NP-MRD: Showing NP-Card for 7-hydroxy-6-(hydroxymethyl)-1-(5-methoxy-4-oxoheptan-2-yl)-3a,6,9a,11a-tetramethyl-4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-3-one (NP0221068)

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Record Information

Version

1.0

Created at

2022-09-05 22:33:02 UTC

Updated at

2022-09-05 22:33:02 UTC

NP-MRD ID

NP0221068

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-hydroxy-6-(hydroxymethyl)-1-(5-methoxy-4-oxoheptan-2-yl)-3a,6,9a,11a-tetramethyl-4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-3-one

Description

5-Hydroxy-6-(hydroxymethyl)-14-(5-methoxy-4-oxoheptan-2-yl)-2,6,11,15-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-1(10),13-dien-12-one belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group. 7-hydroxy-6-(hydroxymethyl)-1-(5-methoxy-4-oxoheptan-2-yl)-3a,6,9a,11a-tetramethyl-4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-3-one is found in Leopoldia comosa. Based on a literature review very few articles have been published on 5-hydroxy-6-(hydroxymethyl)-14-(5-methoxy-4-oxoheptan-2-yl)-2,6,11,15-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-1(10),13-dien-12-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062200332D          

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M  END

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M  END


  Mrv1652309062200332D          

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    9.5145   -8.9918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1168   -9.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7669   -9.7968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7295  -10.0173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1666  -10.7169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3322   -9.0339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7191   -9.5860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9344   -9.3310    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 11 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 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
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 29 33  1  0  0  0  0
 23 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 17 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0221068

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(OC)C(=O)CC(C)C1=CC(=O)C2(C)C3=C(CCC12C)C1(C)CCC(O)C(C)(CO)C1CC3

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O5/c1-8-23(35-7)22(32)15-18(2)21-16-26(34)30(6)20-9-10-24-27(3,19(20)11-14-29(21,30)5)13-12-25(33)28(24,4)17-31/h16,18,23-25,31,33H,8-15,17H2,1-7H3

> <INCHI_KEY>
FTXIRAJSRDWYAK-UHFFFAOYSA-N

> <FORMULA>
C30H46O5

> <MOLECULAR_WEIGHT>
486.693

> <EXACT_MASS>
486.334524581

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
56.50519462057662

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-hydroxy-6-(hydroxymethyl)-14-(5-methoxy-4-oxoheptan-2-yl)-2,6,11,15-tetramethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),13-dien-12-one

> <JCHEM_LOGP>
4.424186910666665

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.269605294754044

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.485011362194463

> <JCHEM_PKA_STRONGEST_BASIC>
-2.785682913964399

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
139.3255

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-6-(hydroxymethyl)-14-(5-methoxy-4-oxoheptan-2-yl)-2,6,11,15-tetramethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),13-dien-12-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       0.511  -9.767   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.051  -9.767   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.821 -11.101   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.051 -12.435   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.511 -12.435   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.361 -11.101   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.131  -9.767   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.131 -12.435   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.671 -12.435   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.441 -11.101   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.441 -13.768   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.815 -15.175   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.959 -16.206   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.798 -17.737   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.293 -15.436   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.454 -16.967   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.757 -15.912   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.902 -14.881   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.582 -13.375   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.117 -12.899   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.973 -13.929   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.497 -12.465   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.367 -15.357   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.046 -13.851   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.511 -14.327   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      15.976 -14.802   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.296 -16.309   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      17.760 -16.785   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      15.151 -17.339   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      16.365 -18.287   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.428 -18.699   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      15.244 -20.005   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      13.687 -16.863   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.542 -17.894   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.078 -17.418   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   21                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17   21                                             
CONECT   16   15                                                            
CONECT   17   15   18   35                                                  
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   11   15   22                                             
CONECT   22   21                                                            
CONECT   23   18   24   25   33                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31   33                                             
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31                                                            
CONECT   33   29   23   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   17                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₆O₅

