NP-MRD: Showing NP-Card for (1s,6s,7s,8as)-7-(2-hydroxypropan-2-yl)-1,4-dimethyl-1,2,3,5,6,7,8,8a-octahydroazulen-6-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate (NP0329927)

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Record Information

Version

2.0

Created at

2022-09-12 14:47:56 UTC

Updated at

2022-09-12 14:47:56 UTC

NP-MRD ID

NP0329927

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,6s,7s,8as)-7-(2-hydroxypropan-2-yl)-1,4-dimethyl-1,2,3,5,6,7,8,8a-octahydroazulen-6-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Description

(4S,5S)-1,10-Didehydro-4beta-methyl-15-norambrosane-8alpha,11-diol 8-[(2E)-3-(3-methoxy-4-hydroxyphenyl)propenoate] belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (1s,6s,7s,8as)-7-(2-hydroxypropan-2-yl)-1,4-dimethyl-1,2,3,5,6,7,8,8a-octahydroazulen-6-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate is found in Thapsia villosa. Based on a literature review very few articles have been published on (4S,5S)-1,10-Didehydro-4beta-methyl-15-norambrosane-8alpha,11-diol 8-[(2E)-3-(3-methoxy-4-hydroxyphenyl)propenoate].

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122216472D          

 30 32  0  0  1  0            999 V2000
    9.3235   -1.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4985   -1.0568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0860   -0.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2610   -0.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8485    0.3722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0235    0.3722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6110    1.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7860    1.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3735    0.3722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3735    1.8011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5485    1.8011    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1906    1.0578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863    0.8742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2027    0.0699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413    1.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566    1.1337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717    1.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566    2.4686    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7017    3.2532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413    2.2136    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3863    2.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906    2.5444    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7050    3.1894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2193    3.8344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3500    2.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0600    3.7038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2610    1.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0860    1.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4985    0.3722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3235    0.3722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309122216472D          

 30 32  0  0  1  0            999 V2000
    9.3235   -1.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4985   -1.0568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0860   -0.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2610   -0.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6110    1.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7860    1.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0329927

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(\C=C\C(=O)O[C@H]2CC(C)=C3CC[C@H](C)[C@@H]3C[C@@H]2C(C)(C)O)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O5/c1-15-6-9-18-16(2)12-22(20(14-19(15)18)25(3,4)28)30-24(27)11-8-17-7-10-21(26)23(13-17)29-5/h7-8,10-11,13,15,19-20,22,26,28H,6,9,12,14H2,1-5H3/b11-8+/t15-,19-,20-,22-/m0/s1

> <INCHI_KEY>
UJHQSMHJLBMXAL-UYVCMBBFSA-N

> <FORMULA>
C25H34O5

> <MOLECULAR_WEIGHT>
414.542

> <EXACT_MASS>
414.240624195

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
47.018600577805614

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,3aS,5S,6S)-5-(2-hydroxypropan-2-yl)-3,8-dimethyl-1,2,3,3a,4,5,6,7-octahydroazulen-6-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

> <JCHEM_LOGP>
4.6446007300000005

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.98452616303225

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.867756979290434

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8055697080632607

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
118.82339999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,6S,7S,8aS)-7-(2-hydroxypropan-2-yl)-1,4-dimethyl-1,2,3,5,6,7,8,8a-octahydroazulen-6-yl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      17.404  -1.973   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      15.864  -1.973   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      15.094  -0.639   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.554  -0.639   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.784   0.695   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.244   0.695   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.474   2.028   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.934   2.028   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.164   0.695   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       8.164   3.362   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.624   3.362   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.956   1.975   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.454   1.632   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.112   0.131   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.250   2.592   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.786   2.116   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.881   3.362   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.786   4.608   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.310   6.073   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.250   4.132   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.454   5.092   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.956   4.750   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.916   5.954   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.876   7.158   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.120   4.993   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.712   6.914   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      13.554   2.028   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.094   2.028   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      15.864   0.695   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      17.404   0.695   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   29                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   27                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   22                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   15   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   11   23                                                  
CONECT   23   22   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23                                                            
CONECT   27    5   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    3   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Value	Source
(4S,5S)-1,10-Didehydro-4b-methyl-15-norambrosane-8a,11-diol 8-[(2E)-3-(3-methoxy-4-hydroxyphenyl)propenoate]	Generator
(4S,5S)-1,10-Didehydro-4b-methyl-15-norambrosane-8a,11-diol 8-[(2E)-3-(3-methoxy-4-hydroxyphenyl)propenoic acid]	Generator
(4S,5S)-1,10-Didehydro-4beta-methyl-15-norambrosane-8alpha,11-diol 8-[(2E)-3-(3-methoxy-4-hydroxyphenyl)propenoic acid]	Generator
(4S,5S)-1,10-Didehydro-4β-methyl-15-norambrosane-8α,11-diol 8-[(2E)-3-(3-methoxy-4-hydroxyphenyl)propenoate]	Generator
(4S,5S)-1,10-Didehydro-4β-methyl-15-norambrosane-8α,11-diol 8-[(2E)-3-(3-methoxy-4-hydroxyphenyl)propenoic acid]	Generator

