NP-MRD: Showing NP-Card for methyl (2r)-3-[(1r,2r,4as,4br,8ar,10as)-2-formyl-2,4b,8,8,10a-pentamethyl-decahydrophenanthren-1-yl]-2-methylpropanoate (NP0165205)

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Record Information

Version

2.0

Created at

2022-09-03 00:16:02 UTC

Updated at

2022-09-03 00:16:02 UTC

NP-MRD ID

NP0165205

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2r)-3-[(1r,2r,4as,4br,8ar,10as)-2-formyl-2,4b,8,8,10a-pentamethyl-decahydrophenanthren-1-yl]-2-methylpropanoate

Description

Methyl (2R)-3-[(1R,2R,4aS,4bR,8aR,10aS)-2-formyl-2,4b,8,8,10a-pentamethyl-tetradecahydrophenanthren-1-yl]-2-methylpropanoate belongs to the class of organic compounds known as isocopalane and spongiane diterpenoids. These are diterpenoids with a structure based on the isocopalane (Tetradecahydro-1,1,4a,7,8,8a-hexamethylphenanthrene) or the 15,16-epoxyisocopalane skeleton. Based on a literature review very few articles have been published on methyl (2R)-3-[(1R,2R,4aS,4bR,8aR,10aS)-2-formyl-2,4b,8,8,10a-pentamethyl-tetradecahydrophenanthren-1-yl]-2-methylpropanoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309032202162D          

 28 30  0  0  1  0            999 V2000
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5737   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1040   -1.8430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0434   -1.8430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2786   -5.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8913   -4.9788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5040   -5.7072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
  9 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  8 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  1  0  0  0
 27 28  2  0  0  0  0
M  END


  Mrv1652309032202162D          

 28 30  0  0  1  0            999 V2000
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5737   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1040   -1.8430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0434   -1.8430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.8592   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2786   -5.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8913   -4.9788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5040   -5.7072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
  9 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  8 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  1  0  0  0
 27 28  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0165205

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@H](C)C[C@H]1[C@@](C)(CC[C@@H]2[C@]1(C)CC[C@@H]1C(C)(C)CCC[C@@]21C)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H42O3/c1-17(21(27)28-7)15-20-23(4,16-26)13-9-19-24(5)12-8-11-22(2,3)18(24)10-14-25(19,20)6/h16-20H,8-15H2,1-7H3/t17-,18-,19+,20+,23+,24-,25+/m1/s1

> <INCHI_KEY>
CYKCDIFKAFHNBW-OMBRQJCQSA-N

> <FORMULA>
C25H42O3

> <MOLECULAR_WEIGHT>
390.608

> <EXACT_MASS>
390.313395212

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
47.15388855854954

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2R)-3-[(1R,2R,4aS,4bR,8aR,10aS)-2-formyl-2,4b,8,8,10a-pentamethyl-tetradecahydrophenanthren-1-yl]-2-methylpropanoate

> <ALOGPS_LOGP>
5.44

> <JCHEM_LOGP>
6.018409245000001

> <ALOGPS_LOGS>
-6.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.777107917843617

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
113.14899999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.45e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2R)-3-[(1R,2R,4aS,4bR,8aR,10aS)-2-formyl-2,4b,8,8,10a-pentamethyl-decahydrophenanthren-1-yl]-2-methylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669  -6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.004  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.994  -3.440   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.014  -3.440   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.338  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.338  -6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.004  -7.700   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.670  -6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.670  -8.470   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.853 -10.546   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.130  -9.294   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.407 -10.653   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   25                                                  
CONECT    9    8   10   11   22                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   20                                                  
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   13   21   22                                             
CONECT   21   20                                                            
CONECT   22   20    9   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24    8   26   27                                             
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Value	Source
Methyl (2R)-3-[(1R,2R,4as,4BR,8ar,10as)-2-formyl-2,4b,8,8,10a-pentamethyl-tetradecahydrophenanthren-1-yl]-2-methylpropanoic acid	Generator

Chemical Formula

C₂₅H₄₂O₃

Average Mass

390.6080 Da

Monoisotopic Mass

390.31340 Da

IUPAC Name

methyl (2R)-3-[(1R,2R,4aS,4bR,8aR,10aS)-2-formyl-2,4b,8,8,10a-pentamethyl-tetradecahydrophenanthren-1-yl]-2-methylpropanoate

