NP-MRD: Showing NP-Card for Dihydrocumambrin A (NP0048525)

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Record Information

Version

2.0

Created at

2022-03-17 20:57:49 UTC

Updated at

2022-03-17 20:57:50 UTC

NP-MRD ID

NP0048525

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dihydrocumambrin A

Description

Dihydrocumambrin A belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Dihydrocumambrin A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Dihydrocumambrin A has been detected, but not quantified in, garland chrysanthemums and herbs and spices. Dihydrocumambrin A is found in Eriocephalus giessii and Polychrysum tadshikorum. This could make dihydrocumambrin a a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061309112D          

 22 24  0  0  0  0            999 V2000
    3.8305   -1.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8656    0.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3431    3.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8217    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534    1.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9881    2.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265    0.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8409   -0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7560    2.9069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9461   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    2.0796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8651    1.7897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  1  1  0  0  0  0
  8  5  2  0  0  0  0
  9  2  1  0  0  0  0
 10  3  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 13  8  1  0  0  0  0
 13 11  1  0  0  0  0
 14  9  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16  9  1  0  0  0  0
 17  4  1  0  0  0  0
 17  7  1  0  0  0  0
 17 11  1  0  0  0  0
 18 10  2  0  0  0  0
 19 16  2  0  0  0  0
 20 17  1  0  0  0  0
 21 10  1  0  0  0  0
 21 12  1  0  0  0  0
 22 15  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048525

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2C(OC1=O)C1C(CC=C1C)C(C)(O)CC2OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H24O5/c1-8-5-6-11-13(8)15-14(9(2)16(19)22-15)12(21-10(3)18)7-17(11,4)20/h5,9,11-15,20H,6-7H2,1-4H3

> <INCHI_KEY>
ACKIMLHJQRKFGM-UHFFFAOYSA-N

> <FORMULA>
C17H24O5

> <MOLECULAR_WEIGHT>
308.3695

> <EXACT_MASS>
308.162373878

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
32.746817302870674

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-hydroxy-3,6,9-trimethyl-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate

> <ALOGPS_LOGP>
1.91

> <JCHEM_LOGP>
0.9312750329999995

> <ALOGPS_LOGS>
-2.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.67057039449124

> <JCHEM_PKA_STRONGEST_BASIC>
-2.942892509449532

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
79.82369999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-3,6,9-trimethyl-2-oxo-3H,3aH,4H,5H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       7.150  -3.052   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.616   1.186   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.507   5.824   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.001   2.381   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.176  -1.200   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.245   0.338   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.073   3.049   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.691  -1.610   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.901   0.338   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.711   4.864   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.803   0.879   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.686   2.381   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.843  -0.325   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.343   0.879   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.303  -0.325   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.970  -1.200   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.461   2.381   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.145   5.426   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.766  -2.160   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       7.803   3.882   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       3.482   3.341   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.455  -1.610   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4   17                                                            
CONECT    5    6    8                                                       
CONECT    6    5   11                                                       
CONECT    7   12   17                                                       
CONECT    8    1    5   13                                                  
CONECT    9    2   14   16                                                  
CONECT   10    3   18   21                                                  
CONECT   11    6   13   17                                                  
CONECT   12    7   14   21                                                  
CONECT   13    8   11   15                                                  
CONECT   14    9   12   15                                                  
CONECT   15   13   14   22                                                  
CONECT   16    9   19   22                                                  
CONECT   17    4    7   11   20                                             
CONECT   18   10                                                            
CONECT   19   16                                                            
CONECT   20   17                                                            
CONECT   21   10   12                                                       
CONECT   22   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
6-Hydroxy-3,6,9-trimethyl-2-oxo-2H,3H,3ah,4H,5H,6H,6ah,7H,9ah,9BH-azuleno[4,5-b]furan-4-yl acetic acid	Generator

Chemical Formula

C₁₇H₂₄O₅

Average Mass

308.3695 Da

Monoisotopic Mass

308.16237 Da

IUPAC Name

6-hydroxy-3,6,9-trimethyl-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate

Traditional Name

6-hydroxy-3,6,9-trimethyl-2-oxo-3H,3aH,4H,5H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl acetate

CAS Registry Number

20482-39-7

SMILES

CC1C2C(OC1=O)C1C(CC=C1C)C(C)(O)CC2OC(C)=O

InChI Identifier

InChI=1S/C17H24O5/c1-8-5-6-11-13(8)15-14(9(2)16(19)22-15)12(21-10(3)18)7-17(11,4)20/h5,9,11-15,20H,6-7H2,1-4H3

InChI Key

ACKIMLHJQRKFGM-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Chrysanthemum coronarium	FooDB	KNAPSACK
Eriocephalus giessii	Plant	KNApSAcK
Polychrysum tadshikorum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Guaiane sesquiterpenoid
Sesquiterpenoid
Dicarboxylic acid or derivatives
Gamma butyrolactone
Cyclic alcohol
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
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	1.91	ALOGPS
logP	0.93	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	14.67	ChemAxon
pKa (Strongest Basic)	-2.9	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	79.82 m³·mol⁻¹	ChemAxon
Polarizability	32.75 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

HMDB0036489

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015386

KNApSAcK ID

C00020480

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

13895575

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Dihydrocumambrin A (NP0048525)

MOL for NP0048525 (Dihydrocumambrin A)

3D MOL for NP0048525 (Dihydrocumambrin A)

3D SDF for NP0048525 (Dihydrocumambrin A)

3D-SDF for NP0048525 (Dihydrocumambrin A)

PDB for NP0048525 (Dihydrocumambrin A)

3D PDB for NP0048525 (Dihydrocumambrin A)

SMILES for NP0048525 (Dihydrocumambrin A)

INCHI for NP0048525 (Dihydrocumambrin A)

Structure for NP0048525 (Dihydrocumambrin A)

3D Structure for NP0048525 (Dihydrocumambrin A)