NP-MRD: Showing NP-Card for (1r,2r,3as,3bs,9br,11ar)-1-[(2r,4e)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2,7,8-trihydroxy-3a,6,9b,11a-tetramethyl-1h,2h,3h,3bh,4h,5h,11h-cyclopenta[a]phenanthren-10-one (NP0238015)

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Record Information

Version

2.0

Created at

2022-09-06 21:19:36 UTC

Updated at

2022-09-06 21:19:37 UTC

NP-MRD ID

NP0238015

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,3as,3bs,9br,11ar)-1-[(2r,4e)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2,7,8-trihydroxy-3a,6,9b,11a-tetramethyl-1h,2h,3h,3bh,4h,5h,11h-cyclopenta[a]phenanthren-10-one

Description

Desacetylfevicordin A belongs to the class of organic compounds known as 11-oxosteroids. These are steroid derivatives carrying a C=O group at the 11-position of the steroid skeleton. (1r,2r,3as,3bs,9br,11ar)-1-[(2r,4e)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2,7,8-trihydroxy-3a,6,9b,11a-tetramethyl-1h,2h,3h,3bh,4h,5h,11h-cyclopenta[a]phenanthren-10-one is found in Phaleria macrocarpa. Based on a literature review very few articles have been published on Desacetylfevicordin A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062223192D          

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M  END

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M  END


  Mrv1652309062223192D          

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    4.4821   -1.1154    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9503   -1.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  6  0  0  0
 19 21  1  6  0  0  0
 19 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
 18 30  1  0  0  0  0
 13 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
  8 35  1  0  0  0  0
 12 35  1  0  0  0  0
 35 36  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0238015

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(O)C(O)=CC2=C1CC[C@H]1[C@]3(C)C[C@@H](O)[C@H]([C@@](C)(O)C(=O)\C=C\C(C)(C)O)[C@@]3(C)CC(=O)[C@@]21C

> <INCHI_IDENTIFIER>
InChI=1S/C29H40O7/c1-15-16-8-9-20-26(4)13-19(31)24(29(7,36)21(32)10-11-25(2,3)35)27(26,5)14-22(33)28(20,6)17(16)12-18(30)23(15)34/h10-12,19-20,24,30-31,34-36H,8-9,13-14H2,1-7H3/b11-10+/t19-,20+,24+,26+,27-,28+,29+/m1/s1

> <INCHI_KEY>
XDSLUVLOHDTQGH-SUBQQBBLSA-N

> <FORMULA>
C29H40O7

> <MOLECULAR_WEIGHT>
500.632

> <EXACT_MASS>
500.277403628

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
54.3930934950806

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,10S,11S,13R,14R,15R)-14-[(2R,4E)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-4,5,13-trihydroxy-1,6,11,15-tetramethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-17-one

> <JCHEM_LOGP>
3.7137512939999997

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.716435513127038

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.718359649485604

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8062198825597706

> <JCHEM_POLAR_SURFACE_AREA>
135.29000000000002

> <JCHEM_REFRACTIVITY>
138.2729

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,10S,11S,13R,14R,15R)-14-[(2R,4E)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-4,5,13-trihydroxy-1,6,11,15-tetramethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-17-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       4.288   1.357   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.811  -0.092   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.819  -1.269   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.303  -0.998   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.342  -2.717   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.349  -3.895   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.858  -2.988   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.851  -1.811   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.327  -0.363   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.320   0.815   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.836   0.544   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.359  -0.905   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.875  -1.176   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.506   0.319   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.091  -0.231   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.366  -1.095   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      14.814  -0.572   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      12.938  -2.574   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.883  -3.790   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.667  -4.735   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      15.099  -2.845   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      14.828  -5.006   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      14.248  -6.432   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      16.354  -4.795   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.299  -6.011   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      18.824  -5.800   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      20.350  -5.590   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      19.035  -7.326   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      18.614  -4.275   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      11.399  -2.624   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.070  -4.010   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.406  -3.802   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.890  -3.531   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       7.897  -4.708   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       8.367  -2.082   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.374  -3.259   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   35                                                  
CONECT    9    8    2   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   35                                                  
CONECT   13   12   14   15   30                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   30                                                  
CONECT   19   18   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26                                                            
CONECT   30   18   13   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    8   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

C₂₉H₄₀O₇

Average Mass

500.6320 Da

Monoisotopic Mass

500.27740 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1=C(O)C(O)=CC2=C1CC[C@H]1[C@]3(C)C[C@@H](O)[C@H]([C@@](C)(O)C(=O)\C=C\C(C)(C)O)[C@@]3(C)CC(=O)[C@@]21C

