NP-MRD: Showing NP-Card for 9-hydroxy-5,9,13-trimethyl-16-methylidene-15-oxo-4,14-dioxatricyclo[11.3.2.0³,⁵]octadec-7-en-12-yl acetate (NP0324619)

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Record Information

Version

2.0

Created at

2022-09-12 04:48:46 UTC

Updated at

2022-09-12 04:48:46 UTC

NP-MRD ID

NP0324619

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-hydroxy-5,9,13-trimethyl-16-methylidene-15-oxo-4,14-dioxatricyclo[11.3.2.0³,⁵]octadec-7-en-12-yl acetate

Description

9-Hydroxy-5,9,13-trimethyl-16-methylidene-15-oxo-4,14-dioxatricyclo[11.3.2.0³,⁵]Octadec-7-en-12-yl acetate belongs to the class of organic compounds known as lactones. These are cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. 9-hydroxy-5,9,13-trimethyl-16-methylidene-15-oxo-4,14-dioxatricyclo[11.3.2.0³,⁵]octadec-7-en-12-yl acetate is found in Sinularia flexibilis and Sinularia querciformis. 9-Hydroxy-5,9,13-trimethyl-16-methylidene-15-oxo-4,14-dioxatricyclo[11.3.2.0³,⁵]Octadec-7-en-12-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004171517302D          

 28 30  0  0  0  0            999 V2000
   -0.3372    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4577    0.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6640   -0.3050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0463    1.0719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8413    0.8512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3413    1.5074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0765    1.8817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9013    1.8999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5830    2.6610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4935    2.4742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6523    1.5584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1808    0.9249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3821    0.1248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2163   -0.6834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0374   -0.6036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5346   -1.4445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7163   -1.3396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9810   -1.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1562   -1.7320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3220   -0.9238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7935   -0.2903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9687   -0.3085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1738   -0.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4687   -0.9647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6700   -1.7648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0365   -2.2933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4210   -2.1063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4392   -2.9311    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
  2  4  1  0  0  0  0
  4  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
  8 10  1  0  0  0  0
 11  8  1  4  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 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
  5 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 19 27  1  0  0  0  0
 27 28  2  0  0  0  0
M  END


  Mrv1533004171517302D          

 28 30  0  0  0  0            999 V2000
   -0.3372    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4577    0.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6640   -0.3050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0463    1.0719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8413    0.8512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3413    1.5074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0765    1.8817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9013    1.8999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5830    2.6610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4935    2.4742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6523    1.5584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1808    0.9249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3821    0.1248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2163   -0.6834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0374   -0.6036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5346   -1.4445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7163   -1.3396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9810   -1.7138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1562   -1.7320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3220   -0.9238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7935   -0.2903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9687   -0.3085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1738   -0.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4687   -0.9647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6700   -1.7648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0365   -2.2933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4210   -2.1063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4392   -2.9311    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
  2  4  1  0  0  0  0
  4  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
  8 10  1  0  0  0  0
 11  8  1  4  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 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
  5 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 19 27  1  0  0  0  0
 27 28  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0324619

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1CCC(C)(O)C=CCC2(C)OC2CC2CCC1(C)OC(=O)C2=C

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O6/c1-14-16-7-12-22(5,28-19(14)24)17(26-15(2)23)8-11-20(3,25)9-6-10-21(4)18(13-16)27-21/h6,9,16-18,25H,1,7-8,10-13H2,2-5H3

> <INCHI_KEY>
SXSOYTHMKCYVOO-UHFFFAOYSA-N

> <FORMULA>
C22H32O6

> <MOLECULAR_WEIGHT>
392.492

> <EXACT_MASS>
392.21988875

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
42.20652568164164

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-hydroxy-5,9,13-trimethyl-16-methylidene-15-oxo-4,14-dioxatricyclo[11.3.2.0³,⁵]octadec-7-en-12-yl acetate

> <ALOGPS_LOGP>
3.12

> <JCHEM_LOGP>
2.9130014096666663

> <ALOGPS_LOGS>
-4.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.689550220937594

