NP-MRD: Showing NP-Card for Agosterol F (NP0070847)

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Record Information

Version

2.0

Created at

2022-04-28 16:16:04 UTC

Updated at

2022-04-28 16:16:04 UTC

NP-MRD ID

NP0070847

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Agosterol F

Description

(1R,2R,5S,6R,7S,8R,11R,14R,15R,17R)-6-(acetyloxy)-5,17-dihydroxy-14-[(2S,3R)-3-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-9-en-8-yl acetate belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups. Agosterol F is found in Acanthodendrilla sp. Based on a literature review very few articles have been published on (1R,2R,5S,6R,7S,8R,11R,14R,15R,17R)-6-(acetyloxy)-5,17-dihydroxy-14-[(2S,3R)-3-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-9-en-8-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282218162D          

 38 41  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282218162D          

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    0.3805    3.0701    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2943    3.8905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5127    4.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0950    2.6576    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8094    3.0701    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5239    2.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2384    3.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9529    2.6576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6673    3.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9529    1.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8094    3.8951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0950    1.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2399    2.1825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2421    1.6068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7051    3.2746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5121    3.1031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0641    3.7162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7670    2.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2150    1.7053    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  6  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  6  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  7 18  1  0  0  0  0
 18 19  1  1  0  0  0
 16 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 15 22  1  6  0  0  0
 20 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 24 30  1  6  0  0  0
 23 31  1  1  0  0  0
 16 32  1  6  0  0  0
  5 33  1  6  0  0  0
  3 34  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
  2 38  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0070847

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C31H50O7/c1-16(2)8-11-23(34)17(3)21-9-10-22-20-14-26(37-18(4)32)28-29(38-19(5)33)24(35)12-13-30(28,6)27(20)25(36)15-31(21,22)7/h14,16-17,21-29,34-36H,8-13,15H2,1-7H3/t17-,21+,22-,23+,24-,25+,26+,27+,28-,29-,30+,31+/m0/s1

> <INCHI_KEY>
NOWCAXXOVHJADO-UKGIDAICSA-N

> <FORMULA>
C31H50O7

> <MOLECULAR_WEIGHT>
534.734

> <EXACT_MASS>
534.35565395

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
88

> <JCHEM_AVERAGE_POLARIZABILITY>
61.17459310275752

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5S,6R,7S,8R,11R,14R,15R,17R)-6-(acetyloxy)-5,17-dihydroxy-14-[(2S,3R)-3-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-yl acetate

> <ALOGPS_LOGP>
3.79

> <JCHEM_LOGP>
3.191406040333331

> <ALOGPS_LOGS>
-4.84

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.477849503078776

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.16077030972232

> <JCHEM_PKA_STRONGEST_BASIC>
-0.23897564825882045

> <JCHEM_POLAR_SURFACE_AREA>
113.29

> <JCHEM_REFRACTIVITY>
144.80570000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.66e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,6R,7S,8R,11R,14R,15R,17R)-6-(acetyloxy)-5,17-dihydroxy-14-[(2S,3R)-3-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-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      -7.198   2.359   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.228   3.503   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.752   4.968   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.246   5.288   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.216   4.144   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.692   2.679   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.709   4.464   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.233   5.929   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.264   7.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.770   6.753   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -6.801   7.897   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -6.325   9.362   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -7.355  10.506   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -4.818   9.682   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.727   6.249   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.697   5.104   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.172   3.640   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.679   3.320   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -3.155   1.855   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.710   5.731   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.549   7.262   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.957   7.583   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.044   4.961   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.378   5.731   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.711   4.961   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.045   5.731   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.379   4.961   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.712   5.731   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.379   3.421   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.378   7.271   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.044   3.421   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.448   4.074   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.185   2.999   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -8.783   6.113   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0     -10.289   5.792   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0     -11.320   6.937   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0     -10.765   4.328   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -9.735   3.183   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   38                                                  
CONECT    3    2    4   34                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   33                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   18                                                  
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    8   16   22                                                  
CONECT   16   15   17   20   32                                             
CONECT   17   16   18                                                       
CONECT   18   17    7   19                                                  
CONECT   19   18                                                            
CONECT   20   16   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21   15                                                       
CONECT   23   20   24   31                                                  
CONECT   24   23   25   30                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   24                                                            
CONECT   31   23                                                            
CONECT   32   16                                                            
CONECT   33    5                                                            
CONECT   34    3   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38    2                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
(1R,2R,5S,6R,7S,8R,11R,14R,15R,17R)-6-(Acetyloxy)-5,17-dihydroxy-14-[(2S,3R)-3-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadec-9-en-8-yl acetic acid	Generator

Chemical Formula

C₃₁H₅₀O₇

Average Mass

534.7340 Da

Monoisotopic Mass

534.35565 Da

IUPAC Name

(1R,2R,5S,6R,7S,8R,11R,14R,15R,17R)-6-(acetyloxy)-5,17-dihydroxy-14-[(2S,3R)-3-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-yl acetate

Traditional Name

(1R,2R,5S,6R,7S,8R,11R,14R,15R,17R)-6-(acetyloxy)-5,17-dihydroxy-14-[(2S,3R)-3-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-yl acetate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C31H50O7/c1-16(2)8-11-23(34)17(3)21-9-10-22-20-14-26(37-18(4)32)28-29(38-19(5)33)24(35)12-13-30(28,6)27(20)25(36)15-31(21,22)7/h14,16-17,21-29,34-36H,8-13,15H2,1-7H3/t17-,21+,22-,23+,24-,25+,26+,27+,28-,29-,30+,31+/m0/s1

InChI Key

NOWCAXXOVHJADO-UKGIDAICSA-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
Acanthodendrilla sp.	Animalia	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears four hydroxyl groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Tetrahydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Cholesterol-skeleton
Cholesterol
Cholestane-skeleton
Tetrahydroxy bile acid, alcohol, or derivatives
22-hydroxysteroid
Steroid ester
1-hydroxysteroid
3-beta-hydroxysteroid
11-hydroxysteroid
11-alpha-hydroxysteroid
Oxosteroid
16-oxosteroid
Hydroxysteroid
3-hydroxysteroid
3-hydroxy-delta-7-steroid
Delta-7-steroid
Dicarboxylic acid or derivatives
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
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	3.79	ALOGPS
logP	3.19	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	14.16	ChemAxon
pKa (Strongest Basic)	-0.24	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	144.81 m³·mol⁻¹	ChemAxon
Polarizability	61.17 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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

163094406

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Agosterol F (NP0070847)

MOL for NP0070847 (Agosterol F)

3D MOL for NP0070847 (Agosterol F)

3D SDF for NP0070847 (Agosterol F)

3D-SDF for NP0070847 (Agosterol F)

PDB for NP0070847 (Agosterol F)

3D PDB for NP0070847 (Agosterol F)

SMILES for NP0070847 (Agosterol F)

INCHI for NP0070847 (Agosterol F)

Structure for NP0070847 (Agosterol F)

3D Structure for NP0070847 (Agosterol F)