NP-MRD: Showing NP-Card for (1r,2s,4ar,5r,8as)-5-hydroxy-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalen-1-yl (2e)-3-phenylprop-2-enoate (NP0225977)

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Record Information

Version

2.0

Created at

2022-09-06 04:51:52 UTC

Updated at

2022-09-06 04:51:52 UTC

NP-MRD ID

NP0225977

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,4ar,5r,8as)-5-hydroxy-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalen-1-yl (2e)-3-phenylprop-2-enoate

Description

(1R,2S,4aR,5R,8aS)-5-hydroxy-4a-methyl-8-methylidene-2-(propan-2-yl)-decahydronaphthalen-1-yl (2E)-3-phenylprop-2-enoate belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. (1r,2s,4ar,5r,8as)-5-hydroxy-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalen-1-yl (2e)-3-phenylprop-2-enoate is found in Brintonia discoidea and Verbesina glabrata. Based on a literature review very few articles have been published on (1R,2S,4aR,5R,8aS)-5-hydroxy-4a-methyl-8-methylidene-2-(propan-2-yl)-decahydronaphthalen-1-yl (2E)-3-phenylprop-2-enoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062206512D          

 27 29  0  0  1  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
    0.7145   -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  1  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3928   -2.9737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 15 27  1  0  0  0  0
 27  2  1  1  0  0  0
  7 27  1  0  0  0  0
M  END


  Mrv1652309062206512D          

 27 29  0  0  1  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
    0.7145   -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  1  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3928   -2.9737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 15 27  1  0  0  0  0
 27  2  1  1  0  0  0
  7 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0225977

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O3/c1-16(2)19-14-15-24(4)20(25)12-10-17(3)22(24)23(19)27-21(26)13-11-18-8-6-5-7-9-18/h5-9,11,13,16,19-20,22-23,25H,3,10,12,14-15H2,1-2,4H3/b13-11+/t19-,20+,22+,23+,24-/m0/s1

> <INCHI_KEY>
VWKORDLHIGIYBW-SDIJUFKJSA-N

> <FORMULA>
C24H32O3

> <MOLECULAR_WEIGHT>
368.517

> <EXACT_MASS>
368.23514489

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
42.63179259234397

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,4aR,5R,8aS)-5-hydroxy-4a-methyl-8-methylidene-2-(propan-2-yl)-decahydronaphthalen-1-yl (2E)-3-phenylprop-2-enoate

> <JCHEM_LOGP>
5.497157457

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.67799890242577

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9396432800789682

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
109.2011

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4aR,5R,8aS)-5-hydroxy-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalen-1-yl (2E)-3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   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       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.200  -5.551   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   27                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9   27                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   11   16   27                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   21                                                       
CONECT   27   15    2    7                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Value	Source
(1R,2S,4AR,5R,8as)-5-hydroxy-4a-methyl-8-methylidene-2-(propan-2-yl)-decahydronaphthalen-1-yl (2E)-3-phenylprop-2-enoic acid	Generator

Chemical Formula

C₂₄H₃₂O₃

Average Mass

368.5170 Da

Monoisotopic Mass

368.23514 Da

IUPAC Name

(1R,2S,4aR,5R,8aS)-5-hydroxy-4a-methyl-8-methylidene-2-(propan-2-yl)-decahydronaphthalen-1-yl (2E)-3-phenylprop-2-enoate

Traditional Name

(1R,2S,4aR,5R,8aS)-5-hydroxy-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalen-1-yl (2E)-3-phenylprop-2-enoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C24H32O3/c1-16(2)19-14-15-24(4)20(25)12-10-17(3)22(24)23(19)27-21(26)13-11-18-8-6-5-7-9-18/h5-9,11,13,16,19-20,22-23,25H,3,10,12,14-15H2,1-2,4H3/b13-11+/t19-,20+,22+,23+,24-/m0/s1

InChI Key

VWKORDLHIGIYBW-SDIJUFKJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Brintonia discoidea	LOTUS Database	35616633
Verbesina glabrata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids

Alternative Parents

Substituents

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid
Cinnamic acid or derivatives
Cinnamic acid ester
Styrene
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
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	5.5	ChemAxon
pKa (Strongest Acidic)	14.68	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	109.2 m³·mol⁻¹	ChemAxon
Polarizability	42.63 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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

14164921

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,4ar,5r,8as)-5-hydroxy-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalen-1-yl (2e)-3-phenylprop-2-enoate (NP0225977)

MOL for NP0225977 ((1r,2s,4ar,5r,8as)-5-hydroxy-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalen-1-yl (2e)-3-phenylprop-2-enoate)

3D MOL for NP0225977 ((1r,2s,4ar,5r,8as)-5-hydroxy-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalen-1-yl (2e)-3-phenylprop-2-enoate)

3D SDF for NP0225977 ((1r,2s,4ar,5r,8as)-5-hydroxy-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalen-1-yl (2e)-3-phenylprop-2-enoate)

3D-SDF for NP0225977 ((1r,2s,4ar,5r,8as)-5-hydroxy-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalen-1-yl (2e)-3-phenylprop-2-enoate)

PDB for NP0225977 ((1r,2s,4ar,5r,8as)-5-hydroxy-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalen-1-yl (2e)-3-phenylprop-2-enoate)

3D PDB for NP0225977 ((1r,2s,4ar,5r,8as)-5-hydroxy-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalen-1-yl (2e)-3-phenylprop-2-enoate)

SMILES for NP0225977 ((1r,2s,4ar,5r,8as)-5-hydroxy-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalen-1-yl (2e)-3-phenylprop-2-enoate)

INCHI for NP0225977 ((1r,2s,4ar,5r,8as)-5-hydroxy-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalen-1-yl (2e)-3-phenylprop-2-enoate)

Structure for NP0225977 ((1r,2s,4ar,5r,8as)-5-hydroxy-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalen-1-yl (2e)-3-phenylprop-2-enoate)

3D Structure for NP0225977 ((1r,2s,4ar,5r,8as)-5-hydroxy-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalen-1-yl (2e)-3-phenylprop-2-enoate)