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 3,4-dimethylpent-2-enoate (NP0231290)

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Record Information

Version

2.0

Created at

2022-09-06 12:05:00 UTC

Updated at

2022-09-06 12:05:01 UTC

NP-MRD ID

NP0231290

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 3,4-dimethylpent-2-enoate

Description

CTK8I0026 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 3,4-dimethylpent-2-enoate is found in Cynanchum caudatum. CTK8I0026 is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004151519152D          

 34 37  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004151519152D          

 34 37  0  0  0  0            999 V2000
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 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 11 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 28 32  1  0  0  0  0
  9 32  1  0  0  0  0
 24 32  1  0  0  0  0
 32 33  1  0  0  0  0
  4 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0231290

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(C)=CC(=O)OC1CC2C3(C)CCC(O)CC3=CCC2(O)C2(O)CCC(C(C)=O)C12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H42O6/c1-16(2)17(3)13-24(31)34-23-15-22-25(5)10-8-20(30)14-19(25)7-11-27(22,32)28(33)12-9-21(18(4)29)26(23,28)6/h7,13,16,20-23,30,32-33H,8-12,14-15H2,1-6H3

> <INCHI_KEY>
SZUXICHIYZJLOY-UHFFFAOYSA-N

> <FORMULA>
C28H42O6

> <MOLECULAR_WEIGHT>
474.638

> <EXACT_MASS>
474.298139072

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
52.66161543865155

> <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 3,4-dimethylpent-2-enoate

> <ALOGPS_LOGP>
2.98

> <JCHEM_LOGP>
3.058144824

> <ALOGPS_LOGS>
-4.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.364167684692

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.009105466319102

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3972422070345134

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
131.00169999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.91e-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 3,4-dimethylpent-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0       9.276  -1.849   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.752  -0.400   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.745   0.777   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.237  -0.129   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.244  -1.307   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.728  -1.036   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.205   0.413   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       3.735  -2.213   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.258  -3.661   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.774  -3.932   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.297  -5.381   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.813  -5.652   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.290  -4.203   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.806  -4.474   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.322  -4.746   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.845  -6.194   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      12.361  -6.465   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       9.853  -7.371   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.337  -7.100   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.344  -8.277   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.828  -8.006   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.305  -6.558   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.312  -7.735   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.789  -6.287   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.678  -7.823   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.573  -7.232   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.298  -6.368   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.726  -4.889   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.781  -3.673   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.362  -2.246   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -0.744  -3.883   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.266  -4.839   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.594  -3.453   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.713   1.319   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   34                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   32                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   22                                                  
CONECT   12   11   13   14   19                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   12   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   11   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   25   26   32                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   32                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   28    9   24   33                                             
CONECT   33   32                                                            
CONECT   34    4                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
14-Acetyl-5,10,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-16-yl 3,4-dimethylpent-2-enoic acid	Generator
14-Acetyl-5,10,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0,.0,]heptadec-7-en-16-yl 3,4-dimethylpent-2-enoic acid	Generator

Chemical Formula

C₂₈H₄₂O₆

Average Mass

474.6380 Da

Monoisotopic Mass

474.29814 Da

IUPAC Name

14-acetyl-5,10,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-16-yl 3,4-dimethylpent-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 3,4-dimethylpent-2-enoate

CAS Registry Number

Not Available

SMILES

CC(C)C(C)=CC(=O)OC1CC2C3(C)CCC(O)CC3=CCC2(O)C2(O)CCC(C(C)=O)C12C

InChI Identifier

InChI=1S/C28H42O6/c1-16(2)17(3)13-24(31)34-23-15-22-25(5)10-8-20(30)14-19(25)7-11-27(22,32)28(33)12-9-21(18(4)29)26(23,28)6/h7,13,16,20-23,30,32-33H,8-12,14-15H2,1-6H3

InChI Key

SZUXICHIYZJLOY-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
Cynanchum caudatum	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
Steroid ester
20-oxosteroid
3-hydroxy-delta-5-steroid
3-hydroxysteroid
Oxosteroid
14-hydroxysteroid
Hydroxysteroid
Delta-5-steroid
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Ketone
Polyol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
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
logP	2.98	ALOGPS
logP	3.06	ChemAxon
logS	-4.2	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	131 m³·mol⁻¹	ChemAxon
Polarizability	52.66 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

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

71436641

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 3,4-dimethylpent-2-enoate (NP0231290)

MOL for NP0231290 (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 3,4-dimethylpent-2-enoate)

3D MOL for NP0231290 (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 3,4-dimethylpent-2-enoate)

3D SDF for NP0231290 (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 3,4-dimethylpent-2-enoate)

3D-SDF for NP0231290 (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 3,4-dimethylpent-2-enoate)

PDB for NP0231290 (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 3,4-dimethylpent-2-enoate)

3D PDB for NP0231290 (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 3,4-dimethylpent-2-enoate)

SMILES for NP0231290 (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 3,4-dimethylpent-2-enoate)

INCHI for NP0231290 (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 3,4-dimethylpent-2-enoate)

Structure for NP0231290 (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 3,4-dimethylpent-2-enoate)

3D Structure for NP0231290 (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 3,4-dimethylpent-2-enoate)