NP-MRD: Showing NP-Card for (1s,2r,4r,5s,9r,10s,11s,12s)-10-hydroxy-2,11-dimethyl-6-methylidene-7-oxo-8-oxatetracyclo[8.3.0.0²,⁴.0⁵,⁹]tridecan-12-yl acetate (NP0317832)

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Record Information

Version

2.0

Created at

2022-09-11 17:56:34 UTC

Updated at

2022-09-11 17:56:35 UTC

NP-MRD ID

NP0317832

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,4r,5s,9r,10s,11s,12s)-10-hydroxy-2,11-dimethyl-6-methylidene-7-oxo-8-oxatetracyclo[8.3.0.0²,⁴.0⁵,⁹]tridecan-12-yl acetate

Description

(1S,2R,4R,5S,9R,10S,11S,12S)-10-hydroxy-2,11-dimethyl-6-methylidene-7-oxo-8-oxatetracyclo[8.3.0.0²,⁴.0⁵,⁹]Tridecan-12-yl acetate belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. (1s,2r,4r,5s,9r,10s,11s,12s)-10-hydroxy-2,11-dimethyl-6-methylidene-7-oxo-8-oxatetracyclo[8.3.0.0²,⁴.0⁵,⁹]tridecan-12-yl acetate is found in Eria mucronata. Based on a literature review very few articles have been published on (1S,2R,4R,5S,9R,10S,11S,12S)-10-hydroxy-2,11-dimethyl-6-methylidene-7-oxo-8-oxatetracyclo[8.3.0.0²,⁴.0⁵,⁹]Tridecan-12-yl acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309112219562D          

 22 25  0  0  1  0            999 V2000
    5.3522   -0.6091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7391   -0.0571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8253    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5398    1.1759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0717    1.0990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5196    0.4859    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9321   -0.2286    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5196   -0.9431    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1071   -1.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6946   -0.9431    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9802   -1.3556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2821   -0.2286    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4752   -0.0571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3889    0.7634    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6745    1.1759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6745    2.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0400    2.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3889    2.4134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1426    1.0990    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3141    1.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6946    0.4859    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0302    1.2395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  2  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 12 21  1  0  0  0  0
  6 21  1  0  0  0  0
 21 22  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0317832

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@H](C[C@H]2[C@]3(C)C[C@@H]3[C@@H]3[C@@H](OC(=O)C3=C)[C@@]12O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O5/c1-7-13-10-6-16(10,4)12-5-11(21-9(3)18)8(2)17(12,20)14(13)22-15(7)19/h8,10-14,20H,1,5-6H2,2-4H3/t8-,10+,11-,12-,13+,14+,16+,17+/m0/s1

> <INCHI_KEY>
UIDYHYYEAGPNQR-CPUVPTDQSA-N

> <FORMULA>
C17H22O5

> <MOLECULAR_WEIGHT>
306.358

> <EXACT_MASS>
306.146723808

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
31.528674940530394

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,4R,5S,9R,10S,11S,12S)-10-hydroxy-2,11-dimethyl-6-methylidene-7-oxo-8-oxatetracyclo[8.3.0.0^{2,4}.0^{5,9}]tridecan-12-yl acetate

> <JCHEM_LOGP>
1.1752748583333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.321062723606996

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5331671646942997

> <JCHEM_POLAR_SURFACE_AREA>
72.83

> <JCHEM_REFRACTIVITY>
76.4552

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4R,5S,9R,10S,11S,12S)-10-hydroxy-2,11-dimethyl-6-methylidene-7-oxo-8-oxatetracyclo[8.3.0.0^{2,4}.0^{5,9}]tridecan-12-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       9.991  -1.137   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.846  -0.107   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.007   1.425   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.341   2.195   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       7.600   2.051   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.570   0.907   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.340  -0.427   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.570  -1.760   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.800  -3.094   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.030  -1.760   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.696  -2.530   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.260  -0.427   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.754  -0.107   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.593   1.425   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.259   2.195   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.259   3.735   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.075   4.505   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.593   4.505   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.000   2.051   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.320   3.558   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.030   0.907   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.656   2.314   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   21                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8   10                                                       
CONECT   10    9    8   11   12                                             
CONECT   11   10                                                            
CONECT   12   10   13   21                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   14   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   12    6   22                                             
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Value	Source
(1S,2R,4R,5S,9R,10S,11S,12S)-10-Hydroxy-2,11-dimethyl-6-methylidene-7-oxo-8-oxatetracyclo[8.3.0.0,.0,]tridecan-12-yl acetic acid	Generator

