NP-MRD: Showing NP-Card for 5-methoxy-3b,6,6,9a,11a-pentamethyl-2,9,11-trioxo-1-(3-oxobut-1-en-1-yl)-1h,4h,5h,5ah,9bh,10h-cyclopenta[a]phenanthren-4-yl acetate (NP0256315)

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Record Information

Version

1.0

Created at

2022-09-07 21:05:46 UTC

Updated at

2022-09-07 21:05:46 UTC

NP-MRD ID

NP0256315

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-methoxy-3b,6,6,9a,11a-pentamethyl-2,9,11-trioxo-1-(3-oxobut-1-en-1-yl)-1h,4h,5h,5ah,9bh,10h-cyclopenta[a]phenanthren-4-yl acetate

Description

8-Methoxy-2,6,6,10,15-pentamethyl-3,13,16-trioxo-14-(3-oxobut-1-en-1-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-4,11-dien-9-yl acetate belongs to the class of organic compounds known as steroid esters. Steroid esters are compounds containing a steroid moiety which bears a carboxylic acid ester group. 5-methoxy-3b,6,6,9a,11a-pentamethyl-2,9,11-trioxo-1-(3-oxobut-1-en-1-yl)-1h,4h,5h,5ah,9bh,10h-cyclopenta[a]phenanthren-4-yl acetate is found in Azadirachta indica. 8-Methoxy-2,6,6,10,15-pentamethyl-3,13,16-trioxo-14-(3-oxobut-1-en-1-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-4,11-dien-9-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231519092D          

 36 39  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004231519092D          

 36 39  0  0  0  0            999 V2000
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  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 18 17  1  4  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
  9 26  1  0  0  0  0
 15 26  1  0  0  0  0
 11 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
  3 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 27 35  1  0  0  0  0
 35 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0256315

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1C(OC(C)=O)C2(C)C(CC(=O)C3(C)C(C=CC(C)=O)C(=O)C=C23)C2(C)C1C(C)(C)C=CC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C29H36O7/c1-15(30)9-10-17-18(32)13-19-27(17,5)22(34)14-20-28(19,6)25(36-16(2)31)23(35-8)24-26(3,4)12-11-21(33)29(20,24)7/h9-13,17,20,23-25H,14H2,1-8H3

> <INCHI_KEY>
KTWGTAQAOGDKCF-UHFFFAOYSA-N

> <FORMULA>
C29H36O7

> <MOLECULAR_WEIGHT>
496.6

> <EXACT_MASS>
496.246103499

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
53.23287817182775

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-methoxy-2,6,6,10,15-pentamethyl-3,13,16-trioxo-14-(3-oxobut-1-en-1-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-4,11-dien-9-yl acetate

> <ALOGPS_LOGP>
3.23

> <JCHEM_LOGP>
3.4424262936666676

> <ALOGPS_LOGS>
-5.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.217648111907383

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.693497180970986

> <JCHEM_PKA_STRONGEST_BASIC>
-4.061460875538479

> <JCHEM_POLAR_SURFACE_AREA>
103.81

> <JCHEM_REFRACTIVITY>
135.6818

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.72e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-methoxy-2,6,6,10,15-pentamethyl-3,13,16-trioxo-14-(3-oxobut-1-en-1-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-4,11-dien-9-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       1.280  -3.304   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.796  -3.033   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.319  -1.585   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.835  -1.314   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.828  -2.491   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.305  -3.939   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.297  -5.117   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.789  -4.210   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.358   0.135   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.351  -1.043   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.366   1.312   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.889   2.761   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.405   3.032   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.928   4.480   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.398   1.854   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.069   3.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.937   1.804   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.882   3.020   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.407   2.809   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.353   4.025   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      13.878   3.815   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      11.772   5.452   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.365   0.325   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.813  -0.198   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.090  -0.539   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.874   0.406   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.850   1.041   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.373   2.489   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.326  -0.407   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.810  -0.678   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.341  -2.124   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.521  -1.452   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.182   0.499   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.341   1.947   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.857   2.218   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.380   3.667   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   29                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    4   10   11   26                                             
CONECT   10    9                                                            
CONECT   11    9   12   27                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17   26                                             
CONECT   16   15                                                            
CONECT   17   15   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   17   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25    9   15                                                  
CONECT   27   11   28   29   35                                             
CONECT   28   27                                                            
CONECT   29   27    3   30                                                  
CONECT   30   29   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   27   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Value	Source
8-Methoxy-2,6,6,10,15-pentamethyl-3,13,16-trioxo-14-(3-oxobut-1-en-1-yl)tetracyclo[8.7.0.0,.0,]heptadeca-4,11-dien-9-yl acetic acid	Generator
8-Methoxy-2,6,6,10,15-pentamethyl-3,13,16-trioxo-14-(3-oxobut-1-en-1-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-4,11-dien-9-yl acetic acid	Generator

