NP-MRD: Showing NP-Card for (3z,5e,9e,11e,17e,19e)-8,14,16-trihydroxy-24-methyl-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one (NP0285309)

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Record Information

Version

2.0

Created at

2022-09-09 13:25:35 UTC

Updated at

2022-09-09 13:25:35 UTC

NP-MRD ID

NP0285309

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3z,5e,9e,11e,17e,19e)-8,14,16-trihydroxy-24-methyl-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one

Description

Macrolactin I 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. Based on a literature review very few articles have been published on Macrolactin I.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309092215252D          

 29 29  0  0  0  0            999 V2000
    3.6922    3.7879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.9717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2193    2.4598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0995    1.6435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7465    1.1316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6267    0.3154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2737   -0.1965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1539   -1.0128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8009   -1.5247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6811   -2.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3281   -2.8528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9143   -2.6453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7944   -3.4615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4414   -3.9734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0276   -3.7659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3807   -3.2540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5005   -2.4377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8535   -1.9259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9733   -1.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3263   -0.5977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5595   -0.9021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4461    0.2185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7991    0.7304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9189    1.5467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2719    2.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3918    2.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1586    3.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2784    3.9954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8056    2.6673    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  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  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
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  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  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
  2 29  1  0  0  0  0
M  END


  Mrv1652309092215252D          

 29 29  0  0  0  0            999 V2000
    3.6922    3.7879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.9717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2193    2.4598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0995    1.6435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7465    1.1316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6267    0.3154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2737   -0.1965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1539   -1.0128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8009   -1.5247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6811   -2.3409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3281   -2.8528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9143   -2.6453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7944   -3.4615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4414   -3.9734    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0276   -3.7659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3807   -3.2540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5005   -2.4377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8535   -1.9259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9733   -1.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3263   -0.5977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5595   -0.9021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4461    0.2185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7991    0.7304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9189    1.5467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2719    2.0586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3918    2.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1586    3.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2784    3.9954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8056    2.6673    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  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  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
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  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  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
  2 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0285309

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC\C=C\C=C\C(O)CC(O)C\C=C\C=C\C(O)C\C=C\C=C/C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C24H34O5/c1-20-13-7-3-2-4-8-16-22(26)19-23(27)17-11-5-9-14-21(25)15-10-6-12-18-24(28)29-20/h2,4-6,8-12,14,16,18,20-23,25-27H,3,7,13,15,17,19H2,1H3/b4-2+,10-6+,11-5+,14-9+,16-8+,18-12-

> <INCHI_KEY>
XXDIJWSZFWZBRM-BPFVYSANSA-N

> <FORMULA>
C24H34O5

> <MOLECULAR_WEIGHT>
402.531

> <EXACT_MASS>
402.240624195

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
46.22677718991807

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3Z,5E,9E,11E,17E,19E)-8,14,16-trihydroxy-24-methyl-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one

> <JCHEM_LOGP>
3.5133448379999987

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.386664363309027

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.629219062823093

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5775923958996727

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
123.47909999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3Z,5E,9E,11E,17E,19E)-8,14,16-trihydroxy-24-methyl-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       6.892   7.071   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   5.547   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.876   4.592   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.652   3.068   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.860   2.112   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.637   0.589   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.844  -0.367   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.621  -1.890   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.828  -2.846   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.605  -4.370   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      11.812  -5.325   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.173  -4.938   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.950  -6.462   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      10.157  -7.417   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.518  -7.030   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.311  -6.074   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.534  -4.550   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.326  -3.595   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.550  -2.071   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.342  -1.116   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.911  -1.684   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.566   0.408   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.358   1.363   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.582   2.887   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.374   3.843   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.598   5.366   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.029   5.934   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.253   7.458   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       5.237   4.979   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   29                                                  
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   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27    2                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₄O₅

Average Mass

402.5310 Da

Monoisotopic Mass

402.24062 Da

IUPAC Name

(3Z,5E,9E,11E,17E,19E)-8,14,16-trihydroxy-24-methyl-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one

Traditional Name

(3Z,5E,9E,11E,17E,19E)-8,14,16-trihydroxy-24-methyl-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one

CAS Registry Number

Not Available

SMILES

CC1CCC\C=C\C=C\C(O)CC(O)C\C=C\C=C\C(O)C\C=C\C=C/C(=O)O1

InChI Identifier

InChI=1S/C24H34O5/c1-20-13-7-3-2-4-8-16-22(26)19-23(27)17-11-5-9-14-21(25)15-10-6-12-18-24(28)29-20/h2,4-6,8-12,14,16,18,20-23,25-27H,3,7,13,15,17,19H2,1H3/b4-2+,10-6+,11-5+,14-9+,16-8+,18-12-

InChI Key

XXDIJWSZFWZBRM-BPFVYSANSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

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
Enoate ester
Alpha,beta-unsaturated carboxylic ester
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	3.51	ChemAxon
pKa (Strongest Acidic)	14.63	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	123.48 m³·mol⁻¹	ChemAxon
Polarizability	46.23 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00015935

Chemspider ID

4906952

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6390938

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3z,5e,9e,11e,17e,19e)-8,14,16-trihydroxy-24-methyl-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one (NP0285309)

MOL for NP0285309 ((3z,5e,9e,11e,17e,19e)-8,14,16-trihydroxy-24-methyl-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one)

3D MOL for NP0285309 ((3z,5e,9e,11e,17e,19e)-8,14,16-trihydroxy-24-methyl-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one)

3D SDF for NP0285309 ((3z,5e,9e,11e,17e,19e)-8,14,16-trihydroxy-24-methyl-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one)

3D-SDF for NP0285309 ((3z,5e,9e,11e,17e,19e)-8,14,16-trihydroxy-24-methyl-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one)

PDB for NP0285309 ((3z,5e,9e,11e,17e,19e)-8,14,16-trihydroxy-24-methyl-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one)

3D PDB for NP0285309 ((3z,5e,9e,11e,17e,19e)-8,14,16-trihydroxy-24-methyl-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one)

SMILES for NP0285309 ((3z,5e,9e,11e,17e,19e)-8,14,16-trihydroxy-24-methyl-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one)

INCHI for NP0285309 ((3z,5e,9e,11e,17e,19e)-8,14,16-trihydroxy-24-methyl-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one)

Structure for NP0285309 ((3z,5e,9e,11e,17e,19e)-8,14,16-trihydroxy-24-methyl-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one)

3D Structure for NP0285309 ((3z,5e,9e,11e,17e,19e)-8,14,16-trihydroxy-24-methyl-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one)