NP-MRD: Showing NP-Card for 3-{[(3s,3as,5as,6s,7s,9ar,9br)-3-(dimethoxymethyl)-3,3a,6,7,9a-pentamethyl-octahydro-1h-cyclopenta[a]naphthalen-6-yl]methyl}-4-hydroxybenzoic acid (NP0158337)

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Record Information

Version

2.0

Created at

2022-09-02 15:54:16 UTC

Updated at

2022-09-02 15:54:16 UTC

NP-MRD ID

NP0158337

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-{[(3s,3as,5as,6s,7s,9ar,9br)-3-(dimethoxymethyl)-3,3a,6,7,9a-pentamethyl-octahydro-1h-cyclopenta[a]naphthalen-6-yl]methyl}-4-hydroxybenzoic acid

Description

3-{[(3S,3aS,5aS,6S,7S,9aR,9bR)-3-(dimethoxymethyl)-3,3a,6,7,9a-pentamethyl-dodecahydro-1H-cyclopenta[a]naphthalen-6-yl]methyl}-4-hydroxybenzoic acid belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review very few articles have been published on 3-{[(3S,3aS,5aS,6S,7S,9aR,9bR)-3-(dimethoxymethyl)-3,3a,6,7,9a-pentamethyl-dodecahydro-1H-cyclopenta[a]naphthalen-6-yl]methyl}-4-hydroxybenzoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022217542D          

 34 37  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309022217542D          

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  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 21 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  0  0  0  0
 16 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 15 33  1  0  0  0  0
 10 33  1  0  0  0  0
 33 34  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0158337

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(OC)[C@@]1(C)CC[C@H]2[C@]1(C)CC[C@H]1[C@@](C)(CC3=CC(=CC=C3O)C(O)=O)[C@@H](C)CC[C@@]21C

> <INCHI_IDENTIFIER>
InChI=1S/C29H44O5/c1-18-10-13-26(2)22(27(18,3)17-20-16-19(24(31)32)8-9-21(20)30)11-14-28(4)23(26)12-15-29(28,5)25(33-6)34-7/h8-9,16,18,22-23,25,30H,10-15,17H2,1-7H3,(H,31,32)/t18-,22+,23+,26+,27-,28-,29+/m0/s1

> <INCHI_KEY>
NGZCNRIYOUJSLA-AZKYYOOMSA-N

> <FORMULA>
C29H44O5

> <MOLECULAR_WEIGHT>
472.666

> <EXACT_MASS>
472.318874517

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
54.44305245499875

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[(3S,3aS,5aS,6S,7S,9aR,9bR)-3-(dimethoxymethyl)-3,3a,6,7,9a-pentamethyl-dodecahydro-1H-cyclopenta[a]naphthalen-6-yl]methyl}-4-hydroxybenzoic acid

> <ALOGPS_LOGP>
6.08

> <JCHEM_LOGP>
6.8566364669999995

> <ALOGPS_LOGS>
-5.98

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.922372274557098

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.376010513256578

> <JCHEM_PKA_STRONGEST_BASIC>
-3.998059310053781

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
133.78529999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.96e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(3S,3aS,5aS,6S,7S,9aR,9bR)-3-(dimethoxymethyl)-3,3a,6,7,9a-pentamethyl-octahydro-1H-cyclopenta[a]naphthalen-6-yl]methyl}-4-hydroxybenzoic acid

> <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      10.609  -1.289   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.070  -1.337   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.258  -0.028   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.986   1.329   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.175   2.638   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.719  -0.076   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.928  -1.602   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.832   1.460   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.406   2.042   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.412   0.866   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.223  -0.443   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.167  -1.660   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.495  -1.800   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.956  -1.848   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.145  -0.539   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.606  -0.587   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.920  -2.095   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.824  -1.159   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.044  -2.683   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.166  -3.636   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.054  -5.160   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.156  -6.112   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.586  -5.541   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.936  -7.637   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.484  -5.731   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.694  -4.779   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.474  -3.255   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -3.684  -2.302   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.206   0.722   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.745   0.674   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.522   2.079   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.062   2.127   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.873   0.818   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.601   2.175   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7    8   11                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   33                                                  
CONECT   11   10    6   12   13                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   33                                                  
CONECT   16   15   17   18   29                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   27                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   25                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   21   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   19   28                                                  
CONECT   28   27                                                            
CONECT   29   16   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   15   10   34                                             
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
3-{[(3S,3as,5as,6S,7S,9ar,9BR)-3-(dimethoxymethyl)-3,3a,6,7,9a-pentamethyl-dodecahydro-1H-cyclopenta[a]naphthalen-6-yl]methyl}-4-hydroxybenzoate	Generator

Chemical Formula

C₂₉H₄₄O₅

Average Mass

472.6660 Da

Monoisotopic Mass

472.31887 Da

IUPAC Name

3-{[(3S,3aS,5aS,6S,7S,9aR,9bR)-3-(dimethoxymethyl)-3,3a,6,7,9a-pentamethyl-dodecahydro-1H-cyclopenta[a]naphthalen-6-yl]methyl}-4-hydroxybenzoic acid

