NP-MRD: Showing NP-Card for 2-(2-{[(13r,14s,16s)-17-amino-5,13,14,16-tetrahydroxy-3,7-dimethylheptadecan-4-yl]oxy}-2-oxoethyl)butanedioic acid (NP0254863)

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Record Information

Version

2.0

Created at

2022-09-07 19:09:06 UTC

Updated at

2022-09-07 19:09:07 UTC

NP-MRD ID

NP0254863

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(2-{[(13r,14s,16s)-17-amino-5,13,14,16-tetrahydroxy-3,7-dimethylheptadecan-4-yl]oxy}-2-oxoethyl)butanedioic acid

Description

AAL-Toxin belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. 2-(2-{[(13r,14s,16s)-17-amino-5,13,14,16-tetrahydroxy-3,7-dimethylheptadecan-4-yl]oxy}-2-oxoethyl)butanedioic acid is found in Alternaria alternata. 2-(2-{[(13r,14s,16s)-17-amino-5,13,14,16-tetrahydroxy-3,7-dimethylheptadecan-4-yl]oxy}-2-oxoethyl)butanedioic acid was first documented in 2020 (PMID: 33379271). Based on a literature review a small amount of articles have been published on AAL-Toxin (PMID: 35205922) (PMID: 33922952) (PMID: 31161714).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072221092D          

 36 35  0  0  1  0            999 V2000
   13.9954    8.9052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9954    8.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.4243    8.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7099    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9954    6.4302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2809    6.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2809    7.6677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309072221092D          

 36 35  0  0  1  0            999 V2000
   13.9954    8.9052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   21.8546    7.6677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5690    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2835    6.8427    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.2835    7.6677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9980    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7124    6.8427    0.0000 N   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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 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
 10 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0254863

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C(OC(=O)CC(CC(O)=O)C(O)=O)C(O)CC(C)CCCCC[C@@H](O)[C@@H](O)C[C@H](O)CN

> <INCHI_IDENTIFIER>
InChI=1S/C25H47NO10/c1-4-16(3)24(36-23(33)12-17(25(34)35)11-22(31)32)21(30)10-15(2)8-6-5-7-9-19(28)20(29)13-18(27)14-26/h15-21,24,27-30H,4-14,26H2,1-3H3,(H,31,32)(H,34,35)/t15?,16?,17?,18-,19+,20-,21?,24?/m0/s1

> <INCHI_KEY>
DOFQASYPBACFKP-UMSUPTIDSA-N

> <FORMULA>
C25H47NO10

> <MOLECULAR_WEIGHT>
521.648

> <EXACT_MASS>
521.319996717

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
56.86067834712791

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(2-{[(13R,14S,16S)-17-amino-5,13,14,16-tetrahydroxy-3,7-dimethylheptadecan-4-yl]oxy}-2-oxoethyl)butanedioic acid

> <JCHEM_LOGP>
-1.4243775299910577

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
5.179262584309889

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6765302649360754

> <JCHEM_PKA_STRONGEST_BASIC>
9.288231469946558

> <JCHEM_POLAR_SURFACE_AREA>
207.83999999999997

> <JCHEM_REFRACTIVITY>
130.89119999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-(2-{[(13R,14S,16S)-17-amino-5,13,14,16-tetrahydroxy-3,7-dimethylheptadecan-4-yl]oxy}-2-oxoethyl)butanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      26.125  16.623   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      26.125  15.083   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      27.458  14.313   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      28.792  15.083   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      27.458  12.773   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      26.125  12.003   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      24.791  12.773   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      24.791  14.313   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      23.457  12.003   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.124  12.773   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      20.790  12.003   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      19.456  12.773   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      18.123  12.003   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      19.456  14.313   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      22.124  14.313   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      20.790  15.083   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      23.457  15.083   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      28.792  12.003   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      28.792  10.463   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      30.126  12.773   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      31.459  12.003   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      31.459  10.463   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      32.793  12.773   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      34.127  12.003   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      35.460  12.773   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      36.794  12.003   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      38.128  12.773   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      39.462  12.003   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      39.462  10.463   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      40.795  12.773   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      40.795  14.313   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      42.129  12.003   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      43.463  12.773   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      43.463  14.313   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      44.796  12.003   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0      46.130  12.773   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   18                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   10   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    5   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₄₇NO₁₀

Average Mass

521.6480 Da

Monoisotopic Mass

521.32000 Da

IUPAC Name

2-(2-{[(13R,14S,16S)-17-amino-5,13,14,16-tetrahydroxy-3,7-dimethylheptadecan-4-yl]oxy}-2-oxoethyl)butanedioic acid

Traditional Name

2-(2-{[(13R,14S,16S)-17-amino-5,13,14,16-tetrahydroxy-3,7-dimethylheptadecan-4-yl]oxy}-2-oxoethyl)butanedioic acid

CAS Registry Number

Not Available

SMILES

CCC(C)C(OC(=O)CC(CC(O)=O)C(O)=O)C(O)CC(C)CCCCC[C@@H](O)[C@@H](O)C[C@H](O)CN

InChI Identifier

InChI=1S/C25H47NO10/c1-4-16(3)24(36-23(33)12-17(25(34)35)11-22(31)32)21(30)10-15(2)8-6-5-7-9-19(28)20(29)13-18(27)14-26/h15-21,24,27-30H,4-14,26H2,1-3H3,(H,31,32)(H,34,35)/t15?,16?,17?,18-,19+,20-,21?,24?/m0/s1

