NP-MRD: Showing NP-Card for [7-(acetyloxy)-6-[(acetyloxy)methyl]-5,6,9-trihydroxy-3b,9b-dimethyl-4-oxo-5h,7h,8h,9h,9ah,10h,11h-phenanthro[1,2-b]furan-5a-yl]methyl acetate (NP0198406)

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Record Information

Version

2.0

Created at

2022-09-04 16:51:07 UTC

Updated at

2022-09-04 16:51:07 UTC

NP-MRD ID

NP0198406

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[7-(acetyloxy)-6-[(acetyloxy)methyl]-5,6,9-trihydroxy-3b,9b-dimethyl-4-oxo-5h,7h,8h,9h,9ah,10h,11h-phenanthro[1,2-b]furan-5a-yl]methyl acetate

Description

[5-(Acetyloxy)-6-[(acetyloxy)methyl]-3,6,8-trihydroxy-1,10-dimethyl-9-oxo-12-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-11(15),13-dien-7-yl]methyl acetate belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations. [7-(acetyloxy)-6-[(acetyloxy)methyl]-5,6,9-trihydroxy-3b,9b-dimethyl-4-oxo-5h,7h,8h,9h,9ah,10h,11h-phenanthro[1,2-b]furan-5a-yl]methyl acetate is found in Teucrium alyssifolium. [5-(Acetyloxy)-6-[(acetyloxy)methyl]-3,6,8-trihydroxy-1,10-dimethyl-9-oxo-12-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-11(15),13-dien-7-yl]methyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241510152D          

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M  END

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  Mrv1533004241510152D          

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  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  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
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 21  2  0  0  0  0
 21 22  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
  6 28  1  0  0  0  0
 12 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
  8 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0198406

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC1(O)C(CC(O)C2C3(C)CCC4=C(OC=C4)C3(C)C(=O)C(O)C12COC(C)=O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O11/c1-13(27)35-11-25-19(17(30)10-18(37-15(3)29)26(25,33)12-36-14(2)28)23(4)8-6-16-7-9-34-22(16)24(23,5)20(31)21(25)32/h7,9,17-19,21,30,32-33H,6,8,10-12H2,1-5H3

> <INCHI_KEY>
CHDGXDIXZWFXLD-UHFFFAOYSA-N

> <FORMULA>
C26H34O11

> <MOLECULAR_WEIGHT>
522.547

> <EXACT_MASS>
522.210111915

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
52.68922227729526

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[5-(acetyloxy)-6-[(acetyloxy)methyl]-3,6,8-trihydroxy-1,10-dimethyl-9-oxo-12-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-11(15),13-dien-7-yl]methyl acetate

> <ALOGPS_LOGP>
0.94

> <JCHEM_LOGP>
-0.4086562570000016

> <ALOGPS_LOGS>
-3.05

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.16303143284853

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.779688976753707

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8224964571697755

> <JCHEM_POLAR_SURFACE_AREA>
169.79999999999998

> <JCHEM_REFRACTIVITY>
124.21879999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.70e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[5-(acetyloxy)-6-[(acetyloxy)methyl]-3,6,8-trihydroxy-1,10-dimethyl-9-oxo-12-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-11(15),13-dien-7-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -3.185  -7.618   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.207  -8.136   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.846  -9.925   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -0.518  -7.612   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.521  -6.072   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.810  -5.298   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.341  -6.744   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.182  -4.121   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.341  -2.673   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.857  -2.402   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.380  -0.953   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.850  -3.579   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.366  -3.308   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.373  -2.131   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.889  -1.859   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.405  -1.588   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.398  -2.766   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.937  -2.816   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.365  -4.295   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.090  -5.159   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.874  -4.214   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.358  -4.485   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.351  -5.663   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.835  -5.934   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.828  -7.111   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.319  -6.205   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.796  -7.653   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.326  -5.027   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.803  -6.476   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.287  -6.747   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -0.236  -8.195   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.757  -9.372   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.752  -8.466   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -1.698  -4.392   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -2.691  -3.215   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -4.207  -3.486   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -2.168  -1.766   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   28                                             
CONECT    7    6                                                            
CONECT    8    6    9   34                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   28                                                  
CONECT   13   12   14   15   22                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   17   22                                                  
CONECT   22   21   13   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26    6   12   29                                             
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34    8   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
[5-(Acetyloxy)-6-[(acetyloxy)methyl]-3,6,8-trihydroxy-1,10-dimethyl-9-oxo-12-oxatetracyclo[8.7.0.0,.0,]heptadeca-11(15),13-dien-7-yl]methyl acetic acid	Generator
[5-(Acetyloxy)-6-[(acetyloxy)methyl]-3,6,8-trihydroxy-1,10-dimethyl-9-oxo-12-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-11(15),13-dien-7-yl]methyl acetic acid	Generator

Chemical Formula

C₂₆H₃₄O₁₁

Average Mass

522.5470 Da

Monoisotopic Mass

522.21011 Da

IUPAC Name

[5-(acetyloxy)-6-[(acetyloxy)methyl]-3,6,8-trihydroxy-1,10-dimethyl-9-oxo-12-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-11(15),13-dien-7-yl]methyl acetate

