NP-MRD: Showing NP-Card for 5-[7-(acetyloxy)-4,9-dimethyl-3,11-dioxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-4-en-9-yl]-2-methylpenta-2,4-dienoic acid (NP0221098)

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Record Information

Version

2.0

Created at

2022-09-05 22:35:04 UTC

Updated at

2022-09-05 22:35:04 UTC

NP-MRD ID

NP0221098

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-[7-(acetyloxy)-4,9-dimethyl-3,11-dioxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-4-en-9-yl]-2-methylpenta-2,4-dienoic acid

Description

5-[7-(Acetyloxy)-4,9-dimethyl-3,11-dioxo-10-oxatricyclo[6.3.2.0¹,⁷]Tridec-4-en-9-yl]-2-methylpenta-2,4-dienoic acid belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. 5-[7-(acetyloxy)-4,9-dimethyl-3,11-dioxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-4-en-9-yl]-2-methylpenta-2,4-dienoic acid is found in Pseudolarix amabilis. 5-[7-(Acetyloxy)-4,9-dimethyl-3,11-dioxo-10-oxatricyclo[6.3.2.0¹,⁷]Tridec-4-en-9-yl]-2-methylpenta-2,4-dienoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004251511142D          

 29 31  0  0  0  0            999 V2000
   -1.0003   -0.1448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2016   -0.3514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0188   -1.1464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4580    0.3196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3700   -0.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8655   -0.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6901   -0.8586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2230   -0.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0958   -0.3146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2957    0.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6951    1.4456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3302    0.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5768    0.6237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7971    0.6064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4027   -0.1182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7234   -0.8784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5176   -1.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3139   -1.5925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1873   -0.6198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2282    0.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9147    0.8989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9386   -1.8927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0823   -2.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8550   -3.0409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9911   -3.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3545   -4.3793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7638   -4.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4005   -3.6189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8999   -4.9573    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  5 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
 19 20  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  2  0  0  0  0
 22 17  1  4  0  0  0
 22 23  2  0  0  0  0
 24 23  1  4  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
M  END


  Mrv1533004251511142D          

 29 31  0  0  0  0            999 V2000
   -1.0003   -0.1448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2016   -0.3514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0188   -1.1464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4580    0.3196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3700   -0.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8655   -0.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6901   -0.8586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2230   -0.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0958   -0.3146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2957    0.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6951    1.4456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3302    0.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5768    0.6237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7971    0.6064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4027   -0.1182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7234   -0.8784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5176   -1.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3139   -1.5925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1873   -0.6198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2282    0.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9147    0.8989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9386   -1.8927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0823   -2.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8550   -3.0409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9911   -3.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3545   -4.3793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7638   -4.1436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4005   -3.6189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8999   -4.9573    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  5 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
 19 20  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  2  0  0  0  0
 22 17  1  4  0  0  0
 22 23  2  0  0  0  0
 24 23  1  4  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0221098

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC12CC=C(C)C(=O)CC11CCC2C(C)(OC1=O)C=CC=C(C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H26O7/c1-13-7-11-22(28-15(3)23)17-8-10-21(22,12-16(13)24)19(27)29-20(17,4)9-5-6-14(2)18(25)26/h5-7,9,17H,8,10-12H2,1-4H3,(H,25,26)

> <INCHI_KEY>
UBHOILGODYTXTA-UHFFFAOYSA-N

> <FORMULA>
C22H26O7

> <MOLECULAR_WEIGHT>
402.443

> <EXACT_MASS>
402.167853177

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
41.16831575592521

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[7-(acetyloxy)-4,9-dimethyl-3,11-dioxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-4-en-9-yl]-2-methylpenta-2,4-dienoic acid

> <ALOGPS_LOGP>
2.82

> <JCHEM_LOGP>
2.7094033896666656

> <ALOGPS_LOGS>
-4.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.90317327911383

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.242397964220837

> <JCHEM_PKA_STRONGEST_BASIC>
-4.859162422786965

> <JCHEM_POLAR_SURFACE_AREA>
106.97000000000001

> <JCHEM_REFRACTIVITY>
105.33839999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.37e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[7-(acetyloxy)-4,9-dimethyl-3,11-dioxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-4-en-9-yl]-2-methylpenta-2,4-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      -1.867  -0.270   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.376  -0.656   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.035  -2.140   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.855   0.597   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.557  -0.327   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.482  -1.558   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.022  -1.603   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.016  -0.427   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.646  -0.587   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.152   1.111   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.897   2.698   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.350   1.792   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.943   1.164   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.488   1.132   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.752  -0.221   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.350  -1.640   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.833  -2.056   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.319  -2.973   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.083  -1.157   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.159   0.381   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.441   1.678   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.752  -3.533   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.020  -5.137   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.463  -5.676   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.717  -7.195   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.528  -8.175   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.159  -7.735   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.348  -6.755   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       5.413  -9.254   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   13   16                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    5   14   20                                             
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    5   17                                                  
CONECT   17   16   18   19   22                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   13   21                                                  
CONECT   21   20                                                            
CONECT   22   17   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

