NP-MRD: Showing NP-Card for 3-{6-hydroxy-2,7,13,15-tetramethyl-8,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),9,12,14-tetraen-7-yl}-4a,5-dimethyl-5,6,7,8-tetrahydronaphthalen-2-one (NP0217144)

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Record Information

Version

2.0

Created at

2022-09-05 17:23:21 UTC

Updated at

2022-09-05 17:23:21 UTC

NP-MRD ID

NP0217144

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-{6-hydroxy-2,7,13,15-tetramethyl-8,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),9,12,14-tetraen-7-yl}-4a,5-dimethyl-5,6,7,8-tetrahydronaphthalen-2-one

Description

3-{6-Hydroxy-2,7,13,15-tetramethyl-8,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]Hexadeca-1(15),9(16),10(14),12-tetraen-7-yl}-4a,5-dimethyl-2,4a,5,6,7,8-hexahydronaphthalen-2-one belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. 3-{6-hydroxy-2,7,13,15-tetramethyl-8,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),9,12,14-tetraen-7-yl}-4a,5-dimethyl-5,6,7,8-tetrahydronaphthalen-2-one is found in Ligularia virgaurea. Based on a literature review very few articles have been published on 3-{6-hydroxy-2,7,13,15-tetramethyl-8,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]Hexadeca-1(15),9(16),10(14),12-tetraen-7-yl}-4a,5-dimethyl-2,4a,5,6,7,8-hexahydronaphthalen-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052219232D          

 34 39  0  0  0  0            999 V2000
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M  END

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M  END


  Mrv1652309052219232D          

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 15 16  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 21 27  1  0  0  0  0
 27 28  2  0  0  0  0
 25 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 23 32  1  0  0  0  0
 32 33  1  0  0  0  0
 19 34  1  0  0  0  0
  6 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0217144

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC2C(O)C(C)(OC3=C4OC=C(C)C4=C(C)C1=C23)C1=CC2(C)C(C)CCCC2=CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H36O4/c1-15-10-11-20-25-23(15)18(4)24-16(2)14-33-26(24)27(25)34-30(6,28(20)32)21-13-29(5)17(3)8-7-9-19(29)12-22(21)31/h12-15,17,20,28,32H,7-11H2,1-6H3

> <INCHI_KEY>
PXLCJVXPHFFDDN-UHFFFAOYSA-N

> <FORMULA>
C30H36O4

> <MOLECULAR_WEIGHT>
460.614

> <EXACT_MASS>
460.261359639

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
53.299621934601625

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{6-hydroxy-2,7,13,15-tetramethyl-8,11-dioxatetracyclo[7.6.1.0^{5,16}.0^{10,14}]hexadeca-1(16),9,12,14-tetraen-7-yl}-4a,5-dimethyl-2,4a,5,6,7,8-hexahydronaphthalen-2-one

> <JCHEM_LOGP>
6.557749763666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.042288285109297

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.496001350801716

> <JCHEM_PKA_STRONGEST_BASIC>
-2.794657762641787

> <JCHEM_POLAR_SURFACE_AREA>
59.67

> <JCHEM_REFRACTIVITY>
135.44399999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-{6-hydroxy-2,7,13,15-tetramethyl-8,11-dioxatetracyclo[7.6.1.0^{5,16}.0^{10,14}]hexadeca-1(16),9,12,14-tetraen-7-yl}-4a,5-dimethyl-5,6,7,8-tetrahydronaphthalen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       7.275  -1.941   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.799  -0.476   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.705   0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.799   2.016   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   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       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.000   4.620   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.677   5.800   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.657   5.800   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.174   5.532   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.164   6.712   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.690   5.265   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.637   8.159   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.120   8.427   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.131   7.247   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.614   7.514   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.627   9.339   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.144   9.071   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.670   7.624   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.680   6.445   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.207   4.997   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7   34                                                  
CONECT    7    6    8   16                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    2    5                                                  
CONECT   12    8   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    7   17                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21   34                                             
CONECT   20   19                                                            
CONECT   21   19   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25   32                                             
CONECT   24   23                                                            
CONECT   25   23   26   29                                                  
CONECT   26   25   27                                                       
CONECT   27   26   21   28                                                  
CONECT   28   27                                                            
CONECT   29   25   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   23   33                                                  
CONECT   33   32                                                            
CONECT   34   19    6                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₆O₄

