NP-MRD: Showing NP-Card for [(4ar,4bs,6r,6as,7r,10as,10br,12as)-8-acetyl-7-formyl-6-hydroxy-1,1,6a,10b-tetramethyl-2,3,4,4b,5,6,7,10,10a,11,12,12a-dodecahydrochrysen-4a-yl]methyl acetate (NP0242229)

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Record Information

Version

2.0

Created at

2022-09-07 02:29:41 UTC

Updated at

2022-09-07 02:29:41 UTC

NP-MRD ID

NP0242229

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(4ar,4bs,6r,6as,7r,10as,10br,12as)-8-acetyl-7-formyl-6-hydroxy-1,1,6a,10b-tetramethyl-2,3,4,4b,5,6,7,10,10a,11,12,12a-dodecahydrochrysen-4a-yl]methyl acetate

Description

CHEMBL498448, also known as 12-deacetyl-acmes, belongs to the class of organic compounds known as scalarane sesterterpenoids. These are sesterterpenoids with a structure based on the scalarane backbone. Scalarane is a tetracyclic compound, which is similar the homoandrostane with five methyl groups at the 4-, 4-, 8-, 17-, 17a-positions. [(4ar,4bs,6r,6as,7r,10as,10br,12as)-8-acetyl-7-formyl-6-hydroxy-1,1,6a,10b-tetramethyl-2,3,4,4b,5,6,7,10,10a,11,12,12a-dodecahydrochrysen-4a-yl]methyl acetate is found in Chromolaichma sedna. Based on a literature review very few articles have been published on CHEMBL498448.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072204292D          

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M  END


  Mrv1652309072204292D          

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 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 21 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  2  0  0  0  0
 25 28  1  0  0  0  0
 18 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 33 32  1  6  0  0  0
 16 33  1  0  0  0  0
  6 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0242229

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@]12CCCC(C)(C)[C@@H]1CC[C@@]1(C)[C@@H]3CC=C([C@H](C=O)[C@@]3(C)[C@H](O)C[C@H]21)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H42O5/c1-17(30)19-8-9-22-26(5)13-10-21-25(3,4)11-7-12-28(21,16-33-18(2)31)23(26)14-24(32)27(22,6)20(19)15-29/h8,15,20-24,32H,7,9-14,16H2,1-6H3/t20-,21-,22-,23-,24+,26-,27+,28+/m0/s1

> <INCHI_KEY>
IEEOZJLECXJYTE-WQSMWVCRSA-N

> <FORMULA>
C28H42O5

> <MOLECULAR_WEIGHT>
458.639

> <EXACT_MASS>
458.303224452

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
52.312318954316886

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(4aR,4bS,6R,6aS,7R,10aS,10bR,12aS)-8-acetyl-7-formyl-6-hydroxy-1,1,6a,10b-tetramethyl-1,2,3,4,4a,4b,5,6,6a,7,10,10a,10b,11,12,12a-hexadecahydrochrysen-4a-yl]methyl acetate

> <JCHEM_LOGP>
3.5493976106666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.056697850609556

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.936682264925317

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9492534992901147

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
127.96909999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(4aR,4bS,6R,6aS,7R,10aS,10bR,12aS)-8-acetyl-7-formyl-6-hydroxy-1,1,6a,10b-tetramethyl-2,3,4,4b,5,6,7,10,10a,11,12,12a-dodecahydrochrysen-4a-yl]methyl acetate

> <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       3.171 -11.690   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.180 -10.525   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.692 -10.817   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.676  -9.070   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.684  -7.906   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.180  -6.451   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.171  -7.615   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.659  -7.324   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.155  -5.869   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.163  -4.705   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.842  -3.914   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.712  -3.266   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.676  -4.996   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.684  -3.832   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.196  -4.123   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.700  -5.578   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.708  -4.414   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.212  -5.869   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.220  -4.705   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.733  -4.996   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.237  -6.451   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.749  -6.742   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.757  -5.578   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      13.253  -8.197   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.229  -7.615   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.733  -9.070   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.725 -10.234   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       8.716  -7.324   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.220  -8.779   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.708  -8.488   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.212  -9.943   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.196  -8.197   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.692  -6.742   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                                                       
CONECT    6    5    7   13   33                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10    6   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   33                                             
CONECT   17   16                                                            
CONECT   18   16   19   28                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   25                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   21   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25   18   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   16    6                                                  
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
12-Deacetyl-23-acetoxy-20-methylscalaradial	MeSH
12-Deacetyl-23-acetoxy-20-methyl-12-epi-scalaradial	MeSH
12-Deacetyl-acmes	MeSH

Chemical Formula

C₂₈H₄₂O₅

Average Mass

458.6390 Da

Monoisotopic Mass

458.30322 Da

IUPAC Name

[(4aR,4bS,6R,6aS,7R,10aS,10bR,12aS)-8-acetyl-7-formyl-6-hydroxy-1,1,6a,10b-tetramethyl-1,2,3,4,4a,4b,5,6,6a,7,10,10a,10b,11,12,12a-hexadecahydrochrysen-4a-yl]methyl acetate

