NP-MRD: Showing NP-Card for (1s,3as,5as,6s,9ar,9bs,11as)-1-[(2r,3s)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-6-(hydroxymethyl)-3a,6,9a,11a-tetramethyl-1h,2h,3h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-one (NP0251598)

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Record Information

Version

2.0

Created at

2022-09-07 14:49:53 UTC

Updated at

2022-09-07 14:49:53 UTC

NP-MRD ID

NP0251598

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3as,5as,6s,9ar,9bs,11as)-1-[(2r,3s)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-6-(hydroxymethyl)-3a,6,9a,11a-tetramethyl-1h,2h,3h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-one

Description

(1S,2R,6S,7S,11S,14S,15S)-14-[(2R,3S)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-6-(hydroxymethyl)-2,6,11,15-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-9-en-5-one belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Based on a literature review very few articles have been published on (1S,2R,6S,7S,11S,14S,15S)-14-[(2R,3S)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-6-(hydroxymethyl)-2,6,11,15-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-9-en-5-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072216492D          

 34 37  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv1652309072216492D          

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    5.5171   -2.2259    0.0000 C   0  0  2  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
    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  1  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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 11  9  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  1  0  0  0
 22 23  1  0  0  0  0
 20 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
 27 28  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 16  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 11 33  1  0  0  0  0
 14 33  1  0  0  0  0
 33 34  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0251598

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O4/c1-18(2)16-23(32)26(34)19(3)20-10-14-30(7)22-8-9-24-27(4,21(22)11-15-29(20,30)6)13-12-25(33)28(24,5)17-31/h8,16,19-21,24,26,31,34H,9-15,17H2,1-7H3/t19-,20+,21-,24+,26+,27-,28-,29+,30-/m1/s1

> <INCHI_KEY>
IHPHSDWTJJCKOC-PUCSHBLLSA-N

> <FORMULA>
C30H46O4

> <MOLECULAR_WEIGHT>
470.694

> <EXACT_MASS>
470.339609961

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
55.4322129358875

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,6S,7S,11S,14S,15S)-14-[(2R,3S)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-6-(hydroxymethyl)-2,6,11,15-tetramethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-one

> <JCHEM_LOGP>
5.4205021250000005

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.961430207540438

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.159731640722065

> <JCHEM_PKA_STRONGEST_BASIC>
-2.818717156650714

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
137.79699999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,6S,7S,11S,14S,15S)-14-[(2R,3S)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-6-(hydroxymethyl)-2,6,11,15-tetramethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-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       1.151  -4.015   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.786  -6.657   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.312  -6.868   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.892  -8.295   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.676  -4.226   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       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.159  -1.754   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.323  -0.719   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.185  -1.391   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      15.182   0.149   0.000  0.00  0.00           O+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  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.595  -6.083   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    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   33                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   33                                             
CONECT   15   14                                                            
CONECT   16   14   17   30                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   28                                                  
CONECT   20   19   21   22   24                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22                                                            
CONECT   24   20   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   19   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   16   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   11   14   34                                             
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₆O₄

Average Mass

470.6940 Da

Monoisotopic Mass

470.33961 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C30H46O4/c1-18(2)16-23(32)26(34)19(3)20-10-14-30(7)22-8-9-24-27(4,21(22)11-15-29(20,30)6)13-12-25(33)28(24,5)17-31/h8,16,19-21,24,26,31,34H,9-15,17H2,1-7H3/t19-,20+,21-,24+,26+,27-,28-,29+,30-/m1/s1

InChI Key

IHPHSDWTJJCKOC-PUCSHBLLSA-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 triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Cholesterol-skeleton
Cholestane-skeleton
Hydroxy bile acid, alcohol, or derivatives
Monohydroxy bile acid, alcohol, or derivatives
23-oxosteroid
Bile acid, alcohol, or derivatives
22-hydroxysteroid
3-oxo-delta-7-steroid
3-oxosteroid
3-oxo-5-beta-steroid
Hydroxysteroid
Oxosteroid
Delta-7-steroid
Steroid
Acyloin
Enone
Alpha,beta-unsaturated ketone
Alpha-hydroxy ketone
Acryloyl-group
Ketone
Secondary alcohol
Cyclic ketone
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Primary alcohol
Organooxygen 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

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

162928769

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3as,5as,6s,9ar,9bs,11as)-1-[(2r,3s)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-6-(hydroxymethyl)-3a,6,9a,11a-tetramethyl-1h,2h,3h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-one (NP0251598)

MOL for NP0251598 ((1s,3as,5as,6s,9ar,9bs,11as)-1-[(2r,3s)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-6-(hydroxymethyl)-3a,6,9a,11a-tetramethyl-1h,2h,3h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-one)

3D MOL for NP0251598 ((1s,3as,5as,6s,9ar,9bs,11as)-1-[(2r,3s)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-6-(hydroxymethyl)-3a,6,9a,11a-tetramethyl-1h,2h,3h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-one)

3D SDF for NP0251598 ((1s,3as,5as,6s,9ar,9bs,11as)-1-[(2r,3s)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-6-(hydroxymethyl)-3a,6,9a,11a-tetramethyl-1h,2h,3h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-one)

3D-SDF for NP0251598 ((1s,3as,5as,6s,9ar,9bs,11as)-1-[(2r,3s)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-6-(hydroxymethyl)-3a,6,9a,11a-tetramethyl-1h,2h,3h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-one)

PDB for NP0251598 ((1s,3as,5as,6s,9ar,9bs,11as)-1-[(2r,3s)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-6-(hydroxymethyl)-3a,6,9a,11a-tetramethyl-1h,2h,3h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-one)

3D PDB for NP0251598 ((1s,3as,5as,6s,9ar,9bs,11as)-1-[(2r,3s)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-6-(hydroxymethyl)-3a,6,9a,11a-tetramethyl-1h,2h,3h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-one)

SMILES for NP0251598 ((1s,3as,5as,6s,9ar,9bs,11as)-1-[(2r,3s)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-6-(hydroxymethyl)-3a,6,9a,11a-tetramethyl-1h,2h,3h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-one)

INCHI for NP0251598 ((1s,3as,5as,6s,9ar,9bs,11as)-1-[(2r,3s)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-6-(hydroxymethyl)-3a,6,9a,11a-tetramethyl-1h,2h,3h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-one)

Structure for NP0251598 ((1s,3as,5as,6s,9ar,9bs,11as)-1-[(2r,3s)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-6-(hydroxymethyl)-3a,6,9a,11a-tetramethyl-1h,2h,3h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-one)

3D Structure for NP0251598 ((1s,3as,5as,6s,9ar,9bs,11as)-1-[(2r,3s)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-6-(hydroxymethyl)-3a,6,9a,11a-tetramethyl-1h,2h,3h,5h,5ah,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-one)