NP-MRD: Showing NP-Card for 1-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-2,8-dihydroxy-6,6,9a,11a-tetramethyl-1h,2h,3h,3ah,3bh,4h,8h,9h,9bh,11h-cyclopenta[a]phenanthrene-7,10-dione (NP0178488)

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Record Information

Version

2.0

Created at

2022-09-03 16:29:28 UTC

Updated at

2022-09-03 16:29:28 UTC

NP-MRD ID

NP0178488

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-2,8-dihydroxy-6,6,9a,11a-tetramethyl-1h,2h,3h,3ah,3bh,4h,8h,9h,9bh,11h-cyclopenta[a]phenanthrene-7,10-dione

Description

14-(2,6-Dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-4,13-dihydroxy-2,6,6,15-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-ene-5,17-dione 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. 1-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-2,8-dihydroxy-6,6,9a,11a-tetramethyl-1h,2h,3h,3ah,3bh,4h,8h,9h,9bh,11h-cyclopenta[a]phenanthrene-7,10-dione is found in Helicteres angustifolia. Based on a literature review very few articles have been published on 14-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-4,13-dihydroxy-2,6,6,15-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-ene-5,17-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032218292D          

 36 39  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309032218292D          

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    6.3292   -2.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7686   -3.6325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    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
  5  2  1  4  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 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  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 20 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 17 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 16 35  1  0  0  0  0
 12 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0178488

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)C=CC(=O)C(C)(O)C1C(O)CC2C3CC=C4C(C)(C)C(=O)C(O)CC4(C)C3C(=O)CC12C

> <INCHI_IDENTIFIER>
InChI=1S/C29H42O7/c1-25(2,35)11-10-21(33)29(7,36)23-17(30)12-16-15-8-9-20-26(3,4)24(34)19(32)14-28(20,6)22(15)18(31)13-27(16,23)5/h9-11,15-17,19,22-23,30,32,35-36H,8,12-14H2,1-7H3

> <INCHI_KEY>
JTPLNLNCNOCZIB-UHFFFAOYSA-N

> <FORMULA>
C29H42O7

> <MOLECULAR_WEIGHT>
502.648

> <EXACT_MASS>
502.293053692

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
54.168499167976734

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-4,13-dihydroxy-2,6,6,15-tetramethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,17-dione

> <JCHEM_LOGP>
2.1359452869999993

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.47442288883607

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.7981609896561

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8062198766278517

> <JCHEM_POLAR_SURFACE_AREA>
132.13000000000002

> <JCHEM_REFRACTIVITY>
137.39079999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
14-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-4,13-dihydroxy-2,6,6,15-tetramethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,17-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.320  -5.020   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.206  -5.231   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.005  -6.756   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.416  -3.705   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.731  -5.442   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.312  -6.868   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.837  -7.079   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.417  -8.505   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.998  -6.808   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.566  -4.918   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.851  -2.645   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.323  -0.719   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.185  -1.391   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      15.316  -5.967   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      10.768  -6.781   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9   13   35                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   35                                                  
CONECT   17   16   18   31                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   29                                                  
CONECT   21   20   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   20   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   17   32                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   16   12   36                                             
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₂O₇

Average Mass

502.6480 Da

Monoisotopic Mass

502.29305 Da

IUPAC Name

14-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-4,13-dihydroxy-2,6,6,15-tetramethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,17-dione

Traditional Name

14-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-4,13-dihydroxy-2,6,6,15-tetramethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,17-dione

CAS Registry Number

Not Available

SMILES

CC(C)(O)C=CC(=O)C(C)(O)C1C(O)CC2C3CC=C4C(C)(C)C(=O)C(O)CC4(C)C3C(=O)CC12C

InChI Identifier

InChI=1S/C29H42O7/c1-25(2,35)11-10-21(33)29(7,36)23-17(30)12-16-15-8-9-20-26(3,4)24(34)19(32)14-28(20,6)22(15)18(31)13-27(16,23)5/h9-11,15-17,19,22-23,30,32,35-36H,8,12-14H2,1-7H3

