NP-MRD: Showing NP-Card for (1s,3s,7s,8s,11s,12s,14s,15r,16r)-15-[(2s,3r)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-7,12,16-trimethyl-6-oxopentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-4-en-14-yl acetate (NP0314915)

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Record Information

Version

2.0

Created at

2022-09-11 13:16:58 UTC

Updated at

2022-09-11 13:16:58 UTC

NP-MRD ID

NP0314915

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3s,7s,8s,11s,12s,14s,15r,16r)-15-[(2s,3r)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-7,12,16-trimethyl-6-oxopentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-4-en-14-yl acetate

Description

CHEMBL1941164 belongs to the class of organic compounds known as cycloartanols and derivatives. These are steroids containing a cycloartanol moiety. Based on a literature review very few articles have been published on CHEMBL1941164.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112215162D          

 36 40  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309112215162D          

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    7.5274    4.8094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2165    5.5736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3446    4.6965    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
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  1  0  0  0
 21 20  1  1  0  0  0
  9 21  1  0  0  0  0
 19 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
  7 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
  5 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0314915

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]([C@@H](O)C(=O)C=C(C)C)[C@H]1[C@H](C[C@@]2(C)[C@@H]3CC[C@H]4[C@H](C)C(=O)C=C[C@@]44C[C@@]34CC[C@]12C)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C31H44O5/c1-17(2)14-23(34)27(35)19(4)26-24(36-20(5)32)15-29(7)25-9-8-21-18(3)22(33)10-11-30(21)16-31(25,30)13-12-28(26,29)6/h10-11,14,18-19,21,24-27,35H,8-9,12-13,15-16H2,1-7H3/t18-,19-,21-,24-,25-,26-,27+,28+,29-,30+,31-/m0/s1

> <INCHI_KEY>
LFOGMLHBIASASZ-CNWSIUGMSA-N

> <FORMULA>
C31H44O5

> <MOLECULAR_WEIGHT>
496.688

> <EXACT_MASS>
496.318874517

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
57.762113139317776

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3S,7S,8S,11S,12S,14S,15R,16R)-15-[(2S,3R)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-7,12,16-trimethyl-6-oxopentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadec-4-en-14-yl acetate

> <JCHEM_LOGP>
5.072775116333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.162164970259514

> <JCHEM_PKA_STRONGEST_BASIC>
-3.602669042008488

> <JCHEM_POLAR_SURFACE_AREA>
80.67000000000002

> <JCHEM_REFRACTIVITY>
140.58050000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,7S,8S,11S,12S,14S,15R,16R)-15-[(2S,3R)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-7,12,16-trimethyl-6-oxopentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadec-4-en-14-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      11.241  -0.397   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.418   0.596   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      13.866   0.073   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      12.147   2.112   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.698   2.635   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.424   1.771   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.208   2.716   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.839   1.221   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.692   2.445   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.169   0.996   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.653   0.725   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.660   1.903   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.144   1.632   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.621   0.183   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.151   2.809   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.365   2.538   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.675   4.257   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.191   4.528   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.183   3.351   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.707   4.799   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.699   3.622   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.222   5.071   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.738   5.342   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.731   4.164   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.403   5.550   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.270   4.114   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.216   5.330   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.741   5.119   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.635   6.757   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.110   6.967   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      11.580   7.972   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      11.000   9.399   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      13.106   7.762   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      14.051   8.977   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      13.471  10.404   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      15.577   8.767   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   26                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   24                                             
CONECT    8    7                                                            
CONECT    9    7   10   21                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   12   20   21                                             
CONECT   20   19   21                                                       
CONECT   21   20    9   19   22                                             
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23    7   25   26                                             
CONECT   25   24                                                            
CONECT   26   24    5   27                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₄₄O₅

Average Mass

496.6880 Da

Monoisotopic Mass

496.31887 Da

IUPAC Name

(1S,3S,7S,8S,11S,12S,14S,15R,16R)-15-[(2S,3R)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-7,12,16-trimethyl-6-oxopentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadec-4-en-14-yl acetate

Traditional Name

(1S,3S,7S,8S,11S,12S,14S,15R,16R)-15-[(2S,3R)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-7,12,16-trimethyl-6-oxopentacyclo[9.7.0.0^{1,3}.0^{3,8}.0^{12,16}]octadec-4-en-14-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@H]([C@@H](O)C(=O)C=C(C)C)[C@H]1[C@H](C[C@@]2(C)[C@@H]3CC[C@H]4[C@H](C)C(=O)C=C[C@@]44C[C@@]34CC[C@]12C)OC(C)=O

