NP-MRD: Showing NP-Card for 4,11,13,15-Tetrahydroridentin B (NP0048468)

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Record Information

Version

2.0

Created at

2022-03-17 20:56:56 UTC

Updated at

2022-03-17 20:56:56 UTC

NP-MRD ID

NP0048468

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,11,13,15-Tetrahydroridentin B

Description

4,11,13,15-Tetrahydroridentin B belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. 4,11,13,15-Tetrahydroridentin B is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 4,11,13,15-Tetrahydroridentin B has been detected, but not quantified in, several different foods, such as alcoholic beverages, beverages, coffee and coffee products, dandelions, and tea. 4,11,13,15-Tetrahydroridentin B is found in Taraxacum erythrospermum. This could make 4,11,13,15-tetrahydroridentin b a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241209282D          

 20 22  0  0  0  0            999 V2000
   -1.0814    1.1254    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7959    0.7129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7959   -0.1121    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0814   -0.5246    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3669   -0.1121    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3669    0.7129    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3475    1.1254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3475   -0.5246    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0620   -0.1121    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0620    0.7129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5190   -1.3316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3395   -1.4178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6751   -0.6642    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0814    1.9504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5103   -0.5246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0814   -1.3496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3669    1.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3669   -0.9371    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4820   -0.4927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7520   -2.1323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  6  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  9 10  1  0  0  0  0
  7 10  1  0  0  0  0
  9 13  1  1  0  0  0
  9  8  1  0  0  0  0
  8 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  1 14  1  1  0  0  0
  3 15  1  1  0  0  0
  4 16  1  1  0  0  0
  6 17  1  1  0  0  0
  5 18  1  6  0  0  0
 13 19  1  6  0  0  0
 12 20  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0048468

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12[C@H]3OC(=O)[C@@H](C)[C@@H]3CC[C@@]1(C)[C@H](O)C[C@H](O)[C@@H]2C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O4/c1-7-9-4-5-15(3)11(17)6-10(16)8(2)12(15)13(9)19-14(7)18/h7-13,16-17H,4-6H2,1-3H3/t7-,8-,9-,10-,11+,12+,13-,15-/m0/s1

> <INCHI_KEY>
GAPZIAIPNAGPQZ-UIUPBXLSSA-N

> <FORMULA>
C15H24O4

> <MOLECULAR_WEIGHT>
268.3487

> <EXACT_MASS>
268.167459256

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
29.566983943427516

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,3aS,5aR,6R,8S,9R,9aS,9bS)-6,8-dihydroxy-3,5a,9-trimethyl-dodecahydronaphtho[1,2-b]furan-2-one

> <ALOGPS_LOGP>
0.71

> <JCHEM_LOGP>
1.0295502886666665

> <ALOGPS_LOGS>
-1.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.156543062544007

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.419036502717692

> <JCHEM_PKA_STRONGEST_BASIC>
-2.859808616362498

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
69.6039

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.62e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,3aS,5aR,6R,8S,9R,9aS,9bS)-6,8-dihydroxy-3,5a,9-trimethyl-decahydronaphtho[1,2-b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.019   2.101   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.352   1.331   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.352  -0.209   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.019  -0.979   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.685  -0.209   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.685   1.331   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.649   2.101   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.649  -0.979   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.982  -0.209   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.982   1.331   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.969  -2.486   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.500  -2.647   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.127  -1.240   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.019   3.641   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -4.686  -0.979   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.019  -2.519   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.685   2.871   0.000  0.00  0.00           C+0
HETATM   18  H   UNK     0      -0.685  -1.749   0.000  0.00  0.00           H+0
HETATM   19  C   UNK     0       4.633  -0.920   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.270  -3.980   0.000  0.00  0.00           O+0
CONECT    1    2    6   14                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5   16                                                  
CONECT    5    4    6    8   18                                             
CONECT    6    1    7    5   17                                             
CONECT    7    6   10                                                       
CONECT    8    5    9   11                                                  
CONECT    9   10   13    8                                                  
CONECT   10    9    7                                                       
CONECT   11    8   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13    9   12   19                                                  
CONECT   14    1                                                            
CONECT   15    3                                                            
CONECT   16    4                                                            
CONECT   17    6                                                            
CONECT   18    5                                                            
CONECT   19   13                                                            
CONECT   20   12                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
4alpha(15), 11beta(13)-Tetrahydroridentin b	HMDB

Chemical Formula

C₁₅H₂₄O₄

Average Mass

268.3487 Da

Monoisotopic Mass

268.16746 Da

IUPAC Name

(3S,3aS,5aR,6R,8S,9R,9aS,9bS)-6,8-dihydroxy-3,5a,9-trimethyl-dodecahydronaphtho[1,2-b]furan-2-one

Traditional Name

(3S,3aS,5aR,6R,8S,9R,9aS,9bS)-6,8-dihydroxy-3,5a,9-trimethyl-decahydronaphtho[1,2-b]furan-2-one

CAS Registry Number

75991-58-1

SMILES

[H][C@@]12[C@H]3OC(=O)[C@@H](C)[C@@H]3CC[C@@]1(C)[C@H](O)C[C@H](O)[C@@H]2C

InChI Identifier

InChI=1S/C15H24O4/c1-7-9-4-5-15(3)11(17)6-10(16)8(2)12(15)13(9)19-14(7)18/h7-13,16-17H,4-6H2,1-3H3/t7-,8-,9-,10-,11+,12+,13-,15-/m0/s1

InChI Key

GAPZIAIPNAGPQZ-UIUPBXLSSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Coffea arabica L.	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephora	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Taraxacum erythrospermum	LOTUS Database	35616633
Taraxacum officinale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Eudesmanolides, secoeudesmanolides, and derivatives

Alternative Parents

Substituents

Eudesmanolide
Sesquiterpenoid
Naphthofuran
Gamma butyrolactone
Cyclic alcohol
Tetrahydrofuran
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	0.71	ALOGPS
logP	1.03	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	14.42	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	69.6 m³·mol⁻¹	ChemAxon
Polarizability	29.57 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

HMDB0036150

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015001

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

15540432

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 4,11,13,15-Tetrahydroridentin B (NP0048468)

MOL for NP0048468 (4,11,13,15-Tetrahydroridentin B)

3D MOL for NP0048468 (4,11,13,15-Tetrahydroridentin B)

3D SDF for NP0048468 (4,11,13,15-Tetrahydroridentin B)

3D-SDF for NP0048468 (4,11,13,15-Tetrahydroridentin B)

PDB for NP0048468 (4,11,13,15-Tetrahydroridentin B)

3D PDB for NP0048468 (4,11,13,15-Tetrahydroridentin B)

SMILES for NP0048468 (4,11,13,15-Tetrahydroridentin B)

INCHI for NP0048468 (4,11,13,15-Tetrahydroridentin B)

Structure for NP0048468 (4,11,13,15-Tetrahydroridentin B)

3D Structure for NP0048468 (4,11,13,15-Tetrahydroridentin B)