NP-MRD: Showing NP-Card for (+)-Hyperibone H (NP0079091)

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Record Information

Version

2.0

Created at

2022-04-29 00:09:25 UTC

Updated at

2022-04-29 00:09:25 UTC

NP-MRD ID

NP0079091

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Hyperibone H

Description

(1S,3R,8R,10R)-6-benzoyl-10-[(1E)-3-hydroxy-3-methylbut-1-en-1-yl]-3-(2-hydroxypropan-2-yl)-9,9-dimethyl-8-(3-methylbut-2-en-1-yl)-4-oxatricyclo[6.3.1.0¹,⁵]Dodec-5-ene-7,12-dione belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. (+)-Hyperibone H is found in Hypericum scabrum . Based on a literature review very few articles have been published on (1S,3R,8R,10R)-6-benzoyl-10-[(1E)-3-hydroxy-3-methylbut-1-en-1-yl]-3-(2-hydroxypropan-2-yl)-9,9-dimethyl-8-(3-methylbut-2-en-1-yl)-4-oxatricyclo[6.3.1.0¹,⁵]Dodec-5-ene-7,12-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292202092D          

 39 42  0  0  1  0            999 V2000
    3.5422    0.4268    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0637    1.1222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1651   -0.1818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0135   -0.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  8  9  2  0  0  0  0
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  6 18  1  0  0  0  0
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  5 20  1  0  0  0  0
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 37 39  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304292202092D          

 39 42  0  0  1  0            999 V2000
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    5.1105    2.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6220    3.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1334    3.7551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2693    2.5963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9746    3.6192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7277    0.6326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8453    1.3862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1991   -0.0723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954   -0.8907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7523   -1.3898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6485   -2.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5130   -1.0705    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  1  8  1  0  0  0  0
  8  9  2  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 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
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
  6 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  5 20  1  0  0  0  0
 19 21  1  1  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
  5 25  1  6  0  0  0
  1 25  1  0  0  0  0
 25 26  2  0  0  0  0
  3 27  1  6  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 29 32  1  0  0  0  0
  2 33  1  0  0  0  0
  2 34  1  0  0  0  0
  1 35  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0079091

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CC[C@@]12C(=O)C(C(=O)C3=CC=CC=C3)=C3O[C@H](C[C@]3(C[C@H](\C=C\C(C)(C)O)C1(C)C)C2=O)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C33H42O6/c1-20(2)14-17-33-26(35)24(25(34)21-12-10-9-11-13-21)27-32(28(33)36,19-23(39-27)31(7,8)38)18-22(30(33,5)6)15-16-29(3,4)37/h9-16,22-23,37-38H,17-19H2,1-8H3/b16-15+/t22-,23+,32-,33-/m0/s1

> <INCHI_KEY>
NMACMGKRMBQMHU-XTEWZBTRSA-N

> <FORMULA>
C33H42O6

> <MOLECULAR_WEIGHT>
534.693

> <EXACT_MASS>
534.298139072

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
59.367767573040545

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,8R,10R)-6-benzoyl-10-[(1E)-3-hydroxy-3-methylbut-1-en-1-yl]-3-(2-hydroxypropan-2-yl)-9,9-dimethyl-8-(3-methylbut-2-en-1-yl)-4-oxatricyclo[6.3.1.0^{1,5}]dodec-5-ene-7,12-dione

