NP-MRD: Showing NP-Card for (3e,5s,6e,8s)-1-[(1s,2s,5z,6r)-2-hydroxy-6-(3-hydroxypropyl)-1,2-dimethyl-5-(1-oxopropan-2-ylidene)cyclohexyl]-4,8,12-trimethyltrideca-3,6,11-trien-5-yl acetate (NP0292533)

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Record Information

Version

2.0

Created at

2022-09-10 00:06:29 UTC

Updated at

2022-09-10 00:06:29 UTC

NP-MRD ID

NP0292533

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3e,5s,6e,8s)-1-[(1s,2s,5z,6r)-2-hydroxy-6-(3-hydroxypropyl)-1,2-dimethyl-5-(1-oxopropan-2-ylidene)cyclohexyl]-4,8,12-trimethyltrideca-3,6,11-trien-5-yl acetate

Description

(3E,5S,6E,8S)-1-[(1S,2S,5Z,6R)-2-hydroxy-6-(3-hydroxypropyl)-1,2-dimethyl-5-(1-oxopropan-2-ylidene)cyclohexyl]-4,8,12-trimethyltrideca-3,6,11-trien-5-yl acetate belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units. (3e,5s,6e,8s)-1-[(1s,2s,5z,6r)-2-hydroxy-6-(3-hydroxypropyl)-1,2-dimethyl-5-(1-oxopropan-2-ylidene)cyclohexyl]-4,8,12-trimethyltrideca-3,6,11-trien-5-yl acetate is found in Iris domestica. Based on a literature review very few articles have been published on (3E,5S,6E,8S)-1-[(1S,2S,5Z,6R)-2-hydroxy-6-(3-hydroxypropyl)-1,2-dimethyl-5-(1-oxopropan-2-ylidene)cyclohexyl]-4,8,12-trimethyltrideca-3,6,11-trien-5-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102202062D          

 37 37  0  0  1  0            999 V2000
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 35 37  1  6  0  0  0
M  END

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M  END


  Mrv1652309102202062D          

 37 37  0  0  1  0            999 V2000
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    1.4929    3.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626    2.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  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
    2.1434    2.0625    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
    3.5724    2.0625    0.0000 O   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   -0.4125    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   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8245    0.8538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4372    1.5246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  1  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 23 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 21 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0292533

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C32H52O5/c1-23(2)12-9-13-24(3)16-17-30(37-27(6)35)25(4)14-10-19-31(7)29(15-11-21-33)28(26(5)22-34)18-20-32(31,8)36/h12,14,16-17,22,24,29-30,33,36H,9-11,13,15,18-21H2,1-8H3/b17-16+,25-14+,28-26-/t24-,29+,30-,31-,32-/m0/s1

> <INCHI_KEY>
HLWDNSYLWSVZSK-NIPZDKAFSA-N

> <FORMULA>
C32H52O5

> <MOLECULAR_WEIGHT>
516.763

> <EXACT_MASS>
516.381474774

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
89

> <JCHEM_AVERAGE_POLARIZABILITY>
61.16517252843056

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3E,5S,6E,8S)-1-[(1S,2S,5Z,6R)-2-hydroxy-6-(3-hydroxypropyl)-1,2-dimethyl-5-(1-oxopropan-2-ylidene)cyclohexyl]-4,8,12-trimethyltrideca-3,6,11-trien-5-yl acetate

> <JCHEM_LOGP>
6.035189968666669

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.855571330629395

> <JCHEM_PKA_STRONGEST_BASIC>
-0.27548081364666255

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
155.7235

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3E,5S,6E,8S)-1-[(1S,2S,5Z,6R)-2-hydroxy-6-(3-hydroxypropyl)-1,2-dimethyl-5-(1-oxopropan-2-ylidene)cyclohexyl]-4,8,12-trimethyltrideca-3,6,11-trien-5-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       6.810   6.761   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.293   7.029   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.303   5.849   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.767   8.476   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.250   8.743   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.723  10.191   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.713  11.370   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.186  12.817   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.670  13.085   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.176  13.997   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.650  15.444   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.639  16.624   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.156  16.356   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.146  17.536   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.683  14.909   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.260   7.564   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.743   7.831   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.787   6.117   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.797   4.937   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667   1.540   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       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.539   1.594   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -0.816   2.846   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    5   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   35                                             
CONECT   22   21                                                            
CONECT   23   21   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   23   29   33                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31                                                            
CONECT   33   28   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   21   36   37                                             
CONECT   36   35                                                            
CONECT   37   35                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   74    0
END

View in JSmol

Synonyms

Value	Source
(3E,5S,6E,8S)-1-[(1S,2S,5Z,6R)-2-Hydroxy-6-(3-hydroxypropyl)-1,2-dimethyl-5-(1-oxopropan-2-ylidene)cyclohexyl]-4,8,12-trimethyltrideca-3,6,11-trien-5-yl acetic acid	Generator