InChI Key

JTPLNLNCNOCZIB-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
Helicteres angustifolia	LOTUS Database	35616633

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
Tetrahydroxy bile acid, alcohol, or derivatives
Cholestane-skeleton
25-hydroxysteroid
22-oxosteroid
21-oxosteroid
20-hydroxysteroid
2-hydroxysteroid
3-oxosteroid
Hydroxysteroid
11-oxosteroid
16-hydroxysteroid
Oxosteroid
3-oxo-delta-5-steroid
Delta-5-steroid
Acyloin
Alpha-hydroxy ketone
Acryloyl-group
Tertiary alcohol
Alpha,beta-unsaturated ketone
Enone
Cyclic alcohol
Ketone
Secondary alcohol
Cyclic ketone
Organooxygen compound
Carbonyl group
Organic oxygen compound
Alcohol
Organic oxide
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	2.14	ChemAxon
pKa (Strongest Acidic)	12.8	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	132.13 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	137.39 m³·mol⁻¹	ChemAxon
Polarizability	54.17 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	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

163066851

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-2,8-dihydroxy-6,6,9a,11a-tetramethyl-1h,2h,3h,3ah,3bh,4h,8h,9h,9bh,11h-cyclopenta[a]phenanthrene-7,10-dione (NP0178488)

MOL for NP0178488 (1-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-2,8-dihydroxy-6,6,9a,11a-tetramethyl-1h,2h,3h,3ah,3bh,4h,8h,9h,9bh,11h-cyclopenta[a]phenanthrene-7,10-dione)

3D MOL for NP0178488 (1-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-2,8-dihydroxy-6,6,9a,11a-tetramethyl-1h,2h,3h,3ah,3bh,4h,8h,9h,9bh,11h-cyclopenta[a]phenanthrene-7,10-dione)

3D SDF for NP0178488 (1-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-2,8-dihydroxy-6,6,9a,11a-tetramethyl-1h,2h,3h,3ah,3bh,4h,8h,9h,9bh,11h-cyclopenta[a]phenanthrene-7,10-dione)

3D-SDF for NP0178488 (1-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-2,8-dihydroxy-6,6,9a,11a-tetramethyl-1h,2h,3h,3ah,3bh,4h,8h,9h,9bh,11h-cyclopenta[a]phenanthrene-7,10-dione)

PDB for NP0178488 (1-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-2,8-dihydroxy-6,6,9a,11a-tetramethyl-1h,2h,3h,3ah,3bh,4h,8h,9h,9bh,11h-cyclopenta[a]phenanthrene-7,10-dione)

3D PDB for NP0178488 (1-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-2,8-dihydroxy-6,6,9a,11a-tetramethyl-1h,2h,3h,3ah,3bh,4h,8h,9h,9bh,11h-cyclopenta[a]phenanthrene-7,10-dione)

SMILES for NP0178488 (1-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-2,8-dihydroxy-6,6,9a,11a-tetramethyl-1h,2h,3h,3ah,3bh,4h,8h,9h,9bh,11h-cyclopenta[a]phenanthrene-7,10-dione)

INCHI for NP0178488 (1-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-2,8-dihydroxy-6,6,9a,11a-tetramethyl-1h,2h,3h,3ah,3bh,4h,8h,9h,9bh,11h-cyclopenta[a]phenanthrene-7,10-dione)

Structure for NP0178488 (1-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-2,8-dihydroxy-6,6,9a,11a-tetramethyl-1h,2h,3h,3ah,3bh,4h,8h,9h,9bh,11h-cyclopenta[a]phenanthrene-7,10-dione)

3D Structure for NP0178488 (1-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-2,8-dihydroxy-6,6,9a,11a-tetramethyl-1h,2h,3h,3ah,3bh,4h,8h,9h,9bh,11h-cyclopenta[a]phenanthrene-7,10-dione)