NP-MRD: Showing NP-Card for [(3r,3as,7e,7as)-7-{2-[(1z,3s,5r)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-3-[(2r)-6-methylheptan-2-yl]-hexahydro-1h-inden-3a-yl]methyl acetate (NP0143214)

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Record Information

Version

2.0

Created at

2022-09-01 21:54:51 UTC

Updated at

2022-09-01 21:54:52 UTC

NP-MRD ID

NP0143214

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(3r,3as,7e,7as)-7-{2-[(1z,3s,5r)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-3-[(2r)-6-methylheptan-2-yl]-hexahydro-1h-inden-3a-yl]methyl acetate

Description

18-Acetoxy-1alpha-hydroxyvitamin D3, also known as 18-acetoxy-1a-hydroxycholecalciferol, belongs to the class of organic compounds known as vitamin d and derivatives. Vitamin D and derivatives are compounds containing a secosteroid backbone, usually secoergostane or secocholestane. Thus, 18-acetoxy-1alpha-hydroxyvitamin D3 is considered to be a secosteroid. [(3r,3as,7e,7as)-7-{2-[(1z,3s,5r)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-3-[(2r)-6-methylheptan-2-yl]-hexahydro-1h-inden-3a-yl]methyl acetate is found in Trypanosoma brucei. Based on a literature review very few articles have been published on 18-acetoxy-1alpha-hydroxyvitamin D3.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309012223542D          

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M  END

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M  END


  Mrv1652309012223542D          

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 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 10 16  1  0  0  0  0
  6 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
  3 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
  2 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0143214

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2\C(CCC[C@]12COC(C)=O)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C29H46O4/c1-19(2)8-6-9-20(3)26-13-14-27-23(10-7-15-29(26,27)18-33-22(5)30)11-12-24-16-25(31)17-28(32)21(24)4/h11-12,19-20,25-28,31-32H,4,6-10,13-18H2,1-3,5H3/b23-11+,24-12-/t20-,25-,26-,27+,28+,29+/m1/s1

> <INCHI_KEY>
PXVFRWYXTUOPCC-JORAJEIRSA-N

> <FORMULA>
C29H46O4

> <MOLECULAR_WEIGHT>
458.683

> <EXACT_MASS>
458.339609961

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
55.4358321155348

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(3R,3aS,7E,7aS)-7-{2-[(1Z,3S,5R)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-3-[(2R)-6-methylheptan-2-yl]-octahydro-1H-inden-3a-yl]methyl acetate

> <ALOGPS_LOGP>
6.18

> <JCHEM_LOGP>
4.982209935333335

> <ALOGPS_LOGS>
-5.10

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.288747756074436

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.392873591326058

> <JCHEM_PKA_STRONGEST_BASIC>
-2.75966147201484

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
135.62259999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.61e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(3R,3aS,7E,7aS)-7-{2-[(1Z,3S,5R)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-3-[(2R)-6-methylheptan-2-yl]-hexahydro-1H-inden-3a-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 01-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.255  -1.241   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.761  -0.921   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.237   0.544   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.206   1.688   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.700   1.368   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.669   2.513   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.145   3.977   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.115   5.122   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.391   4.802   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.867   3.337   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.012   4.367   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.692   5.874   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.836   6.904   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.301   6.428   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.516   8.411   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.837   2.192   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.607   0.859   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.113   1.179   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.274   2.711   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.608   3.481   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.608   5.021   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.942   2.711   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.275   3.481   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.609   2.711   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.943   3.481   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.276   2.711   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.943   5.021   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.743   0.864   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -6.774  -0.280   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -8.280   0.040   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -6.298  -1.745   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.791  -2.065   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -4.315  -3.530   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   32                                                  
CONECT    3    2    4   28                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   16                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16   19                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   10    6   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   10   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                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28    3   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31    2   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Value	Source
(5Z,7E)-(1S,3R)-18-Acetoxy-9,10-seco-5,7,10(19)-cholestatriene-1,3-diol	ChEBI
18-Acetoxy-1alpha-hydroxycholecalciferol	ChEBI
18-Acetoxy-1a-hydroxycholecalciferol	Generator
18-Acetoxy-1α-hydroxycholecalciferol	Generator
18-Acetoxy-1a-hydroxyvitamin D3	Generator
18-Acetoxy-1α-hydroxyvitamin D3	Generator