Traditional Name

[5-(acetyloxy)-6-[(acetyloxy)methyl]-3,6,8-trihydroxy-1,10-dimethyl-9-oxo-12-oxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-11(15),13-dien-7-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC1(O)C(CC(O)C2C3(C)CCC4=C(OC=C4)C3(C)C(=O)C(O)C12COC(C)=O)OC(C)=O

InChI Identifier

InChI=1S/C26H34O11/c1-13(27)35-11-25-19(17(30)10-18(37-15(3)29)26(25,33)12-36-14(2)28)23(4)8-6-16-7-9-34-22(16)24(23,5)20(31)21(25)32/h7,9,17-19,21,30,32-33H,6,8,10-12H2,1-5H3

InChI Key

CHDGXDIXZWFXLD-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
Teucrium alyssifolium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Colensane and clerodane diterpenoids

Alternative Parents

Substituents

Clerodane diterpenoid
14-hydroxysteroid
Hydroxysteroid
7-hydroxysteroid
11-hydroxysteroid
Steroid
Naphthofuran
Benzofuran
Tricarboxylic acid or derivatives
Cyclitol or derivatives
Cyclic alcohol
Furan
Heteroaromatic compound
Tertiary alcohol
Ketone
Carboxylic acid ester
Secondary alcohol
Oxacycle
Carboxylic acid derivative
Polyol
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Carbonyl group
Organic oxide
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
logP	0.94	ALOGPS
logP	-0.41	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	11.78	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	169.8 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	124.22 m³·mol⁻¹	ChemAxon
Polarizability	52.69 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [7-(acetyloxy)-6-[(acetyloxy)methyl]-5,6,9-trihydroxy-3b,9b-dimethyl-4-oxo-5h,7h,8h,9h,9ah,10h,11h-phenanthro[1,2-b]furan-5a-yl]methyl acetate (NP0198406)

MOL for NP0198406 ([7-(acetyloxy)-6-[(acetyloxy)methyl]-5,6,9-trihydroxy-3b,9b-dimethyl-4-oxo-5h,7h,8h,9h,9ah,10h,11h-phenanthro[1,2-b]furan-5a-yl]methyl acetate)

3D MOL for NP0198406 ([7-(acetyloxy)-6-[(acetyloxy)methyl]-5,6,9-trihydroxy-3b,9b-dimethyl-4-oxo-5h,7h,8h,9h,9ah,10h,11h-phenanthro[1,2-b]furan-5a-yl]methyl acetate)

3D SDF for NP0198406 ([7-(acetyloxy)-6-[(acetyloxy)methyl]-5,6,9-trihydroxy-3b,9b-dimethyl-4-oxo-5h,7h,8h,9h,9ah,10h,11h-phenanthro[1,2-b]furan-5a-yl]methyl acetate)

3D-SDF for NP0198406 ([7-(acetyloxy)-6-[(acetyloxy)methyl]-5,6,9-trihydroxy-3b,9b-dimethyl-4-oxo-5h,7h,8h,9h,9ah,10h,11h-phenanthro[1,2-b]furan-5a-yl]methyl acetate)

PDB for NP0198406 ([7-(acetyloxy)-6-[(acetyloxy)methyl]-5,6,9-trihydroxy-3b,9b-dimethyl-4-oxo-5h,7h,8h,9h,9ah,10h,11h-phenanthro[1,2-b]furan-5a-yl]methyl acetate)

3D PDB for NP0198406 ([7-(acetyloxy)-6-[(acetyloxy)methyl]-5,6,9-trihydroxy-3b,9b-dimethyl-4-oxo-5h,7h,8h,9h,9ah,10h,11h-phenanthro[1,2-b]furan-5a-yl]methyl acetate)

SMILES for NP0198406 ([7-(acetyloxy)-6-[(acetyloxy)methyl]-5,6,9-trihydroxy-3b,9b-dimethyl-4-oxo-5h,7h,8h,9h,9ah,10h,11h-phenanthro[1,2-b]furan-5a-yl]methyl acetate)

INCHI for NP0198406 ([7-(acetyloxy)-6-[(acetyloxy)methyl]-5,6,9-trihydroxy-3b,9b-dimethyl-4-oxo-5h,7h,8h,9h,9ah,10h,11h-phenanthro[1,2-b]furan-5a-yl]methyl acetate)

Structure for NP0198406 ([7-(acetyloxy)-6-[(acetyloxy)methyl]-5,6,9-trihydroxy-3b,9b-dimethyl-4-oxo-5h,7h,8h,9h,9ah,10h,11h-phenanthro[1,2-b]furan-5a-yl]methyl acetate)

3D Structure for NP0198406 ([7-(acetyloxy)-6-[(acetyloxy)methyl]-5,6,9-trihydroxy-3b,9b-dimethyl-4-oxo-5h,7h,8h,9h,9ah,10h,11h-phenanthro[1,2-b]furan-5a-yl]methyl acetate)