NP-MRD: Showing NP-Card for Cumambrin B (NP0048523)

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Record Information

Version

2.0

Created at

2022-03-17 20:57:48 UTC

Updated at

2022-03-17 20:57:48 UTC

NP-MRD ID

NP0048523

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cumambrin B

Description

Cumambrin B 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. Cumambrin B is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Cumambrin B has been detected, but not quantified in, sweet bay. This could make cumambrin b a potential biomarker for the consumption of these foods. Cumambrin b is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Cumambrin b belongs to guaianolides and derivatives class of compounds. Cumambrin b can be found in sweet bay, which makes cumambrin b a potential biomarker for the consumption of this food product. Cumambrin B is found in Ambrosia cumanensis , Ambrosia psilostachya, Anthemis carpatica, Artemisia cana, Artemisia nova, Artemisia tripartita, Chrysanthemum boreale, Chrysanthemum ornatum, Eriocephalus giessii, Plagius grandis, Polychrysum tadshikorum, Richteria pyrethroides, Tanacetum densum and Tanacetum santolina. Those are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azulenofuran-2-one or a derivative.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652310101707122D          

 19 21  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
    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
    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
    1.8651    1.7897    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
    2.3864   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  7  1  1  0  0  0  0
  7  4  2  0  0  0  0
  8  2  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 11  9  1  0  0  0  0
 12  8  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14  8  1  0  0  0  0
 15  3  1  0  0  0  0
 15  6  1  0  0  0  0
 15  9  1  0  0  0  0
 16 10  1  0  0  0  0
 17 14  2  0  0  0  0
 18 15  1  0  0  0  0
 19 13  1  0  0  0  0
 19 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048523

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CCC2C1C1OC(=O)C(=C)C1C(O)CC2(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O4/c1-7-4-5-9-11(7)13-12(8(2)14(17)19-13)10(16)6-15(9,3)18/h4,9-13,16,18H,2,5-6H2,1,3H3

> <INCHI_KEY>
NKXCPQWCIOWQOE-UHFFFAOYSA-N

> <FORMULA>
C15H20O4

> <MOLECULAR_WEIGHT>
264.3169

> <EXACT_MASS>
264.136159128

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
27.96379236507554

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,6-dihydroxy-6,9-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-2-one

> <ALOGPS_LOGP>
1.13

> <JCHEM_LOGP>
0.6318043270000004

> <ALOGPS_LOGS>
-1.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.082395252460461

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.378983854548459

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9350079812685426

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
70.4756

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.36e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,6-dihydroxy-6,9-dimethyl-3-methylidene-3aH,4H,5H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-OCT-17         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       9.001   2.381   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.176  -1.200   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.245   0.338   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.073   3.049   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.691  -1.610   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.901   0.338   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.803   0.879   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.686   2.381   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.843  -0.325   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.343   0.879   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.303  -0.325   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.970  -1.200   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.461   2.381   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.482   3.341   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.766  -2.161   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       7.803   3.882   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.455  -1.610   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3   15                                                            
CONECT    4    5    7                                                       
CONECT    5    4    9                                                       
CONECT    6   10   15                                                       
CONECT    7    1    4   11                                                  
CONECT    8    2   12   14                                                  
CONECT    9    5   11   15                                                  
CONECT   10    6   12   16                                                  
CONECT   11    7    9   13                                                  
CONECT   12    8   10   13                                                  
CONECT   13   11   12   19                                                  
CONECT   14    8   17   19                                                  
CONECT   15    3    6    9   18                                             
CONECT   16   10                                                            
CONECT   17   14                                                            
CONECT   18   15                                                            
CONECT   19   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₄

Average Mass

264.3169 Da

Monoisotopic Mass

264.13616 Da

IUPAC Name

4,6-dihydroxy-6,9-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-2-one

Traditional Name

4,6-dihydroxy-6,9-dimethyl-3-methylidene-3aH,4H,5H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-2-one

CAS Registry Number

21982-83-2

SMILES

CC1=CCC2C1C1OC(=O)C(=C)C1C(O)CC2(C)O

InChI Identifier

InChI=1S/C15H20O4/c1-7-4-5-9-11(7)13-12(8(2)14(17)19-13)10(16)6-15(9,3)18/h4,9-13,16,18H,2,5-6H2,1,3H3

InChI Key

NKXCPQWCIOWQOE-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ambrosia cumanensis	Plant	KNApSAcK
Ambrosia psilostachya	LOTUS Database	35616633
Anthemis carpatica	Plant	KNApSAcK
Artemisia cana	LOTUS Database	35616633
Artemisia nova	Plant	KNApSAcK
Artemisia tripartita	Plant	KNApSAcK
Chrysanthemum boreale	LOTUS Database	35616633
Chrysanthemum ornatum	LOTUS Database	35616633
Eriocephalus giessii	Plant	KNApSAcK
Laurus nobilis L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Plagius grandis	LOTUS Database	35616633
Polychrysum tadshikorum	LOTUS Database	35616633
Pyrethrum pyrethroides	LOTUS Database	35616633
Tanacetum densum	LOTUS Database	35616633
Tanacetum santolina	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
Gamma butyrolactone
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
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	1.13	ALOGPS
logP	0.63	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	14.38	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	70.48 m³·mol⁻¹	ChemAxon
Polarizability	27.96 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

HMDB0177208

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015384

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

99115

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Cumambrin B (NP0048523)

MOL for NP0048523 (Cumambrin B)

3D MOL for NP0048523 (Cumambrin B)

3D SDF for NP0048523 (Cumambrin B)

3D-SDF for NP0048523 (Cumambrin B)

PDB for NP0048523 (Cumambrin B)

3D PDB for NP0048523 (Cumambrin B)

SMILES for NP0048523 (Cumambrin B)

INCHI for NP0048523 (Cumambrin B)

Structure for NP0048523 (Cumambrin B)

3D Structure for NP0048523 (Cumambrin B)