NP-MRD: Showing NP-Card for (1r,2r,4ar,4bs,6as,7s,9r,10r,10as,12ar)-2-acetyl-1-(carboxymethyl)-7,10-dihydroxy-1,4a,4b,9,10-pentamethyl-3,4,5,6,7,8,9,10a,12,12a-decahydro-2h-chrysene-6a-carboxylic acid (NP0292554)

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Record Information

Version

2.0

Created at

2022-09-10 00:08:04 UTC

Updated at

2022-09-10 00:08:04 UTC

NP-MRD ID

NP0292554

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,4ar,4bs,6as,7s,9r,10r,10as,12ar)-2-acetyl-1-(carboxymethyl)-7,10-dihydroxy-1,4a,4b,9,10-pentamethyl-3,4,5,6,7,8,9,10a,12,12a-decahydro-2h-chrysene-6a-carboxylic acid

Description

4-Oxo-19alpha,22alpha-dihydroxy-3,24-dinor-2,4-secours-12-ene-2,28-dioic acid belongs to the class of organic compounds known as 3-carboxy steroids. These are steroid compounds that carry a carboxyl group at the C3-atom of the steroid backbone. Based on a literature review very few articles have been published on 4-Oxo-19alpha,22alpha-dihydroxy-3,24-dinor-2,4-secours-12-ene-2,28-dioic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102202082D          

 35 38  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309102202082D          

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  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 12 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  1  1  0  0  0
 14 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 13 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  1  0  0  0
  9 30  1  0  0  0  0
  4 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0292554

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@H](O)[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@](C)(CC(O)=O)[C@@H](CC[C@@]34C)C(C)=O)[C@@H]2[C@]1(C)O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H42O7/c1-15-13-20(30)28(23(33)34)12-11-25(4)18(22(28)27(15,6)35)7-8-19-24(3,14-21(31)32)17(16(2)29)9-10-26(19,25)5/h7,15,17,19-20,22,30,35H,8-14H2,1-6H3,(H,31,32)(H,33,34)/t15-,17+,19-,20+,22-,24+,25-,26-,27-,28-/m1/s1

> <INCHI_KEY>
ODUGZVUJDQKEQS-NOHCGYPKSA-N

> <FORMULA>
C28H42O7

> <MOLECULAR_WEIGHT>
490.637

> <EXACT_MASS>
490.293053692

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
53.36779489648222

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,4aR,4bS,6aS,7S,9R,10R,10aS,12aR)-2-acetyl-1-(carboxymethyl)-7,10-dihydroxy-1,4a,4b,9,10-pentamethyl-1,2,3,4,4a,4b,5,6,6a,7,8,9,10,10a,12,12a-hexadecahydrochrysene-6a-carboxylic acid

> <JCHEM_LOGP>
2.7217521106666656

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.78707165775352

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.167107593734035

> <JCHEM_PKA_STRONGEST_BASIC>
-3.040326697672599

> <JCHEM_POLAR_SURFACE_AREA>
132.13

> <JCHEM_REFRACTIVITY>
130.38840000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4aR,4bS,6aS,7S,9R,10R,10aS,12aR)-2-acetyl-1-(carboxymethyl)-7,10-dihydroxy-1,4a,4b,9,10-pentamethyl-3,4,5,6,7,8,9,10a,12,12a-decahydro-2H-chrysene-6a-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.529  -8.197   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.024  -6.742   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -4.033  -5.578   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.512  -6.451   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.008  -4.996   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.504  -4.705   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.512  -5.869   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.016  -4.414   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.008  -7.324   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.016  -8.488   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.529  -8.197   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.033  -6.742   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.545  -6.451   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.049  -4.996   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.553  -3.541   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.545  -2.377   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       8.065  -3.250   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.041  -3.832   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.529  -4.123   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.024  -5.578   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.893  -4.044   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.561  -4.705   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.824  -3.824   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.569  -5.869   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.065  -7.324   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.073  -8.488   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.553  -7.615   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.791  -9.137   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.425  -8.663   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -0.504  -7.615   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.266  -9.137   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.632  -8.663   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.289 -10.165   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.183 -10.618   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -2.417 -11.213   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   30                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   20                                             
CONECT    8    7                                                            
CONECT    9    7   10   30                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14   27                                                  
CONECT   14   13   15   18   22                                             
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   14   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   12    7   21                                             
CONECT   21   20                                                            
CONECT   22   14   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   13   28   29                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30    9    4   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
4-oxo-19a,22a-Dihydroxy-3,24-dinor-2,4-secours-12-ene-2,28-dioate	Generator
4-oxo-19a,22a-Dihydroxy-3,24-dinor-2,4-secours-12-ene-2,28-dioic acid	Generator
4-oxo-19alpha,22alpha-Dihydroxy-3,24-dinor-2,4-secours-12-ene-2,28-dioate	Generator
4-oxo-19Α,22α-dihydroxy-3,24-dinor-2,4-secours-12-ene-2,28-dioate	Generator
4-oxo-19Α,22α-dihydroxy-3,24-dinor-2,4-secours-12-ene-2,28-dioic acid	Generator

Chemical Formula

C₂₈H₄₂O₇

Average Mass

490.6370 Da

Monoisotopic Mass

490.29305 Da

IUPAC Name

(1R,2R,4aR,4bS,6aS,7S,9R,10R,10aS,12aR)-2-acetyl-1-(carboxymethyl)-7,10-dihydroxy-1,4a,4b,9,10-pentamethyl-1,2,3,4,4a,4b,5,6,6a,7,8,9,10,10a,12,12a-hexadecahydrochrysene-6a-carboxylic acid