InChI Key

DOFQASYPBACFKP-UMSUPTIDSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Alternaria alternata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
1,2-aminoalcohol
Amino acid or derivatives
Carboxylic acid ester
Amino acid
Secondary alcohol
Carboxylic acid
Polyol
Organic nitrogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Amine
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	-1.4	ChemAxon
pKa (Strongest Acidic)	3.68	ChemAxon
pKa (Strongest Basic)	9.29	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	207.84 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	130.89 m³·mol⁻¹	ChemAxon
Polarizability	56.86 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	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

78445645

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139583962

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang H, Guo Y, Luo Z, Gao L, Li R, Zhang Y, Kalaji HM, Qiang S, Chen S: Recent Advances in Alternaria Phytotoxins: A Review of Their Occurrence, Structure, Bioactivity, and Biosynthesis. J Fungi (Basel). 2022 Feb 9;8(2):168. doi: 10.3390/jof8020168. [PubMed:35205922 ]
Shi J, Zhang M, Gao L, Yang Q, Kalaji HM, Qiang S, Strasser RJ, Chen S: Tenuazonic Acid-Triggered Cell Death Is the Essential Prerequisite for Alternaria alternata (Fr.) Keissler to Infect Successfully Host Ageratina adenophora. Cells. 2021 Apr 25;10(5):1010. doi: 10.3390/cells10051010. [PubMed:33922952 ]
Tsuzuki R, Cabrera Pintado RM, Biondi Thorndike JA, Gutierrez Reynoso DL, Amasifuen Guerra CA, Guerrero Abad JC, Aragon Caballero LM, Huarhua Zaquinaula MH, Ureta Sierra C, Alberca Cruz OI, Elespuru Suna MG, Blas Sevillano RH, Torres Arias IC, Flores Ticona J, de Baldarrago FC, Perez ER, Hozum T, Saito H, Kotera S, Akagi Y, Kodama M, Komatsu K, Arie T: Mutations Found in the Asc1 Gene That Confer Susceptibility to the AAL-Toxin in Ancestral Tomatoes from Peru and Mexico. Plants (Basel). 2020 Dec 28;10(1):47. doi: 10.3390/plants10010047. [PubMed:33379271 ]
Shao Z, Zhao Y, Liu L, Chen S, Li C, Meng F, Liu H, Hu S, Wang J, Wang Q: Overexpression of FBR41 enhances resistance to sphinganine analog mycotoxin-induced cell death and Alternaria stem canker in tomato. Plant Biotechnol J. 2020 Jan;18(1):141-154. doi: 10.1111/pbi.13182. Epub 2019 Jun 20. [PubMed:31161714 ]
LOTUS database [Link]

Showing NP-Card for 2-(2-{[(13r,14s,16s)-17-amino-5,13,14,16-tetrahydroxy-3,7-dimethylheptadecan-4-yl]oxy}-2-oxoethyl)butanedioic acid (NP0254863)

MOL for NP0254863 (2-(2-{[(13r,14s,16s)-17-amino-5,13,14,16-tetrahydroxy-3,7-dimethylheptadecan-4-yl]oxy}-2-oxoethyl)butanedioic acid)

3D MOL for NP0254863 (2-(2-{[(13r,14s,16s)-17-amino-5,13,14,16-tetrahydroxy-3,7-dimethylheptadecan-4-yl]oxy}-2-oxoethyl)butanedioic acid)

3D SDF for NP0254863 (2-(2-{[(13r,14s,16s)-17-amino-5,13,14,16-tetrahydroxy-3,7-dimethylheptadecan-4-yl]oxy}-2-oxoethyl)butanedioic acid)

3D-SDF for NP0254863 (2-(2-{[(13r,14s,16s)-17-amino-5,13,14,16-tetrahydroxy-3,7-dimethylheptadecan-4-yl]oxy}-2-oxoethyl)butanedioic acid)

PDB for NP0254863 (2-(2-{[(13r,14s,16s)-17-amino-5,13,14,16-tetrahydroxy-3,7-dimethylheptadecan-4-yl]oxy}-2-oxoethyl)butanedioic acid)

3D PDB for NP0254863 (2-(2-{[(13r,14s,16s)-17-amino-5,13,14,16-tetrahydroxy-3,7-dimethylheptadecan-4-yl]oxy}-2-oxoethyl)butanedioic acid)

SMILES for NP0254863 (2-(2-{[(13r,14s,16s)-17-amino-5,13,14,16-tetrahydroxy-3,7-dimethylheptadecan-4-yl]oxy}-2-oxoethyl)butanedioic acid)

INCHI for NP0254863 (2-(2-{[(13r,14s,16s)-17-amino-5,13,14,16-tetrahydroxy-3,7-dimethylheptadecan-4-yl]oxy}-2-oxoethyl)butanedioic acid)

Structure for NP0254863 (2-(2-{[(13r,14s,16s)-17-amino-5,13,14,16-tetrahydroxy-3,7-dimethylheptadecan-4-yl]oxy}-2-oxoethyl)butanedioic acid)

3D Structure for NP0254863 (2-(2-{[(13r,14s,16s)-17-amino-5,13,14,16-tetrahydroxy-3,7-dimethylheptadecan-4-yl]oxy}-2-oxoethyl)butanedioic acid)