NP-MRD: Showing NP-Card for ethyl (1s,2r,4s,9s,10s,13r,14r)-4-hydroxy-2,14-dimethyl-13-[(2r)-6-methylheptan-2-yl]-5,8-dioxotetracyclo[7.7.0.0²,⁶.0¹⁰,¹⁴]hexadec-6-ene-4-carboxylate (NP0240686)

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Record Information

Version

2.0

Created at

2022-09-07 00:34:20 UTC

Updated at

2022-09-07 00:34:20 UTC

NP-MRD ID

NP0240686

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ethyl (1s,2r,4s,9s,10s,13r,14r)-4-hydroxy-2,14-dimethyl-13-[(2r)-6-methylheptan-2-yl]-5,8-dioxotetracyclo[7.7.0.0²,⁶.0¹⁰,¹⁴]hexadec-6-ene-4-carboxylate

Description

2Alpha-Hydroxy-4,7-dioxo-2,4-cyclo-3,4-secocholesta-5-ene-3-oic acid ethyl ester belongs to the class of organic compounds known as androstane steroids. These are steroids with a structure based on the 19-carbon androstane skeleton. ethyl (1s,2r,4s,9s,10s,13r,14r)-4-hydroxy-2,14-dimethyl-13-[(2r)-6-methylheptan-2-yl]-5,8-dioxotetracyclo[7.7.0.0²,⁶.0¹⁰,¹⁴]hexadec-6-ene-4-carboxylate is found in Acanthella cavernosa. Based on a literature review very few articles have been published on 2alpha-Hydroxy-4,7-dioxo-2,4-cyclo-3,4-secocholesta-5-ene-3-oic acid ethyl ester.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072202342D          

 34 37  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309072202342D          

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  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 15 13  1  6  0  0  0
 15 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 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
 11 33  1  0  0  0  0
  6 33  1  0  0  0  0
 33 34  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0240686

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOC(=O)[C@]1(O)C[C@]2(C)[C@H]3CC[C@]4(C)[C@H](CC[C@H]4[C@@H]3C(=O)C=C2C1=O)[C@H](C)CCCC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C29H44O5/c1-7-34-26(32)29(33)16-28(6)21-13-14-27(5)19(18(4)10-8-9-17(2)3)11-12-20(27)24(21)23(30)15-22(28)25(29)31/h15,17-21,24,33H,7-14,16H2,1-6H3/t18-,19-,20+,21+,24+,27-,28-,29+/m1/s1

> <INCHI_KEY>
VAPIYJYATDCKSY-XFTXXRCBSA-N

> <FORMULA>
C29H44O5

> <MOLECULAR_WEIGHT>
472.666

> <EXACT_MASS>
472.318874517

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
56.15643696557741

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
ethyl (1S,2R,4S,9S,10S,13R,14R)-4-hydroxy-2,14-dimethyl-13-[(2R)-6-methylheptan-2-yl]-5,8-dioxotetracyclo[7.7.0.0^{2,6}.0^{10,14}]hexadec-6-ene-4-carboxylate

> <JCHEM_LOGP>
6.314205899333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.645319993802925

> <JCHEM_PKA_STRONGEST_BASIC>
-4.7035370347106005

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
132.8926

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
ethyl (1S,2R,4S,9S,10S,13R,14R)-4-hydroxy-2,14-dimethyl-13-[(2R)-6-methylheptan-2-yl]-5,8-dioxotetracyclo[7.7.0.0^{2,6}.0^{10,14}]hexadec-6-ene-4-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       6.731  13.212   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.324  13.838   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.078  12.933   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.671  13.559   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.510  15.091   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.425  12.654   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.655  13.988   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.456  11.510   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.686  10.176   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.217  10.015   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.179  10.496   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.851   9.352   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.375   7.887   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.406   6.743   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.131   7.567   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.161   8.711   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.668   8.391   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.144   6.927   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.113   5.782   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.578   5.306   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.607   6.102   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.837   4.769   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.867   3.624   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.274   4.251   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.608   3.481   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.608   1.941   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.942   4.251   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.275   3.481   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.609   4.251   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.943   3.481   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.276   4.251   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.943   1.941   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.018  12.028   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -1.315  12.798   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8   33                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11   16                                             
CONECT   10    9                                                            
CONECT   11    9   12   33                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   21                                                  
CONECT   16   15    9   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21   24                                             
CONECT   20   19                                                            
CONECT   21   19   15   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   19   25                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   11    6   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
2a-Hydroxy-4,7-dioxo-2,4-cyclo-3,4-secocholesta-5-ene-3-Oate ethyl ester	Generator
2a-Hydroxy-4,7-dioxo-2,4-cyclo-3,4-secocholesta-5-ene-3-Oic acid ethyl ester	Generator
2alpha-Hydroxy-4,7-dioxo-2,4-cyclo-3,4-secocholesta-5-ene-3-Oate ethyl ester	Generator
2Α-hydroxy-4,7-dioxo-2,4-cyclo-3,4-secocholesta-5-ene-3-Oate ethyl ester	Generator
2Α-hydroxy-4,7-dioxo-2,4-cyclo-3,4-secocholesta-5-ene-3-Oic acid ethyl ester	Generator

