NP-MRD: Showing NP-Card for (6r)-6-[(1s,3as,5ar,7r,9ar,9bs)-7-hydroxy-1,3a,6,6,9a-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthren-1-yl]-2-methylidene-4-oxoheptanoic acid (NP0290388)

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Record Information

Version

2.0

Created at

2022-09-09 21:03:05 UTC

Updated at

2022-09-09 21:03:06 UTC

NP-MRD ID

NP0290388

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6r)-6-[(1s,3as,5ar,7r,9ar,9bs)-7-hydroxy-1,3a,6,6,9a-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthren-1-yl]-2-methylidene-4-oxoheptanoic acid

Description

Abiesatrine C belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton. Based on a literature review very few articles have been published on Abiesatrine C.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092223032D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309092223032D          

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 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 18 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 15  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 13 31  1  0  0  0  0
  9 31  1  0  0  0  0
  2 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0290388

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CC(=O)CC(=C)C(O)=O)[C@]1(C)CC[C@]2(C)C1=CC[C@@H]1C2=CC[C@H]2C(C)(C)[C@H](O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O4/c1-18(26(33)34)16-20(31)17-19(2)28(5)14-15-30(7)22-8-10-23-27(3,4)25(32)12-13-29(23,6)21(22)9-11-24(28)30/h8,11,19,21,23,25,32H,1,9-10,12-17H2,2-7H3,(H,33,34)/t19-,21-,23+,25-,28+,29-,30+/m1/s1

> <INCHI_KEY>
MFSMECUSKAWISS-ZQBDBAJISA-N

> <FORMULA>
C30H44O4

> <MOLECULAR_WEIGHT>
468.678

> <EXACT_MASS>
468.323959897

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
54.132145161074654

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6R)-6-[(1S,2R,5R,7R,11S,14S)-5-hydroxy-2,6,6,11,14-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-9,15-dien-14-yl]-2-methylidene-4-oxoheptanoic acid

> <JCHEM_LOGP>
5.415159408333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.777681877312396

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.526178292585159

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8068040735863565

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
136.9474

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(6R)-6-[(1S,2R,5R,7R,11S,14S)-5-hydroxy-2,6,6,11,14-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-9,15-dien-14-yl]-2-methylidene-4-oxoheptanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      13.148  -3.340   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.148  -4.880   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.814  -5.650   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.480  -4.880   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      10.480  -3.340   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       9.147  -5.650   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.813  -4.880   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.813  -3.340   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.479  -5.650   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.853  -4.244   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.384  -6.896   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.479  -8.142   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.015  -7.666   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.176  -9.198   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.681  -8.436   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.681  -9.976   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.347 -10.746   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.013  -9.976   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.320 -10.746   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.670 -11.926   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.310 -11.926   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.654  -9.976   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.988 -10.746   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.654  -8.436   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.320  -7.666   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.013  -8.436   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.013  -6.896   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.347  -7.666   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.347  -6.126   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.681  -5.356   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.015  -6.126   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.481  -5.650   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      15.815  -4.880   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      14.481  -7.190   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   32                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11   31                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   31                                             
CONECT   14   13                                                            
CONECT   15   13   16   28                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   26                                                  
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   18   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   15   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   13    9                                                  
CONECT   32    2   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₄O₄

Average Mass

468.6780 Da

Monoisotopic Mass

468.32396 Da

IUPAC Name

(6R)-6-[(1S,2R,5R,7R,11S,14S)-5-hydroxy-2,6,6,11,14-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-9,15-dien-14-yl]-2-methylidene-4-oxoheptanoic acid

Traditional Name

(6R)-6-[(1S,2R,5R,7R,11S,14S)-5-hydroxy-2,6,6,11,14-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-9,15-dien-14-yl]-2-methylidene-4-oxoheptanoic acid

