NP-MRD: Showing NP-Card for Integristerone A 25-acetate (NP0080261)

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Record Information

Version

2.0

Created at

2022-04-29 01:18:40 UTC

Updated at

2022-04-29 01:18:40 UTC

NP-MRD ID

NP0080261

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Integristerone A 25-acetate

Description

Integristerone A 25-acetate belongs to the class of organic compounds known as hydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or derivatives bearing at least hydroxyl group. Integristerone A 25-acetate is found in Silene brahuica and Zoanthus sp.. Integristerone A 25-acetate was first documented in 2002 (PMID: 12193031). Based on a literature review very few articles have been published on Integristerone A 25-acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652304292203182D          

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M  END

     RDKit          3D

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M  END

  Mrv1652304292203182D          

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   -4.5236    5.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3981    2.9880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0592    4.1438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5151    2.2220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2124    3.2347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1073    2.8462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9451    0.5269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6232    2.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399    1.2325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7793    2.7844    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
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  5  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  2  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
 15 16  1  0  0  0  0
  8 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 13 19  1  0  0  0  0
 17 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 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
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 24 30  1  0  0  0  0
 21 31  1  1  0  0  0
 20 32  1  1  0  0  0
 20 33  1  1  0  0  0
 14 34  1  6  0  0  0
 13 35  1  1  0  0  0
  5 36  1  6  0  0  0
  2 37  1  6  0  0  0
  1 38  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0080261

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC(C)(C)CC[C@@H](O)[C@](C)(O)[C@H]1CC[C@@]2(O)C3=CC(=O)[C@@H]4C[C@@H](O)[C@@H](O)[C@@H](O)[C@]4(C)[C@H]3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C29H46O9/c1-15(30)38-25(2,3)10-9-22(33)28(6,36)21-8-12-29(37)17-13-19(31)18-14-20(32)23(34)24(35)27(18,5)16(17)7-11-26(21,29)4/h13,16,18,20-24,32-37H,7-12,14H2,1-6H3/t16-,18-,20+,21-,22+,23+,24+,26+,27+,28+,29+/m0/s1

> <INCHI_KEY>
QMXDANIONYZQEX-NAIDWPAJSA-N

> <FORMULA>
C29H46O9

> <MOLECULAR_WEIGHT>
538.678

> <EXACT_MASS>
538.314183061

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
58.52746000120261

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5R,6R)-5,6-dihydroxy-2-methyl-6-[(1R,2R,3S,4R,5R,7R,11S,14S,15R)-3,4,5,11-tetrahydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-14-yl]heptan-2-yl acetate

> <ALOGPS_LOGP>
1.11

> <JCHEM_LOGP>
0.13199146800000183

> <ALOGPS_LOGS>
-3.05

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.451417032604489

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.871504692558968

> <JCHEM_PKA_STRONGEST_BASIC>
-3.192911912866929

> <JCHEM_POLAR_SURFACE_AREA>
164.75

> <JCHEM_REFRACTIVITY>
139.2348

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.82e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5R,6R)-5,6-dihydroxy-2-methyl-6-[(1R,2R,3S,4R,5R,7R,11S,14S,15R)-3,4,5,11-tetrahydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-14-yl]heptan-2-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       7.929   4.020   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.452   2.572   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.459   1.394   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.943   1.666   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.420   3.114   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.413   4.291   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.889   5.740   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.904   3.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.911   2.208   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.434   0.759   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.950   0.488   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.474  -0.960   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.395   2.479   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.872   3.927   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.865   5.104   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.381   4.833   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.667   3.877   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.095   2.398   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.179   1.534   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.612   5.093   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.557   6.309   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.083   6.098   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.028   7.314   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.554   7.103   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.764   8.629   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -8.079   6.893   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -9.024   8.108   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0     -10.550   7.898   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -8.444   9.535   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -6.343   5.578   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.977   7.735   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -2.828   4.148   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.396   6.038   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       0.200   5.313   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.764   0.984   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       4.897   4.562   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       9.968   2.301   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       8.921   5.197   0.000  0.00  0.00           O+0
CONECT    1    2    6   38                                                  
CONECT    2    1    3   37                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    8   36                                             
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9   16                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10    4   12                                                  
CONECT   12   11                                                            
CONECT   13    9   14   19   35                                             
CONECT   14   13   15   17   34                                             
CONECT   15   14   16                                                       
CONECT   16   15    8                                                       
CONECT   17   14   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18   13                                                       
CONECT   20   17   21   32   33                                             
CONECT   21   20   22   31                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26   30                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   24                                                            
CONECT   31   21                                                            
CONECT   32   20                                                            
CONECT   33   20                                                            
CONECT   34   14                                                            
CONECT   35   13                                                            
CONECT   36    5                                                            
CONECT   37    2                                                            
CONECT   38    1                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
Integristerone a 25-acetic acid	Generator

