MiMeDB: Showing metabocard for (+)-(2S,3S,4aS)-altenuene-3-acetoxy ester (MMDBc0004823)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-14 22:40:13 UTC

Update Date

2022-08-31 06:23:02 UTC

Metabolite ID

MMDBc0004823

Metabolite Identification

Common Name

(+)-(2S,3S,4aS)-altenuene-3-acetoxy ester

Description

(+)-(2S,3S,4aS)-altenuene-3-acetoxy ester belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position (+)-(2S,3S,4aS)-altenuene-3-acetoxy ester is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152100402D          

 26 28  0  0  1  0            999 V2000
   -1.4586   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6336   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -0.1105    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3164   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4914   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -1.5395    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2211   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914   -0.1105    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914   -1.5395    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  0  0  0  0
  9  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  4  1  0  0  0  0
 11  6  2  0  0  0  0
 11 10  1  0  0  0  0
 12  6  1  0  0  0  0
 13  5  2  0  0  0  0
 14  7  1  0  0  0  0
 14 12  1  0  0  0  0
 15 10  2  0  0  0  0
 15 13  1  0  0  0  0
 16 15  1  0  0  0  0
 17  2  1  6  0  0  0
 17  7  1  0  0  0  0
 17 11  1  0  0  0  0
 18  8  2  0  0  0  0
 12 19  1  1  0  0  0
 20 13  1  0  0  0  0
 21 16  2  0  0  0  0
 22  3  1  0  0  0  0
 22  9  1  0  0  0  0
 23  8  1  0  0  0  0
 14 23  1  6  0  0  0
 24 16  1  0  0  0  0
 24 17  1  0  0  0  0
 12 25  1  6  0  0  0
 14 26  1  1  0  0  0
M  END


  Mrv1652305152100402D          

 26 28  0  0  1  0            999 V2000
   -1.4586   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6336   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3164   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -0.1105    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3164   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4914   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -1.5395    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2211   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7289    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2211   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914   -0.1105    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1914   -1.5395    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  0  0  0  0
  9  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  4  1  0  0  0  0
 11  6  2  0  0  0  0
 11 10  1  0  0  0  0
 12  6  1  0  0  0  0
 13  5  2  0  0  0  0
 14  7  1  0  0  0  0
 14 12  1  0  0  0  0
 15 10  2  0  0  0  0
 15 13  1  0  0  0  0
 16 15  1  0  0  0  0
 17  2  1  6  0  0  0
 17  7  1  0  0  0  0
 17 11  1  0  0  0  0
 18  8  2  0  0  0  0
 12 19  1  1  0  0  0
 20 13  1  0  0  0  0
 21 16  2  0  0  0  0
 22  3  1  0  0  0  0
 22  9  1  0  0  0  0
 23  8  1  0  0  0  0
 14 23  1  6  0  0  0
 24 16  1  0  0  0  0
 24 17  1  0  0  0  0
 12 25  1  6  0  0  0
 14 26  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0004823

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@]1(O)C=C2C3=C(C(O)=CC(OC)=C3)C(=O)O[C@@]2(C)C[C@]1([H])OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H18O7/c1-8(18)23-14-7-17(2)11(6-12(14)19)10-4-9(22-3)5-13(20)15(10)16(21)24-17/h4-6,12,14,19-20H,7H2,1-3H3/t12-,14-,17-/m0/s1

> <INCHI_KEY>
NRCQFDXVYVENDF-JDFRZJQESA-N

> <FORMULA>
C17H18O7

> <MOLECULAR_WEIGHT>
334.324

> <EXACT_MASS>
334.10525292

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
33.219304699906786

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,4aS)-2,7-dihydroxy-9-methoxy-4a-methyl-6-oxo-2H,3H,4H,4aH,6H-benzo[c]chromen-3-yl acetate

> <ALOGPS_LOGP>
1.62

> <JCHEM_LOGP>
1.4445886880000003

> <ALOGPS_LOGS>
-2.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.75369101989341

