NP-MRD: Showing NP-Card for 3beta-Hydroxycinnamolide (NP0049324)

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Record Information

Version

2.0

Created at

2022-03-17 21:10:39 UTC

Updated at

2022-03-17 21:10:39 UTC

NP-MRD ID

NP0049324

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3beta-Hydroxycinnamolide

Description

3Beta-Hydroxycinnamolide belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. 3Beta-Hydroxycinnamolide is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3beta-Hydroxycinnamolide has been detected, but not quantified in, mushrooms. 3beta-Hydroxycinnamolide is found in Marasmius oreades , Polyporus arcularius and Warburgia stuhlmannii. This could make 3beta-hydroxycinnamolide a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061310532D          

 18 20  0  0  0  0            999 V2000
    0.4930    1.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4416    1.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9291   -0.3403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4083    1.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837    1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1045   -0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963   -0.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983    1.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3637    0.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1101    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995    0.8656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3245    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5391    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9347    0.4640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2295    1.3982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6601    0.0428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  7  6  1  0  0  0  0
  9  4  2  0  0  0  0
 10  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 13  9  1  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15  3  1  0  0  0  0
 15  7  1  0  0  0  0
 15 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16 12  1  0  0  0  0
 17 13  2  0  0  0  0
 18  8  1  0  0  0  0
 18 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049324

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C(O)CCC2(C)C3COC(=O)C3=CCC12

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O3/c1-14(2)11-5-4-9-10(8-18-13(9)17)15(11,3)7-6-12(14)16/h4,10-12,16H,5-8H2,1-3H3

> <INCHI_KEY>
BXRHNOVSIVSFJG-UHFFFAOYSA-N

> <FORMULA>
C15H22O3

> <MOLECULAR_WEIGHT>
250.3334

> <EXACT_MASS>
250.15689457

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.47357860524702

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-6,6,9a-trimethyl-1H,3H,5H,5aH,6H,7H,8H,9H,9aH,9bH-naphtho[1,2-c]furan-3-one

> <ALOGPS_LOGP>
3.08

> <JCHEM_LOGP>
2.2223947609999994

> <ALOGPS_LOGS>
-2.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.55417804443019

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8068021470996082

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
69.14120000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.63e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-hydroxy-6,6,9a-trimethyl-1H,5H,5aH,7H,8H,9H,9bH-naphtho[1,2-c]furan-3-one

> <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       0.920   3.635   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.824   2.699   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.601  -0.635   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.495   3.340   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.956   3.388   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.522  -0.539   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.062  -0.587   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.406  -0.502   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.223   1.983   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.412   0.674   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.145   2.079   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.206   0.818   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.719   1.616   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.606   2.127   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.873   0.722   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.745   0.866   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       7.895   2.610   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.832   0.080   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3   15                                                            
CONECT    4    5    9                                                       
CONECT    5    4   11                                                       
CONECT    6    7   12                                                       
CONECT    7    6   15                                                       
CONECT    8   10   18                                                       
CONECT    9    4   10   13                                                  
CONECT   10    8    9   15                                                  
CONECT   11    5   14   15                                                  
CONECT   12    6   14   16                                                  
CONECT   13    9   17   18                                                  
CONECT   14    1    2   11   12                                             
CONECT   15    3    7   10   11                                             
CONECT   16   12                                                            
CONECT   17   13                                                            
CONECT   18    8   13                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Value	Source
3b-Hydroxycinnamolide	Generator
3Β-hydroxycinnamolide	Generator
3beta-Hydroxycinnamolide	MeSH
3-Hydroxycinnamolide	MeSH

Chemical Formula

C₁₅H₂₂O₃

Average Mass

250.3334 Da

Monoisotopic Mass

250.15689 Da

IUPAC Name

7-hydroxy-6,6,9a-trimethyl-1H,3H,5H,5aH,6H,7H,8H,9H,9aH,9bH-naphtho[1,2-c]furan-3-one

Traditional Name

7-hydroxy-6,6,9a-trimethyl-1H,5H,5aH,7H,8H,9H,9bH-naphtho[1,2-c]furan-3-one

CAS Registry Number

Not Available

SMILES

CC1(C)C(O)CCC2(C)C3COC(=O)C3=CCC12

InChI Identifier

InChI=1S/C15H22O3/c1-14(2)11-5-4-9-10(8-18-13(9)17)15(11,3)7-6-12(14)16/h4,10-12,16H,5-8H2,1-3H3

InChI Key

BXRHNOVSIVSFJG-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Agaricus bisporus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Marasmius oreades	Fungi	KNApSAcK
Pleurotus ostreatus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Polyporus arcularius	LOTUS Database	35616633
Warburgia stuhlmannii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
Gamma butyrolactone
Cyclic alcohol
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
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	3.08	ALOGPS
logP	2.22	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	19.55	ChemAxon
pKa (Strongest Basic)	-0.81	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.14 m³·mol⁻¹	ChemAxon
Polarizability	27.47 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

HMDB0039156

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018676

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

14433053

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3beta-Hydroxycinnamolide (NP0049324)

MOL for NP0049324 (3beta-Hydroxycinnamolide)

3D MOL for NP0049324 (3beta-Hydroxycinnamolide)

3D SDF for NP0049324 (3beta-Hydroxycinnamolide)

3D-SDF for NP0049324 (3beta-Hydroxycinnamolide)

PDB for NP0049324 (3beta-Hydroxycinnamolide)

3D PDB for NP0049324 (3beta-Hydroxycinnamolide)

SMILES for NP0049324 (3beta-Hydroxycinnamolide)

INCHI for NP0049324 (3beta-Hydroxycinnamolide)

Structure for NP0049324 (3beta-Hydroxycinnamolide)

3D Structure for NP0049324 (3beta-Hydroxycinnamolide)