Traditional Name

(1R,2R,4aR,4bS,6aS,7S,9R,10R,10aS,12aR)-2-acetyl-1-(carboxymethyl)-7,10-dihydroxy-1,4a,4b,9,10-pentamethyl-3,4,5,6,7,8,9,10a,12,12a-decahydro-2H-chrysene-6a-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@H](O)[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@](C)(CC(O)=O)[C@@H](CC[C@@]34C)C(C)=O)[C@@H]2[C@]1(C)O)C(O)=O

InChI Identifier

InChI=1S/C28H42O7/c1-15-13-20(30)28(23(33)34)12-11-25(4)18(22(28)27(15,6)35)7-8-19-24(3,14-21(31)32)17(16(2)29)9-10-26(19,25)5/h7,15,17,19-20,22,30,35H,8-14H2,1-6H3,(H,31,32)(H,33,34)/t15-,17+,19-,20+,22-,24+,25-,26-,27-,28-/m1/s1

InChI Key

ODUGZVUJDQKEQS-NOHCGYPKSA-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 3-carboxy steroids. These are steroid compounds that carry a carboxyl group at the C3-atom of the steroid backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid acids

Direct Parent

3-carboxy steroids

Alternative Parents

Substituents

3-carboxy steroid
Diterpenoid
16-hydroxysteroid
Oxosteroid
17-oxosteroid
16-oxosteroid
Hydroxysteroid
Beta-hydroxy acid
Dicarboxylic acid or derivatives
Hydroxy acid
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Ketone
Carboxylic acid
Carboxylic acid derivative
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
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
logP	2.72	ChemAxon
pKa (Strongest Acidic)	4.17	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	132.13 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	130.39 m³·mol⁻¹	ChemAxon
Polarizability	53.37 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	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

9744194

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11569424

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,4ar,4bs,6as,7s,9r,10r,10as,12ar)-2-acetyl-1-(carboxymethyl)-7,10-dihydroxy-1,4a,4b,9,10-pentamethyl-3,4,5,6,7,8,9,10a,12,12a-decahydro-2h-chrysene-6a-carboxylic acid (NP0292554)

MOL for NP0292554 ((1r,2r,4ar,4bs,6as,7s,9r,10r,10as,12ar)-2-acetyl-1-(carboxymethyl)-7,10-dihydroxy-1,4a,4b,9,10-pentamethyl-3,4,5,6,7,8,9,10a,12,12a-decahydro-2h-chrysene-6a-carboxylic acid)

3D MOL for NP0292554 ((1r,2r,4ar,4bs,6as,7s,9r,10r,10as,12ar)-2-acetyl-1-(carboxymethyl)-7,10-dihydroxy-1,4a,4b,9,10-pentamethyl-3,4,5,6,7,8,9,10a,12,12a-decahydro-2h-chrysene-6a-carboxylic acid)

3D SDF for NP0292554 ((1r,2r,4ar,4bs,6as,7s,9r,10r,10as,12ar)-2-acetyl-1-(carboxymethyl)-7,10-dihydroxy-1,4a,4b,9,10-pentamethyl-3,4,5,6,7,8,9,10a,12,12a-decahydro-2h-chrysene-6a-carboxylic acid)

3D-SDF for NP0292554 ((1r,2r,4ar,4bs,6as,7s,9r,10r,10as,12ar)-2-acetyl-1-(carboxymethyl)-7,10-dihydroxy-1,4a,4b,9,10-pentamethyl-3,4,5,6,7,8,9,10a,12,12a-decahydro-2h-chrysene-6a-carboxylic acid)

PDB for NP0292554 ((1r,2r,4ar,4bs,6as,7s,9r,10r,10as,12ar)-2-acetyl-1-(carboxymethyl)-7,10-dihydroxy-1,4a,4b,9,10-pentamethyl-3,4,5,6,7,8,9,10a,12,12a-decahydro-2h-chrysene-6a-carboxylic acid)

3D PDB for NP0292554 ((1r,2r,4ar,4bs,6as,7s,9r,10r,10as,12ar)-2-acetyl-1-(carboxymethyl)-7,10-dihydroxy-1,4a,4b,9,10-pentamethyl-3,4,5,6,7,8,9,10a,12,12a-decahydro-2h-chrysene-6a-carboxylic acid)

SMILES for NP0292554 ((1r,2r,4ar,4bs,6as,7s,9r,10r,10as,12ar)-2-acetyl-1-(carboxymethyl)-7,10-dihydroxy-1,4a,4b,9,10-pentamethyl-3,4,5,6,7,8,9,10a,12,12a-decahydro-2h-chrysene-6a-carboxylic acid)

INCHI for NP0292554 ((1r,2r,4ar,4bs,6as,7s,9r,10r,10as,12ar)-2-acetyl-1-(carboxymethyl)-7,10-dihydroxy-1,4a,4b,9,10-pentamethyl-3,4,5,6,7,8,9,10a,12,12a-decahydro-2h-chrysene-6a-carboxylic acid)

Structure for NP0292554 ((1r,2r,4ar,4bs,6as,7s,9r,10r,10as,12ar)-2-acetyl-1-(carboxymethyl)-7,10-dihydroxy-1,4a,4b,9,10-pentamethyl-3,4,5,6,7,8,9,10a,12,12a-decahydro-2h-chrysene-6a-carboxylic acid)

3D Structure for NP0292554 ((1r,2r,4ar,4bs,6as,7s,9r,10r,10as,12ar)-2-acetyl-1-(carboxymethyl)-7,10-dihydroxy-1,4a,4b,9,10-pentamethyl-3,4,5,6,7,8,9,10a,12,12a-decahydro-2h-chrysene-6a-carboxylic acid)