NP-MRD: Showing NP-Card for (1s,3ar,5s,6r,7s,7ar)-1-[(1r)-1-(acetyloxy)ethyl]-6-{[(2s)-2-methylbutanoyl]oxy}-4-methylidene-7-[(2s)-2-methyloxiran-2-yl]-2-oxo-hexahydro-1h-inden-5-yl (2e)-3-methylpent-2-enoate (NP0275220)

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Record Information

Version

2.0

Created at

2022-09-08 22:53:28 UTC

Updated at

2022-09-08 22:53:28 UTC

NP-MRD ID

NP0275220

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3ar,5s,6r,7s,7ar)-1-[(1r)-1-(acetyloxy)ethyl]-6-{[(2s)-2-methylbutanoyl]oxy}-4-methylidene-7-[(2s)-2-methyloxiran-2-yl]-2-oxo-hexahydro-1h-inden-5-yl (2e)-3-methylpent-2-enoate

Description

CHEMBL3298992 belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (1s,3ar,5s,6r,7s,7ar)-1-[(1r)-1-(acetyloxy)ethyl]-6-{[(2s)-2-methylbutanoyl]oxy}-4-methylidene-7-[(2s)-2-methyloxiran-2-yl]-2-oxo-hexahydro-1h-inden-5-yl (2e)-3-methylpent-2-enoate is found in Pittocaulon bombycophole and Pittocaulon filare. Based on a literature review very few articles have been published on CHEMBL3298992.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092200532D          

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  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  3 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 12 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 21 24  1  1  0  0  0
 20 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  1  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 26 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 36 35  1  1  0  0  0
  2 36  1  0  0  0  0
 25 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0275220

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](C)C(=O)O[C@H]1[C@@H](OC(=O)\C=C(/C)CC)C(=C)[C@@H]2CC(=O)[C@H]([C@@H](C)OC(C)=O)[C@H]2[C@@H]1[C@@]1(C)CO1

> <INCHI_IDENTIFIER>
InChI=1S/C28H40O8/c1-9-14(3)11-21(31)35-25-16(5)19-12-20(30)22(17(6)34-18(7)29)23(19)24(28(8)13-33-28)26(25)36-27(32)15(4)10-2/h11,15,17,19,22-26H,5,9-10,12-13H2,1-4,6-8H3/b14-11+/t15-,17+,19-,22-,23-,24-,25-,26+,28+/m0/s1

> <INCHI_KEY>
RKAGQEAKHTWMEU-RXXFTBEBSA-N

> <FORMULA>
C28H40O8

> <MOLECULAR_WEIGHT>
504.62

> <EXACT_MASS>
504.272318248

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
54.449393783109215

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3aR,5S,6R,7S,7aR)-1-[(1R)-1-(acetyloxy)ethyl]-6-{[(2S)-2-methylbutanoyl]oxy}-4-methylidene-7-[(2S)-2-methyloxiran-2-yl]-2-oxo-octahydro-1H-inden-5-yl (2E)-3-methylpent-2-enoate

> <JCHEM_LOGP>
4.2129785056666655

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.58067681794959

> <JCHEM_PKA_STRONGEST_BASIC>
-4.20078335975837

> <JCHEM_POLAR_SURFACE_AREA>
108.5

> <JCHEM_REFRACTIVITY>
131.96770000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3aR,5S,6R,7S,7aR)-1-[(1R)-1-(acetyloxy)ethyl]-6-{[(2S)-2-methylbutanoyl]oxy}-4-methylidene-7-[(2S)-2-methyloxiran-2-yl]-2-oxo-hexahydro-1H-inden-5-yl (2E)-3-methylpent-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -6.668   5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.335   3.080   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -4.001   5.390   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -5.335   6.160   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.001   0.770   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.667   3.080   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   0.770   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      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -8.185  -1.037   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.152  -1.037   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -6.142  -2.217   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -9.467   1.064   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -9.943  -0.401   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -11.449  -0.721   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -8.912  -1.545   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -9.388  -3.010   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -8.358  -4.154   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0     -10.894  -3.330   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0     -10.372   2.310   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0     -11.912   2.310   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -9.467   3.556   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -8.002   3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   36                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10                                                            
CONECT   12    3   13   20                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20   12   21   25                                                  
CONECT   21   20   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   21                                                       
CONECT   25   20   26   36                                                  
CONECT   26   25   27   33                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   26   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35    2   25                                                  
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₀O₈

Average Mass

504.6200 Da

Monoisotopic Mass

504.27232 Da

IUPAC Name

(1S,3aR,5S,6R,7S,7aR)-1-[(1R)-1-(acetyloxy)ethyl]-6-{[(2S)-2-methylbutanoyl]oxy}-4-methylidene-7-[(2S)-2-methyloxiran-2-yl]-2-oxo-octahydro-1H-inden-5-yl (2E)-3-methylpent-2-enoate

Traditional Name

(1S,3aR,5S,6R,7S,7aR)-1-[(1R)-1-(acetyloxy)ethyl]-6-{[(2S)-2-methylbutanoyl]oxy}-4-methylidene-7-[(2S)-2-methyloxiran-2-yl]-2-oxo-hexahydro-1H-inden-5-yl (2E)-3-methylpent-2-enoate

