NP-MRD: Showing NP-Card for (-)-Muzigadial (NP0051786)

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Record Information

Version

2.0

Created at

2022-04-27 23:01:15 UTC

Updated at

2022-04-27 23:01:15 UTC

NP-MRD ID

NP0051786

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Muzigadial

Description

Canellal, also known as muzigadial, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (-)-Muzigadial is found in Canella winterana , Warburghia ugandensis, Warburgia salutaris and Warburgia ugandensis. (-)-Muzigadial was first documented in 1998 (PMID: 9626931). Canellal is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
    2.1122    1.8620    0.8199 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6370    0.8786    0.0891 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5194   -0.1629   -0.4322 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8400   -0.1015    0.3018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8877   -1.5175   -0.1693 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4809   -1.5592   -0.6599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4054   -0.5334    0.0146 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6007   -0.9075    1.4363 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1879    0.8303   -0.1969 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5872    1.9249    0.4821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0053    1.7863    0.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5088    0.7048   -0.4333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9316    0.7033   -0.7887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6652    1.7243   -0.6065 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7501   -0.5418   -0.6898 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5140   -0.6679   -2.0671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5955   -1.6870   -0.2779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9860   -1.8568    0.8640 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5036    2.6706    1.2459 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1878    1.8902    1.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7082   -0.0830   -1.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4011   -1.0404    0.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6442   -0.0539    1.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4451    0.7332   -0.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0062   -1.7413    0.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4752   -2.2551   -0.7423 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0939   -2.5781   -0.5403 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4950   -1.3486   -1.7524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4731   -0.4447    1.9320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2807   -0.6990    2.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7491   -2.0060    1.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0917    1.0350   -1.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1661    2.9068    0.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5245    1.8787    1.5852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6574    2.6594    0.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4276   -0.1491   -1.2172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5291    0.2033   -2.5237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9211   -2.4570   -0.9911 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 12 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  2  0
 15  7  1  0
  7  8  1  1
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  1  0
  3  2  1  0
  2  1  2  3
  7  9  1  0
  2  9  1  0
  9 32  1  6
 10 33  1  0
 10 34  1  0
 11 35  1  0
 13 36  1  0
 16 37  1  0
 17 38  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  6 27  1  0
  6 28  1  0
  5 25  1  0
  5 26  1  0
  3 21  1  6
  4 22  1  0
  4 23  1  0
  4 24  1  0
  1 19  1  0
  1 20  1  0
M  END


  Mrv1652309272006272D          

 19 20  0  0  0  0            999 V2000
 9999.638910001.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.351910001.4548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.065510001.8673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.065510001.0423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.779110000.6257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.492710000.2152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9263 9998.1426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4972 9998.9699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6389 9998.5584    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.925010000.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.210510000.2116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2105 9999.3865    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.9250 9998.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6395 9999.3865    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.639510000.2116    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.351410000.6242    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.3514 9998.9742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0659 9999.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.065910000.2117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0  0  0  0
  5  6  2  0  0  0  0
 10 11  1  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 19  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 16  2  1  0  0  0  0
 16  4  1  6  0  0  0
 19  5  1  0  0  0  0
 13  7  2  0  0  0  0
 12  8  1  1  0  0  0
 16 15  1  0  0  0  0
 15  1  1  1  0  0  0
 14 17  1  0  0  0  0
 14  9  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0051786

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC=C(C=O)[C@](O)(C=O)[C@@]1(C)CC[C@H](C)C2=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-10-6-7-14(3)13(11(10)2)5-4-12(8-16)15(14,18)9-17/h4,8-10,13,18H,2,5-7H2,1,3H3/t10-,13-,14-,15+/m0/s1

> <INCHI_KEY>
LDAIOVKPAKFZHM-FBUXBERBSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.322

> <EXACT_MASS>
248.141244504

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
26.87008468157393

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4aS,6S,8aS)-1-hydroxy-6,8a-dimethyl-5-methylidene-1,4,4a,5,6,7,8,8a-octahydronaphthalene-1,2-dicarbaldehyde

> <ALOGPS_LOGP>
2.39

> <JCHEM_LOGP>
1.580427671333334

> <ALOGPS_LOGS>
-2.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.055220893205437

