NP-MRD: Showing NP-Card for 1-acetyl-3a,3b,7-trihydroxy-9a,11a-dimethyl-1h,2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl 3-phenylprop-2-enoate (NP0219911)

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Record Information

Version

2.0

Created at

2022-09-05 21:03:31 UTC

Updated at

2022-09-05 21:03:31 UTC

NP-MRD ID

NP0219911

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-acetyl-3a,3b,7-trihydroxy-9a,11a-dimethyl-1h,2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl 3-phenylprop-2-enoate

Description

14-Acetyl-5,10,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-16-yl 3-phenylprop-2-enoate belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. 1-acetyl-3a,3b,7-trihydroxy-9a,11a-dimethyl-1h,2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl 3-phenylprop-2-enoate is found in Asclepias tuberosa. 14-Acetyl-5,10,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-16-yl 3-phenylprop-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191516372D          

 36 40  0  0  0  0            999 V2000
    2.8728   -3.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004191516372D          

 36 40  0  0  0  0            999 V2000
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    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  2  0  0  0  0
  2  4  1  0  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  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
  9 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 27 25  1  4  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 29 34  1  0  0  0  0
 23 35  1  0  0  0  0
  4 35  1  0  0  0  0
  7 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0219911

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)C1CCC2(O)C1(C)C(CC1C3(C)CCC(O)CC3=CCC21O)OC(=O)C=CC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H38O6/c1-19(31)23-13-16-30(35)28(23,3)25(36-26(33)10-9-20-7-5-4-6-8-20)18-24-27(2)14-12-22(32)17-21(27)11-15-29(24,30)34/h4-11,22-25,32,34-35H,12-18H2,1-3H3

> <INCHI_KEY>
JSEOJMNUDFVEQJ-UHFFFAOYSA-N

> <FORMULA>
C30H38O6

> <MOLECULAR_WEIGHT>
494.628

> <EXACT_MASS>
494.266838944

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
53.09357859712122

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
14-acetyl-5,10,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-16-yl 3-phenylprop-2-enoate

> <ALOGPS_LOGP>
3.17

> <JCHEM_LOGP>
3.2996997636666667

> <ALOGPS_LOGS>
-4.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.36416778641447

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.009105493420137

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3972422311332444

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
137.6651

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.00e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-acetyl-5,10,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-16-yl 3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.257  -5.652   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.159  -1.754   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.725  -1.551   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.736  -7.323   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.729  -8.500   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.245  -8.229   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.206  -9.949   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.198 -11.126   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.675 -12.574   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.668 -13.752   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.145 -15.200   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.629 -15.471   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.636 -14.294   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.159 -12.845   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   36  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   35                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   35                                             
CONECT    8    7                                                            
CONECT    9    7   10   11   21                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   13   20   21                                             
CONECT   20   19                                                            
CONECT   21   19    9   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   35                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   29                                                       
CONECT   35   23    4    7   36                                             
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
14-Acetyl-5,10,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadec-7-en-16-yl 3-phenylprop-2-enoic acid	Generator

Chemical Formula

C₃₀H₃₈O₆

Average Mass

494.6280 Da

Monoisotopic Mass

494.26684 Da

IUPAC Name

14-acetyl-5,10,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-16-yl 3-phenylprop-2-enoate

Traditional Name

14-acetyl-5,10,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-16-yl 3-phenylprop-2-enoate

CAS Registry Number

Not Available

SMILES

CC(=O)C1CCC2(O)C1(C)C(CC1C3(C)CCC(O)CC3=CCC21O)OC(=O)C=CC1=CC=CC=C1

InChI Identifier

InChI=1S/C30H38O6/c1-19(31)23-13-16-30(35)28(23,3)25(36-26(33)10-9-20-7-5-4-6-8-20)18-24-27(2)14-12-22(32)17-21(27)11-15-29(24,30)34/h4-11,22-25,32,34-35H,12-18H2,1-3H3

InChI Key

JSEOJMNUDFVEQJ-UHFFFAOYSA-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
Asclepias tuberosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Pregnane steroids

Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives

Alternative Parents

Substituents

Progestogin-skeleton
20-oxosteroid
Steroid ester
3-hydroxy-delta-5-steroid
3-hydroxysteroid
Hydroxysteroid
14-hydroxysteroid
Oxosteroid
Delta-5-steroid
Cinnamic acid ester
Cinnamic acid or derivatives
Styrene
Monocyclic benzene moiety
Benzenoid
Tertiary alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Ketone
Polyol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Alcohol
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
logP	3.17	ALOGPS
logP	3.3	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	13.01	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	137.67 m³·mol⁻¹	ChemAxon
Polarizability	53.09 Å³	ChemAxon
Number of Rings	5	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

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

71437478

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1-acetyl-3a,3b,7-trihydroxy-9a,11a-dimethyl-1h,2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl 3-phenylprop-2-enoate (NP0219911)

MOL for NP0219911 (1-acetyl-3a,3b,7-trihydroxy-9a,11a-dimethyl-1h,2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl 3-phenylprop-2-enoate)

3D MOL for NP0219911 (1-acetyl-3a,3b,7-trihydroxy-9a,11a-dimethyl-1h,2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl 3-phenylprop-2-enoate)

3D SDF for NP0219911 (1-acetyl-3a,3b,7-trihydroxy-9a,11a-dimethyl-1h,2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl 3-phenylprop-2-enoate)

3D-SDF for NP0219911 (1-acetyl-3a,3b,7-trihydroxy-9a,11a-dimethyl-1h,2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl 3-phenylprop-2-enoate)

PDB for NP0219911 (1-acetyl-3a,3b,7-trihydroxy-9a,11a-dimethyl-1h,2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl 3-phenylprop-2-enoate)

3D PDB for NP0219911 (1-acetyl-3a,3b,7-trihydroxy-9a,11a-dimethyl-1h,2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl 3-phenylprop-2-enoate)

SMILES for NP0219911 (1-acetyl-3a,3b,7-trihydroxy-9a,11a-dimethyl-1h,2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl 3-phenylprop-2-enoate)

INCHI for NP0219911 (1-acetyl-3a,3b,7-trihydroxy-9a,11a-dimethyl-1h,2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl 3-phenylprop-2-enoate)

Structure for NP0219911 (1-acetyl-3a,3b,7-trihydroxy-9a,11a-dimethyl-1h,2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl 3-phenylprop-2-enoate)

3D Structure for NP0219911 (1-acetyl-3a,3b,7-trihydroxy-9a,11a-dimethyl-1h,2h,3h,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl 3-phenylprop-2-enoate)