NP-MRD: Showing NP-Card for (4ar,5r,6r,6as,7r,11as,11br)-6-(acetyloxy)-4a-hydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-5-yl (2e)-3-phenylprop-2-enoate (NP0325389)

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Record Information

Version

2.0

Created at

2022-09-12 06:06:41 UTC

Updated at

2022-09-12 06:06:41 UTC

NP-MRD ID

NP0325389

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

CHEMBL1097166 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 CHEMBL1097166.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122208062D          

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  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  9 13  2  0  0  0  0
 13 14  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  1  0  0  0
  7 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 16 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 32 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0325389

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C31H38O6/c1-19-22-14-17-35-24(22)18-23-26(19)27(36-20(2)32)28(31(34)29(3,4)15-9-16-30(23,31)5)37-25(33)13-12-21-10-7-6-8-11-21/h6-8,10-14,17,19,23,26-28,34H,9,15-16,18H2,1-5H3/b13-12+/t19-,23-,26-,27+,28+,30+,31+/m0/s1

> <INCHI_KEY>
NQXXHQFQXKHFLH-JLTDNTAYSA-N

> <FORMULA>
C31H38O6

> <MOLECULAR_WEIGHT>
506.639

> <EXACT_MASS>
506.266838944

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
55.95705333563616

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,7R,8R,9R,10S,11R)-9-(acetyloxy)-7-hydroxy-2,6,6,11-tetramethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-dien-8-yl (2E)-3-phenylprop-2-enoate

> <JCHEM_LOGP>
5.902641217999998

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.090441362134754

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8204578036360908

> <JCHEM_POLAR_SURFACE_AREA>
85.97

> <JCHEM_REFRACTIVITY>
139.86579999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,7R,8R,9R,10S,11R)-9-(acetyloxy)-7-hydroxy-2,6,6,11-tetramethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-dien-8-yl (2E)-3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       2.284   6.829   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.800   7.100   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.950   8.012   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.419   5.386   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.896   3.938   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.889   2.761   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.366   1.312   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.358   0.135   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.874   0.406   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.090  -0.539   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.365   0.325   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.937   1.804   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.398   1.854   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.405   3.032   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.928   4.480   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.850   1.041   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.842  -0.136   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.326  -0.407   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.810  -0.678   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.182   0.499   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.341   1.947   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.337   3.487   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.176   2.211   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.857   2.218   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.864   3.396   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.380   3.667   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.387   4.844   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.911   6.292   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.427   6.564   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.918   7.470   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.598   7.199   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.591   8.376   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -3.107   8.105   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -4.099   9.282   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.576  10.731   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.060  11.002   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -1.068   9.824   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   26                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    9   14                                                  
CONECT   14   13    6   15                                                  
CONECT   15   14                                                            
CONECT   16    7   17   18   24                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21   16   25   26                                             
CONECT   25   24                                                            
CONECT   26   24    5   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   32                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₃₈O₆

Average Mass

506.6390 Da

Monoisotopic Mass

506.26684 Da

IUPAC Name

(1S,2R,7R,8R,9R,10S,11R)-9-(acetyloxy)-7-hydroxy-2,6,6,11-tetramethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-dien-8-yl (2E)-3-phenylprop-2-enoate

Traditional Name

(1S,2R,7R,8R,9R,10S,11R)-9-(acetyloxy)-7-hydroxy-2,6,6,11-tetramethyl-15-oxatetracyclo[8.7.0.0^{2,7}.0^{12,16}]heptadeca-12(16),13-dien-8-yl (2E)-3-phenylprop-2-enoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C31H38O6/c1-19-22-14-17-35-24(22)18-23-26(19)27(36-20(2)32)28(31(34)29(3,4)15-9-16-30(23,31)5)37-25(33)13-12-21-10-7-6-8-11-21/h6-8,10-14,17,19,23,26-28,34H,9,15-16,18H2,1-5H3/b13-12+/t19-,23-,26-,27+,28+,30+,31+/m0/s1

InChI Key

NQXXHQFQXKHFLH-JLTDNTAYSA-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
Cinnamic acid or derivatives
Cinnamic acid ester
Benzofuran
Styrene
Fatty acid ester
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Fatty acyl
Benzenoid
Tertiary alcohol
Furan
Cyclic alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Heteroaromatic compound
Carboxylic acid ester
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Alcohol
Carbonyl group
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
logP	5.9	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	139.87 m³·mol⁻¹	ChemAxon
Polarizability	55.96 Å³	ChemAxon
Number of Rings	5	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

24672654

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46861633

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)-6-(acetyloxy)-4a-hydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-5-yl (2e)-3-phenylprop-2-enoate (NP0325389)

MOL for NP0325389 ((4ar,5r,6r,6as,7r,11as,11br)-6-(acetyloxy)-4a-hydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-5-yl (2e)-3-phenylprop-2-enoate)

3D MOL for NP0325389 ((4ar,5r,6r,6as,7r,11as,11br)-6-(acetyloxy)-4a-hydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-5-yl (2e)-3-phenylprop-2-enoate)

3D SDF for NP0325389 ((4ar,5r,6r,6as,7r,11as,11br)-6-(acetyloxy)-4a-hydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-5-yl (2e)-3-phenylprop-2-enoate)

3D-SDF for NP0325389 ((4ar,5r,6r,6as,7r,11as,11br)-6-(acetyloxy)-4a-hydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-5-yl (2e)-3-phenylprop-2-enoate)

PDB for NP0325389 ((4ar,5r,6r,6as,7r,11as,11br)-6-(acetyloxy)-4a-hydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-5-yl (2e)-3-phenylprop-2-enoate)

3D PDB for NP0325389 ((4ar,5r,6r,6as,7r,11as,11br)-6-(acetyloxy)-4a-hydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-5-yl (2e)-3-phenylprop-2-enoate)

SMILES for NP0325389 ((4ar,5r,6r,6as,7r,11as,11br)-6-(acetyloxy)-4a-hydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-5-yl (2e)-3-phenylprop-2-enoate)

INCHI for NP0325389 ((4ar,5r,6r,6as,7r,11as,11br)-6-(acetyloxy)-4a-hydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-5-yl (2e)-3-phenylprop-2-enoate)

Structure for NP0325389 ((4ar,5r,6r,6as,7r,11as,11br)-6-(acetyloxy)-4a-hydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-5-yl (2e)-3-phenylprop-2-enoate)

3D Structure for NP0325389 ((4ar,5r,6r,6as,7r,11as,11br)-6-(acetyloxy)-4a-hydroxy-4,4,7,11b-tetramethyl-1h,2h,3h,5h,6h,6ah,7h,11h,11ah-phenanthro[3,2-b]furan-5-yl (2e)-3-phenylprop-2-enoate)