NP-MRD: Showing NP-Card for (4ar,5r,6r,6as,7r,11as,11br)-5-(benzoyloxy)-4a-hydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-6-yl benzoate (NP0219432)

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Record Information

Version

1.0

Created at

2022-09-05 20:24:55 UTC

Updated at

2022-09-05 20:24:55 UTC

NP-MRD ID

NP0219432

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4ar,5r,6r,6as,7r,11as,11br)-5-(benzoyloxy)-4a-hydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-6-yl benzoate

Description

CHEMBL1095680 belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Based on a literature review very few articles have been published on CHEMBL1095680.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052222242D          

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M  END

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M  END


  Mrv1652309052222242D          

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   -0.8522   -3.6622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3204   -3.0315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -0.3634    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4630   -0.9941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1807   -1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6302   -0.3595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    0.2673    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0584    0.8980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  3  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
 10  9  1  6  0  0  0
  2 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
 11 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  2  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
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 25 30  1  0  0  0  0
 21 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
  9 39  1  0  0  0  0
 31 39  1  0  0  0  0
 39 40  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0219432

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1[C@@H]2[C@@H](OC(=O)C3=CC=CC=C3)[C@@H](OC(=O)C3=CC=CC=C3)[C@@]3(O)C(C)(C)CCC[C@]3(C)[C@H]2CC2=C1C=CO2

> <INCHI_IDENTIFIER>
InChI=1S/C34H38O6/c1-21-24-16-19-38-26(24)20-25-27(21)28(39-30(35)22-12-7-5-8-13-22)29(40-31(36)23-14-9-6-10-15-23)34(37)32(2,3)17-11-18-33(25,34)4/h5-10,12-16,19,21,25,27-29,37H,11,17-18,20H2,1-4H3/t21-,25-,27-,28+,29+,33+,34+/m0/s1

> <INCHI_KEY>
ZLUDDZRRFBOSTI-RLZZOFBFSA-N

> <FORMULA>
C34H38O6

> <MOLECULAR_WEIGHT>
542.672

> <EXACT_MASS>
542.266838944

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
59.469715334404086

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,7R,8R,9R,10S,11R)-8-(benzoyloxy)-7-hydroxy-2,6,6,11-tetramethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-dien-9-yl benzoate

> <JCHEM_LOGP>
7.418224786999998

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.090393552431774

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8204574200142223

> <JCHEM_POLAR_SURFACE_AREA>
85.97000000000001

> <JCHEM_REFRACTIVITY>
150.7906

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,7R,8R,9R,10S,11R)-8-(benzoyloxy)-7-hydroxy-2,6,6,11-tetramethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-dien-9-yl benzoate

> <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       6.928  -2.940   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.405  -1.492   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.398  -0.314   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.937  -0.264   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.365   1.215   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.090   2.079   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.874   1.134   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.358   1.405   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.366   0.228   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.889  -1.221   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.896  -2.398   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.419  -3.846   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.018  -5.301   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.502  -5.030   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.950  -6.472   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.466  -6.743   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.989  -8.191   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.996  -9.369   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.480  -9.098   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.957  -7.649   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.380  -2.127   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.387  -3.304   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.911  -4.752   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.427  -5.024   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.918  -5.930   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.441  -7.378   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.448  -8.556   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.068  -8.284   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.591  -6.836   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.598  -5.659   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.857  -0.678   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.864  -1.856   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.341  -0.407   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.337  -1.947   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.176  -0.671   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.182   1.041   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.810   2.218   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.850   0.499   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       3.842   1.676   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    3    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   39                                                  
CONECT   10    9    2   11                                                  
CONECT   11   10   12   21                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
CONECT   21   11   22   31                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   25                                                       
CONECT   31   21   32   33   39                                             
CONECT   32   31                                                            
CONECT   33   31   34   35   36                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   33   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38    9   31   40                                             
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₄H₃₈O₆

Average Mass

542.6720 Da

Monoisotopic Mass

542.26684 Da

IUPAC Name

(1S,2R,7R,8R,9R,10S,11R)-8-(benzoyloxy)-7-hydroxy-2,6,6,11-tetramethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-dien-9-yl benzoate

Traditional Name

(1S,2R,7R,8R,9R,10S,11R)-8-(benzoyloxy)-7-hydroxy-2,6,6,11-tetramethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-dien-9-yl benzoate

CAS Registry Number

Not Available

SMILES

C[C@@H]1[C@@H]2[C@@H](OC(=O)C3=CC=CC=C3)[C@@H](OC(=O)C3=CC=CC=C3)[C@@]3(O)C(C)(C)CCC[C@]3(C)[C@H]2CC2=C1C=CO2

InChI Identifier

InChI=1S/C34H38O6/c1-21-24-16-19-38-26(24)20-25-27(21)28(39-30(35)22-12-7-5-8-13-22)29(40-31(36)23-14-9-6-10-15-23)34(37)32(2,3)17-11-18-33(25,34)4/h5-10,12-16,19,21,25,27-29,37H,11,17-18,20H2,1-4H3/t21-,25-,27-,28+,29+,33+,34+/m0/s1

InChI Key

ZLUDDZRRFBOSTI-RLZZOFBFSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Naphthofuran
Benzoate ester
Benzofuran
Benzoic acid or derivatives
Benzoyl
Monocyclic benzene moiety
Benzenoid
Dicarboxylic acid or derivatives
Heteroaromatic compound
Tertiary alcohol
Cyclic alcohol
Furan
Carboxylic acid ester
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxygen compound
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	7.42	ChemAxon
pKa (Strongest Acidic)	13.09	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	85.97 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	150.79 m³·mol⁻¹	ChemAxon
Polarizability	59.47 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	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

24677178

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46861634

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4ar,5r,6r,6as,7r,11as,11br)-5-(benzoyloxy)-4a-hydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-6-yl benzoate (NP0219432)

MOL for NP0219432 ((4ar,5r,6r,6as,7r,11as,11br)-5-(benzoyloxy)-4a-hydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-6-yl benzoate)

3D MOL for NP0219432 ((4ar,5r,6r,6as,7r,11as,11br)-5-(benzoyloxy)-4a-hydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-6-yl benzoate)

3D SDF for NP0219432 ((4ar,5r,6r,6as,7r,11as,11br)-5-(benzoyloxy)-4a-hydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-6-yl benzoate)

3D-SDF for NP0219432 ((4ar,5r,6r,6as,7r,11as,11br)-5-(benzoyloxy)-4a-hydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-6-yl benzoate)

PDB for NP0219432 ((4ar,5r,6r,6as,7r,11as,11br)-5-(benzoyloxy)-4a-hydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-6-yl benzoate)

3D PDB for NP0219432 ((4ar,5r,6r,6as,7r,11as,11br)-5-(benzoyloxy)-4a-hydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-6-yl benzoate)

SMILES for NP0219432 ((4ar,5r,6r,6as,7r,11as,11br)-5-(benzoyloxy)-4a-hydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-6-yl benzoate)

INCHI for NP0219432 ((4ar,5r,6r,6as,7r,11as,11br)-5-(benzoyloxy)-4a-hydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-6-yl benzoate)

Structure for NP0219432 ((4ar,5r,6r,6as,7r,11as,11br)-5-(benzoyloxy)-4a-hydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-6-yl benzoate)

3D Structure for NP0219432 ((4ar,5r,6r,6as,7r,11as,11br)-5-(benzoyloxy)-4a-hydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-6-yl benzoate)