NP-MRD: Showing NP-Card for 3-[(1s,4as,5s,6s,8as)-5-(2,5-dihydroxy-3-methylbenzoyl)-5,6,8a-trimethyl-2-(propan-2-ylidene)-hexahydro-1h-naphthalen-1-yl]propanoic acid (NP0283835)

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Record Information

Version

2.0

Created at

2022-09-09 11:16:05 UTC

Updated at

2022-09-09 11:16:05 UTC

NP-MRD ID

NP0283835

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[(1s,4as,5s,6s,8as)-5-(2,5-dihydroxy-3-methylbenzoyl)-5,6,8a-trimethyl-2-(propan-2-ylidene)-hexahydro-1h-naphthalen-1-yl]propanoic acid

Description

3-[(1S,4aS,5S,6S,8aS)-5-(2,5-dihydroxy-3-methylbenzoyl)-5,6,8a-trimethyl-2-(propan-2-ylidene)-decahydronaphthalen-1-yl]propanoic acid belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 3-[(1s,4as,5s,6s,8as)-5-(2,5-dihydroxy-3-methylbenzoyl)-5,6,8a-trimethyl-2-(propan-2-ylidene)-hexahydro-1h-naphthalen-1-yl]propanoic acid is found in Stypopodium zonale. Based on a literature review very few articles have been published on 3-[(1S,4aS,5S,6S,8aS)-5-(2,5-dihydroxy-3-methylbenzoyl)-5,6,8a-trimethyl-2-(propan-2-ylidene)-decahydronaphthalen-1-yl]propanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092213162D          

 32 34  0  0  1  0            999 V2000
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309092213162D          

 32 34  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0283835

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC[C@@]2(C)[C@H](CCC(O)=O)C(CC[C@@H]2[C@@]1(C)C(=O)C1=CC(O)=CC(C)=C1O)=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O5/c1-15(2)19-7-9-22-26(5,21(19)8-10-23(29)30)12-11-17(4)27(22,6)25(32)20-14-18(28)13-16(3)24(20)31/h13-14,17,21-22,28,31H,7-12H2,1-6H3,(H,29,30)/t17-,21+,22-,26-,27-/m0/s1

> <INCHI_KEY>
GKCQTPZPJOJIQY-WOIGANAZSA-N

> <FORMULA>
C27H38O5

> <MOLECULAR_WEIGHT>
442.596

> <EXACT_MASS>
442.271924324

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
50.67046432116831

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(1S,4aS,5S,6S,8aS)-5-(2,5-dihydroxy-3-methylbenzoyl)-5,6,8a-trimethyl-2-(propan-2-ylidene)-decahydronaphthalen-1-yl]propanoic acid

> <JCHEM_LOGP>
6.768500649666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.411243571827528

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.560297968590053

> <JCHEM_PKA_STRONGEST_BASIC>
-5.112420818363604

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
126.38529999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-[(1S,4aS,5S,6S,8aS)-5-(2,5-dihydroxy-3-methylbenzoyl)-5,6,8a-trimethyl-2-(propan-2-ylidene)-hexahydro-1H-naphthalen-1-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.390  -4.440   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.944  -4.440   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.405  -4.493   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.760  -5.746   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.300  -5.692   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.116  -6.998   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.655  -6.944   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.393  -8.358   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.854  -8.411   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.131  -9.771   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.037  -7.105   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.498  -7.159   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   27                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   14                                                  
CONECT    8    7    9   10   27                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    7   15   16                                             
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   18   26                                                  
CONECT   26   25                                                            
CONECT   27    8    4   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Value	Source
3-[(1S,4AS,5S,6S,8as)-5-(2,5-dihydroxy-3-methylbenzoyl)-5,6,8a-trimethyl-2-(propan-2-ylidene)-decahydronaphthalen-1-yl]propanoate	Generator

Chemical Formula

C₂₇H₃₈O₅

Average Mass

442.5960 Da

Monoisotopic Mass

442.27192 Da

IUPAC Name

3-[(1S,4aS,5S,6S,8aS)-5-(2,5-dihydroxy-3-methylbenzoyl)-5,6,8a-trimethyl-2-(propan-2-ylidene)-decahydronaphthalen-1-yl]propanoic acid

Traditional Name

3-[(1S,4aS,5S,6S,8aS)-5-(2,5-dihydroxy-3-methylbenzoyl)-5,6,8a-trimethyl-2-(propan-2-ylidene)-hexahydro-1H-naphthalen-1-yl]propanoic acid

