NP-MRD: Showing NP-Card for Myricanol (NP0046026)

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Record Information

Version

2.0

Created at

2022-03-17 19:47:11 UTC

Updated at

2022-03-17 19:47:11 UTC

NP-MRD ID

NP0046026

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Myricanol

Description

Myricanol belongs to the class of organic compounds known as meta,meta-bridged biphenyls. These are cyclic diarylheptanoids where the two aryl groups are linked to each other by an ether group conjugated to their 3-position. Myricanol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Myricanol has been detected, but not quantified in, anises. Myricanol is found in Morella cerifera, Morella esculenta, Morella nana, Myrica rubra , Myrica arborea, Myrica nagi and Nageia nagi. This could make myricanol a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652310051712402D          

 26 28  0  0  0  0            999 V2000
    1.2846    3.6392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6280    3.6013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5323   -0.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9557   -1.1849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7702   -0.0715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7781   -1.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5356    0.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6483    1.4689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0681   -0.6353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2934    2.2137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3583    0.8543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6376    0.9432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1808    0.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8353    0.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2456   -0.5702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0035    1.5991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1810    1.6641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4710    2.2788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3720    1.4336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5545    2.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7316    2.1761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6005   -1.3150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1161    3.0235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4508    1.3738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8246    3.0155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2684    2.8588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  2  0  0  0  0
 13  7  1  0  0  0  0
 13  8  1  0  0  0  0
 13 11  2  0  0  0  0
 14  5  1  0  0  0  0
 14 12  2  0  0  0  0
 15  6  1  0  0  0  0
 15  9  1  0  0  0  0
 16 11  1  0  0  0  0
 17 12  1  0  0  0  0
 17 16  1  0  0  0  0
 18 10  1  0  0  0  0
 18 16  2  0  0  0  0
 19 14  1  0  0  0  0
 20 17  2  0  0  0  0
 21 19  2  0  0  0  0
 21 20  1  0  0  0  0
 22 15  1  0  0  0  0
 23 18  1  0  0  0  0
 24 19  1  0  0  0  0
 25  1  1  0  0  0  0
 25 20  1  0  0  0  0
 26  2  1  0  0  0  0
 26 21  1  0  0  0  0
M  END


  Mrv1652310051712402D          

 26 28  0  0  0  0            999 V2000
    1.2846    3.6392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6280    3.6013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5323   -0.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9557   -1.1849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7702   -0.0715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7781   -1.2499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5356    0.0444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6483    1.4689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0681   -0.6353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2934    2.2137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3583    0.8543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6376    0.9432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1808    0.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8353    0.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2456   -0.5702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0035    1.5991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1810    1.6641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4710    2.2788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3720    1.4336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5545    2.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7316    2.1761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6005   -1.3150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1161    3.0235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4508    1.3738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8246    3.0155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2684    2.8588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  2  0  0  0  0
 13  7  1  0  0  0  0
 13  8  1  0  0  0  0
 13 11  2  0  0  0  0
 14  5  1  0  0  0  0
 14 12  2  0  0  0  0
 15  6  1  0  0  0  0
 15  9  1  0  0  0  0
 16 11  1  0  0  0  0
 17 12  1  0  0  0  0
 17 16  1  0  0  0  0
 18 10  1  0  0  0  0
 18 16  2  0  0  0  0
 19 14  1  0  0  0  0
 20 17  2  0  0  0  0
 21 19  2  0  0  0  0
 21 20  1  0  0  0  0
 22 15  1  0  0  0  0
 23 18  1  0  0  0  0
 24 19  1  0  0  0  0
 25  1  1  0  0  0  0
 25 20  1  0  0  0  0
 26  2  1  0  0  0  0
 26 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046026

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C2=CC(=C1OC)C1=C(O)C=CC(CCC(O)CCCC2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H26O5/c1-25-20-17-12-14(19(24)21(20)26-2)5-3-4-6-15(22)9-7-13-8-10-18(23)16(17)11-13/h8,10-12,15,22-24H,3-7,9H2,1-2H3

> <INCHI_KEY>
SBGBAZQAEOWGFT-UHFFFAOYSA-N

> <FORMULA>
C21H26O5

> <MOLECULAR_WEIGHT>
358.4281

> <EXACT_MASS>
358.178023942

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
37.951730269664495

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
16,17-dimethoxytricyclo[12.3.1.1^{2,6}]nonadeca-1(17),2,4,6(19),14(18),15-hexaene-3,9,15-triol

