NP-MRD: Showing NP-Card for (2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r,6r)-3,6-bis(acetyloxy)icosanoate (NP0184834)

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Record Information

Version

1.0

Created at

2022-09-04 00:03:52 UTC

Updated at

2022-09-04 00:03:52 UTC

NP-MRD ID

NP0184834

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r,6r)-3,6-bis(acetyloxy)icosanoate

Description

Oncidinol belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. (2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r,6r)-3,6-bis(acetyloxy)icosanoate is found in Gomesa radicans. It was first documented in 2007 (PMID: 17530390). Based on a literature review a significant number of articles have been published on Oncidinol (PMID: 36057450) (PMID: 36057449) (PMID: 36057448) (PMID: 36057447).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042202032D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309042202032D          

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   26.4730    7.8592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1874    8.2717    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   27.1874    9.0967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9019    9.5092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9019    7.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6164    8.2717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.3309    7.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0453    8.2717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3309    7.0342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3296    9.0967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6151    9.5092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9006    9.0967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6151   10.3342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1862    7.0342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9006    6.6217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6151    7.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9006    5.7967    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
  8  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  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 23 22  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 18 31  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 15 35  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0184834

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCC[C@H](CC[C@H](CC(=O)O[C@@H](CO)COC(C)=O)OC(C)=O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H52O9/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-26(36-24(3)32)18-19-27(37-25(4)33)20-29(34)38-28(21-30)22-35-23(2)31/h26-28,30H,5-22H2,1-4H3/t26-,27-,28+/m1/s1

> <INCHI_KEY>
OJFMDENMLJWYEW-FCEKVYKBSA-N

> <FORMULA>
C29H52O9

> <MOLECULAR_WEIGHT>
544.726

> <EXACT_MASS>
544.361133254

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
90

> <JCHEM_AVERAGE_POLARIZABILITY>
64.08068452608623

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-1-(acetyloxy)-3-hydroxypropan-2-yl (3R,6R)-3,6-bis(acetyloxy)icosanoate

> <JCHEM_LOGP>
5.566161176666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.57778225057017

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9834780436006065

> <JCHEM_POLAR_SURFACE_AREA>
125.43000000000004

> <JCHEM_REFRACTIVITY>
143.15099999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
28

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-1-(acetyloxy)-3-hydroxypropan-2-yl (3R,6R)-3,6-bis(acetyloxy)icosanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      22.743  14.670   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.076  15.440   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      25.410  14.670   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      26.744  15.440   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      28.077  14.670   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      29.411  15.440   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      30.745  14.670   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      32.078  15.440   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      33.412  14.670   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      34.746  15.440   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      36.079  14.670   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      37.413  15.440   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      38.747  14.670   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      40.080  15.440   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      41.414  14.670   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      42.748  15.440   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      44.082  14.670   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      45.415  15.440   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      46.749  14.670   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      48.083  15.440   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      48.083  16.980   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      49.416  14.670   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      50.750  15.440   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      50.750  16.980   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      52.084  17.750   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      52.084  14.670   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      53.417  15.440   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      54.751  14.670   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      56.085  15.440   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      54.751  13.130   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      45.415  16.980   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      44.082  17.750   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      42.748  16.980   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      44.082  19.290   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      41.414  13.130   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      42.748  12.360   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      44.082  13.130   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      42.748  10.820   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   35                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   31                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   18   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   15   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₅₂O₉

Average Mass

544.7260 Da

Monoisotopic Mass

544.36113 Da

IUPAC Name

(2S)-1-(acetyloxy)-3-hydroxypropan-2-yl (3R,6R)-3,6-bis(acetyloxy)icosanoate

Traditional Name

(2S)-1-(acetyloxy)-3-hydroxypropan-2-yl (3R,6R)-3,6-bis(acetyloxy)icosanoate

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCC[C@H](CC[C@H](CC(=O)O[C@@H](CO)COC(C)=O)OC(C)=O)OC(C)=O

