NP-MRD: Showing NP-Card for 1-(acetyloxy)-4-(3-hydroxy-3-methylpent-4-en-1-yl)-3,4a,8,8-tetramethyl-1,2,5,6,7,8a-hexahydronaphthalen-2-yl acetate (NP0186473)

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Record Information

Version

2.0

Created at

2022-09-04 02:20:03 UTC

Updated at

2022-09-04 02:20:03 UTC

NP-MRD ID

NP0186473

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-(acetyloxy)-4-(3-hydroxy-3-methylpent-4-en-1-yl)-3,4a,8,8-tetramethyl-1,2,5,6,7,8a-hexahydronaphthalen-2-yl acetate

Description

(6B,7b,13R)-6,7-Diacetoxy-8,14-labdadiene-13-ol belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units (6b,7b,13R)-6,7-Diacetoxy-8,14-labdadiene-13-ol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (6b,7b,13R)-6,7-Diacetoxy-8,14-labdadiene-13-ol has been detected, but not quantified in, fruits and herbs and spices. 1-(acetyloxy)-4-(3-hydroxy-3-methylpent-4-en-1-yl)-3,4a,8,8-tetramethyl-1,2,5,6,7,8a-hexahydronaphthalen-2-yl acetate is found in Vitex agnus-castus. This could make (6b,7b,13R)-6,7-diacetoxy-8,14-labdadiene-13-ol a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061308212D          

 29 30  0  0  0  0            999 V2000
    2.1434    4.5375    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
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131   -1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6737   -1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    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
    2.8579    0.0000    0.0000 C   0  0  0  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    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  2  0  0  0  0
 12 10  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15  2  1  0  0  0  0
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 18 15  2  0  0  0  0
 19 15  1  0  0  0  0
 20 19  1  0  0  0  0
 21 20  1  0  0  0  0
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 22 21  1  0  0  0  0
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 29 20  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv0541 05061308212D          

 29 30  0  0  0  0            999 V2000
    2.1434    4.5375    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
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131   -1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6737   -1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0329    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0186473

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1C(OC(C)=O)C(C)=C(CCC(C)(O)C=C)C2(C)CCCC(C)(C)C12

> <INCHI_IDENTIFIER>
InChI=1S/C24H38O5/c1-9-23(7,27)14-11-18-15(2)19(28-16(3)25)20(29-17(4)26)21-22(5,6)12-10-13-24(18,21)8/h9,19-21,27H,1,10-14H2,2-8H3

> <INCHI_KEY>
JVKGUKYXQMTNOK-UHFFFAOYSA-N

> <FORMULA>
C24H38O5

> <MOLECULAR_WEIGHT>
406.5555

> <EXACT_MASS>
406.271924326

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
46.00546823045014

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(acetyloxy)-4-(3-hydroxy-3-methylpent-4-en-1-yl)-3,4a,8,8-tetramethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-yl acetate

> <ALOGPS_LOGP>
4.66

> <JCHEM_LOGP>
3.857317984666667

> <ALOGPS_LOGS>
-5.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.365501852772883

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3267277080245825

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
112.98719999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.54e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(acetyloxy)-4-(3-hydroxy-3-methylpent-4-en-1-yl)-3,4a,8,8-tetramethyl-1,2,5,6,7,8a-hexahydronaphthalen-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.011  -1.950   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.991  -1.950   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.875   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      10.669   1.540   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       3.795   6.160   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   15                                                            
CONECT    3   16                                                            
CONECT    4   17                                                            
CONECT    5   22                                                            
CONECT    6   22                                                            
CONECT    7   23                                                            
CONECT    8   24                                                            
CONECT    9    1   23                                                       
CONECT   10   12   13                                                       
CONECT   11   14   18                                                       
CONECT   12   10   22                                                       
CONECT   13   10   24                                                       
CONECT   14   11   23                                                       
CONECT   15    2   18   19                                                  
CONECT   16    3   25   28                                                  
CONECT   17    4   26   29                                                  
CONECT   18   11   15   24                                                  
CONECT   19   15   20   28                                                  
CONECT   20   19   21   29                                                  
CONECT   21   20   22   24                                                  
CONECT   22    5    6   12   21                                             
CONECT   23    7    9   14   27                                             
CONECT   24    8   13   18   21                                             
CONECT   25   16                                                            
CONECT   26   17                                                            
CONECT   27   23                                                            
CONECT   28   16   19                                                       
CONECT   29   17   20                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   60    0
END

