NP-MRD: Showing NP-Card for 10'-Acetoxy-1'-epilycoserone (NP0063007)

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Record Information

Version

2.0

Created at

2022-04-28 07:31:26 UTC

Updated at

2022-04-28 07:31:26 UTC

NP-MRD ID

NP0063007

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10'-Acetoxy-1'-epilycoserone

Description

(2R)-1-[(1S,4aS,7S,7aR)-1-(4-hydroxy-5-methyl-2-oxo-2H-chromen-3-yl)-4,7-dimethyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-3-yl]-3-methyl-1-oxobutan-2-yl acetate belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. 10'-Acetoxy-1'-epilycoserone is found in Aphyllocladus denticulatus. Based on a literature review very few articles have been published on (2R)-1-[(1S,4aS,7S,7aR)-1-(4-hydroxy-5-methyl-2-oxo-2H-chromen-3-yl)-4,7-dimethyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-3-yl]-3-methyl-1-oxobutan-2-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282209312D          

 34 37  0  0  1  0            999 V2000
    4.7079    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5645    3.3000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5645    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
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 14 32  1  0  0  0  0
 32 33  1  6  0  0  0
  8 34  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282209312D          

 34 37  0  0  1  0            999 V2000
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    3.9934    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0063007

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@H](OC(C)=O)C(=O)C1=C(C)[C@H]2CC[C@H](C)[C@H]2[C@H](O1)C1=C(O)C2=C(C)C=CC=C2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O7/c1-12(2)24(32-16(6)28)23(30)25-15(5)17-11-10-14(4)19(17)26(34-25)21-22(29)20-13(3)8-7-9-18(20)33-27(21)31/h7-9,12,14,17,19,24,26,29H,10-11H2,1-6H3/t14-,17+,19+,24+,26-/m0/s1

> <INCHI_KEY>
AJDYNTCJXHLYJW-GNXCKYAISA-N

> <FORMULA>
C27H32O7

> <MOLECULAR_WEIGHT>
468.546

> <EXACT_MASS>
468.21480337

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
49.73528078909417

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-1-[(1S,4aS,7S,7aR)-1-(4-hydroxy-5-methyl-2-oxo-2H-chromen-3-yl)-4,7-dimethyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-3-yl]-3-methyl-1-oxobutan-2-yl acetate

> <ALOGPS_LOGP>
3.50

> <JCHEM_LOGP>
4.294122758000002

> <ALOGPS_LOGS>
-4.88

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.025347736844513

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.544489805527641

> <JCHEM_PKA_STRONGEST_BASIC>
-4.9684261849326825

> <JCHEM_POLAR_SURFACE_AREA>
99.13000000000001

> <JCHEM_REFRACTIVITY>
127.11959999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.18e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-1-[(1S,4aS,7S,7aR)-1-(4-hydroxy-5-methyl-2-oxochromen-3-yl)-4,7-dimethyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-3-yl]-3-methyl-1-oxobutan-2-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       8.788  13.090   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.454  13.860   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.121  13.090   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.121  11.550   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.454  10.780   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.788  11.550   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.122  10.780   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.454   9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.121   8.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.787   9.240   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.453   8.470   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       4.787  10.780   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.121   6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.787   6.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.787   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.121   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.454   4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.454   6.160   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.788   3.850   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.122   4.620   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.788   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.122   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.122   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.455   2.310   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.454   1.540   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.121  -0.770   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.322   4.144   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.417   5.390   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.322   6.636   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.846   8.101   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       8.788   8.470   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9   34                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    4                                                       
CONECT   13    9   14   18                                                  
CONECT   14   13   15   32                                                  
CONECT   15   14   16   30                                                  
CONECT   16   15   17   29                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   13                                                       
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   25                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   21   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   16                                                            
CONECT   30   15   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   14   33                                                  
CONECT   33   32                                                            
CONECT   34    8                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
(2R)-1-[(1S,4AS,7S,7ar)-1-(4-hydroxy-5-methyl-2-oxo-2H-chromen-3-yl)-4,7-dimethyl-1H,4ah,5H,6H,7H,7ah-cyclopenta[c]pyran-3-yl]-3-methyl-1-oxobutan-2-yl acetic acid	Generator

Chemical Formula

C₂₇H₃₂O₇

Average Mass

468.5460 Da

Monoisotopic Mass

468.21480 Da

IUPAC Name

(2R)-1-[(1S,4aS,7S,7aR)-1-(4-hydroxy-5-methyl-2-oxo-2H-chromen-3-yl)-4,7-dimethyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-3-yl]-3-methyl-1-oxobutan-2-yl acetate

Traditional Name

(2R)-1-[(1S,4aS,7S,7aR)-1-(4-hydroxy-5-methyl-2-oxochromen-3-yl)-4,7-dimethyl-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-3-yl]-3-methyl-1-oxobutan-2-yl acetate

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H](OC(C)=O)C(=O)C1=C(C)[C@H]2CC[C@H](C)[C@H]2[C@H](O1)C1=C(O)C2=C(C)C=CC=C2OC1=O

InChI Identifier

InChI=1S/C27H32O7/c1-12(2)24(32-16(6)28)23(30)25-15(5)17-11-10-14(4)19(17)26(34-25)21-22(29)20-13(3)8-7-9-18(20)33-27(21)31/h7-9,12,14,17,19,24,26,29H,10-11H2,1-6H3/t14-,17+,19+,24+,26-/m0/s1

InChI Key

AJDYNTCJXHLYJW-GNXCKYAISA-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
Aphyllocladus denticulatus	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Sesquiterpenoid
Hydroxycoumarin
4-hydroxycoumarin
Iridoid-skeleton
Coumarin
1-benzopyran
Benzopyran
Alpha-acyloxy ketone
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	3.5	ALOGPS
logP	4.29	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	5.54	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	99.13 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	127.12 m³·mol⁻¹	ChemAxon
Polarizability	49.74 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

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

162874772

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 10'-Acetoxy-1'-epilycoserone (NP0063007)

MOL for NP0063007 (10'-Acetoxy-1'-epilycoserone)

3D MOL for NP0063007 (10'-Acetoxy-1'-epilycoserone)

3D SDF for NP0063007 (10'-Acetoxy-1'-epilycoserone)

3D-SDF for NP0063007 (10'-Acetoxy-1'-epilycoserone)

PDB for NP0063007 (10'-Acetoxy-1'-epilycoserone)

3D PDB for NP0063007 (10'-Acetoxy-1'-epilycoserone)

SMILES for NP0063007 (10'-Acetoxy-1'-epilycoserone)

INCHI for NP0063007 (10'-Acetoxy-1'-epilycoserone)

Structure for NP0063007 (10'-Acetoxy-1'-epilycoserone)

3D Structure for NP0063007 (10'-Acetoxy-1'-epilycoserone)