NP-MRD: Showing NP-Card for (3s)-5-[(1s,4ar,6r,8ar)-6-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpentanoic acid (NP0319952)

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Record Information

Version

2.0

Created at

2022-09-11 21:15:17 UTC

Updated at

2022-09-11 21:15:18 UTC

NP-MRD ID

NP0319952

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s)-5-[(1s,4ar,6r,8ar)-6-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpentanoic acid

Description

SCHEMBL3486760 belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. (3s)-5-[(1s,4ar,6r,8ar)-6-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpentanoic acid is found in Hardwickia binata. Based on a literature review very few articles have been published on SCHEMBL3486760.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112223152D          

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M  END

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  Mrv1652309112223152D          

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 27 28  1  0  0  0  0
 28 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  2  0  0  0  0
 32 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0319952

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](CC[C@H]1C(C)=CC[C@H]2C(C)(C)[C@@H](CC[C@]12C)OC(=O)\C=C\C1=CC=C(O)C=C1)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H40O5/c1-19(18-26(31)32)6-13-23-20(2)7-14-24-28(3,4)25(16-17-29(23,24)5)34-27(33)15-10-21-8-11-22(30)12-9-21/h7-12,15,19,23-25,30H,6,13-14,16-18H2,1-5H3,(H,31,32)/b15-10+/t19-,23-,24-,25+,29+/m0/s1

> <INCHI_KEY>
NXBXXIQYAWOZQT-BKKSLFJISA-N

> <FORMULA>
C29H40O5

> <MOLECULAR_WEIGHT>
468.634

> <EXACT_MASS>
468.287574388

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
54.19696405870631

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-5-[(1S,4aR,6R,8aR)-6-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-methylpentanoic acid

> <JCHEM_LOGP>
6.966999978333331

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.39862343378665

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.718328639776816

> <JCHEM_PKA_STRONGEST_BASIC>
-5.954731874963881

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
135.23110000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-5-[(1S,4aR,6R,8aR)-6-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpentanoic acid

> <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       2.667  -1.540   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       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.151   4.353   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.141   6.067   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.335   7.700   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.668   6.930   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  10.010   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  11.550   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  12.320   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  13.860   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  14.630   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.001  16.170   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.335  13.860   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335  12.320   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      12.003   0.770   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      10.669  -1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   24                                                  
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6   10   22                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   15                                                       
CONECT   22    9   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23    5   25   26                                             
CONECT   25   24                                                            
CONECT   26   24    2   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₀O₅

Average Mass

468.6340 Da

Monoisotopic Mass

468.28757 Da

IUPAC Name

(3S)-5-[(1S,4aR,6R,8aR)-6-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-methylpentanoic acid

Traditional Name

(3S)-5-[(1S,4aR,6R,8aR)-6-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpentanoic acid

CAS Registry Number

Not Available

SMILES

C[C@@H](CC[C@H]1C(C)=CC[C@H]2C(C)(C)[C@@H](CC[C@]12C)OC(=O)\C=C\C1=CC=C(O)C=C1)CC(O)=O

InChI Identifier

InChI=1S/C29H40O5/c1-19(18-26(31)32)6-13-23-20(2)7-14-24-28(3,4)25(16-17-29(23,24)5)34-27(33)15-10-21-8-11-22(30)12-9-21/h7-12,15,19,23-25,30H,6,13-14,16-18H2,1-5H3,(H,31,32)/b15-10+/t19-,23-,24-,25+,29+/m0/s1

InChI Key

NXBXXIQYAWOZQT-BKKSLFJISA-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
Hardwickia binata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Labdane diterpenoid
Diterpenoid
Coumaric acid ester
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Styrene
Phenol
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
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	6.97	ChemAxon
pKa (Strongest Acidic)	4.72	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	135.23 m³·mol⁻¹	ChemAxon
Polarizability	54.2 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

10194486

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21581294

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s)-5-[(1s,4ar,6r,8ar)-6-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpentanoic acid (NP0319952)

MOL for NP0319952 ((3s)-5-[(1s,4ar,6r,8ar)-6-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpentanoic acid)

3D MOL for NP0319952 ((3s)-5-[(1s,4ar,6r,8ar)-6-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpentanoic acid)

3D SDF for NP0319952 ((3s)-5-[(1s,4ar,6r,8ar)-6-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpentanoic acid)

3D-SDF for NP0319952 ((3s)-5-[(1s,4ar,6r,8ar)-6-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpentanoic acid)

PDB for NP0319952 ((3s)-5-[(1s,4ar,6r,8ar)-6-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpentanoic acid)

3D PDB for NP0319952 ((3s)-5-[(1s,4ar,6r,8ar)-6-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpentanoic acid)

SMILES for NP0319952 ((3s)-5-[(1s,4ar,6r,8ar)-6-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpentanoic acid)

INCHI for NP0319952 ((3s)-5-[(1s,4ar,6r,8ar)-6-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpentanoic acid)

Structure for NP0319952 ((3s)-5-[(1s,4ar,6r,8ar)-6-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpentanoic acid)

3D Structure for NP0319952 ((3s)-5-[(1s,4ar,6r,8ar)-6-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-3-methylpentanoic acid)