NP-MRD: Showing NP-Card for 14,20-dihydroxy-17-(3-hydroxy-6-methylheptan-2-yl)-2,6,6,18-tetramethyl-5,7-dioxapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]icos-12-en-11-one (NP0328810)

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Record Information

Version

2.0

Created at

2022-09-12 12:37:11 UTC

Updated at

2022-09-12 12:37:12 UTC

NP-MRD ID

NP0328810

Secondary Accession Numbers

None

Natural Product Identification

Common Name

14,20-dihydroxy-17-(3-hydroxy-6-methylheptan-2-yl)-2,6,6,18-tetramethyl-5,7-dioxapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]icos-12-en-11-one

Description

14,20-Dihydroxy-17-(3-hydroxy-6-methylheptan-2-yl)-2,6,6,18-tetramethyl-5,7-dioxapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]Icos-12-en-11-one belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups. 14,20-Dihydroxy-17-(3-hydroxy-6-methylheptan-2-yl)-2,6,6,18-tetramethyl-5,7-dioxapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]Icos-12-en-11-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191516232D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004191516232D          

 36 40  0  0  0  0            999 V2000
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    9.7788   -1.7358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4981   -2.8036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4069   -2.6361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7128   -2.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9170   -2.4074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3308   -1.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1211   -2.6247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5350   -2.0441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3252   -2.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9114   -3.4226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5294   -3.0593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9432   -2.4787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6512   -3.2503    0.0000 C   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 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
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 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
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 21 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 19 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 15 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 10 35  1  0  0  0  0
 13 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0328810

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CCC(O)C(C)C1CCC2(O)C3=CC(=O)C4CC5OC(C)(C)OC5CC4(C)C3C(O)CC12C

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O6/c1-16(2)8-9-21(31)17(3)18-10-11-30(34)20-12-22(32)19-13-24-25(36-27(4,5)35-24)15-28(19,6)26(20)23(33)14-29(18,30)7/h12,16-19,21,23-26,31,33-34H,8-11,13-15H2,1-7H3

> <INCHI_KEY>
XYTZXEVAVMSUGS-UHFFFAOYSA-N

> <FORMULA>
C30H48O6

> <MOLECULAR_WEIGHT>
504.708

> <EXACT_MASS>
504.345089266

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
57.635125853684485

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14,20-dihydroxy-17-(3-hydroxy-6-methylheptan-2-yl)-2,6,6,18-tetramethyl-5,7-dioxapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]icos-12-en-11-one

> <ALOGPS_LOGP>
3.15

> <JCHEM_LOGP>
3.5559827433333324

> <ALOGPS_LOGS>
-4.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.884769335361575

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.73579661920067

> <JCHEM_PKA_STRONGEST_BASIC>
-0.839957131176554

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
139.3881

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.10e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14,20-dihydroxy-17-(3-hydroxy-6-methylheptan-2-yl)-2,6,6,18-tetramethyl-5,7-dioxapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]icos-12-en-11-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      -1.289  -8.382   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.249  -8.455   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.955  -9.824   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.082  -7.159   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.620  -7.233   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.452  -5.937   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.747  -4.568   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.991  -6.010   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.696  -7.379   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.823  -4.715   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.264  -3.280   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.457  -2.305   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.752  -3.138   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.986  -1.615   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.238  -2.732   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.629  -1.242   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.115  -0.837   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      11.506   0.653   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      12.209  -1.921   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.695  -1.515   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.789  -2.599   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      16.326  -2.511   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      16.885  -3.946   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.254  -3.240   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.730  -5.233   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      15.693  -4.921   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      14.397  -4.088   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.912  -4.494   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.818  -3.410   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.426  -4.899   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.332  -3.816   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.940  -5.305   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      11.035  -6.389   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       8.455  -5.711   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.361  -4.627   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.816  -6.067   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   35                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   35                                             
CONECT   14   13                                                            
CONECT   15   13   16   31                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   29                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23   27                                                       
CONECT   27   26   21   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   19   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   15   32                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   10   13   36                                             
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₈O₆

