NP-MRD: Showing NP-Card for (2z,6r)-6-[(3as,5ar,7r,9ar,9br)-7-hydroxy-3a,6,6,9a,11-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid (NP0197638)

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Record Information

Version

2.0

Created at

2022-09-04 15:56:29 UTC

Updated at

2022-09-04 15:56:29 UTC

NP-MRD ID

NP0197638

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2z,6r)-6-[(3as,5ar,7r,9ar,9br)-7-hydroxy-3a,6,6,9a,11-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid

Description

Ananosic acid A, also known as ananosate a, belongs to the class of organic compounds known as steroid acids. Steroid acids are compounds containing a carboxyl group attached to a steroid backbone. (2z,6r)-6-[(3as,5ar,7r,9ar,9br)-7-hydroxy-3a,6,6,9a,11-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid is found in Kadsura coccinea. (2z,6r)-6-[(3as,5ar,7r,9ar,9br)-7-hydroxy-3a,6,6,9a,11-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid was first documented in 2001 (PMID: 11738422). Based on a literature review very few articles have been published on Ananosic acid A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042217562D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309042217562D          

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  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 13 25  1  0  0  0  0
 17 25  1  0  0  0  0
 25 26  1  1  0  0  0
 14 27  1  0  0  0  0
  9 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
  8 30  1  0  0  0  0
  2 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0197638

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CC\C=C(\C)C(O)=O)C1=C2C(C)C[C@H]3C(=CC[C@H]4C(C)(C)[C@H](O)CC[C@]34C)[C@]2(C)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O3/c1-18(9-8-10-19(2)27(32)33)21-13-15-30(7)22-11-12-24-28(4,5)25(31)14-16-29(24,6)23(22)17-20(3)26(21)30/h10-11,18,20,23-25,31H,8-9,12-17H2,1-7H3,(H,32,33)/b19-10-/t18-,20?,23+,24+,25-,29-,30+/m1/s1

> <INCHI_KEY>
KNYVORLBUHFUJF-JTZQQAANSA-N

> <FORMULA>
C30H46O3

> <MOLECULAR_WEIGHT>
454.695

> <EXACT_MASS>
454.344695341

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
54.65542200986005

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z,6R)-6-[(1R,2R,5R,7R,11S)-5-hydroxy-2,6,6,11,16-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-9,14-dien-14-yl]-2-methylhept-2-enoic acid

> <JCHEM_LOGP>
6.479757614999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.55417898220883

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.596548598263199

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8068038288546248

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
137.18540000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2Z,6R)-6-[(1R,2R,5R,7R,11S)-5-hydroxy-2,6,6,11,16-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-9,14-dien-14-yl]-2-methylhept-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       4.633 -12.574   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.053 -11.147   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.998  -9.932   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.417  -8.505   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.736  -7.323   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.323  -0.719   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.185  -1.391   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.159  -1.754   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.527 -10.937   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.582 -12.153   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       1.947  -9.510   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   30                                                  
CONECT    9    8   10   27                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   25                                                  
CONECT   14   13   15   27                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   25                                                  
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   13   17   26                                             
CONECT   26   25                                                            
CONECT   27   14    9   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29    8                                                       
CONECT   31    2   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
Ananosate a	Generator

Chemical Formula

C₃₀H₄₆O₃

Average Mass

454.6950 Da

Monoisotopic Mass

454.34470 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@H](CC\C=C(\C)C(O)=O)C1=C2C(C)C[C@H]3C(=CC[C@H]4C(C)(C)[C@H](O)CC[C@]34C)[C@]2(C)CC1

InChI Identifier

InChI=1S/C30H46O3/c1-18(9-8-10-19(2)27(32)33)21-13-15-30(7)22-11-12-24-28(4,5)25(31)14-16-29(24,6)23(22)17-20(3)26(21)30/h10-11,18,20,23-25,31H,8-9,12-17H2,1-7H3,(H,32,33)/b19-10-/t18-,20?,23+,24+,25-,29-,30+/m1/s1

InChI Key

KNYVORLBUHFUJF-JTZQQAANSA-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
Kadsura coccinea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroid acids. Steroid acids are compounds containing a carboxyl group attached to a steroid backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid acids

Direct Parent

Steroid acids

Alternative Parents

Substituents

Steroid acid
3-hydroxy-delta-7-steroid
3-hydroxysteroid
14-alpha-methylsteroid
3-alpha-hydroxysteroid
Hydroxysteroid
Delta-7-steroid
Medium-chain fatty acid
Branched fatty acid
Methyl-branched fatty acid
Hydroxy fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Cyclic alcohol
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Alcohol
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

C00036722

Chemspider ID

23327063

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44559523

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chen YG, Xie YY, Cheng KF, Cheung KK, Qin GW: Compounds from Kadsura ananosma. Phytochemistry. 2001 Dec;58(8):1277-80. doi: 10.1016/s0031-9422(01)00319-3. [PubMed:11738422 ]
LOTUS database [Link]

Showing NP-Card for (2z,6r)-6-[(3as,5ar,7r,9ar,9br)-7-hydroxy-3a,6,6,9a,11-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid (NP0197638)

MOL for NP0197638 ((2z,6r)-6-[(3as,5ar,7r,9ar,9br)-7-hydroxy-3a,6,6,9a,11-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid)

3D MOL for NP0197638 ((2z,6r)-6-[(3as,5ar,7r,9ar,9br)-7-hydroxy-3a,6,6,9a,11-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid)

3D SDF for NP0197638 ((2z,6r)-6-[(3as,5ar,7r,9ar,9br)-7-hydroxy-3a,6,6,9a,11-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid)

3D-SDF for NP0197638 ((2z,6r)-6-[(3as,5ar,7r,9ar,9br)-7-hydroxy-3a,6,6,9a,11-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid)

PDB for NP0197638 ((2z,6r)-6-[(3as,5ar,7r,9ar,9br)-7-hydroxy-3a,6,6,9a,11-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid)

3D PDB for NP0197638 ((2z,6r)-6-[(3as,5ar,7r,9ar,9br)-7-hydroxy-3a,6,6,9a,11-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid)

SMILES for NP0197638 ((2z,6r)-6-[(3as,5ar,7r,9ar,9br)-7-hydroxy-3a,6,6,9a,11-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid)

INCHI for NP0197638 ((2z,6r)-6-[(3as,5ar,7r,9ar,9br)-7-hydroxy-3a,6,6,9a,11-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid)

Structure for NP0197638 ((2z,6r)-6-[(3as,5ar,7r,9ar,9br)-7-hydroxy-3a,6,6,9a,11-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid)

3D Structure for NP0197638 ((2z,6r)-6-[(3as,5ar,7r,9ar,9br)-7-hydroxy-3a,6,6,9a,11-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid)