NP-MRD: Showing NP-Card for (6z)-4-(acetyloxy)-3-isopropyl-6,10-dimethyl-11-oxabicyclo[8.1.0]undec-6-en-2-yl 3,4,5-trimethoxybenzoate (NP0151091)

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Record Information

Version

2.0

Created at

2022-09-02 07:21:06 UTC

Updated at

2022-09-02 07:21:06 UTC

NP-MRD ID

NP0151091

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6z)-4-(acetyloxy)-3-isopropyl-6,10-dimethyl-11-oxabicyclo[8.1.0]undec-6-en-2-yl 3,4,5-trimethoxybenzoate

Description

Involucrin belongs to the class of organic compounds known as germacrane sesquiterpenoids. These are sesquiterpenoids having the germacrane skeleton, with a structure characterized by a cyclodecane ring substituted with an isopropyl and two methyl groups. (6z)-4-(acetyloxy)-3-isopropyl-6,10-dimethyl-11-oxabicyclo[8.1.0]undec-6-en-2-yl 3,4,5-trimethoxybenzoate is found in Ferula leucographa. (6z)-4-(acetyloxy)-3-isopropyl-6,10-dimethyl-11-oxabicyclo[8.1.0]undec-6-en-2-yl 3,4,5-trimethoxybenzoate was first documented in 2022 (PMID: 36047814). Based on a literature review a small amount of articles have been published on Involucrin (PMID: 35988588) (PMID: 35961432) (PMID: 35948609) (PMID: 35928950).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022209212D          

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 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
  9 28  1  0  0  0  0
 25 28  1  0  0  0  0
  5 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 33  2  0  0  0  0
  3 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0151091

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(OC)=C1OC)C(=O)OC1C2OC2(C)CC\C=C(C)/CC(OC(C)=O)C1C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C27H38O8/c1-15(2)22-19(33-17(4)28)12-16(3)10-9-11-27(5)25(35-27)24(22)34-26(29)18-13-20(30-6)23(32-8)21(14-18)31-7/h10,13-15,19,22,24-25H,9,11-12H2,1-8H3/b16-10-

> <INCHI_KEY>
FSBLXTAIINGBJY-YBEGLDIGSA-N

> <FORMULA>
C27H38O8

> <MOLECULAR_WEIGHT>
490.593

> <EXACT_MASS>
490.256668184

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
53.09152706784421

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6Z)-4-(acetyloxy)-6,10-dimethyl-3-(propan-2-yl)-11-oxabicyclo[8.1.0]undec-6-en-2-yl 3,4,5-trimethoxybenzoate

> <ALOGPS_LOGP>
4.70

> <JCHEM_LOGP>
4.447691014333332

> <ALOGPS_LOGS>
-5.43

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.035980168237462

> <JCHEM_POLAR_SURFACE_AREA>
92.82000000000001

> <JCHEM_REFRACTIVITY>
130.4842

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.81e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6Z)-4-(acetyloxy)-3-isopropyl-6,10-dimethyl-11-oxabicyclo[8.1.0]undec-6-en-2-yl 3,4,5-trimethoxybenzoate

> <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      -0.445   3.850   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.889   4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.223   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.556   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.890   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.224   4.620   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.224   6.160   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       7.558   3.850   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.558   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.891   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.891   3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.518   4.487   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.265   4.487   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.225   2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.225   3.850   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      11.559   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.559   6.160   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.892   3.850   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      11.559   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.559   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.892  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.225  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.891  -0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.558  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.224  -0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.454  -1.334   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.890   0.770   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.224   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.890   2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.556   1.540   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.556  -0.000   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.223  -0.770   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.223   2.310   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.889   1.540   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       0.889  -0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   33                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   29                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   28                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   14   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27    9   25                                                  
CONECT   29    5   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30    3   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₈O₈

Average Mass

490.5930 Da

Monoisotopic Mass

490.25667 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1OC)C(=O)OC1C2OC2(C)CC\C=C(C)/CC(OC(C)=O)C1C(C)C

InChI Identifier

InChI=1S/C27H38O8/c1-15(2)22-19(33-17(4)28)12-16(3)10-9-11-27(5)25(35-27)24(22)34-26(29)18-13-20(30-6)23(32-8)21(14-18)31-7/h10,13-15,19,22,24-25H,9,11-12H2,1-8H3/b16-10-

InChI Key

FSBLXTAIINGBJY-YBEGLDIGSA-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
Ferula leucographa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacrane sesquiterpenoids. These are sesquiterpenoids having the germacrane skeleton, with a structure characterized by a cyclodecane ring substituted with an isopropyl and two methyl groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Germacrane sesquiterpenoids

Alternative Parents

Substituents

Germacrane sesquiterpenoid
Gallic acid or derivatives
P-methoxybenzoic acid or derivatives
M-methoxybenzoic acid or derivatives
Benzoate ester
Benzoic acid or derivatives
Phenoxy compound
Methoxybenzene
Phenol ether
Benzoyl
Anisole
Alkyl aryl ether
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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

4941666

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Involucrin

METLIN ID

Not Available

PubChem Compound

6437078

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hewitt B, Batt J, Shelton RM, Cooper PR, Landini G, Lucas RA, Wiench M, Milward MR: A 3D Printed Device for In Vitro Generation of Stratified Epithelia at the Air-Liquid Interface. Tissue Eng Part C Methods. 2022 Nov;28(11):599-609. doi: 10.1089/ten.TEC.2022.0130. Epub 2022 Oct 11. [PubMed:36047814 ]
Kim JH, Ahn S, Ghosh P, Rhee DK: Immunization with a Pneumococcal pep27 Mutant Strain Alleviates Atopic Dermatitis through the Upregulation of Regulatory T-Cell Activity and Epithelial Barrier Function and Suppressing TSLP Expression. J Invest Dermatol. 2023 Jan;143(1):115-123.e6. doi: 10.1016/j.jid.2022.07.021. Epub 2022 Aug 18. [PubMed:35988588 ]
Talabot-Ayer D, Diaz-Barreiro A, Modarressi A, Palmer G: Epigenetic remodeling of downstream enhancer regions is linked to selective expression of the IL1F10 gene in differentiated human keratinocytes. Gene. 2022 Oct 30;842:146800. doi: 10.1016/j.gene.2022.146800. Epub 2022 Aug 10. [PubMed:35961432 ]
Sachslehner AP, Eckhart L: Evolutionary diversification of epidermal barrier genes in amphibians. Sci Rep. 2022 Aug 10;12(1):13634. doi: 10.1038/s41598-022-18053-7. [PubMed:35948609 ]
Jones CFE, Di Cio S, Connelly JT, Gautrot JE: Design of an Integrated Microvascularized Human Skin-on-a-Chip Tissue Equivalent Model. Front Bioeng Biotechnol. 2022 Jul 19;10:915702. doi: 10.3389/fbioe.2022.915702. eCollection 2022. [PubMed:35928950 ]
LOTUS database [Link]

Showing NP-Card for (6z)-4-(acetyloxy)-3-isopropyl-6,10-dimethyl-11-oxabicyclo[8.1.0]undec-6-en-2-yl 3,4,5-trimethoxybenzoate (NP0151091)

MOL for NP0151091 ((6z)-4-(acetyloxy)-3-isopropyl-6,10-dimethyl-11-oxabicyclo[8.1.0]undec-6-en-2-yl 3,4,5-trimethoxybenzoate)

3D MOL for NP0151091 ((6z)-4-(acetyloxy)-3-isopropyl-6,10-dimethyl-11-oxabicyclo[8.1.0]undec-6-en-2-yl 3,4,5-trimethoxybenzoate)

3D SDF for NP0151091 ((6z)-4-(acetyloxy)-3-isopropyl-6,10-dimethyl-11-oxabicyclo[8.1.0]undec-6-en-2-yl 3,4,5-trimethoxybenzoate)

3D-SDF for NP0151091 ((6z)-4-(acetyloxy)-3-isopropyl-6,10-dimethyl-11-oxabicyclo[8.1.0]undec-6-en-2-yl 3,4,5-trimethoxybenzoate)

PDB for NP0151091 ((6z)-4-(acetyloxy)-3-isopropyl-6,10-dimethyl-11-oxabicyclo[8.1.0]undec-6-en-2-yl 3,4,5-trimethoxybenzoate)

3D PDB for NP0151091 ((6z)-4-(acetyloxy)-3-isopropyl-6,10-dimethyl-11-oxabicyclo[8.1.0]undec-6-en-2-yl 3,4,5-trimethoxybenzoate)

SMILES for NP0151091 ((6z)-4-(acetyloxy)-3-isopropyl-6,10-dimethyl-11-oxabicyclo[8.1.0]undec-6-en-2-yl 3,4,5-trimethoxybenzoate)

INCHI for NP0151091 ((6z)-4-(acetyloxy)-3-isopropyl-6,10-dimethyl-11-oxabicyclo[8.1.0]undec-6-en-2-yl 3,4,5-trimethoxybenzoate)

Structure for NP0151091 ((6z)-4-(acetyloxy)-3-isopropyl-6,10-dimethyl-11-oxabicyclo[8.1.0]undec-6-en-2-yl 3,4,5-trimethoxybenzoate)

3D Structure for NP0151091 ((6z)-4-(acetyloxy)-3-isopropyl-6,10-dimethyl-11-oxabicyclo[8.1.0]undec-6-en-2-yl 3,4,5-trimethoxybenzoate)