NP-MRD: Showing NP-Card for 24R-Acetoxy-3beta,25-dihydroxycycloartane (NP0074934)

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Record Information

Version

2.0

Created at

2022-04-28 20:14:02 UTC

Updated at

2022-04-28 20:14:02 UTC

NP-MRD ID

NP0074934

Secondary Accession Numbers

None

Natural Product Identification

Common Name

24R-Acetoxy-3beta,25-dihydroxycycloartane

Description

(24R)-24-Acetoxycycloartane-3beta,25-diol belongs to the class of organic compounds known as cycloartanols and derivatives. These are steroids containing a cycloartanol moiety. 24R-Acetoxy-3beta,25-dihydroxycycloartane is found in Dysoxylum malabaricum. Based on a literature review very few articles have been published on (24R)-24-Acetoxycycloartane-3beta,25-diol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282222142D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282222142D          

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    6.2670   -0.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7953    0.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3420   -0.7223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2266    1.4573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0438    1.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5502    1.9958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3547    0.5803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2685    1.1446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6083    0.4982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7705   -1.8210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0924    0.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8921   -2.1544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1635   -2.4176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6242   -1.1154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
  4 10  1  1  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 15 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
 21 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 18 30  1  6  0  0  0
 12 31  1  1  0  0  0
 11 32  1  6  0  0  0
  7 33  1  1  0  0  0
  5 33  1  1  0  0  0
  3 34  1  0  0  0  0
  3 35  1  0  0  0  0
  2 36  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0074934

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CC[C@@H](OC(C)=O)C(C)(C)O)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@@H]4[C@]5(C[C@@]35CC[C@]12C)CC[C@H](O)C4(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C32H54O4/c1-20(9-12-26(28(5,6)35)36-21(2)33)22-13-15-30(8)24-11-10-23-27(3,4)25(34)14-16-31(23)19-32(24,31)18-17-29(22,30)7/h20,22-26,34-35H,9-19H2,1-8H3/t20-,22-,23+,24+,25+,26-,29-,30+,31-,32+/m1/s1

> <INCHI_KEY>
HPQKOKRQWLFMFP-FQWGTIQDSA-N

> <FORMULA>
C32H54O4

> <MOLECULAR_WEIGHT>
502.78

> <EXACT_MASS>
502.402210219

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
90

> <JCHEM_AVERAGE_POLARIZABILITY>
61.413342384582464

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,6R)-2-hydroxy-6-[(1S,3R,6S,8R,11S,12S,15R,16R)-6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-15-yl]-2-methylheptan-3-yl acetate

> <ALOGPS_LOGP>
5.70

> <JCHEM_LOGP>
5.848348979000002

> <ALOGPS_LOGS>
-6.48

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.489408976606935

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.302827647836942

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351322225363057

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
143.53230000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.68e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,6R)-2-hydroxy-6-[(1S,3R,6S,8R,11S,12S,15R,16R)-6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-15-yl]-2-methylheptan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -0.993  -0.363   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.516  -1.811   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.523  -2.988   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.993  -2.717   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.516  -1.269   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.523  -0.092   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.032  -0.998   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.025  -2.175   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.501  -3.624   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.985  -3.895   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.541  -1.904   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.064  -0.456   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.071   0.722   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.555   0.451   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.603  -0.506   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.031  -1.985   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.756  -2.849   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.548   0.710   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.074   0.499   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.019   1.715   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.544   1.505   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.125   0.078   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.698  -0.502   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.551   0.658   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      13.705  -1.348   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      13.490   2.720   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      15.015   2.510   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      15.960   3.726   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      15.595   1.083   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.968   2.137   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.736   0.930   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.172  -3.399   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.039   0.179   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.665  -4.022   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.305  -4.513   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -3.032  -2.082   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   36                                                  
CONECT    3    2    4   34   35                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   33                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   14   33                                             
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12   17   32                                             
CONECT   12   11   13   15   31                                             
CONECT   13   12   14                                                       
CONECT   14   13    7                                                       
CONECT   15   12   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   11                                                       
CONECT   18   15   19   30                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22                                                            
CONECT   26   21   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   18                                                            
CONECT   31   12                                                            
CONECT   32   11                                                            
CONECT   33    7    5                                                       
CONECT   34    3                                                            
CONECT   35    3                                                            
CONECT   36    2                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
(24R)-24-Acetoxycycloartane-3b,25-diol	Generator
(24R)-24-Acetoxycycloartane-3β,25-diol	Generator