CAS Registry Number

Not Available

SMILES

CC[C@H](C)C(=O)O[C@H]1[C@@H](OC(=O)\C=C(/C)CC)C(=C)[C@@H]2CC(=O)[C@H]([C@@H](C)OC(C)=O)[C@H]2[C@@H]1[C@@]1(C)CO1

InChI Identifier

InChI=1S/C28H40O8/c1-9-14(3)11-21(31)35-25-16(5)19-12-20(30)22(17(6)34-18(7)29)23(19)24(28(8)13-33-28)26(25)36-27(32)15(4)10-2/h11,15,17,19,22-26H,5,9-10,12-13H2,1-4,6-8H3/b14-11+/t15-,17+,19-,22-,23-,24-,25-,26+,28+/m0/s1

InChI Key

RKAGQEAKHTWMEU-RXXFTBEBSA-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
Pittocaulon bombycophole	LOTUS Database	35616633
Pittocaulon filare	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
Oplopane sesquiterpenoid
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Ketone
Cyclic ketone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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
logP	4.21	ChemAxon
pKa (Strongest Acidic)	18.58	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	108.5 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	131.97 m³·mol⁻¹	ChemAxon
Polarizability	54.45 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

34245843

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

90683362

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3ar,5s,6r,7s,7ar)-1-[(1r)-1-(acetyloxy)ethyl]-6-{[(2s)-2-methylbutanoyl]oxy}-4-methylidene-7-[(2s)-2-methyloxiran-2-yl]-2-oxo-hexahydro-1h-inden-5-yl (2e)-3-methylpent-2-enoate (NP0275220)

MOL for NP0275220 ((1s,3ar,5s,6r,7s,7ar)-1-[(1r)-1-(acetyloxy)ethyl]-6-{[(2s)-2-methylbutanoyl]oxy}-4-methylidene-7-[(2s)-2-methyloxiran-2-yl]-2-oxo-hexahydro-1h-inden-5-yl (2e)-3-methylpent-2-enoate)

3D MOL for NP0275220 ((1s,3ar,5s,6r,7s,7ar)-1-[(1r)-1-(acetyloxy)ethyl]-6-{[(2s)-2-methylbutanoyl]oxy}-4-methylidene-7-[(2s)-2-methyloxiran-2-yl]-2-oxo-hexahydro-1h-inden-5-yl (2e)-3-methylpent-2-enoate)

3D SDF for NP0275220 ((1s,3ar,5s,6r,7s,7ar)-1-[(1r)-1-(acetyloxy)ethyl]-6-{[(2s)-2-methylbutanoyl]oxy}-4-methylidene-7-[(2s)-2-methyloxiran-2-yl]-2-oxo-hexahydro-1h-inden-5-yl (2e)-3-methylpent-2-enoate)

3D-SDF for NP0275220 ((1s,3ar,5s,6r,7s,7ar)-1-[(1r)-1-(acetyloxy)ethyl]-6-{[(2s)-2-methylbutanoyl]oxy}-4-methylidene-7-[(2s)-2-methyloxiran-2-yl]-2-oxo-hexahydro-1h-inden-5-yl (2e)-3-methylpent-2-enoate)

PDB for NP0275220 ((1s,3ar,5s,6r,7s,7ar)-1-[(1r)-1-(acetyloxy)ethyl]-6-{[(2s)-2-methylbutanoyl]oxy}-4-methylidene-7-[(2s)-2-methyloxiran-2-yl]-2-oxo-hexahydro-1h-inden-5-yl (2e)-3-methylpent-2-enoate)

3D PDB for NP0275220 ((1s,3ar,5s,6r,7s,7ar)-1-[(1r)-1-(acetyloxy)ethyl]-6-{[(2s)-2-methylbutanoyl]oxy}-4-methylidene-7-[(2s)-2-methyloxiran-2-yl]-2-oxo-hexahydro-1h-inden-5-yl (2e)-3-methylpent-2-enoate)

SMILES for NP0275220 ((1s,3ar,5s,6r,7s,7ar)-1-[(1r)-1-(acetyloxy)ethyl]-6-{[(2s)-2-methylbutanoyl]oxy}-4-methylidene-7-[(2s)-2-methyloxiran-2-yl]-2-oxo-hexahydro-1h-inden-5-yl (2e)-3-methylpent-2-enoate)

INCHI for NP0275220 ((1s,3ar,5s,6r,7s,7ar)-1-[(1r)-1-(acetyloxy)ethyl]-6-{[(2s)-2-methylbutanoyl]oxy}-4-methylidene-7-[(2s)-2-methyloxiran-2-yl]-2-oxo-hexahydro-1h-inden-5-yl (2e)-3-methylpent-2-enoate)

Structure for NP0275220 ((1s,3ar,5s,6r,7s,7ar)-1-[(1r)-1-(acetyloxy)ethyl]-6-{[(2s)-2-methylbutanoyl]oxy}-4-methylidene-7-[(2s)-2-methyloxiran-2-yl]-2-oxo-hexahydro-1h-inden-5-yl (2e)-3-methylpent-2-enoate)

3D Structure for NP0275220 ((1s,3ar,5s,6r,7s,7ar)-1-[(1r)-1-(acetyloxy)ethyl]-6-{[(2s)-2-methylbutanoyl]oxy}-4-methylidene-7-[(2s)-2-methyloxiran-2-yl]-2-oxo-hexahydro-1h-inden-5-yl (2e)-3-methylpent-2-enoate)