NP-MRD: Showing NP-Card for (-)-3-O-Acetylanthothecanolide (NP0074196)

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Record Information

Version

2.0

Created at

2022-04-28 19:21:48 UTC

Updated at

2022-04-28 19:21:48 UTC

NP-MRD ID

NP0074196

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-3-O-Acetylanthothecanolide

Description

(1R,2S,6R,7S,10R,11S,16S,18S,19R,20R)-6-(furan-3-yl)-2,19,20-trihydroxy-7,17,17-trimethyl-4,14-dioxo-5,13,21-trioxahexacyclo[17.2.1.0¹,¹⁰.0²,⁷.0¹¹,¹⁶.0¹¹,²⁰]Docosan-18-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. (-)-3-O-Acetylanthothecanolide is found in Khaya anthotheca. Based on a literature review very few articles have been published on (1R,2S,6R,7S,10R,11S,16S,18S,19R,20R)-6-(furan-3-yl)-2,19,20-trihydroxy-7,17,17-trimethyl-4,14-dioxo-5,13,21-trioxahexacyclo[17.2.1.0¹,¹⁰.0²,⁷.0¹¹,¹⁶.0¹¹,²⁰]Docosan-18-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282221212D          

 39 45  0  0  1  0            999 V2000
    0.1077    2.7361    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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  1 39  1  1  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282221212D          

 39 45  0  0  1  0            999 V2000
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    2.5090   -1.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2049   -1.5264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9985   -2.3252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1750   -2.3757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8725   -1.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7400    1.7536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7803   -0.7147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2609    3.5467    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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  1  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  7 13  1  0  0  0  0
  7 14  1  0  0  0  0
  6 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
  5 19  1  1  0  0  0
  5 20  1  0  0  0  0
  1 20  1  0  0  0  0
 20 21  1  0  0  0  0
  3 21  1  1  0  0  0
 20 22  1  1  0  0  0
  4 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  3 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 25 31  1  0  0  0  0
 31 32  1  1  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 32 36  1  0  0  0  0
 26 37  1  1  0  0  0
 25 38  1  1  0  0  0
  1 39  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0074196

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1[C@]2(O)C[C@@]34O[C@]2(O)[C@]2(COC(=O)C[C@H]2C1(C)C)[C@H]3CC[C@@]1(C)[C@@H](OC(=O)C[C@@]41O)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H34O11/c1-14(29)37-21-22(2,3)17-9-18(30)36-13-24(17)16-5-7-23(4)20(15-6-8-35-11-15)38-19(31)10-27(23,33)26(16)12-25(21,32)28(24,34)39-26/h6,8,11,16-17,20-21,32-34H,5,7,9-10,12-13H2,1-4H3/t16-,17+,20+,21+,23+,24-,25-,26-,27+,28-/m1/s1

> <INCHI_KEY>
NKDXTBIRGROVAP-GDJRKFDVSA-N

> <FORMULA>
C28H34O11

> <MOLECULAR_WEIGHT>
546.569

> <EXACT_MASS>
546.210111915

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
53.86815438247409

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,6R,7S,10R,11S,16S,18S,19R,20R)-6-(furan-3-yl)-2,19,20-trihydroxy-7,17,17-trimethyl-4,14-dioxo-5,13,21-trioxahexacyclo[17.2.1.0^{1,10}.0^{2,7}.0^{11,16}.0^{11,20}]docosan-18-yl acetate

> <ALOGPS_LOGP>
1.11

> <JCHEM_LOGP>
0.46882028999999864

> <ALOGPS_LOGS>
-2.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.526679110523876

