NP-MRD: Showing NP-Card for 2-[(2e)-4-[(1r,4's,4ar,7ar)-4'-hydroxy-4a,5',5',7a-tetramethyl-6,7-dihydro-5h-spiro[cyclopenta[c]pyran-1,2'-oxolan]-3-yl]-3-methylbut-2-en-1-yl]-6-methylbenzene-1,4-diol (NP0320376)

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Record Information

Version

2.0

Created at

2022-09-11 21:59:22 UTC

Updated at

2022-09-11 21:59:22 UTC

NP-MRD ID

NP0320376

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(2e)-4-[(1r,4's,4ar,7ar)-4'-hydroxy-4a,5',5',7a-tetramethyl-6,7-dihydro-5h-spiro[cyclopenta[c]pyran-1,2'-oxolan]-3-yl]-3-methylbut-2-en-1-yl]-6-methylbenzene-1,4-diol

Description

2-[(2E)-3-{[(1R,4'S,4aR,7aR)-4'-hydroxy-4a,5',5',7a-tetramethyl-5,6,7,7a-tetrahydro-4aH-spiro[cyclopenta[c]pyran-1,2'-oxolane]-3-yl]methyl}but-2-en-1-yl]-6-methylbenzene-1,4-diol belongs to the class of organic compounds known as prenylated hydroquinones. These are quinones with a structure characterized by the hydroquinone ring substituted by an prenyl side-chain. 2-[(2e)-4-[(1r,4's,4ar,7ar)-4'-hydroxy-4a,5',5',7a-tetramethyl-6,7-dihydro-5h-spiro[cyclopenta[c]pyran-1,2'-oxolan]-3-yl]-3-methylbut-2-en-1-yl]-6-methylbenzene-1,4-diol is found in Cystoseira amentacea. Based on a literature review very few articles have been published on 2-[(2E)-3-{[(1R,4'S,4aR,7aR)-4'-hydroxy-4a,5',5',7a-tetramethyl-5,6,7,7a-tetrahydro-4aH-spiro[cyclopenta[c]pyran-1,2'-oxolane]-3-yl]methyl}but-2-en-1-yl]-6-methylbenzene-1,4-diol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112223592D          

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M  END

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M  END


  Mrv1652309112223592D          

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M  END
> <DATABASE_ID>
NP0320376

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(CC1=C[C@@]2(C)CCC[C@@]2(C)[C@]2(C[C@H](O)C(C)(C)O2)O1)=C/CC1=CC(O)=CC(C)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O5/c1-17(8-9-19-14-20(28)13-18(2)23(19)30)12-21-15-25(5)10-7-11-26(25,6)27(31-21)16-22(29)24(3,4)32-27/h8,13-15,22,28-30H,7,9-12,16H2,1-6H3/b17-8+/t22-,25+,26+,27+/m0/s1

> <INCHI_KEY>
NAGGUTLYHIBWFX-YVIGTYCOSA-N

> <FORMULA>
C27H38O5

> <MOLECULAR_WEIGHT>
442.596

> <EXACT_MASS>
442.271924324

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
49.12690800857831

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2E)-3-{[(1R,4'S,4aR,7aR)-4'-hydroxy-4a,5',5',7a-tetramethyl-5,6,7,7a-tetrahydro-4aH-spiro[cyclopenta[c]pyran-1,2'-oxolane]-3-yl]methyl}but-2-en-1-yl]-6-methylbenzene-1,4-diol

> <JCHEM_LOGP>
5.826683827666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.648330363819705

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.784944781675037

> <JCHEM_PKA_STRONGEST_BASIC>
-3.310973844491646

> <JCHEM_POLAR_SURFACE_AREA>
79.15

> <JCHEM_REFRACTIVITY>
127.9735

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2E)-3-[(1R,4'S,4aR,7aR)-4'-hydroxy-4a,5',5',7a-tetramethyl-6,7-dihydro-5H-spiro[cyclopenta[c]pyran-1,2'-oxolane]-3-ylmethyl]but-2-en-1-yl]-6-methylbenzene-1,4-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       6.359   9.568   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.627   8.051   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.075   7.525   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.254   8.516   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.701   7.989   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.881   8.980   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.328   8.454   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      14.507   9.444   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      13.596   6.937   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.417   5.947   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.685   4.430   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.970   6.473   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.790   5.483   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.448   7.061   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.716   5.544   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.164   5.018   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.432   3.502   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.708   4.363   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.738   2.686   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.366   1.192   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.830   1.084   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.252   2.511   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.578   1.127   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.805   3.037   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.913   1.501   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.485   0.924   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.114  -0.571   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.495   2.103   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.426   0.995   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.281   3.051   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.311   3.409   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       4.537   4.554   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    5   13                                                  
CONECT   13   12                                                            
CONECT   14    2   15                                                       
CONECT   15   14   16   32                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19   22                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   25   31   32                                             
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28   24                                                       
CONECT   32   24   15                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₈O₅

Average Mass

442.5960 Da

Monoisotopic Mass

442.27192 Da

IUPAC Name

2-[(2E)-3-{[(1R,4'S,4aR,7aR)-4'-hydroxy-4a,5',5',7a-tetramethyl-5,6,7,7a-tetrahydro-4aH-spiro[cyclopenta[c]pyran-1,2'-oxolane]-3-yl]methyl}but-2-en-1-yl]-6-methylbenzene-1,4-diol

Traditional Name

2-[(2E)-3-[(1R,4'S,4aR,7aR)-4'-hydroxy-4a,5',5',7a-tetramethyl-6,7-dihydro-5H-spiro[cyclopenta[c]pyran-1,2'-oxolane]-3-ylmethyl]but-2-en-1-yl]-6-methylbenzene-1,4-diol