Chemical Formula

C₃₂H₅₂O₅

Average Mass

516.7630 Da

Monoisotopic Mass

516.38147 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C32H52O5/c1-23(2)12-9-13-24(3)16-17-30(37-27(6)35)25(4)14-10-19-31(7)29(15-11-21-33)28(26(5)22-34)18-20-32(31,8)36/h12,14,16-17,22,24,29-30,33,36H,9-11,13,15,18-21H2,1-8H3/b17-16+,25-14+,28-26-/t24-,29+,30-,31-,32-/m0/s1

InChI Key

HLWDNSYLWSVZSK-NIPZDKAFSA-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
Iris domestica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Sesterterpenoids

Alternative Parents

Substituents

Sesterterpenoid
Fatty alcohol ester
Tertiary alcohol
Enal
Cyclic alcohol
Alpha,beta-unsaturated aldehyde
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxygen compound
Primary alcohol
Organooxygen compound
Alcohol
Carbonyl group
Aldehyde
Organic oxide
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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

163185246

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3e,5s,6e,8s)-1-[(1s,2s,5z,6r)-2-hydroxy-6-(3-hydroxypropyl)-1,2-dimethyl-5-(1-oxopropan-2-ylidene)cyclohexyl]-4,8,12-trimethyltrideca-3,6,11-trien-5-yl acetate (NP0292533)

MOL for NP0292533 ((3e,5s,6e,8s)-1-[(1s,2s,5z,6r)-2-hydroxy-6-(3-hydroxypropyl)-1,2-dimethyl-5-(1-oxopropan-2-ylidene)cyclohexyl]-4,8,12-trimethyltrideca-3,6,11-trien-5-yl acetate)

3D MOL for NP0292533 ((3e,5s,6e,8s)-1-[(1s,2s,5z,6r)-2-hydroxy-6-(3-hydroxypropyl)-1,2-dimethyl-5-(1-oxopropan-2-ylidene)cyclohexyl]-4,8,12-trimethyltrideca-3,6,11-trien-5-yl acetate)

3D SDF for NP0292533 ((3e,5s,6e,8s)-1-[(1s,2s,5z,6r)-2-hydroxy-6-(3-hydroxypropyl)-1,2-dimethyl-5-(1-oxopropan-2-ylidene)cyclohexyl]-4,8,12-trimethyltrideca-3,6,11-trien-5-yl acetate)

3D-SDF for NP0292533 ((3e,5s,6e,8s)-1-[(1s,2s,5z,6r)-2-hydroxy-6-(3-hydroxypropyl)-1,2-dimethyl-5-(1-oxopropan-2-ylidene)cyclohexyl]-4,8,12-trimethyltrideca-3,6,11-trien-5-yl acetate)

PDB for NP0292533 ((3e,5s,6e,8s)-1-[(1s,2s,5z,6r)-2-hydroxy-6-(3-hydroxypropyl)-1,2-dimethyl-5-(1-oxopropan-2-ylidene)cyclohexyl]-4,8,12-trimethyltrideca-3,6,11-trien-5-yl acetate)

3D PDB for NP0292533 ((3e,5s,6e,8s)-1-[(1s,2s,5z,6r)-2-hydroxy-6-(3-hydroxypropyl)-1,2-dimethyl-5-(1-oxopropan-2-ylidene)cyclohexyl]-4,8,12-trimethyltrideca-3,6,11-trien-5-yl acetate)

SMILES for NP0292533 ((3e,5s,6e,8s)-1-[(1s,2s,5z,6r)-2-hydroxy-6-(3-hydroxypropyl)-1,2-dimethyl-5-(1-oxopropan-2-ylidene)cyclohexyl]-4,8,12-trimethyltrideca-3,6,11-trien-5-yl acetate)

INCHI for NP0292533 ((3e,5s,6e,8s)-1-[(1s,2s,5z,6r)-2-hydroxy-6-(3-hydroxypropyl)-1,2-dimethyl-5-(1-oxopropan-2-ylidene)cyclohexyl]-4,8,12-trimethyltrideca-3,6,11-trien-5-yl acetate)

Structure for NP0292533 ((3e,5s,6e,8s)-1-[(1s,2s,5z,6r)-2-hydroxy-6-(3-hydroxypropyl)-1,2-dimethyl-5-(1-oxopropan-2-ylidene)cyclohexyl]-4,8,12-trimethyltrideca-3,6,11-trien-5-yl acetate)

3D Structure for NP0292533 ((3e,5s,6e,8s)-1-[(1s,2s,5z,6r)-2-hydroxy-6-(3-hydroxypropyl)-1,2-dimethyl-5-(1-oxopropan-2-ylidene)cyclohexyl]-4,8,12-trimethyltrideca-3,6,11-trien-5-yl acetate)