NP-MRD: Showing NP-Card for (3as,4r,7ar)-5-(2-hydroxy-2-methylpropyl)-6-[(2e)-4-(2-hydroxy-5-methoxy-3-methylphenyl)-2-methylbut-2-en-1-yl]-3a,7a-dimethyl-2,3,4,7-tetrahydro-1h-inden-4-ol (NP0153774)

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Record Information

Version

2.0

Created at

2022-09-02 10:29:44 UTC

Updated at

2022-09-02 10:29:45 UTC

NP-MRD ID

NP0153774

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3as,4r,7ar)-5-(2-hydroxy-2-methylpropyl)-6-[(2e)-4-(2-hydroxy-5-methoxy-3-methylphenyl)-2-methylbut-2-en-1-yl]-3a,7a-dimethyl-2,3,4,7-tetrahydro-1h-inden-4-ol

Description

(3AS,4R,7aR)-5-(2-hydroxy-2-methylpropyl)-6-[(2E)-4-(2-hydroxy-5-methoxy-3-methylphenyl)-2-methylbut-2-en-1-yl]-3a,7a-dimethyl-2,3,3a,4,7,7a-hexahydro-1H-inden-4-ol belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. (3as,4r,7ar)-5-(2-hydroxy-2-methylpropyl)-6-[(2e)-4-(2-hydroxy-5-methoxy-3-methylphenyl)-2-methylbut-2-en-1-yl]-3a,7a-dimethyl-2,3,4,7-tetrahydro-1h-inden-4-ol is found in Cystoseira baccata. Based on a literature review very few articles have been published on (3aS,4R,7aR)-5-(2-hydroxy-2-methylpropyl)-6-[(2E)-4-(2-hydroxy-5-methoxy-3-methylphenyl)-2-methylbut-2-en-1-yl]-3a,7a-dimethyl-2,3,3a,4,7,7a-hexahydro-1H-inden-4-ol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022212292D          

 32 34  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309022212292D          

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 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 15 31  1  0  0  0  0
  9 32  2  0  0  0  0
  3 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0153774

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(C)=C(O)C(C\C=C(/C)CC2=C(CC(C)(C)O)[C@@H](O)[C@@]3(C)CCC[C@]3(C)C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H42O4/c1-18(9-10-20-15-22(32-7)14-19(2)24(20)29)13-21-16-27(5)11-8-12-28(27,6)25(30)23(21)17-26(3,4)31/h9,14-15,25,29-31H,8,10-13,16-17H2,1-7H3/b18-9+/t25-,27-,28-/m1/s1

> <INCHI_KEY>
LBLHHROBLKNZGS-BSLDVHQESA-N

> <FORMULA>
C28H42O4

> <MOLECULAR_WEIGHT>
442.64

> <EXACT_MASS>
442.308309832

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
51.538827462049866

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3aS,4R,7aR)-5-(2-hydroxy-2-methylpropyl)-6-[(2E)-4-(2-hydroxy-5-methoxy-3-methylphenyl)-2-methylbut-2-en-1-yl]-3a,7a-dimethyl-2,3,3a,4,7,7a-hexahydro-1H-inden-4-ol

> <ALOGPS_LOGP>
5.18

> <JCHEM_LOGP>
5.423029255666668

> <ALOGPS_LOGS>
-5.24

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.094843342493455

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.110227643468036

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6579584815672685

> <JCHEM_POLAR_SURFACE_AREA>
69.92

> <JCHEM_REFRACTIVITY>
132.46390000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.54e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,4R,7aR)-5-(2-hydroxy-2-methylpropyl)-6-[(2E)-4-(2-hydroxy-5-methoxy-3-methylphenyl)-2-methylbut-2-en-1-yl]-3a,7a-dimethyl-2,3,4,7-tetrahydro-1H-inden-4-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      12.926  13.623   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      11.592  12.853   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.592  11.313   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.926  10.543   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.926   9.003   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.260   8.233   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.592   8.233   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      11.592   6.693   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      10.259   9.003   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.925   8.233   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.925   6.693   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.258   6.693   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.591   1.303   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.925   2.073   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.259   2.843   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.695   0.739   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.155   3.407   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.924  -0.237   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.429   0.541   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.429   5.144   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.259  10.543   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   32                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   32                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   31                                                  
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18                                                            
CONECT   22   16   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26   29                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   24   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   15                                                       
CONECT   32    9    3                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₂O₄

Average Mass

442.6400 Da

Monoisotopic Mass

442.30831 Da

IUPAC Name

(3aS,4R,7aR)-5-(2-hydroxy-2-methylpropyl)-6-[(2E)-4-(2-hydroxy-5-methoxy-3-methylphenyl)-2-methylbut-2-en-1-yl]-3a,7a-dimethyl-2,3,3a,4,7,7a-hexahydro-1H-inden-4-ol

Traditional Name

(3aS,4R,7aR)-5-(2-hydroxy-2-methylpropyl)-6-[(2E)-4-(2-hydroxy-5-methoxy-3-methylphenyl)-2-methylbut-2-en-1-yl]-3a,7a-dimethyl-2,3,4,7-tetrahydro-1H-inden-4-ol