CAS Registry Number

Not Available

SMILES

C\C(CC1=C[C@@]2(C)CCC[C@@]2(C)[C@]2(C[C@H](O)C(C)(C)O2)O1)=C/CC1=CC(O)=CC(C)=C1O

InChI Identifier

InChI=1S/C27H38O5/c1-17(8-9-19-14-20(28)13-18(2)23(19)30)12-21-15-25(5)10-7-11-26(25,6)27(31-21)16-22(29)24(3,4)32-27/h8,13-15,22,28-30H,7,9-12,16H2,1-6H3/b17-8+/t22-,25+,26+,27+/m0/s1

InChI Key

NAGGUTLYHIBWFX-YVIGTYCOSA-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
Cystoseira amentacea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prenylated hydroquinones. These are quinones with a structure characterized by the hydroquinone ring substituted by an prenyl side-chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Prenylated hydroquinones

Alternative Parents

Substituents

Prenylbenzoquinol
Hydroquinone
M-cresol
O-cresol
1-hydroxy-2-unsubstituted benzenoid
Ketal
Phenol
Toluene
Monosaccharide
Monocyclic benzene moiety
Benzenoid
Oxolane
Secondary alcohol
Acetal
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxygen 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	5.83	ChemAxon
pKa (Strongest Acidic)	9.78	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	79.15 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	127.97 m³·mol⁻¹	ChemAxon
Polarizability	49.13 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	No	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

10298844

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21681090

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[(2e)-4-[(1r,4's,4ar,7ar)-4'-hydroxy-4a,5',5',7a-tetramethyl-6,7-dihydro-5h-spiro[cyclopenta[c]pyran-1,2'-oxolan]-3-yl]-3-methylbut-2-en-1-yl]-6-methylbenzene-1,4-diol (NP0320376)

MOL for NP0320376 (2-[(2e)-4-[(1r,4's,4ar,7ar)-4'-hydroxy-4a,5',5',7a-tetramethyl-6,7-dihydro-5h-spiro[cyclopenta[c]pyran-1,2'-oxolan]-3-yl]-3-methylbut-2-en-1-yl]-6-methylbenzene-1,4-diol)

3D MOL for NP0320376 (2-[(2e)-4-[(1r,4's,4ar,7ar)-4'-hydroxy-4a,5',5',7a-tetramethyl-6,7-dihydro-5h-spiro[cyclopenta[c]pyran-1,2'-oxolan]-3-yl]-3-methylbut-2-en-1-yl]-6-methylbenzene-1,4-diol)

3D SDF for NP0320376 (2-[(2e)-4-[(1r,4's,4ar,7ar)-4'-hydroxy-4a,5',5',7a-tetramethyl-6,7-dihydro-5h-spiro[cyclopenta[c]pyran-1,2'-oxolan]-3-yl]-3-methylbut-2-en-1-yl]-6-methylbenzene-1,4-diol)

3D-SDF for NP0320376 (2-[(2e)-4-[(1r,4's,4ar,7ar)-4'-hydroxy-4a,5',5',7a-tetramethyl-6,7-dihydro-5h-spiro[cyclopenta[c]pyran-1,2'-oxolan]-3-yl]-3-methylbut-2-en-1-yl]-6-methylbenzene-1,4-diol)

PDB for NP0320376 (2-[(2e)-4-[(1r,4's,4ar,7ar)-4'-hydroxy-4a,5',5',7a-tetramethyl-6,7-dihydro-5h-spiro[cyclopenta[c]pyran-1,2'-oxolan]-3-yl]-3-methylbut-2-en-1-yl]-6-methylbenzene-1,4-diol)

3D PDB for NP0320376 (2-[(2e)-4-[(1r,4's,4ar,7ar)-4'-hydroxy-4a,5',5',7a-tetramethyl-6,7-dihydro-5h-spiro[cyclopenta[c]pyran-1,2'-oxolan]-3-yl]-3-methylbut-2-en-1-yl]-6-methylbenzene-1,4-diol)

SMILES for NP0320376 (2-[(2e)-4-[(1r,4's,4ar,7ar)-4'-hydroxy-4a,5',5',7a-tetramethyl-6,7-dihydro-5h-spiro[cyclopenta[c]pyran-1,2'-oxolan]-3-yl]-3-methylbut-2-en-1-yl]-6-methylbenzene-1,4-diol)

INCHI for NP0320376 (2-[(2e)-4-[(1r,4's,4ar,7ar)-4'-hydroxy-4a,5',5',7a-tetramethyl-6,7-dihydro-5h-spiro[cyclopenta[c]pyran-1,2'-oxolan]-3-yl]-3-methylbut-2-en-1-yl]-6-methylbenzene-1,4-diol)

Structure for NP0320376 (2-[(2e)-4-[(1r,4's,4ar,7ar)-4'-hydroxy-4a,5',5',7a-tetramethyl-6,7-dihydro-5h-spiro[cyclopenta[c]pyran-1,2'-oxolan]-3-yl]-3-methylbut-2-en-1-yl]-6-methylbenzene-1,4-diol)

3D Structure for NP0320376 (2-[(2e)-4-[(1r,4's,4ar,7ar)-4'-hydroxy-4a,5',5',7a-tetramethyl-6,7-dihydro-5h-spiro[cyclopenta[c]pyran-1,2'-oxolan]-3-yl]-3-methylbut-2-en-1-yl]-6-methylbenzene-1,4-diol)