Traditional Name

3-{[(3S,3aS,5aS,6S,7S,9aR,9bR)-3-(dimethoxymethyl)-3,3a,6,7,9a-pentamethyl-octahydro-1H-cyclopenta[a]naphthalen-6-yl]methyl}-4-hydroxybenzoic acid

CAS Registry Number

Not Available

SMILES

COC(OC)[C@@]1(C)CC[C@H]2[C@]1(C)CC[C@H]1[C@@](C)(CC3=CC(=CC=C3O)C(O)=O)[C@@H](C)CC[C@@]21C

InChI Identifier

InChI=1S/C29H44O5/c1-18-10-13-26(2)22(27(18,3)17-20-16-19(24(31)32)8-9-21(20)30)11-14-28(4)23(26)12-15-29(28,5)25(33-6)34-7/h8-9,16,18,22-23,25,30H,10-15,17H2,1-7H3,(H,31,32)/t18-,22+,23+,26+,27-,28-,29+/m0/s1

InChI Key

NGZCNRIYOUJSLA-AZKYYOOMSA-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 sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Hydroxybenzoic acid
Benzoic acid or derivatives
Benzoic acid
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxylic acid
Carboxylic acid derivative
Acetal
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen 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	6.08	ALOGPS
logP	6.86	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	4.38	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	133.79 m³·mol⁻¹	ChemAxon
Polarizability	54.44 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	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

163186965

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-{[(3s,3as,5as,6s,7s,9ar,9br)-3-(dimethoxymethyl)-3,3a,6,7,9a-pentamethyl-octahydro-1h-cyclopenta[a]naphthalen-6-yl]methyl}-4-hydroxybenzoic acid (NP0158337)

MOL for NP0158337 (3-{[(3s,3as,5as,6s,7s,9ar,9br)-3-(dimethoxymethyl)-3,3a,6,7,9a-pentamethyl-octahydro-1h-cyclopenta[a]naphthalen-6-yl]methyl}-4-hydroxybenzoic acid)

3D MOL for NP0158337 (3-{[(3s,3as,5as,6s,7s,9ar,9br)-3-(dimethoxymethyl)-3,3a,6,7,9a-pentamethyl-octahydro-1h-cyclopenta[a]naphthalen-6-yl]methyl}-4-hydroxybenzoic acid)

3D SDF for NP0158337 (3-{[(3s,3as,5as,6s,7s,9ar,9br)-3-(dimethoxymethyl)-3,3a,6,7,9a-pentamethyl-octahydro-1h-cyclopenta[a]naphthalen-6-yl]methyl}-4-hydroxybenzoic acid)

3D-SDF for NP0158337 (3-{[(3s,3as,5as,6s,7s,9ar,9br)-3-(dimethoxymethyl)-3,3a,6,7,9a-pentamethyl-octahydro-1h-cyclopenta[a]naphthalen-6-yl]methyl}-4-hydroxybenzoic acid)

PDB for NP0158337 (3-{[(3s,3as,5as,6s,7s,9ar,9br)-3-(dimethoxymethyl)-3,3a,6,7,9a-pentamethyl-octahydro-1h-cyclopenta[a]naphthalen-6-yl]methyl}-4-hydroxybenzoic acid)

3D PDB for NP0158337 (3-{[(3s,3as,5as,6s,7s,9ar,9br)-3-(dimethoxymethyl)-3,3a,6,7,9a-pentamethyl-octahydro-1h-cyclopenta[a]naphthalen-6-yl]methyl}-4-hydroxybenzoic acid)

SMILES for NP0158337 (3-{[(3s,3as,5as,6s,7s,9ar,9br)-3-(dimethoxymethyl)-3,3a,6,7,9a-pentamethyl-octahydro-1h-cyclopenta[a]naphthalen-6-yl]methyl}-4-hydroxybenzoic acid)

INCHI for NP0158337 (3-{[(3s,3as,5as,6s,7s,9ar,9br)-3-(dimethoxymethyl)-3,3a,6,7,9a-pentamethyl-octahydro-1h-cyclopenta[a]naphthalen-6-yl]methyl}-4-hydroxybenzoic acid)

Structure for NP0158337 (3-{[(3s,3as,5as,6s,7s,9ar,9br)-3-(dimethoxymethyl)-3,3a,6,7,9a-pentamethyl-octahydro-1h-cyclopenta[a]naphthalen-6-yl]methyl}-4-hydroxybenzoic acid)

3D Structure for NP0158337 (3-{[(3s,3as,5as,6s,7s,9ar,9br)-3-(dimethoxymethyl)-3,3a,6,7,9a-pentamethyl-octahydro-1h-cyclopenta[a]naphthalen-6-yl]methyl}-4-hydroxybenzoic acid)