NP-MRD: Showing NP-Card for Epicitreodiol (NP0057234)

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Record Information

Version

2.0

Created at

2022-04-28 02:43:38 UTC

Updated at

2022-04-28 02:43:38 UTC

NP-MRD ID

NP0057234

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Epicitreodiol

Description

Epi-Citreodiol belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. Epicitreodiol is found in Penicillium citreo-viride B and Streptomyces rochei. Based on a literature review very few articles have been published on epi-Citreodiol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 32  0  0  0  0  0  0  0  0999 V2000
    5.9678   -0.8867    0.3233 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7476   -0.2660    0.0112 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5735   -0.7115    0.5933 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6501   -1.6686    1.3898 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3347   -0.0565    0.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3208    1.0686   -0.6941 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2156   -0.4703    0.8012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0163    0.2164    0.4353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2001   -0.1305    0.9357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4615    0.5373    0.5909 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2828    1.8663   -0.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1687    0.7527    1.7957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3596   -0.3154   -0.2729 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7496   -1.5778    0.5016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5475    0.3816   -0.4899 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0310   -1.1072    1.4047 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9951   -1.8466   -0.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7807   -0.1954    0.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3679    1.3435   -0.9940 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8116    0.7604   -1.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8006    1.9637   -0.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2246   -1.2798    1.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0331    1.0432   -0.2614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2111   -0.9549    1.6353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7774    1.7553   -1.0464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6810    2.5693    0.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2915    2.2990   -0.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7949    0.1711    2.5214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9208   -0.5718   -1.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8461   -2.0419    0.9100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4398   -1.3462    1.3135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2742   -2.2567   -0.2046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7656    0.9553    0.3102 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  1  1
 10 13  1  0
 13 14  1  0
 13 15  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  6 19  1  0
  6 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  6
 14 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
M  END


  Mrv1652304282204432D          

 15 14  0  0  1  0            999 V2000
    2.4750    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8250   -1.4289    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  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
  7  9  1  6  0  0  0
  6 10  1  1  0  0  0
  6 11  1  1  0  0  0
  2 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0057234

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(\C)=C\C=C\[C@](C)(O)[C@@H](C)O

> <INCHI_IDENTIFIER>
InChI=1S/C11H18O4/c1-8(10(13)15-4)6-5-7-11(3,14)9(2)12/h5-7,9,12,14H,1-4H3/b7-5+,8-6+/t9-,11+/m1/s1

> <INCHI_KEY>
VRPFJYGFBAJGLE-SUTNNJMISA-N

> <FORMULA>
C11H18O4

> <MOLECULAR_WEIGHT>
214.261

> <EXACT_MASS>
214.12050906

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
23.531448908877486

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2E,4E,6S,7R)-6,7-dihydroxy-2,6-dimethylocta-2,4-dienoate

> <ALOGPS_LOGP>
1.10

> <JCHEM_LOGP>
1.0076214336666671

> <ALOGPS_LOGS>
-1.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.124726369968876

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.572925099956265

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1439525654006006

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
59.203900000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.97e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2E,4E,6S,7R)-6,7-dihydroxy-2,6-dimethylocta-2,4-dienoate

> <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       4.620   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.540  -2.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.080  -2.667   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.770  -4.001   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.564  -2.104   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.850   4.001   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       6.160   2.667   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   10   11                                             
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    6                                                            
CONECT   11    6                                                            
CONECT   12    2   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

View in JSmol

Synonyms

Value	Source
Citreodiol	MeSH

Chemical Formula

C₁₁H₁₈O₄

Average Mass

214.2610 Da

Monoisotopic Mass

214.12051 Da

IUPAC Name

methyl (2E,4E,6S,7R)-6,7-dihydroxy-2,6-dimethylocta-2,4-dienoate

Traditional Name

methyl (2E,4E,6S,7R)-6,7-dihydroxy-2,6-dimethylocta-2,4-dienoate

CAS Registry Number

Not Available

SMILES

COC(=O)C(\C)=C\C=C\[C@](C)(O)[C@@H](C)O

InChI Identifier

InChI=1S/C11H18O4/c1-8(10(13)15-4)6-5-7-11(3,14)9(2)12/h5-7,9,12,14H,1-4H3/b7-5+,8-6+/t9-,11+/m1/s1

InChI Key

VRPFJYGFBAJGLE-SUTNNJMISA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Penicillium citreo-viride B	Fungi	KNApSAcK
Streptomyces rochei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Fatty alcohols

Alternative Parents

Substituents

Fatty alcohol
Fatty acid ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tertiary alcohol
1,2-diol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Alcohol
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	1.1	ALOGPS
logP	1.01	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	13.57	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	59.2 m³·mol⁻¹	ChemAxon
Polarizability	23.53 Å³	ChemAxon
Number of Rings	0	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

75549890

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44477651

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Epicitreodiol (NP0057234)

MOL for NP0057234 (Epicitreodiol)

3D MOL for NP0057234 (Epicitreodiol)

3D SDF for NP0057234 (Epicitreodiol)

3D-SDF for NP0057234 (Epicitreodiol)

PDB for NP0057234 (Epicitreodiol)

3D PDB for NP0057234 (Epicitreodiol)

SMILES for NP0057234 (Epicitreodiol)

INCHI for NP0057234 (Epicitreodiol)

Structure for NP0057234 (Epicitreodiol)

3D Structure for NP0057234 (Epicitreodiol)