InChI Identifier

InChI=1S/C29H40O7/c1-15-16-8-9-20-26(4)13-19(31)24(29(7,36)21(32)10-11-25(2,3)35)27(26,5)14-22(33)28(20,6)17(16)12-18(30)23(15)34/h10-12,19-20,24,30-31,34-36H,8-9,13-14H2,1-7H3/b11-10+/t19-,20+,24+,26+,27-,28+,29+/m1/s1

InChI Key

XDSLUVLOHDTQGH-SUBQQBBLSA-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
Phaleria macrocarpa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 11-oxosteroids. These are steroid derivatives carrying a C=O group at the 11-position of the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Oxosteroids

Direct Parent

11-oxosteroids

Alternative Parents

Substituents

25-hydroxysteroid
20-hydroxysteroid
3-hydroxysteroid
2-hydroxysteroid
Hydroxysteroid
11-oxosteroid
16-alpha-hydroxysteroid
16-hydroxysteroid
14-alpha-methylsteroid
Phenanthrene
Tetralin
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Acyloin
Tertiary alcohol
Alpha,beta-unsaturated ketone
Alpha-hydroxy ketone
Acryloyl-group
Enone
Cyclic alcohol
Secondary alcohol
Ketone
Polyol
Organic oxide
Organic oxygen compound
Organooxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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

28284905

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101839558

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,3as,3bs,9br,11ar)-1-[(2r,4e)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2,7,8-trihydroxy-3a,6,9b,11a-tetramethyl-1h,2h,3h,3bh,4h,5h,11h-cyclopenta[a]phenanthren-10-one (NP0238015)

MOL for NP0238015 ((1r,2r,3as,3bs,9br,11ar)-1-[(2r,4e)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2,7,8-trihydroxy-3a,6,9b,11a-tetramethyl-1h,2h,3h,3bh,4h,5h,11h-cyclopenta[a]phenanthren-10-one)

3D MOL for NP0238015 ((1r,2r,3as,3bs,9br,11ar)-1-[(2r,4e)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2,7,8-trihydroxy-3a,6,9b,11a-tetramethyl-1h,2h,3h,3bh,4h,5h,11h-cyclopenta[a]phenanthren-10-one)

3D SDF for NP0238015 ((1r,2r,3as,3bs,9br,11ar)-1-[(2r,4e)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2,7,8-trihydroxy-3a,6,9b,11a-tetramethyl-1h,2h,3h,3bh,4h,5h,11h-cyclopenta[a]phenanthren-10-one)

3D-SDF for NP0238015 ((1r,2r,3as,3bs,9br,11ar)-1-[(2r,4e)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2,7,8-trihydroxy-3a,6,9b,11a-tetramethyl-1h,2h,3h,3bh,4h,5h,11h-cyclopenta[a]phenanthren-10-one)

PDB for NP0238015 ((1r,2r,3as,3bs,9br,11ar)-1-[(2r,4e)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2,7,8-trihydroxy-3a,6,9b,11a-tetramethyl-1h,2h,3h,3bh,4h,5h,11h-cyclopenta[a]phenanthren-10-one)

3D PDB for NP0238015 ((1r,2r,3as,3bs,9br,11ar)-1-[(2r,4e)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2,7,8-trihydroxy-3a,6,9b,11a-tetramethyl-1h,2h,3h,3bh,4h,5h,11h-cyclopenta[a]phenanthren-10-one)

SMILES for NP0238015 ((1r,2r,3as,3bs,9br,11ar)-1-[(2r,4e)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2,7,8-trihydroxy-3a,6,9b,11a-tetramethyl-1h,2h,3h,3bh,4h,5h,11h-cyclopenta[a]phenanthren-10-one)

INCHI for NP0238015 ((1r,2r,3as,3bs,9br,11ar)-1-[(2r,4e)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2,7,8-trihydroxy-3a,6,9b,11a-tetramethyl-1h,2h,3h,3bh,4h,5h,11h-cyclopenta[a]phenanthren-10-one)

Structure for NP0238015 ((1r,2r,3as,3bs,9br,11ar)-1-[(2r,4e)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2,7,8-trihydroxy-3a,6,9b,11a-tetramethyl-1h,2h,3h,3bh,4h,5h,11h-cyclopenta[a]phenanthren-10-one)

3D Structure for NP0238015 ((1r,2r,3as,3bs,9br,11ar)-1-[(2r,4e)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2,7,8-trihydroxy-3a,6,9b,11a-tetramethyl-1h,2h,3h,3bh,4h,5h,11h-cyclopenta[a]phenanthren-10-one)