Traditional Name

methyl (2R)-3-[(1R,2R,4aS,4bR,8aR,10aS)-2-formyl-2,4b,8,8,10a-pentamethyl-decahydrophenanthren-1-yl]-2-methylpropanoate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@H](C)C[C@H]1[C@@](C)(CC[C@@H]2[C@]1(C)CC[C@@H]1C(C)(C)CCC[C@@]21C)C=O

InChI Identifier

InChI=1S/C25H42O3/c1-17(21(27)28-7)15-20-23(4,16-26)13-9-19-24(5)12-8-11-22(2,3)18(24)10-14-25(19,20)6/h16-20H,8-15H2,1-7H3/t17-,18-,19+,20+,23+,24-,25+/m1/s1

InChI Key

CYKCDIFKAFHNBW-OMBRQJCQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isocopalane and spongiane diterpenoids. These are diterpenoids with a structure based on the isocopalane (Tetradecahydro-1,1,4a,7,8,8a-hexamethylphenanthrene) or the 15,16-epoxyisocopalane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Isocopalane and spongiane diterpenoids

Alternative Parents

Substituents

Isocopalane diterpenoid
18-oxosteroid
Oxosteroid
Steroid
Hydrophenanthrene
Phenanthrene
Fatty acid ester
Fatty acyl
Methyl ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aldehyde
Carbonyl group
Organooxygen compound
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	5.44	ALOGPS
logP	6.02	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	113.15 m³·mol⁻¹	ChemAxon
Polarizability	47.15 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

162861780

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (2r)-3-[(1r,2r,4as,4br,8ar,10as)-2-formyl-2,4b,8,8,10a-pentamethyl-decahydrophenanthren-1-yl]-2-methylpropanoate (NP0165205)

MOL for NP0165205 (methyl (2r)-3-[(1r,2r,4as,4br,8ar,10as)-2-formyl-2,4b,8,8,10a-pentamethyl-decahydrophenanthren-1-yl]-2-methylpropanoate)

3D MOL for NP0165205 (methyl (2r)-3-[(1r,2r,4as,4br,8ar,10as)-2-formyl-2,4b,8,8,10a-pentamethyl-decahydrophenanthren-1-yl]-2-methylpropanoate)

3D SDF for NP0165205 (methyl (2r)-3-[(1r,2r,4as,4br,8ar,10as)-2-formyl-2,4b,8,8,10a-pentamethyl-decahydrophenanthren-1-yl]-2-methylpropanoate)

3D-SDF for NP0165205 (methyl (2r)-3-[(1r,2r,4as,4br,8ar,10as)-2-formyl-2,4b,8,8,10a-pentamethyl-decahydrophenanthren-1-yl]-2-methylpropanoate)

PDB for NP0165205 (methyl (2r)-3-[(1r,2r,4as,4br,8ar,10as)-2-formyl-2,4b,8,8,10a-pentamethyl-decahydrophenanthren-1-yl]-2-methylpropanoate)

3D PDB for NP0165205 (methyl (2r)-3-[(1r,2r,4as,4br,8ar,10as)-2-formyl-2,4b,8,8,10a-pentamethyl-decahydrophenanthren-1-yl]-2-methylpropanoate)

SMILES for NP0165205 (methyl (2r)-3-[(1r,2r,4as,4br,8ar,10as)-2-formyl-2,4b,8,8,10a-pentamethyl-decahydrophenanthren-1-yl]-2-methylpropanoate)

INCHI for NP0165205 (methyl (2r)-3-[(1r,2r,4as,4br,8ar,10as)-2-formyl-2,4b,8,8,10a-pentamethyl-decahydrophenanthren-1-yl]-2-methylpropanoate)

Structure for NP0165205 (methyl (2r)-3-[(1r,2r,4as,4br,8ar,10as)-2-formyl-2,4b,8,8,10a-pentamethyl-decahydrophenanthren-1-yl]-2-methylpropanoate)

3D Structure for NP0165205 (methyl (2r)-3-[(1r,2r,4as,4br,8ar,10as)-2-formyl-2,4b,8,8,10a-pentamethyl-decahydrophenanthren-1-yl]-2-methylpropanoate)