Chemical Formula

C₂₉H₄₄O₅

Average Mass

472.6660 Da

Monoisotopic Mass

472.31887 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCOC(=O)[C@]1(O)C[C@]2(C)[C@H]3CC[C@]4(C)[C@H](CC[C@H]4[C@@H]3C(=O)C=C2C1=O)[C@H](C)CCCC(C)C

InChI Identifier

InChI=1S/C29H44O5/c1-7-34-26(32)29(33)16-28(6)21-13-14-27(5)19(18(4)10-8-9-17(2)3)11-12-20(27)24(21)23(30)15-22(28)25(29)31/h15,17-21,24,33H,7-14,16H2,1-6H3/t18-,19-,20+,21+,24+,27-,28-,29+/m1/s1

InChI Key

VAPIYJYATDCKSY-XFTXXRCBSA-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
Acanthella cavernosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as androstane steroids. These are steroids with a structure based on the 19-carbon androstane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androstane steroids

Alternative Parents

Substituents

Androstane-skeleton
Cyclohexenone
Acyloin
Tertiary alcohol
Cyclic alcohol
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
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

Not Available

Chemspider ID

27023818

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25180581

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for ethyl (1s,2r,4s,9s,10s,13r,14r)-4-hydroxy-2,14-dimethyl-13-[(2r)-6-methylheptan-2-yl]-5,8-dioxotetracyclo[7.7.0.0²,⁶.0¹⁰,¹⁴]hexadec-6-ene-4-carboxylate (NP0240686)

MOL for NP0240686 (ethyl (1s,2r,4s,9s,10s,13r,14r)-4-hydroxy-2,14-dimethyl-13-[(2r)-6-methylheptan-2-yl]-5,8-dioxotetracyclo[7.7.0.0²,⁶.0¹⁰,¹⁴]hexadec-6-ene-4-carboxylate)

3D MOL for NP0240686 (ethyl (1s,2r,4s,9s,10s,13r,14r)-4-hydroxy-2,14-dimethyl-13-[(2r)-6-methylheptan-2-yl]-5,8-dioxotetracyclo[7.7.0.0²,⁶.0¹⁰,¹⁴]hexadec-6-ene-4-carboxylate)

3D SDF for NP0240686 (ethyl (1s,2r,4s,9s,10s,13r,14r)-4-hydroxy-2,14-dimethyl-13-[(2r)-6-methylheptan-2-yl]-5,8-dioxotetracyclo[7.7.0.0²,⁶.0¹⁰,¹⁴]hexadec-6-ene-4-carboxylate)

3D-SDF for NP0240686 (ethyl (1s,2r,4s,9s,10s,13r,14r)-4-hydroxy-2,14-dimethyl-13-[(2r)-6-methylheptan-2-yl]-5,8-dioxotetracyclo[7.7.0.0²,⁶.0¹⁰,¹⁴]hexadec-6-ene-4-carboxylate)

PDB for NP0240686 (ethyl (1s,2r,4s,9s,10s,13r,14r)-4-hydroxy-2,14-dimethyl-13-[(2r)-6-methylheptan-2-yl]-5,8-dioxotetracyclo[7.7.0.0²,⁶.0¹⁰,¹⁴]hexadec-6-ene-4-carboxylate)

3D PDB for NP0240686 (ethyl (1s,2r,4s,9s,10s,13r,14r)-4-hydroxy-2,14-dimethyl-13-[(2r)-6-methylheptan-2-yl]-5,8-dioxotetracyclo[7.7.0.0²,⁶.0¹⁰,¹⁴]hexadec-6-ene-4-carboxylate)

SMILES for NP0240686 (ethyl (1s,2r,4s,9s,10s,13r,14r)-4-hydroxy-2,14-dimethyl-13-[(2r)-6-methylheptan-2-yl]-5,8-dioxotetracyclo[7.7.0.0²,⁶.0¹⁰,¹⁴]hexadec-6-ene-4-carboxylate)

INCHI for NP0240686 (ethyl (1s,2r,4s,9s,10s,13r,14r)-4-hydroxy-2,14-dimethyl-13-[(2r)-6-methylheptan-2-yl]-5,8-dioxotetracyclo[7.7.0.0²,⁶.0¹⁰,¹⁴]hexadec-6-ene-4-carboxylate)

Structure for NP0240686 (ethyl (1s,2r,4s,9s,10s,13r,14r)-4-hydroxy-2,14-dimethyl-13-[(2r)-6-methylheptan-2-yl]-5,8-dioxotetracyclo[7.7.0.0²,⁶.0¹⁰,¹⁴]hexadec-6-ene-4-carboxylate)

3D Structure for NP0240686 (ethyl (1s,2r,4s,9s,10s,13r,14r)-4-hydroxy-2,14-dimethyl-13-[(2r)-6-methylheptan-2-yl]-5,8-dioxotetracyclo[7.7.0.0²,⁶.0¹⁰,¹⁴]hexadec-6-ene-4-carboxylate)