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.48699403031668

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8763236561907926

> <JCHEM_POLAR_SURFACE_AREA>
161.96

> <JCHEM_REFRACTIVITY>
127.34609999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.12e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,6R,7S,10R,11S,16S,18S,19R,20R)-6-(furan-3-yl)-2,19,20-trihydroxy-7,17,17-trimethyl-4,14-dioxo-5,13,21-trioxahexacyclo[17.2.1.0^{1,10}.0^{2,7}.0^{11,16}.0^{11,20}]docosan-18-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       0.201   5.107   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.171   4.603   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.864   2.919   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.712   1.785   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.731   2.350   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.279   2.604   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.618   4.184   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.437   5.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.921   6.772   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -3.429   7.084   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.912   8.546   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.453   5.934   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.131   3.898   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.708   5.272   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.300   1.313   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.838  -0.183   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.886  -1.312   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.354  -0.524   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.470   0.753   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.024   3.740   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.296   4.699   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.488   4.220   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.700   0.117   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.960  -0.670   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.211   0.202   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.117   1.739   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.401   2.589   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.779   1.902   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       7.063   2.753   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       5.873   0.365   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.589  -0.485   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.683  -2.022   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.982  -2.849   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.597  -4.340   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       4.060  -4.435   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.495  -3.002   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       3.248   3.273   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       3.323  -1.334   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       0.487   6.621   0.000  0.00  0.00           O+0
CONECT    1    2    8   20   39                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   21   26                                             
CONECT    4    3    5   23                                                  
CONECT    5    4    6   19   20                                             
CONECT    6    5    7   15                                                  
CONECT    7    6    8   13   14                                             
CONECT    8    7    1    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    7                                                            
CONECT   14    7                                                            
CONECT   15    6   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18    5                                                       
CONECT   20    5    1   21   22                                             
CONECT   21   20    3                                                       
CONECT   22   20                                                            
CONECT   23    4   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   31   38                                             
CONECT   26   25    3   27   37                                             
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   25   32                                                  
CONECT   32   31   33   36                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   32                                                       
CONECT   37   26                                                            
CONECT   38   25                                                            
CONECT   39    1                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   90    0
END

View in JSmol

Synonyms

Value	Source
(1R,2S,6R,7S,10R,11S,16S,18S,19R,20R)-6-(Furan-3-yl)-2,19,20-trihydroxy-7,17,17-trimethyl-4,14-dioxo-5,13,21-trioxahexacyclo[17.2.1.0,.0,.0,.0,]docosan-18-yl acetic acid	Generator

Chemical Formula

C₂₈H₃₄O₁₁

Average Mass

546.5690 Da

Monoisotopic Mass

546.21011 Da

IUPAC Name

(1R,2S,6R,7S,10R,11S,16S,18S,19R,20R)-6-(furan-3-yl)-2,19,20-trihydroxy-7,17,17-trimethyl-4,14-dioxo-5,13,21-trioxahexacyclo[17.2.1.0^{1,10}.0^{2,7}.0^{11,16}.0^{11,20}]docosan-18-yl acetate

Traditional Name

(1R,2S,6R,7S,10R,11S,16S,18S,19R,20R)-6-(furan-3-yl)-2,19,20-trihydroxy-7,17,17-trimethyl-4,14-dioxo-5,13,21-trioxahexacyclo[17.2.1.0^{1,10}.0^{2,7}.0^{11,16}.0^{11,20}]docosan-18-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1[C@]2(O)C[C@@]34O[C@]2(O)[C@]2(COC(=O)C[C@H]2C1(C)C)[C@H]3CC[C@@]1(C)[C@@H](OC(=O)C[C@@]41O)C1=COC=C1

InChI Identifier

InChI=1S/C28H34O11/c1-14(29)37-21-22(2,3)17-9-18(30)36-13-24(17)16-5-7-23(4)20(15-6-8-35-11-15)38-19(31)10-27(23,33)26(16)12-25(21,32)28(24,34)39-26/h6,8,11,16-17,20-21,32-34H,5,7,9-10,12-13H2,1-4H3/t16-,17+,20+,21+,23+,24-,25-,26-,27+,28-/m1/s1

InChI Key

NKDXTBIRGROVAP-GDJRKFDVSA-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
Khaya anthotheca	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
Naphthopyran
Naphthalene
Tricarboxylic acid or derivatives
Delta_valerolactone
Delta valerolactone
Pyran
Oxane
Heteroaromatic compound
Tetrahydrofuran
Tertiary alcohol
Furan
Cyclic alcohol
Lactone
Hemiacetal
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	1.11	ALOGPS
logP	0.47	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	10.49	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	161.96 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	127.35 m³·mol⁻¹	ChemAxon
Polarizability	53.87 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	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

163035595

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (-)-3-O-Acetylanthothecanolide (NP0074196)

MOL for NP0074196 ((-)-3-O-Acetylanthothecanolide)

3D MOL for NP0074196 ((-)-3-O-Acetylanthothecanolide)

3D SDF for NP0074196 ((-)-3-O-Acetylanthothecanolide)

3D-SDF for NP0074196 ((-)-3-O-Acetylanthothecanolide)

PDB for NP0074196 ((-)-3-O-Acetylanthothecanolide)

3D PDB for NP0074196 ((-)-3-O-Acetylanthothecanolide)

SMILES for NP0074196 ((-)-3-O-Acetylanthothecanolide)

INCHI for NP0074196 ((-)-3-O-Acetylanthothecanolide)

Structure for NP0074196 ((-)-3-O-Acetylanthothecanolide)

3D Structure for NP0074196 ((-)-3-O-Acetylanthothecanolide)