NP-MRD: Showing NP-Card for (17e,19e,21e,23e,25e)-4,6,10,12,14,16-hexahydroxy-3,15,27,28-tetramethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one (NP0324254)

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Record Information

Version

2.0

Created at

2022-09-12 04:13:03 UTC

Updated at

2022-09-12 04:13:04 UTC

NP-MRD ID

NP0324254

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(17e,19e,21e,23e,25e)-4,6,10,12,14,16-hexahydroxy-3,15,27,28-tetramethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one

Description

AB023a, also known as xisomab 3G3, belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. (17e,19e,21e,23e,25e)-4,6,10,12,14,16-hexahydroxy-3,15,27,28-tetramethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one was first documented in 1993 (PMID: 8468239). Based on a literature review very few articles have been published on AB023a (PMID: 8468240).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122206132D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309122206132D          

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    4.8062   -3.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1051   -2.6473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3779   -3.0371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1310   -1.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4299   -1.3879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7028   -1.7777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4559   -0.5634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7547   -0.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7807    0.6960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0796    1.1308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3525    0.7410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1055    1.9554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4044    2.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6773    2.0004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4304    3.2148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7292    3.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1575    3.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1834    4.4292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8586    3.1698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5857    3.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6117    4.3842    0.0000 C   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 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  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
  2 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0324254

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(=O)C(C)C(O)CC(O)CCCC(O)CC(O)CC(O)C(C)C(O)\C=C\C=C\C=C\C=C\C=C\C1C

> <INCHI_IDENTIFIER>
InChI=1S/C31H50O8/c1-21-14-11-9-7-5-6-8-10-12-17-28(35)22(2)29(36)20-27(34)18-25(32)15-13-16-26(33)19-30(37)23(3)31(38)39-24(21)4/h5-12,14,17,21-30,32-37H,13,15-16,18-20H2,1-4H3/b6-5+,9-7+,10-8+,14-11+,17-12+

> <INCHI_KEY>
RXFPIRNYTBRDOG-LHKSPRDVSA-N

> <FORMULA>
C31H50O8

> <MOLECULAR_WEIGHT>
550.733

> <EXACT_MASS>
550.35056857

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
89

> <JCHEM_AVERAGE_POLARIZABILITY>
63.65649259449081

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(17E,19E,21E,23E,25E)-4,6,10,12,14,16-hexahydroxy-3,15,27,28-tetramethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one

> <JCHEM_LOGP>
2.0692077400000004

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.466548375449417

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.02874323541803

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7209504321796585

> <JCHEM_POLAR_SURFACE_AREA>
147.68

> <JCHEM_REFRACTIVITY>
159.13000000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(17E,19E,21E,23E,25E)-4,6,10,12,14,16-hexahydroxy-3,15,27,28-tetramethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       9.359   6.561   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   5.833   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.954   4.294   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.262   3.482   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.214   1.943   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.523   1.131   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.474  -0.408   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.783  -1.220   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.735  -2.759   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.043  -3.570   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.995  -5.110   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.638  -5.837   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.589  -7.376   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      12.898  -8.188   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      10.232  -8.104   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.183  -9.643   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.923  -7.292   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.566  -8.020   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.972  -5.753   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.663  -4.942   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.306  -5.669   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.711  -3.402   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.402  -2.591   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.045  -3.318   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.451  -1.052   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.142  -0.240   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.191   1.299   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.882   2.111   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.525   1.383   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.930   3.650   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.622   4.462   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.264   3.734   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       2.670   6.001   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.361   6.813   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.027   6.729   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.076   8.268   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       5.336   5.917   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       6.693   6.645   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.742   8.184   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   38                                                  
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   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37    2   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   78    0
END

View in JSmol

Synonyms

Value	Source
Xisomab 3g3	MeSH

Chemical Formula

C₃₁H₅₀O₈

Average Mass

550.7330 Da

Monoisotopic Mass

550.35057 Da

IUPAC Name

(17E,19E,21E,23E,25E)-4,6,10,12,14,16-hexahydroxy-3,15,27,28-tetramethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one

Traditional Name

(17E,19E,21E,23E,25E)-4,6,10,12,14,16-hexahydroxy-3,15,27,28-tetramethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one

CAS Registry Number

Not Available

SMILES

CC1OC(=O)C(C)C(O)CC(O)CCCC(O)CC(O)CC(O)C(C)C(O)\C=C\C=C\C=C\C=C\C=C\C1C

InChI Identifier

InChI=1S/C31H50O8/c1-21-14-11-9-7-5-6-8-10-12-17-28(35)22(2)29(36)20-27(34)18-25(32)15-13-16-26(33)19-30(37)23(3)31(38)39-24(21)4/h5-12,14,17,21-30,32-37H,13,15-16,18-20H2,1-4H3/b6-5+,9-7+,10-8+,14-11+,17-12+

InChI Key

RXFPIRNYTBRDOG-LHKSPRDVSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Polyol
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Carbonyl group
Alcohol
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	2.07	ChemAxon
pKa (Strongest Acidic)	14.03	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	147.68 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	159.13 m³·mol⁻¹	ChemAxon
Polarizability	63.66 Å³	ChemAxon
Number of Rings	1	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

4976367

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6474366

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Cidaria D, Borgonovi G, Pirali G: AB023, novel polyene antibiotics. I. Taxonomy of the producing organism, fermentation and antifungal activity. J Antibiot (Tokyo). 1993 Feb;46(2):251-4. doi: 10.7164/antibiotics.46.251. [PubMed:8468239 ]
Bortolo R, Spera S, Gugliemetti G, Cassani G: AB023, novel polyene antibiotics. II. Isolation and structure determination. J Antibiot (Tokyo). 1993 Feb;46(2):255-64. doi: 10.7164/antibiotics.46.255. [PubMed:8468240 ]
LOTUS database [Link]

Showing NP-Card for (17e,19e,21e,23e,25e)-4,6,10,12,14,16-hexahydroxy-3,15,27,28-tetramethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one (NP0324254)

MOL for NP0324254 ((17e,19e,21e,23e,25e)-4,6,10,12,14,16-hexahydroxy-3,15,27,28-tetramethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one)

3D MOL for NP0324254 ((17e,19e,21e,23e,25e)-4,6,10,12,14,16-hexahydroxy-3,15,27,28-tetramethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one)

3D SDF for NP0324254 ((17e,19e,21e,23e,25e)-4,6,10,12,14,16-hexahydroxy-3,15,27,28-tetramethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one)

3D-SDF for NP0324254 ((17e,19e,21e,23e,25e)-4,6,10,12,14,16-hexahydroxy-3,15,27,28-tetramethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one)

PDB for NP0324254 ((17e,19e,21e,23e,25e)-4,6,10,12,14,16-hexahydroxy-3,15,27,28-tetramethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one)

3D PDB for NP0324254 ((17e,19e,21e,23e,25e)-4,6,10,12,14,16-hexahydroxy-3,15,27,28-tetramethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one)

SMILES for NP0324254 ((17e,19e,21e,23e,25e)-4,6,10,12,14,16-hexahydroxy-3,15,27,28-tetramethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one)

INCHI for NP0324254 ((17e,19e,21e,23e,25e)-4,6,10,12,14,16-hexahydroxy-3,15,27,28-tetramethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one)

Structure for NP0324254 ((17e,19e,21e,23e,25e)-4,6,10,12,14,16-hexahydroxy-3,15,27,28-tetramethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one)

3D Structure for NP0324254 ((17e,19e,21e,23e,25e)-4,6,10,12,14,16-hexahydroxy-3,15,27,28-tetramethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one)