View in JSmol

Synonyms

Value	Source
5-[7-(Acetyloxy)-4,9-dimethyl-3,11-dioxo-10-oxatricyclo[6.3.2.0,]tridec-4-en-9-yl]-2-methylpenta-2,4-dienoate	Generator
5-[7-(Acetyloxy)-4,9-dimethyl-3,11-dioxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-4-en-9-yl]-2-methylpenta-2,4-dienoate	Generator

Chemical Formula

C₂₂H₂₆O₇

Average Mass

402.4430 Da

Monoisotopic Mass

402.16785 Da

IUPAC Name

5-[7-(acetyloxy)-4,9-dimethyl-3,11-dioxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-4-en-9-yl]-2-methylpenta-2,4-dienoic acid

Traditional Name

5-[7-(acetyloxy)-4,9-dimethyl-3,11-dioxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-4-en-9-yl]-2-methylpenta-2,4-dienoic acid

CAS Registry Number

Not Available

SMILES

CC(=O)OC12CC=C(C)C(=O)CC11CCC2C(C)(OC1=O)C=CC=C(C)C(O)=O

InChI Identifier

InChI=1S/C22H26O7/c1-13-7-11-22(28-15(3)23)17-8-10-21(22,12-16(13)24)19(27)29-20(17,4)9-5-6-14(2)18(25)26/h5-7,9,17H,8,10-12H2,1-4H3,(H,25,26)

InChI Key

UBHOILGODYTXTA-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Pseudolarix amabilis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Prenyldaucane diterpenoid
Tricarboxylic acid or derivatives
Caprolactone
Delta valerolactone
Delta_valerolactone
Oxepane
Oxane
Carboxylic acid ester
Ketone
Lactone
Cyclic ketone
Oxacycle
Carboxylic acid
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organooxygen compound
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	2.82	ALOGPS
logP	2.71	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	4.24	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	106.97 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	105.34 m³·mol⁻¹	ChemAxon
Polarizability	41.17 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-[7-(acetyloxy)-4,9-dimethyl-3,11-dioxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-4-en-9-yl]-2-methylpenta-2,4-dienoic acid (NP0221098)

MOL for NP0221098 (5-[7-(acetyloxy)-4,9-dimethyl-3,11-dioxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-4-en-9-yl]-2-methylpenta-2,4-dienoic acid)

3D MOL for NP0221098 (5-[7-(acetyloxy)-4,9-dimethyl-3,11-dioxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-4-en-9-yl]-2-methylpenta-2,4-dienoic acid)

3D SDF for NP0221098 (5-[7-(acetyloxy)-4,9-dimethyl-3,11-dioxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-4-en-9-yl]-2-methylpenta-2,4-dienoic acid)

3D-SDF for NP0221098 (5-[7-(acetyloxy)-4,9-dimethyl-3,11-dioxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-4-en-9-yl]-2-methylpenta-2,4-dienoic acid)

PDB for NP0221098 (5-[7-(acetyloxy)-4,9-dimethyl-3,11-dioxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-4-en-9-yl]-2-methylpenta-2,4-dienoic acid)

3D PDB for NP0221098 (5-[7-(acetyloxy)-4,9-dimethyl-3,11-dioxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-4-en-9-yl]-2-methylpenta-2,4-dienoic acid)

SMILES for NP0221098 (5-[7-(acetyloxy)-4,9-dimethyl-3,11-dioxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-4-en-9-yl]-2-methylpenta-2,4-dienoic acid)

INCHI for NP0221098 (5-[7-(acetyloxy)-4,9-dimethyl-3,11-dioxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-4-en-9-yl]-2-methylpenta-2,4-dienoic acid)

Structure for NP0221098 (5-[7-(acetyloxy)-4,9-dimethyl-3,11-dioxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-4-en-9-yl]-2-methylpenta-2,4-dienoic acid)

3D Structure for NP0221098 (5-[7-(acetyloxy)-4,9-dimethyl-3,11-dioxo-10-oxatricyclo[6.3.2.0¹,⁷]tridec-4-en-9-yl]-2-methylpenta-2,4-dienoic acid)