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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 20:31:36 UTC

Update Date

2022-09-22 18:34:49 UTC

HMDB ID

HMDB0341338

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Marrubiin

Description

Marrubiin belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Based on a literature review a significant number of articles have been published on Marrubiin.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309092223092D          

 27 30  0  0  1  0            999 V2000
    1.6051   -0.3412    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6913    0.4793    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9377    0.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8514   -0.6767    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7652   -1.4972    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0978   -1.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5189   -1.1617    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9802   -1.8456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9254   -1.7347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1250   -2.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9180   -2.7626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5681   -2.2547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2521   -2.7161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0247   -3.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2002   -3.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2725   -0.8261    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3019   -1.6506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1987   -1.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8661   -0.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7799    0.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0262    0.4793    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6393    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7713    1.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2562    1.9314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9463    1.2639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3588   -0.0056    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0732   -0.4181    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  6  0  0  0
  4  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 11 15  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
  2 25  1  0  0  0  0
 21 26  1  0  0  0  0
  2 26  1  0  0  0  0
 16 26  1  0  0  0  0
 26 27  1  6  0  0  0
M  END


  Mrv1652309092223092D          

 27 30  0  0  1  0            999 V2000
    1.6051   -0.3412    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6913    0.4793    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9377    0.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8514   -0.6767    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7652   -1.4972    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0978   -1.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5189   -1.1617    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9802   -1.8456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9254   -1.7347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1250   -2.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9180   -2.7626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5681   -2.2547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2521   -2.7161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0247   -3.5091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2002   -3.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2725   -0.8261    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3019   -1.6506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1987   -1.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8661   -0.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7799    0.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0262    0.4793    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6393    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7713    1.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2562    1.9314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9463    1.2639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3588   -0.0056    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0732   -0.4181    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  6  0  0  0
  4  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 11 15  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
  2 25  1  0  0  0  0
 21 26  1  0  0  0  0
  2 26  1  0  0  0  0
 16 26  1  0  0  0  0
 26 27  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0341338

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12C[C@@]([H])(C)[C@](O)(CCC3=COC=C3)[C@@]3(C)CCC[C@](C)(C(=O)O1)[C@]23[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O4/c1-13-11-15-16-18(2,17(21)24-15)7-4-8-19(16,3)20(13,22)9-5-14-6-10-23-12-14/h6,10,12-13,15-16,22H,4-5,7-9,11H2,1-3H3/t13-,15-,16+,18+,19+,20-/m1/s1

> <INCHI_KEY>
HQLLRHCTVDVUJB-OBHOOXMTSA-N

> <FORMULA>
C20H28O4

> <MOLECULAR_WEIGHT>
332.44

> <EXACT_MASS>
332.198759382

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
36.07430960744018

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4S,8S,9R,10R,12R)-9-[2-(furan-3-yl)ethyl]-9-hydroxy-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0^{4,12}]dodecan-3-one

> <JCHEM_LOGP>
3.757252853666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.171482542909505

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7860097992315023

> <JCHEM_POLAR_SURFACE_AREA>
59.67

> <JCHEM_REFRACTIVITY>
89.77799999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4S,8S,9R,10R,12R)-9-[2-(furan-3-yl)ethyl]-9-hydroxy-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0^{4,12}]dodecan-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  H   UNK     0       2.996  -0.637   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       3.157   0.895   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.750   0.268   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.589  -1.263   0.000  0.00  0.00           C+0
HETATM    5  H   UNK     0       1.428  -2.795   0.000  0.00  0.00           H+0
HETATM    6  C   UNK     0       0.182  -1.890   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.835  -2.168   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.696  -3.445   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.727  -3.238   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.100  -4.732   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.580  -5.157   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.794  -4.209   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.071  -5.070   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.646  -6.550   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.107  -6.604   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.242  -1.542   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.297  -3.081   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.971  -2.168   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.217  -1.263   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.056   0.268   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.649   0.895   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.793   1.925   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.173   2.359   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.078   3.605   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       3.633   2.359   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.403  -0.010   0.000  0.00  0.00           C+0
HETATM   27  H   UNK     0       5.737  -0.780   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   25   26                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    6    7                                             
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    4    8    9   16                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   11                                                       
CONECT   16    7   17   18   26                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   26                                             
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23    2                                                       
CONECT   26   21    2   16   27                                             
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₀H₂₈O₄

Average Molecular Weight

332.44

Monoisotopic Molecular Weight

332.198759382

IUPAC Name

(1R,4S,8S,9R,10R,12R)-9-[2-(furan-3-yl)ethyl]-9-hydroxy-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0^{4,12}]dodecan-3-one

Traditional Name

(1R,4S,8S,9R,10R,12R)-9-[2-(furan-3-yl)ethyl]-9-hydroxy-4,8,10-trimethyl-2-oxatricyclo[6.3.1.0^{4,12}]dodecan-3-one

CAS Registry Number

Not Available

SMILES

[H][C@]12C[C@@]([H])(C)[C@](O)(CCC3=COC=C3)[C@@]3(C)CCC[C@](C)(C(=O)O1)[C@]23[H]

InChI Identifier

InChI=1S/C20H28O4/c1-13-11-15-16-18(2,17(21)24-15)7-4-8-19(16,3)20(13,22)9-5-14-6-10-23-12-14/h6,10,12-13,15-16,22H,4-5,7-9,11H2,1-3H3/t13-,15-,16+,18+,19+,20-/m1/s1

InChI Key

HQLLRHCTVDVUJB-OBHOOXMTSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Cyclic alcohol
Furan
Heteroaromatic compound
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

gamma-lactone (CHEBI:6696 )
Diterpenoids (C20) (C09128 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.76	ChemAxon
pKa (Strongest Acidic)	14.17	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59.67 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	89.78 m³·mol⁻¹	ChemAxon
Polarizability	36.07 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Retention Times

Not Available

Predicted Kovats Retention Indices

Not Available

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00003452

Chemspider ID

66118

KEGG Compound ID

C09128

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73401

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1699721

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simon-Manso Y, Marupaka R, Yan X, Liang Y, Telu KH, Mirokhin Y, Stein SE: Mass Spectrometry Fingerprints of Small-Molecule Metabolites in Biofluids: Building a Spectral Library of Recurrent Spectra for Urine Analysis. Anal Chem. 2019 Sep 17;91(18):12021-12029. doi: 10.1021/acs.analchem.9b02977. Epub 2019 Aug 30. [PubMed:31424920 ]

Showing metabocard for Marrubiin (HMDB0341338)

MOL for HMDB0341338 (Marrubiin)

3D MOL for HMDB0341338 (Marrubiin)

3D SDF for HMDB0341338 (Marrubiin)

3D-SDF for HMDB0341338 (Marrubiin)

PDB for HMDB0341338 (Marrubiin)

3D PDB for HMDB0341338 (Marrubiin)

SMILES for HMDB0341338 (Marrubiin)

INCHI for HMDB0341338 (Marrubiin)

Structure for HMDB0341338 (Marrubiin)

3D Structure for HMDB0341338 (Marrubiin)

Predicted Retention Times

Predicted Kovats Retention Indices