CAS Registry Number

Not Available

SMILES

C[C@H](CC(=O)CC(=C)C(O)=O)[C@]1(C)CC[C@]2(C)C1=CC[C@@H]1C2=CC[C@H]2C(C)(C)[C@H](O)CC[C@]12C

InChI Identifier

InChI=1S/C30H44O4/c1-18(26(33)34)16-20(31)17-19(2)28(5)14-15-30(7)22-8-10-23-27(3,4)25(32)12-13-29(23,6)21(22)9-11-24(28)30/h8,11,19,21,23,25,32H,1,9-10,12-17H2,2-7H3,(H,33,34)/t19-,21-,23+,25-,28+,29-,30+/m1/s1

InChI Key

MFSMECUSKAWISS-ZQBDBAJISA-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 oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Oxosteroids

Direct Parent

Oxosteroids

Alternative Parents

Substituents

23-oxosteroid
3-hydroxy-delta-7-steroid
3-hydroxysteroid
14-alpha-methylsteroid
Hydroxysteroid
3-alpha-hydroxysteroid
Oxosteroid
Delta-7-steroid
Medium-chain keto acid
Gamma-keto acid
Branched fatty acid
Methyl-branched fatty acid
Hydroxy fatty acid
Fatty acyl
Unsaturated fatty acid
Keto acid
Cyclic alcohol
Secondary alcohol
Ketone
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organic oxide
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	5.42	ChemAxon
pKa (Strongest Acidic)	4.53	ChemAxon
pKa (Strongest Basic)	-0.81	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	136.95 m³·mol⁻¹	ChemAxon
Polarizability	54.13 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	Yes	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

46243631

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (6r)-6-[(1s,3as,5ar,7r,9ar,9bs)-7-hydroxy-1,3a,6,6,9a-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthren-1-yl]-2-methylidene-4-oxoheptanoic acid (NP0290388)

MOL for NP0290388 ((6r)-6-[(1s,3as,5ar,7r,9ar,9bs)-7-hydroxy-1,3a,6,6,9a-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthren-1-yl]-2-methylidene-4-oxoheptanoic acid)

3D MOL for NP0290388 ((6r)-6-[(1s,3as,5ar,7r,9ar,9bs)-7-hydroxy-1,3a,6,6,9a-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthren-1-yl]-2-methylidene-4-oxoheptanoic acid)

3D SDF for NP0290388 ((6r)-6-[(1s,3as,5ar,7r,9ar,9bs)-7-hydroxy-1,3a,6,6,9a-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthren-1-yl]-2-methylidene-4-oxoheptanoic acid)

3D-SDF for NP0290388 ((6r)-6-[(1s,3as,5ar,7r,9ar,9bs)-7-hydroxy-1,3a,6,6,9a-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthren-1-yl]-2-methylidene-4-oxoheptanoic acid)

PDB for NP0290388 ((6r)-6-[(1s,3as,5ar,7r,9ar,9bs)-7-hydroxy-1,3a,6,6,9a-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthren-1-yl]-2-methylidene-4-oxoheptanoic acid)

3D PDB for NP0290388 ((6r)-6-[(1s,3as,5ar,7r,9ar,9bs)-7-hydroxy-1,3a,6,6,9a-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthren-1-yl]-2-methylidene-4-oxoheptanoic acid)

SMILES for NP0290388 ((6r)-6-[(1s,3as,5ar,7r,9ar,9bs)-7-hydroxy-1,3a,6,6,9a-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthren-1-yl]-2-methylidene-4-oxoheptanoic acid)

INCHI for NP0290388 ((6r)-6-[(1s,3as,5ar,7r,9ar,9bs)-7-hydroxy-1,3a,6,6,9a-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthren-1-yl]-2-methylidene-4-oxoheptanoic acid)

Structure for NP0290388 ((6r)-6-[(1s,3as,5ar,7r,9ar,9bs)-7-hydroxy-1,3a,6,6,9a-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthren-1-yl]-2-methylidene-4-oxoheptanoic acid)

3D Structure for NP0290388 ((6r)-6-[(1s,3as,5ar,7r,9ar,9bs)-7-hydroxy-1,3a,6,6,9a-pentamethyl-2h,3h,5h,5ah,7h,8h,9h,9bh,10h-cyclopenta[a]phenanthren-1-yl]-2-methylidene-4-oxoheptanoic acid)