NP-MRD: Showing NP-Card for 12-ethyl-8-hydroxy-5-(2-hydroxybutyl)-2,9-dimethyl-4,11,17-trioxabicyclo[12.2.1]heptadecane-3,10-dione (NP0249507)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 12:04:47 UTC

Updated at

2022-09-07 12:04:47 UTC

NP-MRD ID

NP0249507

Secondary Accession Numbers

None

Natural Product Identification

Common Name

12-ethyl-8-hydroxy-5-(2-hydroxybutyl)-2,9-dimethyl-4,11,17-trioxabicyclo[12.2.1]heptadecane-3,10-dione

Description

12-Ethyl-8-hydroxy-5-(2-hydroxybutyl)-2,9-dimethyl-4,11,17-trioxabicyclo[12.2.1]Heptadecane-3,10-dione 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. 12-ethyl-8-hydroxy-5-(2-hydroxybutyl)-2,9-dimethyl-4,11,17-trioxabicyclo[12.2.1]heptadecane-3,10-dione is found in Streptomyces griseus. 12-Ethyl-8-hydroxy-5-(2-hydroxybutyl)-2,9-dimethyl-4,11,17-trioxabicyclo[12.2.1]Heptadecane-3,10-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004191517302D          

 29 30  0  0  0  0            999 V2000
    7.7502    3.6578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0256    2.8801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4897    2.2528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6786    2.4032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7651    1.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2293    0.8478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5490    0.0035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2652   -0.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0973   -1.2136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6520   -1.8242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2772   -1.3034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9154   -0.5620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6474   -1.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8887   -2.7392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8397   -1.7823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2903   -2.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5487   -3.1813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3564   -3.3493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4826   -2.2298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2242   -1.4463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5079   -1.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6759   -0.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5152   -0.0473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7735   -0.8308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0645    0.5682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8061    1.3517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8722    0.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1306   -0.3833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4215    1.0157    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
  3  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
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 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
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 20 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
  6 29  1  0  0  0  0
M  END


  Mrv1533004191517302D          

 29 30  0  0  0  0            999 V2000
    7.7502    3.6578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0256    2.8801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4897    2.2528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6786    2.4032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7651    1.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2293    0.8478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5490    0.0035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2652   -0.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0973   -1.2136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6520   -1.8242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2772   -1.3034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9154   -0.5620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6474   -1.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8887   -2.7392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8397   -1.7823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2903   -2.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5487   -3.1813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3564   -3.3493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4826   -2.2298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2242   -1.4463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5079   -1.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6759   -0.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5152   -0.0473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7735   -0.8308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0645    0.5682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8061    1.3517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8722    0.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1306   -0.3833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4215    1.0157    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
  3  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
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 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
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 20 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
  6 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0249507

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(O)CC1CCC(O)C(C)C(=O)OC(CC)CC2CCC(O2)C(C)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C22H38O7/c1-5-15(23)11-17-7-9-19(24)13(3)21(25)28-16(6-2)12-18-8-10-20(27-18)14(4)22(26)29-17/h13-20,23-24H,5-12H2,1-4H3

> <INCHI_KEY>
LCVDIZRTXONOQH-UHFFFAOYSA-N

> <FORMULA>
C22H38O7

> <MOLECULAR_WEIGHT>
414.539

> <EXACT_MASS>
414.261753564

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
45.94351834653856

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
12-ethyl-8-hydroxy-5-(2-hydroxybutyl)-2,9-dimethyl-4,11,17-trioxabicyclo[12.2.1]heptadecane-3,10-dione

> <ALOGPS_LOGP>
2.16

> <JCHEM_LOGP>
2.6008756996666658

> <ALOGPS_LOGS>
-2.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.308493841526296

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.577225884410119

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7175946707616783

> <JCHEM_POLAR_SURFACE_AREA>
102.29

> <JCHEM_REFRACTIVITY>
107.23149999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.70e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-ethyl-8-hydroxy-5-(2-hydroxybutyl)-2,9-dimethyl-4,11,17-trioxabicyclo[12.2.1]heptadecane-3,10-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      14.467   6.828   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.981   5.376   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.981   4.205   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      12.467   4.486   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      14.495   2.753   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.495   1.583   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.091   0.006   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.428  -0.758   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.115  -2.265   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      16.150  -3.405   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      13.584  -2.433   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.909  -1.049   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.408  -3.640   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      12.859  -5.113   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      10.901  -3.327   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.875  -4.476   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.358  -5.938   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.865  -6.252   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.368  -4.162   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.885  -2.700   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.548  -1.936   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.862  -0.428   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.428  -0.088   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.911  -1.551   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.454   1.061   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.971   2.523   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.961   0.747   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      11.444  -0.715   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      11.987   1.896   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   29                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21   24                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23   20                                                       
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27    6                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₈O₇