Average Mass

504.7080 Da

Monoisotopic Mass

504.34509 Da

IUPAC Name

14,20-dihydroxy-17-(3-hydroxy-6-methylheptan-2-yl)-2,6,6,18-tetramethyl-5,7-dioxapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]icos-12-en-11-one

Traditional Name

14,20-dihydroxy-17-(3-hydroxy-6-methylheptan-2-yl)-2,6,6,18-tetramethyl-5,7-dioxapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]icos-12-en-11-one

CAS Registry Number

Not Available

SMILES

CC(C)CCC(O)C(C)C1CCC2(O)C3=CC(=O)C4CC5OC(C)(C)OC5CC4(C)C3C(O)CC12C

InChI Identifier

InChI=1S/C30H48O6/c1-16(2)8-9-21(31)17(3)18-10-11-30(34)20-12-22(32)19-13-24-25(36-27(4,5)35-24)15-28(19,6)26(20)23(33)14-29(18,30)7/h12,16-19,21,23-26,31,33-34H,8-11,13-15H2,1-7H3

InChI Key

XYTZXEVAVMSUGS-UHFFFAOYSA-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

Not Available

Chemical Taxonomy

Description

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

Trihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Cholesterol
Cholestane-skeleton
Ecdysteroid
Trihydroxy bile acid, alcohol, or derivatives
22-hydroxysteroid
6-oxosteroid
11-hydroxysteroid
14-hydroxysteroid
Oxosteroid
Hydroxysteroid
Delta-7-steroid
Ketal
Cyclohexenone
Meta-dioxolane
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Ketone
Organoheterocyclic compound
Oxacycle
Acetal
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Alcohol
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	3.15	ALOGPS
logP	3.56	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	13.74	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	139.39 m³·mol⁻¹	ChemAxon
Polarizability	57.64 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 14,20-dihydroxy-17-(3-hydroxy-6-methylheptan-2-yl)-2,6,6,18-tetramethyl-5,7-dioxapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]icos-12-en-11-one (NP0328810)

MOL for NP0328810 (14,20-dihydroxy-17-(3-hydroxy-6-methylheptan-2-yl)-2,6,6,18-tetramethyl-5,7-dioxapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]icos-12-en-11-one)

3D MOL for NP0328810 (14,20-dihydroxy-17-(3-hydroxy-6-methylheptan-2-yl)-2,6,6,18-tetramethyl-5,7-dioxapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]icos-12-en-11-one)

3D SDF for NP0328810 (14,20-dihydroxy-17-(3-hydroxy-6-methylheptan-2-yl)-2,6,6,18-tetramethyl-5,7-dioxapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]icos-12-en-11-one)

3D-SDF for NP0328810 (14,20-dihydroxy-17-(3-hydroxy-6-methylheptan-2-yl)-2,6,6,18-tetramethyl-5,7-dioxapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]icos-12-en-11-one)

PDB for NP0328810 (14,20-dihydroxy-17-(3-hydroxy-6-methylheptan-2-yl)-2,6,6,18-tetramethyl-5,7-dioxapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]icos-12-en-11-one)

3D PDB for NP0328810 (14,20-dihydroxy-17-(3-hydroxy-6-methylheptan-2-yl)-2,6,6,18-tetramethyl-5,7-dioxapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]icos-12-en-11-one)

SMILES for NP0328810 (14,20-dihydroxy-17-(3-hydroxy-6-methylheptan-2-yl)-2,6,6,18-tetramethyl-5,7-dioxapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]icos-12-en-11-one)

INCHI for NP0328810 (14,20-dihydroxy-17-(3-hydroxy-6-methylheptan-2-yl)-2,6,6,18-tetramethyl-5,7-dioxapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]icos-12-en-11-one)

Structure for NP0328810 (14,20-dihydroxy-17-(3-hydroxy-6-methylheptan-2-yl)-2,6,6,18-tetramethyl-5,7-dioxapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]icos-12-en-11-one)

3D Structure for NP0328810 (14,20-dihydroxy-17-(3-hydroxy-6-methylheptan-2-yl)-2,6,6,18-tetramethyl-5,7-dioxapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]icos-12-en-11-one)