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9345907333618957

> <JCHEM_POLAR_SURFACE_AREA>
85.36000000000001

> <JCHEM_REFRACTIVITY>
104.36479999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.31e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-hydroxy-5,9,13-trimethyl-16-methylidene-15-oxo-4,14-dioxatricyclo[11.3.2.0³,⁵]octadec-7-en-12-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -0.629   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.854   0.922   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.240  -0.569   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.953   2.001   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.437   1.589   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.370   2.814   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.743   3.512   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.282   3.546   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.688   4.967   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.388   4.619   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.684   2.909   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.671   1.726   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.047   0.233   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.737  -1.276   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.270  -1.127   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.331  -2.696   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.804  -2.501   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.431  -3.199   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.892  -3.233   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.201  -1.725   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.215  -0.542   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.675  -0.576   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.191  -0.164   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.742  -1.801   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.117  -3.294   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.935  -4.281   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.519  -3.932   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.553  -5.471   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   22                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   14   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   27                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21    5   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   19   28                                                  
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Value	Source
9-Hydroxy-5,9,13-trimethyl-16-methylidene-15-oxo-4,14-dioxatricyclo[11.3.2.0,]octadec-7-en-12-yl acetic acid	Generator
9-Hydroxy-5,9,13-trimethyl-16-methylidene-15-oxo-4,14-dioxatricyclo[11.3.2.0³,⁵]octadec-7-en-12-yl acetic acid	Generator

Chemical Formula

C₂₂H₃₂O₆

Average Mass

392.4920 Da

Monoisotopic Mass

392.21989 Da

IUPAC Name

9-hydroxy-5,9,13-trimethyl-16-methylidene-15-oxo-4,14-dioxatricyclo[11.3.2.0³,⁵]octadec-7-en-12-yl acetate

Traditional Name

9-hydroxy-5,9,13-trimethyl-16-methylidene-15-oxo-4,14-dioxatricyclo[11.3.2.0³,⁵]octadec-7-en-12-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CCC(C)(O)C=CCC2(C)OC2CC2CCC1(C)OC(=O)C2=C

InChI Identifier

InChI=1S/C22H32O6/c1-14-16-7-12-22(5,28-19(14)24)17(26-15(2)23)8-11-20(3,25)9-6-10-21(4)18(13-16)27-21/h6,9,16-18,25H,1,7-8,10-13H2,2-5H3

InChI Key

SXSOYTHMKCYVOO-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Sinularia flexibilis	LOTUS Database	35616633
Sinularia querciformis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lactones. These are cyclic esters of hydroxy carboxylic acids, containing a 1-oxacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Not Available

Direct Parent

Lactones

Alternative Parents

Substituents

Caprolactone
Oxepane
Dicarboxylic acid or derivatives
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
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	3.12	ALOGPS
logP	2.91	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	14.69	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	85.36 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	104.36 m³·mol⁻¹	ChemAxon
Polarizability	42.21 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

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

75040005

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 9-hydroxy-5,9,13-trimethyl-16-methylidene-15-oxo-4,14-dioxatricyclo[11.3.2.0³,⁵]octadec-7-en-12-yl acetate (NP0324619)

MOL for NP0324619 (9-hydroxy-5,9,13-trimethyl-16-methylidene-15-oxo-4,14-dioxatricyclo[11.3.2.0³,⁵]octadec-7-en-12-yl acetate)

3D MOL for NP0324619 (9-hydroxy-5,9,13-trimethyl-16-methylidene-15-oxo-4,14-dioxatricyclo[11.3.2.0³,⁵]octadec-7-en-12-yl acetate)

3D SDF for NP0324619 (9-hydroxy-5,9,13-trimethyl-16-methylidene-15-oxo-4,14-dioxatricyclo[11.3.2.0³,⁵]octadec-7-en-12-yl acetate)

3D-SDF for NP0324619 (9-hydroxy-5,9,13-trimethyl-16-methylidene-15-oxo-4,14-dioxatricyclo[11.3.2.0³,⁵]octadec-7-en-12-yl acetate)

PDB for NP0324619 (9-hydroxy-5,9,13-trimethyl-16-methylidene-15-oxo-4,14-dioxatricyclo[11.3.2.0³,⁵]octadec-7-en-12-yl acetate)

3D PDB for NP0324619 (9-hydroxy-5,9,13-trimethyl-16-methylidene-15-oxo-4,14-dioxatricyclo[11.3.2.0³,⁵]octadec-7-en-12-yl acetate)

SMILES for NP0324619 (9-hydroxy-5,9,13-trimethyl-16-methylidene-15-oxo-4,14-dioxatricyclo[11.3.2.0³,⁵]octadec-7-en-12-yl acetate)

INCHI for NP0324619 (9-hydroxy-5,9,13-trimethyl-16-methylidene-15-oxo-4,14-dioxatricyclo[11.3.2.0³,⁵]octadec-7-en-12-yl acetate)

Structure for NP0324619 (9-hydroxy-5,9,13-trimethyl-16-methylidene-15-oxo-4,14-dioxatricyclo[11.3.2.0³,⁵]octadec-7-en-12-yl acetate)

3D Structure for NP0324619 (9-hydroxy-5,9,13-trimethyl-16-methylidene-15-oxo-4,14-dioxatricyclo[11.3.2.0³,⁵]octadec-7-en-12-yl acetate)