Average Mass

460.6140 Da

Monoisotopic Mass

460.26136 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1CCC2C(O)C(C)(OC3=C4OC=C(C)C4=C(C)C1=C23)C1=CC2(C)C(C)CCCC2=CC1=O

InChI Identifier

InChI=1S/C30H36O4/c1-15-10-11-20-25-23(15)18(4)24-16(2)14-33-26(24)27(25)34-30(6,28(20)32)21-13-29(5)17(3)8-7-9-19(29)12-22(21)31/h12-15,17,20,28,32H,7-11H2,1-6H3

InChI Key

PXLCJVXPHFFDDN-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Ligularia virgaurea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Eremophilane sesquiterpenoid
Naphthofuran
Chromane
Benzopyran
1-benzopyran
Tetralin
Benzofuran
Alkyl aryl ether
Benzenoid
Heteroaromatic compound
Furan
Cyclic ketone
Secondary alcohol
Ketone
Oxacycle
Ether
Organoheterocyclic compound
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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

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

162966113

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-{6-hydroxy-2,7,13,15-tetramethyl-8,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),9,12,14-tetraen-7-yl}-4a,5-dimethyl-5,6,7,8-tetrahydronaphthalen-2-one (NP0217144)

MOL for NP0217144 (3-{6-hydroxy-2,7,13,15-tetramethyl-8,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),9,12,14-tetraen-7-yl}-4a,5-dimethyl-5,6,7,8-tetrahydronaphthalen-2-one)

3D MOL for NP0217144 (3-{6-hydroxy-2,7,13,15-tetramethyl-8,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),9,12,14-tetraen-7-yl}-4a,5-dimethyl-5,6,7,8-tetrahydronaphthalen-2-one)

3D SDF for NP0217144 (3-{6-hydroxy-2,7,13,15-tetramethyl-8,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),9,12,14-tetraen-7-yl}-4a,5-dimethyl-5,6,7,8-tetrahydronaphthalen-2-one)

3D-SDF for NP0217144 (3-{6-hydroxy-2,7,13,15-tetramethyl-8,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),9,12,14-tetraen-7-yl}-4a,5-dimethyl-5,6,7,8-tetrahydronaphthalen-2-one)

PDB for NP0217144 (3-{6-hydroxy-2,7,13,15-tetramethyl-8,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),9,12,14-tetraen-7-yl}-4a,5-dimethyl-5,6,7,8-tetrahydronaphthalen-2-one)

3D PDB for NP0217144 (3-{6-hydroxy-2,7,13,15-tetramethyl-8,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),9,12,14-tetraen-7-yl}-4a,5-dimethyl-5,6,7,8-tetrahydronaphthalen-2-one)

SMILES for NP0217144 (3-{6-hydroxy-2,7,13,15-tetramethyl-8,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),9,12,14-tetraen-7-yl}-4a,5-dimethyl-5,6,7,8-tetrahydronaphthalen-2-one)

INCHI for NP0217144 (3-{6-hydroxy-2,7,13,15-tetramethyl-8,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),9,12,14-tetraen-7-yl}-4a,5-dimethyl-5,6,7,8-tetrahydronaphthalen-2-one)

Structure for NP0217144 (3-{6-hydroxy-2,7,13,15-tetramethyl-8,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),9,12,14-tetraen-7-yl}-4a,5-dimethyl-5,6,7,8-tetrahydronaphthalen-2-one)

3D Structure for NP0217144 (3-{6-hydroxy-2,7,13,15-tetramethyl-8,11-dioxatetracyclo[7.6.1.0⁵,¹⁶.0¹⁰,¹⁴]hexadeca-1(16),9,12,14-tetraen-7-yl}-4a,5-dimethyl-5,6,7,8-tetrahydronaphthalen-2-one)