NP-MRD: Showing NP-Card for (3e,6r,9e,11s,12r,14r)-11,12-dihydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8-dione (NP0225992)

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Record Information

Version

2.0

Created at

2022-09-06 04:52:56 UTC

Updated at

2022-09-06 04:52:56 UTC

NP-MRD ID

NP0225992

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3e,6r,9e,11s,12r,14r)-11,12-dihydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8-dione

Description

10-Epi-Colletodiol, also known as colletodiol, 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. (3e,6r,9e,11s,12r,14r)-11,12-dihydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8-dione is found in Colletotrichum truncatum and Dichotomopilus funicola. (3e,6r,9e,11s,12r,14r)-11,12-dihydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8-dione was first documented in 1998 (PMID: 9549884). Based on a literature review very few articles have been published on 10-epi-Colletodiol.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062206522D          

 20 20  0  0  1  0            999 V2000
    2.0562    1.6647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.8851    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5963    1.0410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1364    0.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8664   -0.3622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4064   -0.9858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2166   -0.8299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1364   -1.7654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3263   -1.9213    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0562   -2.7008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -1.2976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9760   -1.4535    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7060   -2.2331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4360   -0.8299    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3742   -0.9858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7060   -0.0503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1659    0.5733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4360    1.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1041    1.9765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2461    1.5088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  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  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 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
 18 20  1  0  0  0  0
  2 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0225992

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C\C=C\C(=O)O[C@H](C)C[C@@H](O)[C@@H](O)\C=C\C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C14H20O6/c1-9-4-3-5-13(17)20-10(2)8-12(16)11(15)6-7-14(18)19-9/h3,5-7,9-12,15-16H,4,8H2,1-2H3/b5-3+,7-6+/t9-,10-,11+,12-/m1/s1

> <INCHI_KEY>
SHQHOHRUGBYJBS-DACQJQBYSA-N

> <FORMULA>
C14H20O6

> <MOLECULAR_WEIGHT>
284.308

> <EXACT_MASS>
284.125988364

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
28.579289368445036

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E,6R,9E,11S,12R,14R)-11,12-dihydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8-dione

> <JCHEM_LOGP>
0.994332286666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.080026497119071

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.591665488061839

> <JCHEM_PKA_STRONGEST_BASIC>
-3.207262876492682

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
72.87780000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3E,6R,9E,11S,12R,14R)-11,12-dihydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       3.838   3.107   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.334   1.652   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.846   1.943   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.855   0.779   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.351  -0.676   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.359  -1.840   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.871  -1.549   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       5.855  -3.295   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.342  -3.586   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.838  -5.042   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.334  -2.422   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.822  -2.713   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.318  -4.168   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.814  -1.549   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.698  -1.840   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.318  -0.094   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.310   1.070   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.814   2.525   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.194   3.689   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.326   2.816   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    2                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol

Synonyms

Value	Source
Colletodiol	MeSH

Chemical Formula

C₁₄H₂₀O₆

Average Mass

284.3080 Da

Monoisotopic Mass

284.12599 Da

IUPAC Name

(3E,6R,9E,11S,12R,14R)-11,12-dihydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8-dione

Traditional Name

(3E,6R,9E,11S,12R,14R)-11,12-dihydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8-dione

CAS Registry Number

Not Available

SMILES

C[C@@H]1C\C=C\C(=O)O[C@H](C)C[C@@H](O)[C@@H](O)\C=C\C(=O)O1

InChI Identifier

InChI=1S/C14H20O6/c1-9-4-3-5-13(17)20-10(2)8-12(16)11(15)6-7-14(18)19-9/h3,5-7,9-12,15-16H,4,8H2,1-2H3/b5-3+,7-6+/t9-,10-,11+,12-/m1/s1

InChI Key

SHQHOHRUGBYJBS-DACQJQBYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Colletotrichum truncatum	LOTUS Database	35616633
Dichotomopilus funicola	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
Alpha,beta-unsaturated carboxylic ester
Enoate ester
1,2-diol
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Organooxygen 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	0.99	ChemAxon
pKa (Strongest Acidic)	13.59	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	72.88 m³·mol⁻¹	ChemAxon
Polarizability	28.58 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

78436422

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10469093

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fujimoto H, Nagano J, Yamaguchi K, Yamazaki M: Immunosuppressive components from an Ascomycete, Diplogelasinospora grovesii. Chem Pharm Bull (Tokyo). 1998 Mar;46(3):423-9. doi: 10.1248/cpb.46.423. [PubMed:9549884 ]
LOTUS database [Link]

Showing NP-Card for (3e,6r,9e,11s,12r,14r)-11,12-dihydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8-dione (NP0225992)

MOL for NP0225992 ((3e,6r,9e,11s,12r,14r)-11,12-dihydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8-dione)

3D MOL for NP0225992 ((3e,6r,9e,11s,12r,14r)-11,12-dihydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8-dione)

3D SDF for NP0225992 ((3e,6r,9e,11s,12r,14r)-11,12-dihydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8-dione)

3D-SDF for NP0225992 ((3e,6r,9e,11s,12r,14r)-11,12-dihydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8-dione)

PDB for NP0225992 ((3e,6r,9e,11s,12r,14r)-11,12-dihydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8-dione)

3D PDB for NP0225992 ((3e,6r,9e,11s,12r,14r)-11,12-dihydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8-dione)

SMILES for NP0225992 ((3e,6r,9e,11s,12r,14r)-11,12-dihydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8-dione)

INCHI for NP0225992 ((3e,6r,9e,11s,12r,14r)-11,12-dihydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8-dione)

Structure for NP0225992 ((3e,6r,9e,11s,12r,14r)-11,12-dihydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8-dione)

3D Structure for NP0225992 ((3e,6r,9e,11s,12r,14r)-11,12-dihydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8-dione)