> <JCHEM_PKA_STRONGEST_BASIC>
-4.086846381311941

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
70.2037

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
muzigadial

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8665.9938668.608   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8667.3248669.382   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8668.6568670.152   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8668.6568668.612   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8669.9888667.835   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    8671.3208667.068   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8664.6628663.200   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8661.9958664.744   0.000  0.00  0.00           C+0
HETATM    9  H   UNK     0    8665.9938663.976   0.000  0.00  0.00           H+0
HETATM   10  C   UNK     0    8664.6608667.832   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8663.3268667.062   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8663.3268665.521   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8664.6608664.752   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8665.9948665.521   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8665.9948667.062   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8667.3238667.832   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8667.3238664.752   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8668.6568665.522   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8668.6568667.062   0.000  0.00  0.00           C+0
CONECT    1   15                                                            
CONECT    2    3   16                                                       
CONECT    3    2                                                            
CONECT    4   16                                                            
CONECT    5    6   19                                                       
CONECT    6    5                                                            
CONECT    7   13                                                            
CONECT    8   12                                                            
CONECT    9   14                                                            
CONECT   10   11   15                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13    8                                                  
CONECT   13   12   14    7                                                  
CONECT   14   13   15   17    9                                             
CONECT   15   10   14   16    1                                             
CONECT   16   19    2    4   15                                             
CONECT   17   18   14                                                       
CONECT   18   17   19                                                       
CONECT   19   16   18    5                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Value	Source
Muzigadial	Kegg
(1alpha,4Aalpha,6beta,8abeta)-(+-)-isomer OF muzigadial	MeSH
(-)-Muzigadial	PhytoBank
Canellal	PhytoBank

Chemical Formula

C₁₅H₂₀O₃

Average Mass

248.3220 Da

Monoisotopic Mass

248.14124 Da

IUPAC Name

(1S,4aS,6S,8aS)-1-hydroxy-6,8a-dimethyl-5-methylidene-1,4,4a,5,6,7,8,8a-octahydronaphthalene-1,2-dicarbaldehyde

Traditional Name

muzigadial

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC=C(C=O)[C@](O)(C=O)[C@@]1(C)CC[C@H](C)C2=C

InChI Identifier

InChI=1S/C15H20O3/c1-10-6-7-14(3)13(11(10)2)5-4-12(8-16)15(14,18)9-17/h4,8-10,13,18H,2,5-7H2,1,3H3/t10-,13-,14-,15+/m0/s1

InChI Key

LDAIOVKPAKFZHM-FBUXBERBSA-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
Canella winterana	Plant	KNApSAcK
Warburghia ugandensis	-	KNApSAcK
Warburgia salutaris	Plant	KNApSAcK
Warburgia ugandensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Tertiary alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

sesquiterpenoid (CHEBI:3355 )
Farnesenes (C09626 )

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	2.39	ALOGPS
logP	1.58	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	12.06	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	70.2 m³·mol⁻¹	ChemAxon
Polarizability	26.87 Å³	ChemAxon
Number of Rings	2	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00003107

Chemspider ID

390798

KEGG Compound ID

C09626

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442346

PDB ID

Not Available

ChEBI ID

3355

Good Scents ID

Not Available

References

General References

Rastogi N, Abaul J, Goh KS, Devallois A, Philogene E, Bourgeois P: Antimycobacterial activity of chemically defined natural substances from the Caribbean flora in Guadeloupe. FEMS Immunol Med Microbiol. 1998 Apr;20(4):267-73. doi: 10.1111/j.1574-695X.1998.tb01136.x. [PubMed:9626931 ]

Showing NP-Card for (-)-Muzigadial (NP0051786)

MOL for NP0051786 ((-)-Muzigadial)

3D MOL for NP0051786 ((-)-Muzigadial)

3D SDF for NP0051786 ((-)-Muzigadial)

3D-SDF for NP0051786 ((-)-Muzigadial)

PDB for NP0051786 ((-)-Muzigadial)

3D PDB for NP0051786 ((-)-Muzigadial)

SMILES for NP0051786 ((-)-Muzigadial)

INCHI for NP0051786 ((-)-Muzigadial)

Structure for NP0051786 ((-)-Muzigadial)

3D Structure for NP0051786 ((-)-Muzigadial)