NP-MRD: Showing NP-Card for (+)-Myrrhanone B (NP0072259)

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Record Information

Version

2.0

Created at

2022-04-28 17:37:19 UTC

Updated at

2022-04-28 17:37:20 UTC

NP-MRD ID

NP0072259

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Myrrhanone B

Description

(2E,6E,10E)-13-[(1R,2R,4aR,8aR)-2-hydroxy-2,5,5,8a-tetramethyl-6-oxo-decahydronaphthalen-1-yl]-2,6,10-trimethyltrideca-2,6,10-trienoic acid belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (+)-Myrrhanone B is found in Balsamodendron mukul HOOK. and Commiphora mukul . Based on a literature review very few articles have been published on (2E,6E,10E)-13-[(1R,2R,4aR,8aR)-2-hydroxy-2,5,5,8a-tetramethyl-6-oxo-decahydronaphthalen-1-yl]-2,6,10-trimethyltrideca-2,6,10-trienoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282219372D          

 34 35  0  0  1  0            999 V2000
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  4 33  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652304282219372D          

 34 35  0  0  1  0            999 V2000
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  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  1  0  0  0
  9 12  1  1  0  0  0
  9 13  1  6  0  0  0
  8 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 25 29  1  0  0  0  0
 21 30  1  0  0  0  0
 17 31  1  0  0  0  0
  6 32  1  6  0  0  0
  4 33  1  0  0  0  0
  4 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0072259

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O4/c1-21(13-9-15-23(3)27(32)33)11-8-12-22(2)14-10-16-25-29(6)19-18-26(31)28(4,5)24(29)17-20-30(25,7)34/h11,14-15,24-25,34H,8-10,12-13,16-20H2,1-7H3,(H,32,33)/b21-11+,22-14+,23-15+/t24-,25+,29+,30+/m0/s1

> <INCHI_KEY>
RLNHWDNOTXLOJQ-JMLPEAIGSA-N

> <FORMULA>
C30H48O4

> <MOLECULAR_WEIGHT>
472.71

> <EXACT_MASS>
472.355260026

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
57.8746888603389

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,6E,10E)-13-[(1R,2R,4aR,8aR)-2-hydroxy-2,5,5,8a-tetramethyl-6-oxo-decahydronaphthalen-1-yl]-2,6,10-trimethyltrideca-2,6,10-trienoic acid

> <ALOGPS_LOGP>
6.72

> <JCHEM_LOGP>
7.316357976666666

> <ALOGPS_LOGS>
-5.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.94298494487467

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.0711590355696154

> <JCHEM_PKA_STRONGEST_BASIC>
-0.43545688979153907

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
142.19930000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.10e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,6E,10E)-13-[(1R,2R,4aR,8aR)-2-hydroxy-2,5,5,8a-tetramethyl-6-oxo-hexahydronaphthalen-1-yl]-2,6,10-trimethyltrideca-2,6,10-trienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.817   0.536   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.540  -0.716   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002  10.780   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.336  11.550   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.336  13.090   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.669  13.860   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.669  15.400   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.336  16.170   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      12.003  16.170   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      12.003  13.090   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.723  -4.440   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.723  -4.440   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   33   34                                             
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8   32                                             
CONECT    7    6    1                                                       
CONECT    8    6    9   14                                                  
CONECT    9    8   10   12   13                                             
CONECT   10    9   11                                                       
CONECT   11   10    5                                                       
CONECT   12    9                                                            
CONECT   13    9                                                            
CONECT   14    8   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   31                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   30                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   29                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   25                                                            
CONECT   30   21                                                            
CONECT   31   17                                                            
CONECT   32    6                                                            
CONECT   33    4                                                            
CONECT   34    4                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   70    0
END

View in JSmol

Synonyms

Value	Source
(2E,6E,10E)-13-[(1R,2R,4AR,8ar)-2-hydroxy-2,5,5,8a-tetramethyl-6-oxo-decahydronaphthalen-1-yl]-2,6,10-trimethyltrideca-2,6,10-trienoate	Generator

Chemical Formula

C₃₀H₄₈O₄

Average Mass

472.7100 Da

Monoisotopic Mass

472.35526 Da

IUPAC Name

(2E,6E,10E)-13-[(1R,2R,4aR,8aR)-2-hydroxy-2,5,5,8a-tetramethyl-6-oxo-decahydronaphthalen-1-yl]-2,6,10-trimethyltrideca-2,6,10-trienoic acid

Traditional Name

(2E,6E,10E)-13-[(1R,2R,4aR,8aR)-2-hydroxy-2,5,5,8a-tetramethyl-6-oxo-hexahydronaphthalen-1-yl]-2,6,10-trimethyltrideca-2,6,10-trienoic acid

CAS Registry Number

Not Available

SMILES

C\C(CC\C=C(/C)CC\C=C(/C)C(O)=O)=C/CC[C@H]1[C@](C)(O)CC[C@H]2C(C)(C)C(=O)CC[C@@]12C

InChI Identifier

InChI=1S/C30H48O4/c1-21(13-9-15-23(3)27(32)33)11-8-12-22(2)14-10-16-25-29(6)19-18-26(31)28(4,5)24(29)17-20-30(25,7)34/h11,14-15,24-25,34H,8-10,12-13,16-20H2,1-7H3,(H,32,33)/b21-11+,22-14+,23-15+/t24-,25+,29+,30+/m0/s1

InChI Key

RLNHWDNOTXLOJQ-JMLPEAIGSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Balsamodendron mukul HOOK.	Plant	KNApSAcK
Commiphora mukul	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Long-chain fatty acid
Methyl-branched fatty acid
Hydroxy fatty acid
Branched fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Tertiary alcohol
Cyclic alcohol
Cyclic ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	6.72	ALOGPS
logP	7.32	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	5.07	ChemAxon
pKa (Strongest Basic)	-0.44	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	142.2 m³·mol⁻¹	ChemAxon
Polarizability	57.87 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

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

162876648

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (+)-Myrrhanone B (NP0072259)

MOL for NP0072259 ((+)-Myrrhanone B)

3D MOL for NP0072259 ((+)-Myrrhanone B)

3D SDF for NP0072259 ((+)-Myrrhanone B)

3D-SDF for NP0072259 ((+)-Myrrhanone B)

PDB for NP0072259 ((+)-Myrrhanone B)

3D PDB for NP0072259 ((+)-Myrrhanone B)

SMILES for NP0072259 ((+)-Myrrhanone B)

INCHI for NP0072259 ((+)-Myrrhanone B)

Structure for NP0072259 ((+)-Myrrhanone B)

3D Structure for NP0072259 ((+)-Myrrhanone B)