CAS Registry Number

Not Available

SMILES

C[C@H]1CC[C@@]2(C)[C@H](CCC(O)=O)C(CC[C@@H]2[C@@]1(C)C(=O)C1=CC(O)=CC(C)=C1O)=C(C)C

InChI Identifier

InChI=1S/C27H38O5/c1-15(2)19-7-9-22-26(5,21(19)8-10-23(29)30)12-11-17(4)27(22,6)25(32)20-14-18(28)13-16(3)24(20)31/h13-14,17,21-22,28,31H,7-12H2,1-6H3,(H,29,30)/t17-,21+,22-,26-,27-/m0/s1

InChI Key

GKCQTPZPJOJIQY-WOIGANAZSA-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
Stypopodium zonale	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Aromatic monoterpenoid
Bicyclic monoterpenoid
Monoterpenoid
Carbocyclic fatty acid
Hydroquinone
M-cresol
Benzoyl
Aryl alkyl ketone
O-cresol
1-hydroxy-2-unsubstituted benzenoid
Hydroxy fatty acid
Toluene
Phenol
Benzenoid
Monocyclic benzene moiety
Fatty acyl
Vinylogous acid
Carboxylic acid
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
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	6.77	ChemAxon
pKa (Strongest Acidic)	4.56	ChemAxon
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	126.39 m³·mol⁻¹	ChemAxon
Polarizability	50.67 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	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

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

162920834

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-[(1s,4as,5s,6s,8as)-5-(2,5-dihydroxy-3-methylbenzoyl)-5,6,8a-trimethyl-2-(propan-2-ylidene)-hexahydro-1h-naphthalen-1-yl]propanoic acid (NP0283835)

MOL for NP0283835 (3-[(1s,4as,5s,6s,8as)-5-(2,5-dihydroxy-3-methylbenzoyl)-5,6,8a-trimethyl-2-(propan-2-ylidene)-hexahydro-1h-naphthalen-1-yl]propanoic acid)

3D MOL for NP0283835 (3-[(1s,4as,5s,6s,8as)-5-(2,5-dihydroxy-3-methylbenzoyl)-5,6,8a-trimethyl-2-(propan-2-ylidene)-hexahydro-1h-naphthalen-1-yl]propanoic acid)

3D SDF for NP0283835 (3-[(1s,4as,5s,6s,8as)-5-(2,5-dihydroxy-3-methylbenzoyl)-5,6,8a-trimethyl-2-(propan-2-ylidene)-hexahydro-1h-naphthalen-1-yl]propanoic acid)

3D-SDF for NP0283835 (3-[(1s,4as,5s,6s,8as)-5-(2,5-dihydroxy-3-methylbenzoyl)-5,6,8a-trimethyl-2-(propan-2-ylidene)-hexahydro-1h-naphthalen-1-yl]propanoic acid)

PDB for NP0283835 (3-[(1s,4as,5s,6s,8as)-5-(2,5-dihydroxy-3-methylbenzoyl)-5,6,8a-trimethyl-2-(propan-2-ylidene)-hexahydro-1h-naphthalen-1-yl]propanoic acid)

3D PDB for NP0283835 (3-[(1s,4as,5s,6s,8as)-5-(2,5-dihydroxy-3-methylbenzoyl)-5,6,8a-trimethyl-2-(propan-2-ylidene)-hexahydro-1h-naphthalen-1-yl]propanoic acid)

SMILES for NP0283835 (3-[(1s,4as,5s,6s,8as)-5-(2,5-dihydroxy-3-methylbenzoyl)-5,6,8a-trimethyl-2-(propan-2-ylidene)-hexahydro-1h-naphthalen-1-yl]propanoic acid)

INCHI for NP0283835 (3-[(1s,4as,5s,6s,8as)-5-(2,5-dihydroxy-3-methylbenzoyl)-5,6,8a-trimethyl-2-(propan-2-ylidene)-hexahydro-1h-naphthalen-1-yl]propanoic acid)

Structure for NP0283835 (3-[(1s,4as,5s,6s,8as)-5-(2,5-dihydroxy-3-methylbenzoyl)-5,6,8a-trimethyl-2-(propan-2-ylidene)-hexahydro-1h-naphthalen-1-yl]propanoic acid)

3D Structure for NP0283835 (3-[(1s,4as,5s,6s,8as)-5-(2,5-dihydroxy-3-methylbenzoyl)-5,6,8a-trimethyl-2-(propan-2-ylidene)-hexahydro-1h-naphthalen-1-yl]propanoic acid)