InChI Identifier

InChI=1S/C29H52O9/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-26(36-24(3)32)18-19-27(37-25(4)33)20-29(34)38-28(21-30)22-35-23(2)31/h26-28,30H,5-22H2,1-4H3/t26-,27-,28+/m1/s1

InChI Key

OJFMDENMLJWYEW-FCEKVYKBSA-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
Gomesa radicans	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
Fatty alcohol ester
1,2-acyl-sn-glycerol
Diacylglycerol
Diradylglycerol
Fatty acid ester
Glycerolipid
Fatty acyl
Carboxylic acid ester
Primary alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Organooxygen compound
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	5.57	ChemAxon
pKa (Strongest Acidic)	14.58	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	125.43 Å²	ChemAxon
Rotatable Bond Count	28	ChemAxon
Refractivity	143.15 m³·mol⁻¹	ChemAxon
Polarizability	64.08 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

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

101758743

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Micalizzi E, Vaudano AE, Ballerini A, Talami F, Giovannini G, Turchi G, Cioclu MC, Giunta L, Meletti S: Ictal Apnea: a prospective monocentric study in patients with epilepsy. Eur J Neurol. 2022 Sep 3. doi: 10.1111/ene.15547. [PubMed:36057450 ]
Jiang S, Guo P, Heo HY, Zhang Y, Wu J, Jin Y, Laterra J, Eberhart CG, Lim M, Blakeley JO: Radiomics analysis of amide proton transfer-weighted and structural MR images for treatment response assessment in malignant gliomas. NMR Biomed. 2022 Sep 3:e4824. doi: 10.1002/nbm.4824. [PubMed:36057449 ]
Agarwal K, Saikia P, Podder I: Metabolic syndrome and Dyslipidemia in xanthelasma palpebrarum and associated risk-factors- a case-control study. J Cosmet Dermatol. 2022 Sep 3. doi: 10.1111/jocd.15353. [PubMed:36057448 ]
Lebel V, Argiropoulos N, Robins S, Charbonneau L, Feeley N: Family-centred care and breastfeeding self-efficacy determined how ready mothers were for their infants to be discharged from a neonatal intensive care unit. Acta Paediatr. 2022 Sep 3. doi: 10.1111/apa.16538. [PubMed:36057447 ]
Reis MG, de Faria DA, dos Santos IA, Amaral Mdo C, Marsaioli AJ: Byrsonic acid--the clue to floral mimicry involving oil-producing flowers and oil-collecting bees. J Chem Ecol. 2007 Jul;33(7):1421-9. doi: 10.1007/s10886-007-9309-y. [PubMed:17530390 ]
LOTUS database [Link]

Showing NP-Card for (2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r,6r)-3,6-bis(acetyloxy)icosanoate (NP0184834)

MOL for NP0184834 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r,6r)-3,6-bis(acetyloxy)icosanoate)

3D MOL for NP0184834 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r,6r)-3,6-bis(acetyloxy)icosanoate)

3D SDF for NP0184834 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r,6r)-3,6-bis(acetyloxy)icosanoate)

3D-SDF for NP0184834 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r,6r)-3,6-bis(acetyloxy)icosanoate)

PDB for NP0184834 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r,6r)-3,6-bis(acetyloxy)icosanoate)

3D PDB for NP0184834 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r,6r)-3,6-bis(acetyloxy)icosanoate)

SMILES for NP0184834 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r,6r)-3,6-bis(acetyloxy)icosanoate)

INCHI for NP0184834 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r,6r)-3,6-bis(acetyloxy)icosanoate)

Structure for NP0184834 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r,6r)-3,6-bis(acetyloxy)icosanoate)

3D Structure for NP0184834 ((2s)-1-(acetyloxy)-3-hydroxypropan-2-yl (3r,6r)-3,6-bis(acetyloxy)icosanoate)