Chemical Formula

C₂₉H₄₆O₄

Average Mass

458.6830 Da

Monoisotopic Mass

458.33961 Da

IUPAC Name

[(3R,3aS,7E,7aS)-7-{2-[(1Z,3S,5R)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-3-[(2R)-6-methylheptan-2-yl]-octahydro-1H-inden-3a-yl]methyl acetate

Traditional Name

[(3R,3aS,7E,7aS)-7-{2-[(1Z,3S,5R)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-3-[(2R)-6-methylheptan-2-yl]-hexahydro-1H-inden-3a-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2\C(CCC[C@]12COC(C)=O)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C

InChI Identifier

InChI=1S/C29H46O4/c1-19(2)8-6-9-20(3)26-13-14-27-23(10-7-15-29(26,27)18-33-22(5)30)11-12-24-16-25(31)17-28(32)21(24)4/h11-12,19-20,25-28,31-32H,4,6-10,13-18H2,1-3,5H3/b23-11+,24-12-/t20-,25-,26-,27+,28+,29+/m1/s1

InChI Key

PXVFRWYXTUOPCC-JORAJEIRSA-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
Trypanosoma brucei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as vitamin d and derivatives. Vitamin D and derivatives are compounds containing a secosteroid backbone, usually secoergostane or secocholestane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Vitamin D and derivatives

Direct Parent

Vitamin D and derivatives

Alternative Parents

Substituents

Triterpenoid
Cyclic alcohol
Secondary alcohol
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

diol (CHEBI:73906 )
D3 vitamins (CHEBI:73906 )
hydroxycalciol (CHEBI:73906 )
Vitamin D3 and derivatives (LMST03020409 )

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	6.18	ALOGPS
logP	4.98	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	14.39	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	135.62 m³·mol⁻¹	ChemAxon
Polarizability	55.44 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

7826457

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9547517

PDB ID

Not Available

ChEBI ID

73906

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(3r,3as,7e,7as)-7-{2-[(1z,3s,5r)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-3-[(2r)-6-methylheptan-2-yl]-hexahydro-1h-inden-3a-yl]methyl acetate (NP0143214)

MOL for NP0143214 ([(3r,3as,7e,7as)-7-{2-[(1z,3s,5r)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-3-[(2r)-6-methylheptan-2-yl]-hexahydro-1h-inden-3a-yl]methyl acetate)

3D MOL for NP0143214 ([(3r,3as,7e,7as)-7-{2-[(1z,3s,5r)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-3-[(2r)-6-methylheptan-2-yl]-hexahydro-1h-inden-3a-yl]methyl acetate)

3D SDF for NP0143214 ([(3r,3as,7e,7as)-7-{2-[(1z,3s,5r)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-3-[(2r)-6-methylheptan-2-yl]-hexahydro-1h-inden-3a-yl]methyl acetate)

3D-SDF for NP0143214 ([(3r,3as,7e,7as)-7-{2-[(1z,3s,5r)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-3-[(2r)-6-methylheptan-2-yl]-hexahydro-1h-inden-3a-yl]methyl acetate)

PDB for NP0143214 ([(3r,3as,7e,7as)-7-{2-[(1z,3s,5r)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-3-[(2r)-6-methylheptan-2-yl]-hexahydro-1h-inden-3a-yl]methyl acetate)

3D PDB for NP0143214 ([(3r,3as,7e,7as)-7-{2-[(1z,3s,5r)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-3-[(2r)-6-methylheptan-2-yl]-hexahydro-1h-inden-3a-yl]methyl acetate)

SMILES for NP0143214 ([(3r,3as,7e,7as)-7-{2-[(1z,3s,5r)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-3-[(2r)-6-methylheptan-2-yl]-hexahydro-1h-inden-3a-yl]methyl acetate)

INCHI for NP0143214 ([(3r,3as,7e,7as)-7-{2-[(1z,3s,5r)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-3-[(2r)-6-methylheptan-2-yl]-hexahydro-1h-inden-3a-yl]methyl acetate)

Structure for NP0143214 ([(3r,3as,7e,7as)-7-{2-[(1z,3s,5r)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-3-[(2r)-6-methylheptan-2-yl]-hexahydro-1h-inden-3a-yl]methyl acetate)

3D Structure for NP0143214 ([(3r,3as,7e,7as)-7-{2-[(1z,3s,5r)-3,5-dihydroxy-2-methylidenecyclohexylidene]ethylidene}-3-[(2r)-6-methylheptan-2-yl]-hexahydro-1h-inden-3a-yl]methyl acetate)