Average Mass

486.6930 Da

Monoisotopic Mass

486.33452 Da

IUPAC Name

5-hydroxy-6-(hydroxymethyl)-14-(5-methoxy-4-oxoheptan-2-yl)-2,6,11,15-tetramethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),13-dien-12-one

Traditional Name

5-hydroxy-6-(hydroxymethyl)-14-(5-methoxy-4-oxoheptan-2-yl)-2,6,11,15-tetramethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),13-dien-12-one

CAS Registry Number

Not Available

SMILES

CCC(OC)C(=O)CC(C)C1=CC(=O)C2(C)C3=C(CCC12C)C1(C)CCC(O)C(C)(CO)C1CC3

InChI Identifier

InChI=1S/C30H46O5/c1-8-23(35-7)22(32)15-18(2)21-16-26(34)30(6)20-9-10-24-27(3,19(20)11-14-29(21,30)5)13-12-25(33)28(24,4)17-31/h16,18,23-25,31,33H,8-15,17H2,1-7H3

InChI Key

FTXIRAJSRDWYAK-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

Species Name	Source	Reference
Muscari comosum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a 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

Monohydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Monohydroxy bile acid, alcohol, or derivatives
23-oxosteroid
3-hydroxysteroid
Hydroxysteroid
15-oxosteroid
Oxosteroid
Cyclic alcohol
Ketone
Secondary alcohol
Ether
Dialkyl ether
Organic oxide
Organooxygen compound
Organic oxygen compound
Alcohol
Carbonyl group
Primary alcohol
Hydrocarbon derivative
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	4.42	ChemAxon
pKa (Strongest Acidic)	14.49	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	139.33 m³·mol⁻¹	ChemAxon
Polarizability	56.51 Å³	ChemAxon
Number of Rings	4	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

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

162955439

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7-hydroxy-6-(hydroxymethyl)-1-(5-methoxy-4-oxoheptan-2-yl)-3a,6,9a,11a-tetramethyl-4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-3-one (NP0221068)

MOL for NP0221068 (7-hydroxy-6-(hydroxymethyl)-1-(5-methoxy-4-oxoheptan-2-yl)-3a,6,9a,11a-tetramethyl-4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-3-one)

3D MOL for NP0221068 (7-hydroxy-6-(hydroxymethyl)-1-(5-methoxy-4-oxoheptan-2-yl)-3a,6,9a,11a-tetramethyl-4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-3-one)

3D SDF for NP0221068 (7-hydroxy-6-(hydroxymethyl)-1-(5-methoxy-4-oxoheptan-2-yl)-3a,6,9a,11a-tetramethyl-4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-3-one)

3D-SDF for NP0221068 (7-hydroxy-6-(hydroxymethyl)-1-(5-methoxy-4-oxoheptan-2-yl)-3a,6,9a,11a-tetramethyl-4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-3-one)

PDB for NP0221068 (7-hydroxy-6-(hydroxymethyl)-1-(5-methoxy-4-oxoheptan-2-yl)-3a,6,9a,11a-tetramethyl-4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-3-one)

3D PDB for NP0221068 (7-hydroxy-6-(hydroxymethyl)-1-(5-methoxy-4-oxoheptan-2-yl)-3a,6,9a,11a-tetramethyl-4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-3-one)

SMILES for NP0221068 (7-hydroxy-6-(hydroxymethyl)-1-(5-methoxy-4-oxoheptan-2-yl)-3a,6,9a,11a-tetramethyl-4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-3-one)

INCHI for NP0221068 (7-hydroxy-6-(hydroxymethyl)-1-(5-methoxy-4-oxoheptan-2-yl)-3a,6,9a,11a-tetramethyl-4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-3-one)

Structure for NP0221068 (7-hydroxy-6-(hydroxymethyl)-1-(5-methoxy-4-oxoheptan-2-yl)-3a,6,9a,11a-tetramethyl-4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-3-one)

3D Structure for NP0221068 (7-hydroxy-6-(hydroxymethyl)-1-(5-methoxy-4-oxoheptan-2-yl)-3a,6,9a,11a-tetramethyl-4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-3-one)