Traditional Name

[(4aR,4bS,6R,6aS,7R,10aS,10bR,12aS)-8-acetyl-7-formyl-6-hydroxy-1,1,6a,10b-tetramethyl-2,3,4,4b,5,6,7,10,10a,11,12,12a-dodecahydrochrysen-4a-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@]12CCCC(C)(C)[C@@H]1CC[C@@]1(C)[C@@H]3CC=C([C@H](C=O)[C@@]3(C)[C@H](O)C[C@H]21)C(C)=O

InChI Identifier

InChI=1S/C28H42O5/c1-17(30)19-8-9-22-26(5)13-10-21-25(3,4)11-7-12-28(21,16-33-18(2)31)23(26)14-24(32)27(22,6)20(19)15-29/h8,15,20-24,32H,7,9-14,16H2,1-6H3/t20-,21-,22-,23-,24+,26-,27+,28+/m0/s1

InChI Key

IEEOZJLECXJYTE-WQSMWVCRSA-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
Chromolaichma sedna	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as scalarane sesterterpenoids. These are sesterterpenoids with a structure based on the scalarane backbone. Scalarane is a tetracyclic compound, which is similar the homoandrostane with five methyl groups at the 4-, 4-, 8-, 17-, 17a-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Scalarane sesterterpenoids

Alternative Parents

Substituents

Scalarane sesterterpenoid
Hydroxysteroid
17-oxosteroid
7-hydroxysteroid
7-alpha-hydroxysteroid
Oxosteroid
Steroid
Cyclic alcohol
Carboxylic acid ester
Ketone
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Aldehyde
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
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	3.55	ChemAxon
pKa (Strongest Acidic)	13.94	ChemAxon
pKa (Strongest Basic)	-2.9	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	5	ChemAxon
Refractivity	127.97 m³·mol⁻¹	ChemAxon
Polarizability	52.31 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

10235614

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21603479

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(4ar,4bs,6r,6as,7r,10as,10br,12as)-8-acetyl-7-formyl-6-hydroxy-1,1,6a,10b-tetramethyl-2,3,4,4b,5,6,7,10,10a,11,12,12a-dodecahydrochrysen-4a-yl]methyl acetate (NP0242229)

MOL for NP0242229 ([(4ar,4bs,6r,6as,7r,10as,10br,12as)-8-acetyl-7-formyl-6-hydroxy-1,1,6a,10b-tetramethyl-2,3,4,4b,5,6,7,10,10a,11,12,12a-dodecahydrochrysen-4a-yl]methyl acetate)

3D MOL for NP0242229 ([(4ar,4bs,6r,6as,7r,10as,10br,12as)-8-acetyl-7-formyl-6-hydroxy-1,1,6a,10b-tetramethyl-2,3,4,4b,5,6,7,10,10a,11,12,12a-dodecahydrochrysen-4a-yl]methyl acetate)

3D SDF for NP0242229 ([(4ar,4bs,6r,6as,7r,10as,10br,12as)-8-acetyl-7-formyl-6-hydroxy-1,1,6a,10b-tetramethyl-2,3,4,4b,5,6,7,10,10a,11,12,12a-dodecahydrochrysen-4a-yl]methyl acetate)

3D-SDF for NP0242229 ([(4ar,4bs,6r,6as,7r,10as,10br,12as)-8-acetyl-7-formyl-6-hydroxy-1,1,6a,10b-tetramethyl-2,3,4,4b,5,6,7,10,10a,11,12,12a-dodecahydrochrysen-4a-yl]methyl acetate)

PDB for NP0242229 ([(4ar,4bs,6r,6as,7r,10as,10br,12as)-8-acetyl-7-formyl-6-hydroxy-1,1,6a,10b-tetramethyl-2,3,4,4b,5,6,7,10,10a,11,12,12a-dodecahydrochrysen-4a-yl]methyl acetate)

3D PDB for NP0242229 ([(4ar,4bs,6r,6as,7r,10as,10br,12as)-8-acetyl-7-formyl-6-hydroxy-1,1,6a,10b-tetramethyl-2,3,4,4b,5,6,7,10,10a,11,12,12a-dodecahydrochrysen-4a-yl]methyl acetate)

SMILES for NP0242229 ([(4ar,4bs,6r,6as,7r,10as,10br,12as)-8-acetyl-7-formyl-6-hydroxy-1,1,6a,10b-tetramethyl-2,3,4,4b,5,6,7,10,10a,11,12,12a-dodecahydrochrysen-4a-yl]methyl acetate)

INCHI for NP0242229 ([(4ar,4bs,6r,6as,7r,10as,10br,12as)-8-acetyl-7-formyl-6-hydroxy-1,1,6a,10b-tetramethyl-2,3,4,4b,5,6,7,10,10a,11,12,12a-dodecahydrochrysen-4a-yl]methyl acetate)

Structure for NP0242229 ([(4ar,4bs,6r,6as,7r,10as,10br,12as)-8-acetyl-7-formyl-6-hydroxy-1,1,6a,10b-tetramethyl-2,3,4,4b,5,6,7,10,10a,11,12,12a-dodecahydrochrysen-4a-yl]methyl acetate)

3D Structure for NP0242229 ([(4ar,4bs,6r,6as,7r,10as,10br,12as)-8-acetyl-7-formyl-6-hydroxy-1,1,6a,10b-tetramethyl-2,3,4,4b,5,6,7,10,10a,11,12,12a-dodecahydrochrysen-4a-yl]methyl acetate)