Chemical Formula

C₃₂H₅₄O₄

Average Mass

502.7800 Da

Monoisotopic Mass

502.40221 Da

IUPAC Name

(3R,6R)-2-hydroxy-6-[(1S,3R,6S,8R,11S,12S,15R,16R)-6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-15-yl]-2-methylheptan-3-yl acetate

Traditional Name

(3R,6R)-2-hydroxy-6-[(1S,3R,6S,8R,11S,12S,15R,16R)-6-hydroxy-7,7,12,16-tetramethylpentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadecan-15-yl]-2-methylheptan-3-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@H](CC[C@@H](OC(C)=O)C(C)(C)O)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@@H]4[C@]5(C[C@@]35CC[C@]12C)CC[C@H](O)C4(C)C

InChI Identifier

InChI=1S/C32H54O4/c1-20(9-12-26(28(5,6)35)36-21(2)33)22-13-15-30(8)24-11-10-23-27(3,4)25(34)14-16-31(23)19-32(24,31)18-17-29(22,30)7/h20,22-26,34-35H,9-19H2,1-8H3/t20-,22-,23+,24+,25+,26-,29-,30+,31-,32+/m1/s1

InChI Key

HPQKOKRQWLFMFP-FQWGTIQDSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Dysoxylum malabaricum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cycloartanols and derivatives. These are steroids containing a cycloartanol moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cycloartanols and derivatives

Direct Parent

Cycloartanols and derivatives

Alternative Parents

Substituents

Cycloartanol-skeleton
9b,19-cyclo-lanostane-skeleton
Cycloartane-skeleton
Triterpenoid
25-hydroxysteroid
Dihydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
Steroid ester
Hydroxysteroid
3-hydroxysteroid
3-beta-hydroxysteroid
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Alcohol
Organooxygen compound
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	5.7	ALOGPS
logP	5.85	ChemAxon
logS	-6.5	ALOGPS
pKa (Strongest Acidic)	14.3	ChemAxon
pKa (Strongest Basic)	-0.84	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	7	ChemAxon
Refractivity	143.53 m³·mol⁻¹	ChemAxon
Polarizability	61.41 Å³	ChemAxon
Number of Rings	5	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

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

101093182

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 24R-Acetoxy-3beta,25-dihydroxycycloartane (NP0074934)

MOL for NP0074934 (24R-Acetoxy-3beta,25-dihydroxycycloartane)

3D MOL for NP0074934 (24R-Acetoxy-3beta,25-dihydroxycycloartane)

3D SDF for NP0074934 (24R-Acetoxy-3beta,25-dihydroxycycloartane)

3D-SDF for NP0074934 (24R-Acetoxy-3beta,25-dihydroxycycloartane)

PDB for NP0074934 (24R-Acetoxy-3beta,25-dihydroxycycloartane)

3D PDB for NP0074934 (24R-Acetoxy-3beta,25-dihydroxycycloartane)

SMILES for NP0074934 (24R-Acetoxy-3beta,25-dihydroxycycloartane)

INCHI for NP0074934 (24R-Acetoxy-3beta,25-dihydroxycycloartane)

Structure for NP0074934 (24R-Acetoxy-3beta,25-dihydroxycycloartane)

3D Structure for NP0074934 (24R-Acetoxy-3beta,25-dihydroxycycloartane)