Chemical Formula

C₂₉H₄₆O₉

Average Mass

538.6780 Da

Monoisotopic Mass

538.31418 Da

IUPAC Name

(5R,6R)-5,6-dihydroxy-2-methyl-6-[(1R,2R,3S,4R,5R,7R,11S,14S,15R)-3,4,5,11-tetrahydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-14-yl]heptan-2-yl acetate

Traditional Name

(5R,6R)-5,6-dihydroxy-2-methyl-6-[(1R,2R,3S,4R,5R,7R,11S,14S,15R)-3,4,5,11-tetrahydroxy-2,15-dimethyl-8-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-14-yl]heptan-2-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC(C)(C)CC[C@@H](O)[C@](C)(O)[C@H]1CC[C@@]2(O)C3=CC(=O)[C@@H]4C[C@@H](O)[C@@H](O)[C@@H](O)[C@]4(C)[C@H]3CC[C@]12C

InChI Identifier

InChI=1S/C29H46O9/c1-15(30)38-25(2,3)10-9-22(33)28(6,36)21-8-12-29(37)17-13-19(31)18-14-20(32)23(34)24(35)27(18,5)16(17)7-11-26(21,29)4/h13,16,18,20-24,32-37H,7-12,14H2,1-6H3/t16-,18-,20+,21-,22+,23+,24+,26+,27+,28+,29+/m0/s1

InChI Key

QMXDANIONYZQEX-NAIDWPAJSA-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
Silene brahuica	LOTUS Database	35616633
Zoanthus sp.	Animalia	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or derivatives bearing at least hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Hydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Hexahydroxy bile acid, alcohol, or derivatives
Cholesterol
Cholesterol-skeleton
Cholestane-skeleton
Ecdysteroid
Hydroxy bile acid, alcohol, or derivatives
22-hydroxysteroid
20-hydroxysteroid
Steroid ester
3-hydroxy-delta-7-steroid
3-hydroxysteroid
1-hydroxysteroid
6-oxosteroid
2-hydroxysteroid
14-hydroxysteroid
Hydroxysteroid
Oxosteroid
3-beta-hydroxysteroid
Delta-7-steroid
Cyclohexenone
Cyclitol or derivatives
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Ketone
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carbonyl group
Organic oxide
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxygen 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	1.11	ALOGPS
logP	0.13	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	12.87	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	164.75 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	139.23 m³·mol⁻¹	ChemAxon
Polarizability	58.53 Å³	ChemAxon
Number of Rings	4	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

C00045323

Chemspider ID

10214052

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21592302

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Suksamrarn A, Jankam A, Tarnchompoo B, Putchakarn S: Ecdysteroids from a Zoanthus sp. J Nat Prod. 2002 Aug;65(8):1194-7. doi: 10.1021/np010645s. [PubMed:12193031 ]

Showing NP-Card for Integristerone A 25-acetate (NP0080261)

MOL for NP0080261 (Integristerone A 25-acetate)

3D MOL for NP0080261 (Integristerone A 25-acetate)

3D SDF for NP0080261 (Integristerone A 25-acetate)

3D-SDF for NP0080261 (Integristerone A 25-acetate)

PDB for NP0080261 (Integristerone A 25-acetate)

3D PDB for NP0080261 (Integristerone A 25-acetate)

SMILES for NP0080261 (Integristerone A 25-acetate)

INCHI for NP0080261 (Integristerone A 25-acetate)

Structure for NP0080261 (Integristerone A 25-acetate)

3D Structure for NP0080261 (Integristerone A 25-acetate)