NP-MRD: Showing NP-Card for Albocycline M-3 (NP0065057)

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Record Information

Version

2.0

Created at

2022-04-28 09:20:11 UTC

Updated at

2022-04-28 09:20:11 UTC

NP-MRD ID

NP0065057

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Albocycline M-3

Description

(5S,8S,9E,12S,13S,14R)-5,12-dihydroxy-8-methoxy-5,9,13,14-tetramethyl-1-oxacyclotetradeca-6,9-dien-2-one 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. Albocycline M-3 is found in Streptomyces bruneogriseus. Based on a literature review very few articles have been published on (5S,8S,9E,12S,13S,14R)-5,12-dihydroxy-8-methoxy-5,9,13,14-tetramethyl-1-oxacyclotetradeca-6,9-dien-2-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282211202D          

 23 23  0  0  1  0            999 V2000
    2.5006   -1.0312    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5006   -1.8562    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7862   -2.2687    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0717   -1.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.2062    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0717    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    1.8562    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5006    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9296    0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3989    2.5847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1735    2.5847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -3.0937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151   -2.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.6187    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  1  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  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
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  1 15  1  0  0  0  0
 10 16  1  6  0  0  0
 10 17  1  1  0  0  0
  7 18  1  1  0  0  0
 18 19  1  0  0  0  0
  6 20  1  0  0  0  0
  3 21  1  1  0  0  0
  2 22  1  1  0  0  0
  1 23  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0065057

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1\C=C\[C@@](C)(O)CCC(=O)O[C@H](C)[C@@H](C)[C@@H](O)C\C=C1/C

> <INCHI_IDENTIFIER>
InChI=1S/C18H30O5/c1-12-6-7-15(19)13(2)14(3)23-17(20)9-11-18(4,21)10-8-16(12)22-5/h6,8,10,13-16,19,21H,7,9,11H2,1-5H3/b10-8+,12-6+/t13-,14-,15+,16+,18-/m1/s1

> <INCHI_KEY>
HYUFUJWFFITERP-PEFZUDOASA-N

> <FORMULA>
C18H30O5

> <MOLECULAR_WEIGHT>
326.433

> <EXACT_MASS>
326.209324066

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
35.982945109250856

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,6E,8S,9E,12S,13S,14R)-5,12-dihydroxy-8-methoxy-5,9,13,14-tetramethyl-1-oxacyclotetradeca-6,9-dien-2-one

> <ALOGPS_LOGP>
1.84

> <JCHEM_LOGP>
1.724561797999998

> <ALOGPS_LOGS>
-2.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.04647942987856

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.429844557428915

> <JCHEM_PKA_STRONGEST_BASIC>
-2.878431005247565

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
90.9598

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.10e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S,6E,8S,9E,12S,13S,14R)-5,12-dihydroxy-8-methoxy-5,9,13,14-tetramethyl-1-oxacyclotetradeca-6,9-dien-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       4.668  -1.925   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.668  -3.465   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.334  -4.235   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.001  -3.465   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.001  -1.925   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.667  -1.155   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.667   0.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.001   1.155   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.001   2.695   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.334   3.465   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.668   2.695   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.668   1.155   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.002   0.385   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.335   1.155   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       6.002  -1.155   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.611   4.825   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.057   4.825   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -0.667   1.155   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.001   0.385   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.667  -1.925   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.334  -5.775   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.002  -4.235   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.334  -1.155   0.000  0.00  0.00           C+0
CONECT    1    2   15   23                                                  
CONECT    2    1    3   22                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   20                                                  
CONECT    7    6    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16   17                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    1                                                       
CONECT   16   10                                                            
CONECT   17   10                                                            
CONECT   18    7   19                                                       
CONECT   19   18                                                            
CONECT   20    6                                                            
CONECT   21    3                                                            
CONECT   22    2                                                            
CONECT   23    1                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₃₀O₅

Average Mass

326.4330 Da

Monoisotopic Mass

326.20932 Da

IUPAC Name

(5S,6E,8S,9E,12S,13S,14R)-5,12-dihydroxy-8-methoxy-5,9,13,14-tetramethyl-1-oxacyclotetradeca-6,9-dien-2-one

Traditional Name

(5S,6E,8S,9E,12S,13S,14R)-5,12-dihydroxy-8-methoxy-5,9,13,14-tetramethyl-1-oxacyclotetradeca-6,9-dien-2-one

CAS Registry Number

Not Available

SMILES

CO[C@H]1\C=C\[C@@](C)(O)CCC(=O)O[C@H](C)[C@@H](C)[C@@H](O)C\C=C1/C

InChI Identifier

InChI=1S/C18H30O5/c1-12-6-7-15(19)13(2)14(3)23-17(20)9-11-18(4,21)10-8-16(12)22-5/h6,8,10,13-16,19,21H,7,9,11H2,1-5H3/b10-8+,12-6+/t13-,14-,15+,16+,18-/m1/s1

InChI Key

HYUFUJWFFITERP-PEFZUDOASA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces bruneogriseus	Bacteria	KNApSAcK

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
Tertiary alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	1.84	ALOGPS
logP	1.72	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	14.43	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	90.96 m³·mol⁻¹	ChemAxon
Polarizability	35.98 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

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

163033273

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Albocycline M-3 (NP0065057)

MOL for NP0065057 (Albocycline M-3)

3D MOL for NP0065057 (Albocycline M-3)

3D SDF for NP0065057 (Albocycline M-3)

3D-SDF for NP0065057 (Albocycline M-3)

PDB for NP0065057 (Albocycline M-3)

3D PDB for NP0065057 (Albocycline M-3)

SMILES for NP0065057 (Albocycline M-3)

INCHI for NP0065057 (Albocycline M-3)

Structure for NP0065057 (Albocycline M-3)

3D Structure for NP0065057 (Albocycline M-3)