InChI Identifier

InChI=1S/C31H44O5/c1-17(2)14-23(34)27(35)19(4)26-24(36-20(5)32)15-29(7)25-9-8-21-18(3)22(33)10-11-30(21)16-31(25,30)13-12-28(26,29)6/h10-11,14,18-19,21,24-27,35H,8-9,12-13,15-16H2,1-7H3/t18-,19-,21-,24-,25-,26-,27+,28+,29-,30+,31-/m0/s1

InChI Key

LFOGMLHBIASASZ-CNWSIUGMSA-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 cycloartanols and derivatives. These are steroids containing a cycloartanol moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cycloartanols and derivatives

Direct Parent

Cycloartanols and derivatives

Alternative Parents

Substituents

Cycloartanol-skeleton
9b,19-cyclo-lanostane-skeleton
Triterpenoid
Hydroxy bile acid, alcohol, or derivatives
Monohydroxy bile acid, alcohol, or derivatives
23-oxosteroid
Bile acid, alcohol, or derivatives
22-hydroxysteroid
Steroid ester
3-oxo-delta-1-steroid
3-oxosteroid
Hydroxysteroid
3-oxo-5-alpha-steroid
Oxosteroid
Delta-1-steroid
Cyclohexenone
Acyloin
Acryloyl-group
Alpha,beta-unsaturated ketone
Enone
Alpha-hydroxy ketone
Ketone
Secondary alcohol
Carboxylic acid ester
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
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
logP	5.07	ChemAxon
pKa (Strongest Acidic)	13.16	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	140.58 m³·mol⁻¹	ChemAxon
Polarizability	57.76 Å³	ChemAxon
Number of Rings	5	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

28492542

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

57332506

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3s,7s,8s,11s,12s,14s,15r,16r)-15-[(2s,3r)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-7,12,16-trimethyl-6-oxopentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-4-en-14-yl acetate (NP0314915)

MOL for NP0314915 ((1s,3s,7s,8s,11s,12s,14s,15r,16r)-15-[(2s,3r)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-7,12,16-trimethyl-6-oxopentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-4-en-14-yl acetate)

3D MOL for NP0314915 ((1s,3s,7s,8s,11s,12s,14s,15r,16r)-15-[(2s,3r)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-7,12,16-trimethyl-6-oxopentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-4-en-14-yl acetate)

3D SDF for NP0314915 ((1s,3s,7s,8s,11s,12s,14s,15r,16r)-15-[(2s,3r)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-7,12,16-trimethyl-6-oxopentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-4-en-14-yl acetate)

3D-SDF for NP0314915 ((1s,3s,7s,8s,11s,12s,14s,15r,16r)-15-[(2s,3r)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-7,12,16-trimethyl-6-oxopentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-4-en-14-yl acetate)

PDB for NP0314915 ((1s,3s,7s,8s,11s,12s,14s,15r,16r)-15-[(2s,3r)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-7,12,16-trimethyl-6-oxopentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-4-en-14-yl acetate)

3D PDB for NP0314915 ((1s,3s,7s,8s,11s,12s,14s,15r,16r)-15-[(2s,3r)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-7,12,16-trimethyl-6-oxopentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-4-en-14-yl acetate)

SMILES for NP0314915 ((1s,3s,7s,8s,11s,12s,14s,15r,16r)-15-[(2s,3r)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-7,12,16-trimethyl-6-oxopentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-4-en-14-yl acetate)

INCHI for NP0314915 ((1s,3s,7s,8s,11s,12s,14s,15r,16r)-15-[(2s,3r)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-7,12,16-trimethyl-6-oxopentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-4-en-14-yl acetate)

Structure for NP0314915 ((1s,3s,7s,8s,11s,12s,14s,15r,16r)-15-[(2s,3r)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-7,12,16-trimethyl-6-oxopentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-4-en-14-yl acetate)

3D Structure for NP0314915 ((1s,3s,7s,8s,11s,12s,14s,15r,16r)-15-[(2s,3r)-3-hydroxy-6-methyl-4-oxohept-5-en-2-yl]-7,12,16-trimethyl-6-oxopentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadec-4-en-14-yl acetate)