Chemical Formula

C₂₉H₃₆O₇

Average Mass

496.6000 Da

Monoisotopic Mass

496.24610 Da

IUPAC Name

8-methoxy-2,6,6,10,15-pentamethyl-3,13,16-trioxo-14-(3-oxobut-1-en-1-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-4,11-dien-9-yl acetate

Traditional Name

8-methoxy-2,6,6,10,15-pentamethyl-3,13,16-trioxo-14-(3-oxobut-1-en-1-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-4,11-dien-9-yl acetate

CAS Registry Number

Not Available

SMILES

COC1C(OC(C)=O)C2(C)C(CC(=O)C3(C)C(C=CC(C)=O)C(=O)C=C23)C2(C)C1C(C)(C)C=CC2=O

InChI Identifier

InChI=1S/C29H36O7/c1-15(30)9-10-17-18(32)13-19-27(17,5)22(34)14-20-28(19,6)25(36-16(2)31)23(35-8)24-26(3,4)12-11-21(33)29(20,24)7/h9-13,17,20,23-25H,14H2,1-8H3

InChI Key

KTWGTAQAOGDKCF-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
Azadirachta indica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroid esters. Steroid esters are compounds containing a steroid moiety which bears a carboxylic acid ester group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid esters

Direct Parent

Steroid esters

Alternative Parents

Substituents

Steroid ester
16-oxosteroid
1-oxosteroid
Oxosteroid
12-oxosteroid
Cyclohexenone
Acryloyl-group
Enone
Alpha,beta-unsaturated ketone
Carboxylic acid ester
Ketone
Cyclic ketone
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
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	3.23	ALOGPS
logP	3.44	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	12.69	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	103.81 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	135.68 m³·mol⁻¹	ChemAxon
Polarizability	53.23 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

73657276

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-methoxy-3b,6,6,9a,11a-pentamethyl-2,9,11-trioxo-1-(3-oxobut-1-en-1-yl)-1h,4h,5h,5ah,9bh,10h-cyclopenta[a]phenanthren-4-yl acetate (NP0256315)

MOL for NP0256315 (5-methoxy-3b,6,6,9a,11a-pentamethyl-2,9,11-trioxo-1-(3-oxobut-1-en-1-yl)-1h,4h,5h,5ah,9bh,10h-cyclopenta[a]phenanthren-4-yl acetate)

3D MOL for NP0256315 (5-methoxy-3b,6,6,9a,11a-pentamethyl-2,9,11-trioxo-1-(3-oxobut-1-en-1-yl)-1h,4h,5h,5ah,9bh,10h-cyclopenta[a]phenanthren-4-yl acetate)

3D SDF for NP0256315 (5-methoxy-3b,6,6,9a,11a-pentamethyl-2,9,11-trioxo-1-(3-oxobut-1-en-1-yl)-1h,4h,5h,5ah,9bh,10h-cyclopenta[a]phenanthren-4-yl acetate)

3D-SDF for NP0256315 (5-methoxy-3b,6,6,9a,11a-pentamethyl-2,9,11-trioxo-1-(3-oxobut-1-en-1-yl)-1h,4h,5h,5ah,9bh,10h-cyclopenta[a]phenanthren-4-yl acetate)

PDB for NP0256315 (5-methoxy-3b,6,6,9a,11a-pentamethyl-2,9,11-trioxo-1-(3-oxobut-1-en-1-yl)-1h,4h,5h,5ah,9bh,10h-cyclopenta[a]phenanthren-4-yl acetate)

3D PDB for NP0256315 (5-methoxy-3b,6,6,9a,11a-pentamethyl-2,9,11-trioxo-1-(3-oxobut-1-en-1-yl)-1h,4h,5h,5ah,9bh,10h-cyclopenta[a]phenanthren-4-yl acetate)

SMILES for NP0256315 (5-methoxy-3b,6,6,9a,11a-pentamethyl-2,9,11-trioxo-1-(3-oxobut-1-en-1-yl)-1h,4h,5h,5ah,9bh,10h-cyclopenta[a]phenanthren-4-yl acetate)

INCHI for NP0256315 (5-methoxy-3b,6,6,9a,11a-pentamethyl-2,9,11-trioxo-1-(3-oxobut-1-en-1-yl)-1h,4h,5h,5ah,9bh,10h-cyclopenta[a]phenanthren-4-yl acetate)

Structure for NP0256315 (5-methoxy-3b,6,6,9a,11a-pentamethyl-2,9,11-trioxo-1-(3-oxobut-1-en-1-yl)-1h,4h,5h,5ah,9bh,10h-cyclopenta[a]phenanthren-4-yl acetate)

3D Structure for NP0256315 (5-methoxy-3b,6,6,9a,11a-pentamethyl-2,9,11-trioxo-1-(3-oxobut-1-en-1-yl)-1h,4h,5h,5ah,9bh,10h-cyclopenta[a]phenanthren-4-yl acetate)