Chemical Formula

C₂₅H₃₄O₅

Average Mass

414.5420 Da

Monoisotopic Mass

414.24062 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=CC(\C=C\C(=O)O[C@H]2CC(C)=C3CC[C@H](C)[C@@H]3C[C@@H]2C(C)(C)O)=CC=C1O

InChI Identifier

InChI=1S/C25H34O5/c1-15-6-9-18-16(2)12-22(20(14-19(15)18)25(3,4)28)30-24(27)11-8-17-7-10-21(26)23(13-17)29-5/h7-8,10-11,13,15,19-20,22,26,28H,6,9,12,14H2,1-5H3/b11-8+/t15-,19-,20-,22-/m0/s1

InChI Key

UJHQSMHJLBMXAL-UYVCMBBFSA-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
Thapsia villosa	LOTUS Database	35616633

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
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Methoxyphenol
Anisole
Phenoxy compound
Phenol ether
Styrene
Methoxybenzene
Phenol
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Ether
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Alcohol
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

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

101609663

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,6s,7s,8as)-7-(2-hydroxypropan-2-yl)-1,4-dimethyl-1,2,3,5,6,7,8,8a-octahydroazulen-6-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate (NP0329927)

MOL for NP0329927 ((1s,6s,7s,8as)-7-(2-hydroxypropan-2-yl)-1,4-dimethyl-1,2,3,5,6,7,8,8a-octahydroazulen-6-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D MOL for NP0329927 ((1s,6s,7s,8as)-7-(2-hydroxypropan-2-yl)-1,4-dimethyl-1,2,3,5,6,7,8,8a-octahydroazulen-6-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D SDF for NP0329927 ((1s,6s,7s,8as)-7-(2-hydroxypropan-2-yl)-1,4-dimethyl-1,2,3,5,6,7,8,8a-octahydroazulen-6-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D-SDF for NP0329927 ((1s,6s,7s,8as)-7-(2-hydroxypropan-2-yl)-1,4-dimethyl-1,2,3,5,6,7,8,8a-octahydroazulen-6-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

PDB for NP0329927 ((1s,6s,7s,8as)-7-(2-hydroxypropan-2-yl)-1,4-dimethyl-1,2,3,5,6,7,8,8a-octahydroazulen-6-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D PDB for NP0329927 ((1s,6s,7s,8as)-7-(2-hydroxypropan-2-yl)-1,4-dimethyl-1,2,3,5,6,7,8,8a-octahydroazulen-6-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

SMILES for NP0329927 ((1s,6s,7s,8as)-7-(2-hydroxypropan-2-yl)-1,4-dimethyl-1,2,3,5,6,7,8,8a-octahydroazulen-6-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

INCHI for NP0329927 ((1s,6s,7s,8as)-7-(2-hydroxypropan-2-yl)-1,4-dimethyl-1,2,3,5,6,7,8,8a-octahydroazulen-6-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

Structure for NP0329927 ((1s,6s,7s,8as)-7-(2-hydroxypropan-2-yl)-1,4-dimethyl-1,2,3,5,6,7,8,8a-octahydroazulen-6-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D Structure for NP0329927 ((1s,6s,7s,8as)-7-(2-hydroxypropan-2-yl)-1,4-dimethyl-1,2,3,5,6,7,8,8a-octahydroazulen-6-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)