Chemical Formula

C₁₇H₂₂O₅

Average Mass

306.3580 Da

Monoisotopic Mass

306.14672 Da

IUPAC Name

(1S,2R,4R,5S,9R,10S,11S,12S)-10-hydroxy-2,11-dimethyl-6-methylidene-7-oxo-8-oxatetracyclo[8.3.0.0^{2,4}.0^{5,9}]tridecan-12-yl acetate

Traditional Name

(1S,2R,4R,5S,9R,10S,11S,12S)-10-hydroxy-2,11-dimethyl-6-methylidene-7-oxo-8-oxatetracyclo[8.3.0.0^{2,4}.0^{5,9}]tridecan-12-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@H](C[C@H]2[C@]3(C)C[C@@H]3[C@@H]3[C@@H](OC(=O)C3=C)[C@@]12O)OC(C)=O

InChI Identifier

InChI=1S/C17H22O5/c1-7-13-10-6-16(10,4)12-5-11(21-9(3)18)8(2)17(12,20)14(13)22-15(7)19/h8,10-14,20H,1,5-6H2,2-4H3/t8-,10+,11-,12-,13+,14+,16+,17+/m0/s1

InChI Key

UIDYHYYEAGPNQR-CPUVPTDQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Eria mucronata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Dicarboxylic acid or derivatives
Gamma butyrolactone
Cyclic alcohol
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Hydrocarbon derivative
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	1.18	ChemAxon
pKa (Strongest Acidic)	13.32	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	76.46 m³·mol⁻¹	ChemAxon
Polarizability	31.53 Å³	ChemAxon
Number of Rings	4	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

163048519

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,4r,5s,9r,10s,11s,12s)-10-hydroxy-2,11-dimethyl-6-methylidene-7-oxo-8-oxatetracyclo[8.3.0.0²,⁴.0⁵,⁹]tridecan-12-yl acetate (NP0317832)

MOL for NP0317832 ((1s,2r,4r,5s,9r,10s,11s,12s)-10-hydroxy-2,11-dimethyl-6-methylidene-7-oxo-8-oxatetracyclo[8.3.0.0²,⁴.0⁵,⁹]tridecan-12-yl acetate)

3D MOL for NP0317832 ((1s,2r,4r,5s,9r,10s,11s,12s)-10-hydroxy-2,11-dimethyl-6-methylidene-7-oxo-8-oxatetracyclo[8.3.0.0²,⁴.0⁵,⁹]tridecan-12-yl acetate)

3D SDF for NP0317832 ((1s,2r,4r,5s,9r,10s,11s,12s)-10-hydroxy-2,11-dimethyl-6-methylidene-7-oxo-8-oxatetracyclo[8.3.0.0²,⁴.0⁵,⁹]tridecan-12-yl acetate)

3D-SDF for NP0317832 ((1s,2r,4r,5s,9r,10s,11s,12s)-10-hydroxy-2,11-dimethyl-6-methylidene-7-oxo-8-oxatetracyclo[8.3.0.0²,⁴.0⁵,⁹]tridecan-12-yl acetate)

PDB for NP0317832 ((1s,2r,4r,5s,9r,10s,11s,12s)-10-hydroxy-2,11-dimethyl-6-methylidene-7-oxo-8-oxatetracyclo[8.3.0.0²,⁴.0⁵,⁹]tridecan-12-yl acetate)

3D PDB for NP0317832 ((1s,2r,4r,5s,9r,10s,11s,12s)-10-hydroxy-2,11-dimethyl-6-methylidene-7-oxo-8-oxatetracyclo[8.3.0.0²,⁴.0⁵,⁹]tridecan-12-yl acetate)

SMILES for NP0317832 ((1s,2r,4r,5s,9r,10s,11s,12s)-10-hydroxy-2,11-dimethyl-6-methylidene-7-oxo-8-oxatetracyclo[8.3.0.0²,⁴.0⁵,⁹]tridecan-12-yl acetate)

INCHI for NP0317832 ((1s,2r,4r,5s,9r,10s,11s,12s)-10-hydroxy-2,11-dimethyl-6-methylidene-7-oxo-8-oxatetracyclo[8.3.0.0²,⁴.0⁵,⁹]tridecan-12-yl acetate)

Structure for NP0317832 ((1s,2r,4r,5s,9r,10s,11s,12s)-10-hydroxy-2,11-dimethyl-6-methylidene-7-oxo-8-oxatetracyclo[8.3.0.0²,⁴.0⁵,⁹]tridecan-12-yl acetate)

3D Structure for NP0317832 ((1s,2r,4r,5s,9r,10s,11s,12s)-10-hydroxy-2,11-dimethyl-6-methylidene-7-oxo-8-oxatetracyclo[8.3.0.0²,⁴.0⁵,⁹]tridecan-12-yl acetate)