> <ALOGPS_LOGP>
4.66

> <JCHEM_LOGP>
5.407151943999999

> <ALOGPS_LOGS>
-5.75

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.681248917952626

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.306605197481137

> <JCHEM_PKA_STRONGEST_BASIC>
-1.625784267358529

> <JCHEM_POLAR_SURFACE_AREA>
100.90000000000002

> <JCHEM_REFRACTIVITY>
154.73070000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.53e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,8R,10R)-6-benzoyl-10-[(1E)-3-hydroxy-3-methylbut-1-en-1-yl]-3-(2-hydroxypropan-2-yl)-9,9-dimethyl-8-(3-methylbut-2-en-1-yl)-4-oxatricyclo[6.3.1.0^{1,5}]dodec-5-ene-7,12-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       6.612   0.797   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.586   2.095   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.061   3.607   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.470   3.767   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.404   2.510   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.469   1.170   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.042  -0.339   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.625  -0.486   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.241  -1.897   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.109  -1.565   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.582  -1.371   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.705  -2.985   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.233  -3.180   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.828  -4.600   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.896  -5.826   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.368  -5.631   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.773  -4.211   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.977   1.566   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.886   3.111   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.326   3.677   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.588   3.941   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.709   4.770   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.418   5.238   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.241   2.643   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.522   1.665   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.466   2.882   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.016   4.815   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.540   4.593   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.494   5.801   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.449   7.010   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.703   4.846   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.286   6.756   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       8.825   1.181   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.045   2.588   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.838  -0.135   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.645  -1.663   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.871  -2.594   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.677  -4.122   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      10.291  -1.998   0.000  0.00  0.00           C+0
CONECT    1    2    8   25   35                                             
CONECT    2    1    3   33   34                                             
CONECT    3    2    4   27                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   20   25                                             
CONECT    6    5    7   18                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    1    9                                                  
CONECT    9    8                                                            
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18    6   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19    5                                                       
CONECT   21   19   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21                                                            
CONECT   25    5    1   26                                                  
CONECT   26   25                                                            
CONECT   27    3   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31   32                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   29                                                            
CONECT   33    2                                                            
CONECT   34    2                                                            
CONECT   35    1   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₃H₄₂O₆

Average Mass

534.6930 Da

Monoisotopic Mass

534.29814 Da

IUPAC Name

(1S,3R,8R,10R)-6-benzoyl-10-[(1E)-3-hydroxy-3-methylbut-1-en-1-yl]-3-(2-hydroxypropan-2-yl)-9,9-dimethyl-8-(3-methylbut-2-en-1-yl)-4-oxatricyclo[6.3.1.0^{1,5}]dodec-5-ene-7,12-dione

Traditional Name

(1S,3R,8R,10R)-6-benzoyl-10-[(1E)-3-hydroxy-3-methylbut-1-en-1-yl]-3-(2-hydroxypropan-2-yl)-9,9-dimethyl-8-(3-methylbut-2-en-1-yl)-4-oxatricyclo[6.3.1.0^{1,5}]dodec-5-ene-7,12-dione

CAS Registry Number

Not Available

SMILES

CC(C)=CC[C@@]12C(=O)C(C(=O)C3=CC=CC=C3)=C3O[C@H](C[C@]3(C[C@H](\C=C\C(C)(C)O)C1(C)C)C2=O)C(C)(C)O

InChI Identifier

InChI=1S/C33H42O6/c1-20(2)14-17-33-26(35)24(25(34)21-12-10-9-11-13-21)27-32(28(33)36,19-23(39-27)31(7,8)38)18-22(30(33,5)6)15-16-29(3,4)37/h9-16,22-23,37-38H,17-19H2,1-8H3/b16-15+/t22-,23+,32-,33-/m0/s1

InChI Key

NMACMGKRMBQMHU-XTEWZBTRSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Hypericum scabrum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Aromatic monoterpenoids

Alternative Parents

Substituents

Aromatic monoterpenoid
Aryl ketone
Benzoyl
Cyclohexenone
Benzenoid
Monocyclic benzene moiety
Vinylogous ester
Tetrahydrofuran
Tertiary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	4.66	ALOGPS
logP	5.41	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	14.31	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	154.73 m³·mol⁻¹	ChemAxon
Polarizability	59.37 Å³	ChemAxon
Number of Rings	4	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

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

163105223

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Hyperibone H (NP0079091)

MOL for NP0079091 ((+)-Hyperibone H)

3D MOL for NP0079091 ((+)-Hyperibone H)

3D SDF for NP0079091 ((+)-Hyperibone H)

3D-SDF for NP0079091 ((+)-Hyperibone H)

PDB for NP0079091 ((+)-Hyperibone H)

3D PDB for NP0079091 ((+)-Hyperibone H)

SMILES for NP0079091 ((+)-Hyperibone H)

INCHI for NP0079091 ((+)-Hyperibone H)

Structure for NP0079091 ((+)-Hyperibone H)

3D Structure for NP0079091 ((+)-Hyperibone H)