NP-MRD: Showing NP-Card for (1r,4r,7r,8s,9r,11s,12s)-7,12-dihydroxy-2,2,4,9-tetramethyl-6-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl acetate (NP0155641)

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Record Information

Version

2.0

Created at

2022-09-02 12:44:30 UTC

Updated at

2022-09-02 12:44:31 UTC

NP-MRD ID

NP0155641

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,4r,7r,8s,9r,11s,12s)-7,12-dihydroxy-2,2,4,9-tetramethyl-6-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl acetate

Description

10-Epi-Dihydrobotrydial belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms. (1r,4r,7r,8s,9r,11s,12s)-7,12-dihydroxy-2,2,4,9-tetramethyl-6-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl acetate is found in Botrytis cinerea. Based on a literature review very few articles have been published on 10-epi-Dihydrobotrydial.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309022214442D          

 22 24  0  0  1  0            999 V2000
   -1.1509    0.0470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4835    0.5319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5697    1.3524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2702    0.1963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9377    0.6813    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8514    1.5017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5189    1.9867    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4326    2.8071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2725    1.6511    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1987    1.9867    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3141    2.8035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8661    1.5017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7799    0.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0262    0.3457    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6393   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7713   -0.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9463   -0.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0325   -1.2594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1393   -0.6105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6913    0.3457    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3588    0.8306    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0732    1.2431    0.0000 O   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
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 20 17  1  6  0  0  0
  5 20  1  0  0  0  0
 20 21  1  0  0  0  0
  9 21  1  6  0  0  0
 14 21  1  0  0  0  0
 21 22  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0155641

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@H](OC(C)=O)[C@H]2C(C)(C)C[C@]3(C)CO[C@@H](O)[C@@H]1[C@@]23O

> <INCHI_IDENTIFIER>
InChI=1S/C17H28O5/c1-9-6-11(22-10(2)18)13-15(3,4)7-16(5)8-21-14(19)12(9)17(13,16)20/h9,11-14,19-20H,6-8H2,1-5H3/t9-,11+,12-,13+,14-,16-,17-/m1/s1

> <INCHI_KEY>
QUGYVDURDBEQRB-VZJVBFQISA-N

> <FORMULA>
C17H28O5

> <MOLECULAR_WEIGHT>
312.406

> <EXACT_MASS>
312.193674002

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
33.76595731927556

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4R,7R,8S,9R,11S,12S)-7,12-dihydroxy-2,2,4,9-tetramethyl-6-oxatricyclo[6.3.1.0^{4,12}]dodecan-11-yl acetate

> <ALOGPS_LOGP>
0.94

> <JCHEM_LOGP>
1.2897931509999991

> <ALOGPS_LOGS>
-2.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.811474880165687

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.078554828291875

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3687689687082853

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
79.6605

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.08e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4R,7R,8S,9R,11S,12S)-7,12-dihydroxy-2,2,4,9-tetramethyl-6-oxatricyclo[6.3.1.0^{4,12}]dodecan-11-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.148   0.088   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.902   0.993   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.063   2.524   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.504   0.366   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.750   1.272   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.589   2.803   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.835   3.708   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.674   5.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.242   3.082   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.971   3.708   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.186   5.233   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       7.217   2.803   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.056   1.272   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.649   0.645   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.793  -0.385   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.173  -0.819   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.633  -0.819   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.794  -2.351   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.127  -1.140   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.157   0.645   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.403   1.550   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.737   2.320   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   20                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   21                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   21                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17    5   21                                                  
CONECT   21   20    9   14   22                                             
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₈O₅

Average Mass

312.4060 Da

Monoisotopic Mass

312.19367 Da

IUPAC Name

(1R,4R,7R,8S,9R,11S,12S)-7,12-dihydroxy-2,2,4,9-tetramethyl-6-oxatricyclo[6.3.1.0^{4,12}]dodecan-11-yl acetate

Traditional Name

(1R,4R,7R,8S,9R,11S,12S)-7,12-dihydroxy-2,2,4,9-tetramethyl-6-oxatricyclo[6.3.1.0^{4,12}]dodecan-11-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@H](OC(C)=O)[C@H]2C(C)(C)C[C@]3(C)CO[C@@H](O)[C@@H]1[C@@]23O

InChI Identifier

InChI=1S/C17H28O5/c1-9-6-11(22-10(2)18)13-15(3,4)7-16(5)8-21-14(19)12(9)17(13,16)20/h9,11-14,19-20H,6-8H2,1-5H3/t9-,11+,12-,13+,14-,16-,17-/m1/s1

InChI Key

QUGYVDURDBEQRB-VZJVBFQISA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Botrytis cinerea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxanes

Sub Class

Not Available

Direct Parent

Oxanes

Alternative Parents

Substituents

Oxane
Tertiary alcohol
Cyclic alcohol
Hemiacetal
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	0.94	ALOGPS
logP	1.29	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	12.08	ChemAxon
pKa (Strongest Basic)	-3.4	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	2	ChemAxon
Refractivity	79.66 m³·mol⁻¹	ChemAxon
Polarizability	33.77 Å³	ChemAxon
Number of Rings	3	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

9004224

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10828924

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,4r,7r,8s,9r,11s,12s)-7,12-dihydroxy-2,2,4,9-tetramethyl-6-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl acetate (NP0155641)

MOL for NP0155641 ((1r,4r,7r,8s,9r,11s,12s)-7,12-dihydroxy-2,2,4,9-tetramethyl-6-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl acetate)

3D MOL for NP0155641 ((1r,4r,7r,8s,9r,11s,12s)-7,12-dihydroxy-2,2,4,9-tetramethyl-6-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl acetate)

3D SDF for NP0155641 ((1r,4r,7r,8s,9r,11s,12s)-7,12-dihydroxy-2,2,4,9-tetramethyl-6-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl acetate)

3D-SDF for NP0155641 ((1r,4r,7r,8s,9r,11s,12s)-7,12-dihydroxy-2,2,4,9-tetramethyl-6-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl acetate)

PDB for NP0155641 ((1r,4r,7r,8s,9r,11s,12s)-7,12-dihydroxy-2,2,4,9-tetramethyl-6-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl acetate)

3D PDB for NP0155641 ((1r,4r,7r,8s,9r,11s,12s)-7,12-dihydroxy-2,2,4,9-tetramethyl-6-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl acetate)

SMILES for NP0155641 ((1r,4r,7r,8s,9r,11s,12s)-7,12-dihydroxy-2,2,4,9-tetramethyl-6-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl acetate)

INCHI for NP0155641 ((1r,4r,7r,8s,9r,11s,12s)-7,12-dihydroxy-2,2,4,9-tetramethyl-6-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl acetate)

Structure for NP0155641 ((1r,4r,7r,8s,9r,11s,12s)-7,12-dihydroxy-2,2,4,9-tetramethyl-6-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl acetate)

3D Structure for NP0155641 ((1r,4r,7r,8s,9r,11s,12s)-7,12-dihydroxy-2,2,4,9-tetramethyl-6-oxatricyclo[6.3.1.0⁴,¹²]dodecan-11-yl acetate)