioxo-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]Icos-13-en-20-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. (+)-7-Deoxo-7beta-acetoxykihadanin A is found in Trichilia elegans and Trichilia elegans ssp. elegans. Based on a literature review very few articles have been published on (1S,2R,4S,7R,8S,11R,12R,18R,20S)-7-[(2R)-2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl]-1,8,12,17,17-pentamethyl-5,15-dioxo-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]Icos-13-en-20-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282222222D          

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M  END

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M  END


  Mrv1652304282222222D          

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    4.1360    1.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4205   -1.3017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1660   -1.2290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3681    1.2941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  6  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  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 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
  9 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  1  0  0  0
 11 23  1  6  0  0  0
 10 23  1  6  0  0  0
  9 24  1  1  0  0  0
  5 25  1  6  0  0  0
  4 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
  2 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
  1 35  1  0  0  0  0
 30 36  1  0  0  0  0
 30 37  1  0  0  0  0
  1 38  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0075048

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1C[C@@H]2[C@](C)(C=CC(=O)OC2(C)C)[C@H]2CC[C@@]3(C)[C@@H](OC(=O)[C@H]4O[C@@]34[C@]12C)C1=CC(=O)O[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H34O10/c1-13(29)34-17-12-16-24(2,3)37-18(30)8-9-25(16,4)15-7-10-26(5)20(14-11-19(31)35-22(14)32)36-23(33)21-28(26,38-21)27(15,17)6/h8-9,11,15-17,20-22,32H,7,10,12H2,1-6H3/t15-,16+,17+,20+,21-,22-,25-,26+,27+,28-/m1/s1

> <INCHI_KEY>
VKZYANGAHYJBJK-LJHJOZSSSA-N

> <FORMULA>
C28H34O10

> <MOLECULAR_WEIGHT>
530.57

> <EXACT_MASS>
530.215197295

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
53.36321641037841

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,4S,7R,8S,11R,12R,18R,20S)-7-[(2R)-2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl]-1,8,12,17,17-pentamethyl-5,15-dioxo-3,6,16-trioxapentacyclo[9.9.0.0^{2,4}.0^{2,8}.0^{12,18}]icos-13-en-20-yl acetate

> <ALOGPS_LOGP>
2.22

> <JCHEM_LOGP>
2.548757053

> <ALOGPS_LOGS>
-4.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.730229434291884

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.303372827545726

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3037719381357915

> <JCHEM_POLAR_SURFACE_AREA>
137.96000000000004

> <JCHEM_REFRACTIVITY>
129.1069

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.90e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4S,7R,8S,11R,12R,18R,20S)-7-[(2R)-2-hydroxy-5-oxo-2H-furan-3-yl]-1,8,12,17,17-pentamethyl-5,15-dioxo-3,6,16-trioxapentacyclo[9.9.0.0^{2,4}.0^{2,8}.0^{12,18}]icos-13-en-20-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       6.882   0.995   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.368  -0.466   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.346  -1.618   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.838  -1.309   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.351   0.152   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.373   1.304   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.886   2.765   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.378   3.074   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.356   1.922   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.842   0.461   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.820  -0.691   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.312  -0.382   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.710  -1.534   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -0.175   1.079   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.847   2.231   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.360   3.692   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.108   4.157   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.119   5.697   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.372   6.593   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.342   6.184   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.256   4.945   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.796   4.956   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.329  -1.000   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.869   3.383   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.201  -1.381   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.816  -2.461   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.303  -3.922   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.811  -4.231   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.281  -5.074   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.814  -0.996   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      10.130  -0.197   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      10.326   1.331   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      11.787   1.818   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       9.253   2.436   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.720   2.287   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.252  -2.430   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.643  -2.294   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.287   2.416   0.000  0.00  0.00           C+0
CONECT    1    2    6   35   38                                             
CONECT    2    1    3   30                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   26                                                  
CONECT    5    4    6   10   25                                             
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   15   24                                             
CONECT   10    9    5   11   23                                             
CONECT   11   10   12   23                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14    9   16                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   16   22                                                  
CONECT   22   21                                                            
CONECT   23   11   10                                                       
CONECT   24    9                                                            
CONECT   25    5                                                            
CONECT   26    4   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30    2   31   36   37                                             
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34    1                                                       
CONECT   36   30                                                            
CONECT   37   30                                                            
CONECT   38    1                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   86    0
END