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.499079069289857

> <JCHEM_PKA_STRONGEST_BASIC>
-3.344121881494165

> <JCHEM_POLAR_SURFACE_AREA>
102.29

> <JCHEM_REFRACTIVITY>
83.4463

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.06e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4aS)-2,7-dihydroxy-9-methoxy-4a-methyl-6-oxo-2H,3H,4H-benzo[c]chromen-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0      -2.723  -2.874   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -4.207   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.057   2.461   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.517  -0.206   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.827  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.437  -0.206   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.897  -2.874   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.183  -2.874   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.057  -0.206   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.747  -1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.207  -1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.897  -0.206   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.057  -2.874   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.127  -1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.517  -2.874   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.747  -4.207   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.437  -2.874   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.413  -4.207   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.127   1.127   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.827  -4.207   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.517  -5.541   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.827   1.127   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -0.413  -1.540   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.207  -4.207   0.000  0.00  0.00           O+0
HETATM   25  H   UNK     0       0.357  -0.206   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.357  -2.874   0.000  0.00  0.00           H+0
CONECT    1    8                                                            
CONECT    2   17                                                            
CONECT    3   22                                                            
CONECT    4    9   10                                                       
CONECT    5    9   13                                                       
CONECT    6   11   12                                                       
CONECT    7   14   17                                                       
CONECT    8    1   18   23                                                  
CONECT    9    4    5   22                                                  
CONECT   10    4   11   15                                                  
CONECT   11    6   10   17                                                  
CONECT   12    6   14   19   25                                             
CONECT   13    5   15   20                                                  
CONECT   14    7   12   23   26                                             
CONECT   15   10   13   16                                                  
CONECT   16   15   21   24                                                  
CONECT   17    2    7   11   24                                             
CONECT   18    8                                                            
CONECT   19   12                                                            
CONECT   20   13                                                            
CONECT   21   16                                                            
CONECT   22    3    9                                                       
CONECT   23    8   14                                                       
CONECT   24   16   17                                                       
CONECT   25   12                                                            
CONECT   26   14                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

Synonyms

Not Available

Molecular Formula

C₁₇H₁₈O₇

Average Mass

334.324

Monoisotopic Mass

334.10525292

IUPAC Name

(2S,3S,4aS)-2,7-dihydroxy-9-methoxy-4a-methyl-6-oxo-2H,3H,4H,4aH,6H-benzo[c]chromen-3-yl acetate

Traditional Name

(2S,3S,4aS)-2,7-dihydroxy-9-methoxy-4a-methyl-6-oxo-2H,3H,4H-benzo[c]chromen-3-yl acetate

CAS Registry Number

Not Available

SMILES

[H][C@]1(O)C=C2C3=C(C(O)=CC(OC)=C3)C(=O)O[C@@]2(C)C[C@]1([H])OC(C)=O

InChI Identifier

InChI=1S/C17H18O7/c1-8(18)23-14-7-17(2)11(6-12(14)19)10-4-9(22-3)5-13(20)15(10)16(21)24-17/h4-6,12,14,19-20H,7H2,1-3H3/t12-,14-,17-/m0/s1

InChI Key

NRCQFDXVYVENDF-JDFRZJQESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

2-benzopyrans

Direct Parent

2-benzopyrans

Alternative Parents

Substituents

2-benzopyran
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Dicarboxylic acid or derivatives
Vinylogous acid
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Ether
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

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.41 g/L	ALOGPS
logP	1.62	ALOGPS
logP	1.44	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	9.5	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	102.29 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	83.45 m³·mol⁻¹	ChemAxon
Polarizability	33.22 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human supragingival plaque	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78442287

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139584230

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for (+)-(2S,3S,4aS)-altenuene-3-acetoxy ester (MMDBc0004823)

MOL for #<Metabolite:0x0000564af3a2efd8>

3D MOL for #<Metabolite:0x0000564af3a2efd8>

3D SDF for #<Metabolite:0x0000564af3a2efd8>

3D-SDF for #<Metabolite:0x0000564af3a2efd8>

PDB for #<Metabolite:0x0000564af3a2efd8>

3D PDB for #<Metabolite:0x0000564af3a2efd8>

SMILES for #<Metabolite:0x0000564af3a2efd8>

INCHI for #<Metabolite:0x0000564af3a2efd8>

Structure for #<Metabolite:0x0000564af3a2efd8>

3D Structure for #<Metabolite:0x0000564af3a2efd8>