CAS Registry Number

Not Available

SMILES

COC1=CC(C)=C(O)C(C\C=C(/C)CC2=C(CC(C)(C)O)[C@@H](O)[C@@]3(C)CCC[C@]3(C)C2)=C1

InChI Identifier

InChI=1S/C28H42O4/c1-18(9-10-20-15-22(32-7)14-19(2)24(20)29)13-21-16-27(5)11-8-12-28(27,6)25(30)23(21)17-26(3,4)31/h9,14-15,25,29-31H,8,10-13,16-17H2,1-7H3/b18-9+/t25-,27-,28-/m1/s1

InChI Key

LBLHHROBLKNZGS-BSLDVHQESA-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
Gongolaria baccata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Methoxyphenol
4-alkoxyphenol
Anisole
Phenoxy compound
O-cresol
Phenol ether
Methoxybenzene
Alkyl aryl ether
Toluene
Monocyclic benzene moiety
Tertiary alcohol
Secondary alcohol
Ether
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	5.18	ALOGPS
logP	5.42	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	10.11	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.92 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	132.46 m³·mol⁻¹	ChemAxon
Polarizability	51.54 Å³	ChemAxon
Number of Rings	3	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

25155862

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3as,4r,7ar)-5-(2-hydroxy-2-methylpropyl)-6-[(2e)-4-(2-hydroxy-5-methoxy-3-methylphenyl)-2-methylbut-2-en-1-yl]-3a,7a-dimethyl-2,3,4,7-tetrahydro-1h-inden-4-ol (NP0153774)

MOL for NP0153774 ((3as,4r,7ar)-5-(2-hydroxy-2-methylpropyl)-6-[(2e)-4-(2-hydroxy-5-methoxy-3-methylphenyl)-2-methylbut-2-en-1-yl]-3a,7a-dimethyl-2,3,4,7-tetrahydro-1h-inden-4-ol)

3D MOL for NP0153774 ((3as,4r,7ar)-5-(2-hydroxy-2-methylpropyl)-6-[(2e)-4-(2-hydroxy-5-methoxy-3-methylphenyl)-2-methylbut-2-en-1-yl]-3a,7a-dimethyl-2,3,4,7-tetrahydro-1h-inden-4-ol)

3D SDF for NP0153774 ((3as,4r,7ar)-5-(2-hydroxy-2-methylpropyl)-6-[(2e)-4-(2-hydroxy-5-methoxy-3-methylphenyl)-2-methylbut-2-en-1-yl]-3a,7a-dimethyl-2,3,4,7-tetrahydro-1h-inden-4-ol)

3D-SDF for NP0153774 ((3as,4r,7ar)-5-(2-hydroxy-2-methylpropyl)-6-[(2e)-4-(2-hydroxy-5-methoxy-3-methylphenyl)-2-methylbut-2-en-1-yl]-3a,7a-dimethyl-2,3,4,7-tetrahydro-1h-inden-4-ol)

PDB for NP0153774 ((3as,4r,7ar)-5-(2-hydroxy-2-methylpropyl)-6-[(2e)-4-(2-hydroxy-5-methoxy-3-methylphenyl)-2-methylbut-2-en-1-yl]-3a,7a-dimethyl-2,3,4,7-tetrahydro-1h-inden-4-ol)

3D PDB for NP0153774 ((3as,4r,7ar)-5-(2-hydroxy-2-methylpropyl)-6-[(2e)-4-(2-hydroxy-5-methoxy-3-methylphenyl)-2-methylbut-2-en-1-yl]-3a,7a-dimethyl-2,3,4,7-tetrahydro-1h-inden-4-ol)

SMILES for NP0153774 ((3as,4r,7ar)-5-(2-hydroxy-2-methylpropyl)-6-[(2e)-4-(2-hydroxy-5-methoxy-3-methylphenyl)-2-methylbut-2-en-1-yl]-3a,7a-dimethyl-2,3,4,7-tetrahydro-1h-inden-4-ol)

INCHI for NP0153774 ((3as,4r,7ar)-5-(2-hydroxy-2-methylpropyl)-6-[(2e)-4-(2-hydroxy-5-methoxy-3-methylphenyl)-2-methylbut-2-en-1-yl]-3a,7a-dimethyl-2,3,4,7-tetrahydro-1h-inden-4-ol)

Structure for NP0153774 ((3as,4r,7ar)-5-(2-hydroxy-2-methylpropyl)-6-[(2e)-4-(2-hydroxy-5-methoxy-3-methylphenyl)-2-methylbut-2-en-1-yl]-3a,7a-dimethyl-2,3,4,7-tetrahydro-1h-inden-4-ol)

3D Structure for NP0153774 ((3as,4r,7ar)-5-(2-hydroxy-2-methylpropyl)-6-[(2e)-4-(2-hydroxy-5-methoxy-3-methylphenyl)-2-methylbut-2-en-1-yl]-3a,7a-dimethyl-2,3,4,7-tetrahydro-1h-inden-4-ol)