View in JSmol

Synonyms

Value	Source
1-(Acetyloxy)-4-(3-hydroxy-3-methylpent-4-en-1-yl)-3,4a,8,8-tetramethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-yl acetic acid	Generator

Chemical Formula

C₂₄H₃₈O₅

Average Mass

406.5555 Da

Monoisotopic Mass

406.27192 Da

IUPAC Name

1-(acetyloxy)-4-(3-hydroxy-3-methylpent-4-en-1-yl)-3,4a,8,8-tetramethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-yl acetate

Traditional Name

1-(acetyloxy)-4-(3-hydroxy-3-methylpent-4-en-1-yl)-3,4a,8,8-tetramethyl-1,2,5,6,7,8a-hexahydronaphthalen-2-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1C(OC(C)=O)C(C)=C(CCC(C)(O)C=C)C2(C)CCCC(C)(C)C12

InChI Identifier

InChI=1S/C24H38O5/c1-9-23(7,27)14-11-18-15(2)19(28-16(3)25)20(29-17(4)26)21-22(5,6)12-10-13-24(18,21)8/h9,19-21,27H,1,10-14H2,2-8H3

InChI Key

JVKGUKYXQMTNOK-UHFFFAOYSA-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
Vitex agnus-castus	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

Diterpenoid
Labdane diterpenoid
Dicarboxylic acid or derivatives
Tertiary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic 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	4.66	ALOGPS
logP	3.86	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	18.37	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	112.99 m³·mol⁻¹	ChemAxon
Polarizability	46.01 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0035288

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013953

KNApSAcK ID

Not Available

Chemspider ID

13197715

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

18008143

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-(acetyloxy)-4-(3-hydroxy-3-methylpent-4-en-1-yl)-3,4a,8,8-tetramethyl-1,2,5,6,7,8a-hexahydronaphthalen-2-yl acetate (NP0186473)

MOL for NP0186473 (1-(acetyloxy)-4-(3-hydroxy-3-methylpent-4-en-1-yl)-3,4a,8,8-tetramethyl-1,2,5,6,7,8a-hexahydronaphthalen-2-yl acetate)

3D MOL for NP0186473 (1-(acetyloxy)-4-(3-hydroxy-3-methylpent-4-en-1-yl)-3,4a,8,8-tetramethyl-1,2,5,6,7,8a-hexahydronaphthalen-2-yl acetate)

3D SDF for NP0186473 (1-(acetyloxy)-4-(3-hydroxy-3-methylpent-4-en-1-yl)-3,4a,8,8-tetramethyl-1,2,5,6,7,8a-hexahydronaphthalen-2-yl acetate)

3D-SDF for NP0186473 (1-(acetyloxy)-4-(3-hydroxy-3-methylpent-4-en-1-yl)-3,4a,8,8-tetramethyl-1,2,5,6,7,8a-hexahydronaphthalen-2-yl acetate)

PDB for NP0186473 (1-(acetyloxy)-4-(3-hydroxy-3-methylpent-4-en-1-yl)-3,4a,8,8-tetramethyl-1,2,5,6,7,8a-hexahydronaphthalen-2-yl acetate)

3D PDB for NP0186473 (1-(acetyloxy)-4-(3-hydroxy-3-methylpent-4-en-1-yl)-3,4a,8,8-tetramethyl-1,2,5,6,7,8a-hexahydronaphthalen-2-yl acetate)

SMILES for NP0186473 (1-(acetyloxy)-4-(3-hydroxy-3-methylpent-4-en-1-yl)-3,4a,8,8-tetramethyl-1,2,5,6,7,8a-hexahydronaphthalen-2-yl acetate)

INCHI for NP0186473 (1-(acetyloxy)-4-(3-hydroxy-3-methylpent-4-en-1-yl)-3,4a,8,8-tetramethyl-1,2,5,6,7,8a-hexahydronaphthalen-2-yl acetate)

Structure for NP0186473 (1-(acetyloxy)-4-(3-hydroxy-3-methylpent-4-en-1-yl)-3,4a,8,8-tetramethyl-1,2,5,6,7,8a-hexahydronaphthalen-2-yl acetate)

3D Structure for NP0186473 (1-(acetyloxy)-4-(3-hydroxy-3-methylpent-4-en-1-yl)-3,4a,8,8-tetramethyl-1,2,5,6,7,8a-hexahydronaphthalen-2-yl acetate)