Average Mass

414.5390 Da

Monoisotopic Mass

414.26175 Da

IUPAC Name

12-ethyl-8-hydroxy-5-(2-hydroxybutyl)-2,9-dimethyl-4,11,17-trioxabicyclo[12.2.1]heptadecane-3,10-dione

Traditional Name

12-ethyl-8-hydroxy-5-(2-hydroxybutyl)-2,9-dimethyl-4,11,17-trioxabicyclo[12.2.1]heptadecane-3,10-dione

CAS Registry Number

Not Available

SMILES

CCC(O)CC1CCC(O)C(C)C(=O)OC(CC)CC2CCC(O2)C(C)C(=O)O1

InChI Identifier

InChI=1S/C22H38O7/c1-5-15(23)11-17-7-9-19(24)13(3)21(25)28-16(6-2)12-18-8-10-20(27-18)14(4)22(26)29-17/h13-20,23-24H,5-12H2,1-4H3

InChI Key

LCVDIZRTXONOQH-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces griseus	LOTUS Database	35616633

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
Dicarboxylic acid or derivatives
Oxolane
Carboxylic acid ester
Lactone
Secondary alcohol
Ether
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	2.16	ALOGPS
logP	2.6	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	14.58	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	102.29 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	107.23 m³·mol⁻¹	ChemAxon
Polarizability	45.94 Å³	ChemAxon
Number of Rings	2	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 12-ethyl-8-hydroxy-5-(2-hydroxybutyl)-2,9-dimethyl-4,11,17-trioxabicyclo[12.2.1]heptadecane-3,10-dione (NP0249507)

MOL for NP0249507 (12-ethyl-8-hydroxy-5-(2-hydroxybutyl)-2,9-dimethyl-4,11,17-trioxabicyclo[12.2.1]heptadecane-3,10-dione)

3D MOL for NP0249507 (12-ethyl-8-hydroxy-5-(2-hydroxybutyl)-2,9-dimethyl-4,11,17-trioxabicyclo[12.2.1]heptadecane-3,10-dione)

3D SDF for NP0249507 (12-ethyl-8-hydroxy-5-(2-hydroxybutyl)-2,9-dimethyl-4,11,17-trioxabicyclo[12.2.1]heptadecane-3,10-dione)

3D-SDF for NP0249507 (12-ethyl-8-hydroxy-5-(2-hydroxybutyl)-2,9-dimethyl-4,11,17-trioxabicyclo[12.2.1]heptadecane-3,10-dione)

PDB for NP0249507 (12-ethyl-8-hydroxy-5-(2-hydroxybutyl)-2,9-dimethyl-4,11,17-trioxabicyclo[12.2.1]heptadecane-3,10-dione)

3D PDB for NP0249507 (12-ethyl-8-hydroxy-5-(2-hydroxybutyl)-2,9-dimethyl-4,11,17-trioxabicyclo[12.2.1]heptadecane-3,10-dione)

SMILES for NP0249507 (12-ethyl-8-hydroxy-5-(2-hydroxybutyl)-2,9-dimethyl-4,11,17-trioxabicyclo[12.2.1]heptadecane-3,10-dione)

INCHI for NP0249507 (12-ethyl-8-hydroxy-5-(2-hydroxybutyl)-2,9-dimethyl-4,11,17-trioxabicyclo[12.2.1]heptadecane-3,10-dione)

Structure for NP0249507 (12-ethyl-8-hydroxy-5-(2-hydroxybutyl)-2,9-dimethyl-4,11,17-trioxabicyclo[12.2.1]heptadecane-3,10-dione)

3D Structure for NP0249507 (12-ethyl-8-hydroxy-5-(2-hydroxybutyl)-2,9-dimethyl-4,11,17-trioxabicyclo[12.2.1]heptadecane-3,10-dione)