NP-MRD: Showing NP-Card for (1r,2s,3ar,4r,7s,7ar)-1-acetyl-4-hydroxy-7-isopropyl-4-methyl-octahydroinden-2-yl acetate (NP0172260)

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Record Information

Version

2.0

Created at

2022-09-03 09:07:31 UTC

Updated at

2022-09-03 09:07:31 UTC

NP-MRD ID

NP0172260

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,3ar,4r,7s,7ar)-1-acetyl-4-hydroxy-7-isopropyl-4-methyl-octahydroinden-2-yl acetate

Description

(1R,2S,3aR,4R,7S,7aR)-1-acetyl-4-hydroxy-4-methyl-7-(propan-2-yl)-octahydro-1H-inden-2-yl acetate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (1r,2s,3ar,4r,7s,7ar)-1-acetyl-4-hydroxy-7-isopropyl-4-methyl-octahydroinden-2-yl acetate is found in Pallenis spinosa. Based on a literature review very few articles have been published on (1R,2S,3aR,4R,7S,7aR)-1-acetyl-4-hydroxy-4-methyl-7-(propan-2-yl)-octahydro-1H-inden-2-yl acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309032211072D          

 21 22  0  0  1  0            999 V2000
   -2.6909   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534   -2.1269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3556    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7429   -2.2514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9683   -2.2514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3984    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054    0.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1536    1.3672    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
  7  6  1  6  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  1  0  0  0
  8 18  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0172260

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@H]1CC[C@@](C)(O)[C@@H]2C[C@H](OC(C)=O)[C@@H]([C@H]12)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H28O4/c1-9(2)12-6-7-17(5,20)13-8-14(21-11(4)19)15(10(3)18)16(12)13/h9,12-16,20H,6-8H2,1-5H3/t12-,13+,14-,15-,16+,17+/m0/s1

> <INCHI_KEY>
YNNDVHBDEXCUNO-RHJCGQNESA-N

> <FORMULA>
C17H28O4

> <MOLECULAR_WEIGHT>
296.407

> <EXACT_MASS>
296.198759382

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
33.35067996197772

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,3aR,4R,7S,7aR)-1-acetyl-4-hydroxy-4-methyl-7-(propan-2-yl)-octahydro-1H-inden-2-yl acetate

> <ALOGPS_LOGP>
1.99

> <JCHEM_LOGP>
1.9753960533333321

> <ALOGPS_LOGS>
-3.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.721923001262525

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.775025434260652

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8971633265859404

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
79.88889999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.28e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3aR,4R,7S,7aR)-1-acetyl-4-hydroxy-7-isopropyl-4-methyl-octahydroinden-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.023  -2.637   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.483  -2.637   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.713  -3.970   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -2.713  -1.303   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.268  -2.549   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.530   1.777   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.197   2.547   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.864   2.547   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.253  -4.203   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.807  -4.203   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.268  -0.057   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.744   1.408   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.250   1.728   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.287   2.552   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   18                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9   18                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    9   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    7   16   17                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    8    5   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Value	Source
(1R,2S,3AR,4R,7S,7ar)-1-acetyl-4-hydroxy-4-methyl-7-(propan-2-yl)-octahydro-1H-inden-2-yl acetic acid	Generator

Chemical Formula

C₁₇H₂₈O₄

Average Mass

296.4070 Da

Monoisotopic Mass

296.19876 Da

IUPAC Name

(1R,2S,3aR,4R,7S,7aR)-1-acetyl-4-hydroxy-4-methyl-7-(propan-2-yl)-octahydro-1H-inden-2-yl acetate

Traditional Name

(1R,2S,3aR,4R,7S,7aR)-1-acetyl-4-hydroxy-7-isopropyl-4-methyl-octahydroinden-2-yl acetate

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H]1CC[C@@](C)(O)[C@@H]2C[C@H](OC(C)=O)[C@@H]([C@H]12)C(C)=O

InChI Identifier

InChI=1S/C17H28O4/c1-9(2)12-6-7-17(5,20)13-8-14(21-11(4)19)15(10(3)18)16(12)13/h9,12-16,20H,6-8H2,1-5H3/t12-,13+,14-,15-,16+,17+/m0/s1

InChI Key

YNNDVHBDEXCUNO-RHJCGQNESA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Pallenis spinosa	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

Oplopane sesquiterpenoid
Sesquiterpenoid
Tertiary alcohol
Cyclic alcohol
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
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	1.99	ALOGPS
logP	1.98	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	14.78	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	79.89 m³·mol⁻¹	ChemAxon
Polarizability	33.35 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

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

162945465

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,3ar,4r,7s,7ar)-1-acetyl-4-hydroxy-7-isopropyl-4-methyl-octahydroinden-2-yl acetate (NP0172260)

MOL for NP0172260 ((1r,2s,3ar,4r,7s,7ar)-1-acetyl-4-hydroxy-7-isopropyl-4-methyl-octahydroinden-2-yl acetate)

3D MOL for NP0172260 ((1r,2s,3ar,4r,7s,7ar)-1-acetyl-4-hydroxy-7-isopropyl-4-methyl-octahydroinden-2-yl acetate)

3D SDF for NP0172260 ((1r,2s,3ar,4r,7s,7ar)-1-acetyl-4-hydroxy-7-isopropyl-4-methyl-octahydroinden-2-yl acetate)

3D-SDF for NP0172260 ((1r,2s,3ar,4r,7s,7ar)-1-acetyl-4-hydroxy-7-isopropyl-4-methyl-octahydroinden-2-yl acetate)

PDB for NP0172260 ((1r,2s,3ar,4r,7s,7ar)-1-acetyl-4-hydroxy-7-isopropyl-4-methyl-octahydroinden-2-yl acetate)

3D PDB for NP0172260 ((1r,2s,3ar,4r,7s,7ar)-1-acetyl-4-hydroxy-7-isopropyl-4-methyl-octahydroinden-2-yl acetate)

SMILES for NP0172260 ((1r,2s,3ar,4r,7s,7ar)-1-acetyl-4-hydroxy-7-isopropyl-4-methyl-octahydroinden-2-yl acetate)

INCHI for NP0172260 ((1r,2s,3ar,4r,7s,7ar)-1-acetyl-4-hydroxy-7-isopropyl-4-methyl-octahydroinden-2-yl acetate)

Structure for NP0172260 ((1r,2s,3ar,4r,7s,7ar)-1-acetyl-4-hydroxy-7-isopropyl-4-methyl-octahydroinden-2-yl acetate)

3D Structure for NP0172260 ((1r,2s,3ar,4r,7s,7ar)-1-acetyl-4-hydroxy-7-isopropyl-4-methyl-octahydroinden-2-yl acetate)