View in JSmol

Synonyms

Value	Source
(1S,2R,4S,7R,8S,11R,12R,18R,20S)-7-[(2R)-2-Hydroxy-5-oxo-2,5-dihydrofuran-3-yl]-1,8,12,17,17-pentamethyl-5,15-dioxo-3,6,16-trioxapentacyclo[9.9.0.0,.0,.0,]icos-13-en-20-yl acetic acid	Generator

Chemical Formula

C₂₈H₃₄O₁₀

Average Mass

530.5700 Da

Monoisotopic Mass

530.21520 Da

IUPAC Name

(1S,2R,4S,7R,8S,11R,12R,18R,20S)-7-[(2R)-2-hydroxy-5-oxo-2,5-dihydrofuran-3-yl]-1,8,12,17,17-pentamethyl-5,15-dioxo-3,6,16-trioxapentacyclo[9.9.0.0^{2,4}.0^{2,8}.0^{12,18}]icos-13-en-20-yl acetate

Traditional Name

(1S,2R,4S,7R,8S,11R,12R,18R,20S)-7-[(2R)-2-hydroxy-5-oxo-2H-furan-3-yl]-1,8,12,17,17-pentamethyl-5,15-dioxo-3,6,16-trioxapentacyclo[9.9.0.0^{2,4}.0^{2,8}.0^{12,18}]icos-13-en-20-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1C[C@@H]2[C@](C)(C=CC(=O)OC2(C)C)[C@H]2CC[C@@]3(C)[C@@H](OC(=O)[C@H]4O[C@@]34[C@]12C)C1=CC(=O)O[C@H]1O

InChI Identifier

InChI=1S/C28H34O10/c1-13(29)34-17-12-16-24(2,3)37-18(30)8-9-25(16,4)15-7-10-26(5)20(14-11-19(31)35-22(14)32)36-23(33)21-28(26,38-21)27(15,17)6/h8-9,11,15-17,20-22,32H,7,10,12H2,1-6H3/t15-,16+,17+,20+,21-,22-,25-,26+,27+,28-/m1/s1

InChI Key

VKZYANGAHYJBJK-LJHJOZSSSA-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
Trichilia elegans	LOTUS Database	35616633
Trichilia elegans ssp. elegans	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
Naphthopyran
Tetracarboxylic acid or derivatives
Naphthalene
1,4-dioxepane
Delta valerolactone
Dioxepane
Delta_valerolactone
2-furanone
Pyran
Oxane
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Hemiacetal
Lactone
Ether
Oxirane
Organoheterocyclic compound
Oxacycle
Dialkyl ether
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
Organic oxide
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
logP	2.22	ALOGPS
logP	2.55	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	5.3	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	137.96 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	129.11 m³·mol⁻¹	ChemAxon
Polarizability	53.36 Å³	ChemAxon
Number of Rings	6	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

553421

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

637835

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (+)-7-Deoxo-7beta-acetoxykihadanin A (NP0075048)

MOL for NP0075048 ((+)-7-Deoxo-7beta-acetoxykihadanin A)

3D MOL for NP0075048 ((+)-7-Deoxo-7beta-acetoxykihadanin A)

3D SDF for NP0075048 ((+)-7-Deoxo-7beta-acetoxykihadanin A)

3D-SDF for NP0075048 ((+)-7-Deoxo-7beta-acetoxykihadanin A)

PDB for NP0075048 ((+)-7-Deoxo-7beta-acetoxykihadanin A)

3D PDB for NP0075048 ((+)-7-Deoxo-7beta-acetoxykihadanin A)

SMILES for NP0075048 ((+)-7-Deoxo-7beta-acetoxykihadanin A)

INCHI for NP0075048 ((+)-7-Deoxo-7beta-acetoxykihadanin A)

Structure for NP0075048 ((+)-7-Deoxo-7beta-acetoxykihadanin A)

3D Structure for NP0075048 ((+)-7-Deoxo-7beta-acetoxykihadanin A)