NP-MRD: Showing NP-Card for (9r)-16-methoxytricyclo[12.3.1.1²,⁶]nonadeca-1(17),2(19),3,5,14(18),15-hexaene-3,9,17-triol (NP0252513)

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Record Information

Version

2.0

Created at

2022-09-07 16:03:10 UTC

Updated at

2022-09-07 16:03:10 UTC

NP-MRD ID

NP0252513

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(9r)-16-methoxytricyclo[12.3.1.1²,⁶]nonadeca-1(17),2(19),3,5,14(18),15-hexaene-3,9,17-triol

Description

(9R)-16-methoxytricyclo[12.3.1.1²,⁶]Nonadeca-1(17),2,4,6(19),14(18),15-hexaene-3,9,17-triol 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. (9r)-16-methoxytricyclo[12.3.1.1²,⁶]nonadeca-1(17),2(19),3,5,14(18),15-hexaene-3,9,17-triol is found in Juglans regia. Based on a literature review very few articles have been published on (9R)-16-methoxytricyclo[12.3.1.1²,⁶]Nonadeca-1(17),2,4,6(19),14(18),15-hexaene-3,9,17-triol.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309072218032D          

 24 26  0  0  1  0            999 V2000
    5.2813   -0.1223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2763    0.7027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5594    1.1109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5544    1.9359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9046    2.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1255    1.9272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8414    1.1526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8474    0.6941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8894   -0.1299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0170    1.1835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7915    1.9771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0487    2.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5034    1.8403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5973    1.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3541    0.6923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4481   -0.1274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0795    3.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8089    3.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8397    4.5245    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1411    4.9634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5691    4.9100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2677    4.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2368    3.6467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9354    3.2078    0.0000 C   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  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
  5 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0252513

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=CC(=C1O)C1=CC(CC[C@H](O)CCCC2)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O4/c1-24-19-12-14-4-2-3-5-15(21)8-6-13-7-9-18(22)16(10-13)17(11-14)20(19)23/h7,9-12,15,21-23H,2-6,8H2,1H3/t15-/m1/s1

> <INCHI_KEY>
AVDQDLSGSIPLPN-OAHLLOKOSA-N

> <FORMULA>
C20H24O4

> <MOLECULAR_WEIGHT>
328.408

> <EXACT_MASS>
328.167459253

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
35.59170619805043

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9R)-16-methoxytricyclo[12.3.1.1^{2,6}]nonadeca-1(17),2(19),3,5,14(18),15-hexaene-3,9,17-triol

> <JCHEM_LOGP>
4.254910943

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.362019636813447

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.504363695858343

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6891361641103897

> <JCHEM_POLAR_SURFACE_AREA>
69.92

> <JCHEM_REFRACTIVITY>
94.5739

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(9R)-16-methoxytricyclo[12.3.1.1^{2,6}]nonadeca-1(17),2(19),3,5,14(18),15-hexaene-3,9,17-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       9.858  -0.228   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.849   1.312   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.511   2.074   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.502   3.614   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.289   4.449   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.834   3.597   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.304   2.152   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.182   1.296   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       7.260  -0.242   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.765   2.209   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.344   3.691   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.958   4.648   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.940   3.435   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.115   1.905   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.528   1.292   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.703  -0.238   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.015   6.187   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.377   6.907   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.434   8.446   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.130   9.265   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.796   9.165   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.100   8.346   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.042   6.807   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.346   5.988   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   24                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
CONECT   10    7   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10   16                                                  
CONECT   16   15                                                            
CONECT   17   12   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23    5                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄O₄

Average Mass

328.4080 Da

Monoisotopic Mass

328.16746 Da

IUPAC Name

(9R)-16-methoxytricyclo[12.3.1.1^{2,6}]nonadeca-1(17),2(19),3,5,14(18),15-hexaene-3,9,17-triol

Traditional Name

(9R)-16-methoxytricyclo[12.3.1.1^{2,6}]nonadeca-1(17),2(19),3,5,14(18),15-hexaene-3,9,17-triol

CAS Registry Number

Not Available

SMILES

COC1=CC2=CC(=C1O)C1=CC(CC[C@H](O)CCCC2)=CC=C1O

InChI Identifier

InChI=1S/C20H24O4/c1-24-19-12-14-4-2-3-5-15(21)8-6-13-7-9-18(22)16(10-13)17(11-14)20(19)23/h7,9-12,15,21-23H,2-6,8H2,1H3/t15-/m1/s1

InChI Key

AVDQDLSGSIPLPN-OAHLLOKOSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Juglans regia	LOTUS Database	35616633

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
Phenol ether
Anisole
1-hydroxy-2-unsubstituted benzenoid
Phenol
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	4.25	ChemAxon
pKa (Strongest Acidic)	9.5	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.92 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	94.57 m³·mol⁻¹	ChemAxon
Polarizability	35.59 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

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

162871159

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (9r)-16-methoxytricyclo[12.3.1.1²,⁶]nonadeca-1(17),2(19),3,5,14(18),15-hexaene-3,9,17-triol (NP0252513)

MOL for NP0252513 ((9r)-16-methoxytricyclo[12.3.1.1²,⁶]nonadeca-1(17),2(19),3,5,14(18),15-hexaene-3,9,17-triol)

3D MOL for NP0252513 ((9r)-16-methoxytricyclo[12.3.1.1²,⁶]nonadeca-1(17),2(19),3,5,14(18),15-hexaene-3,9,17-triol)

3D SDF for NP0252513 ((9r)-16-methoxytricyclo[12.3.1.1²,⁶]nonadeca-1(17),2(19),3,5,14(18),15-hexaene-3,9,17-triol)

3D-SDF for NP0252513 ((9r)-16-methoxytricyclo[12.3.1.1²,⁶]nonadeca-1(17),2(19),3,5,14(18),15-hexaene-3,9,17-triol)

PDB for NP0252513 ((9r)-16-methoxytricyclo[12.3.1.1²,⁶]nonadeca-1(17),2(19),3,5,14(18),15-hexaene-3,9,17-triol)

3D PDB for NP0252513 ((9r)-16-methoxytricyclo[12.3.1.1²,⁶]nonadeca-1(17),2(19),3,5,14(18),15-hexaene-3,9,17-triol)

SMILES for NP0252513 ((9r)-16-methoxytricyclo[12.3.1.1²,⁶]nonadeca-1(17),2(19),3,5,14(18),15-hexaene-3,9,17-triol)

INCHI for NP0252513 ((9r)-16-methoxytricyclo[12.3.1.1²,⁶]nonadeca-1(17),2(19),3,5,14(18),15-hexaene-3,9,17-triol)

Structure for NP0252513 ((9r)-16-methoxytricyclo[12.3.1.1²,⁶]nonadeca-1(17),2(19),3,5,14(18),15-hexaene-3,9,17-triol)

3D Structure for NP0252513 ((9r)-16-methoxytricyclo[12.3.1.1²,⁶]nonadeca-1(17),2(19),3,5,14(18),15-hexaene-3,9,17-triol)