> <ALOGPS_LOGP>
3.16

> <JCHEM_LOGP>
4.0972396773333335

> <ALOGPS_LOGS>
-4.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.414222651370617

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.650266583946536

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6891361697482887

> <JCHEM_POLAR_SURFACE_AREA>
79.15

> <JCHEM_REFRACTIVITY>
101.03709999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.43e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16,17-dimethoxytricyclo[12.3.1.1^{2,6}]nonadeca-1(17),2,4,6(19),14(18),15-hexaene-3,9,15-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-OCT-17         0                                  
HETATM    1  C   UNK     0       2.398   6.793   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.172   6.722   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.860  -0.723   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.651  -2.212   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.438  -0.133   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.186  -2.333   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.467   0.083   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.677   2.742   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.594  -1.186   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.014   4.132   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.269   1.595   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.057   1.761   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.804   1.473   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.559   1.402   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.059  -1.064   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.606   2.985   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.071   3.106   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.479   4.254   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.694   2.676   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.902   4.174   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.366   4.062   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.721  -2.455   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.817   5.644   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -0.841   2.564   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       3.406   5.629   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       0.501   5.336   0.000  0.00  0.00           O+0
CONECT    1   25                                                            
CONECT    2   26                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3   14                                                       
CONECT    6    4   15                                                       
CONECT    7    9   13                                                       
CONECT    8   10   13                                                       
CONECT    9    7   15                                                       
CONECT   10    8   18                                                       
CONECT   11   13   16                                                       
CONECT   12   14   17                                                       
CONECT   13    7    8   11                                                  
CONECT   14    5   12   19                                                  
CONECT   15    6    9   22                                                  
CONECT   16   11   17   18                                                  
CONECT   17   12   16   20                                                  
CONECT   18   10   16   23                                                  
CONECT   19   14   21   24                                                  
CONECT   20   17   21   25                                                  
CONECT   21   19   20   26                                                  
CONECT   22   15                                                            
CONECT   23   18                                                            
CONECT   24   19                                                            
CONECT   25    1   20                                                       
CONECT   26    2   21                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₆O₅

Average Mass

358.4281 Da

Monoisotopic Mass

358.17802 Da

IUPAC Name

16,17-dimethoxytricyclo[12.3.1.1^{2,6}]nonadeca-1(17),2,4,6(19),14(18),15-hexaene-3,9,15-triol

Traditional Name

16,17-dimethoxytricyclo[12.3.1.1^{2,6}]nonadeca-1(17),2,4,6(19),14(18),15-hexaene-3,9,15-triol

CAS Registry Number

33606-81-4

SMILES

COC1=C(O)C2=CC(=C1OC)C1=C(O)C=CC(CCC(O)CCCC2)=C1

InChI Identifier

InChI=1S/C21H26O5/c1-25-20-17-12-14(19(24)21(20)26-2)5-3-4-6-15(22)9-7-13-8-10-18(23)16(17)11-13/h8,10-12,15,22-24H,3-7,9H2,1-2H3

InChI Key

SBGBAZQAEOWGFT-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Morella cerifera	LOTUS Database	35616633
Morella esculenta	LOTUS Database	35616633
Morella nana	LOTUS Database	35616633
Morella rubra	Plant	KNApSAcK
Myrica arborea	Plant	KNApSAcK
Myrica nagi	Plant	KNApSAcK
Nageia nagi	LOTUS Database	35616633
Pimpinella anisum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as meta,meta-bridged biphenyls. These are cyclic diarylheptanoids where the two aryl groups are linked to each other by an ether group conjugated to their 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Diarylheptanoids

Sub Class

Cyclic diarylheptanoids

Direct Parent

Meta,meta-bridged biphenyls

Alternative Parents

Substituents

Meta,meta-bridged biphenyl
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Secondary alcohol
Polyol
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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	3.16	ALOGPS
logP	4.1	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.65	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	79.15 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	101.04 m³·mol⁻¹	ChemAxon
Polarizability	37.95 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

HMDB0150339

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002738

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

5319978

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Myricanol (NP0046026)

MOL for NP0046026 (Myricanol)

3D MOL for NP0046026 (Myricanol)

3D SDF for NP0046026 (Myricanol)

3D-SDF for NP0046026 (Myricanol)

PDB for NP0046026 (Myricanol)

3D PDB for NP0046026 (Myricanol)

SMILES for NP0046026 (Myricanol)

INCHI for NP0046026 (Myricanol)

Structure for NP0046026 (Myricanol)

3D Structure for NP0046026 (Myricanol)