NP-MRD: Showing NP-Card for [(1r,4ar,4br,7s,8ar,10ar)-7-ethenyl-4b-hydroxy-1,4a,7-trimethyl-decahydrophenanthren-1-yl]methyl pentanoate (NP0217304)

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Record Information

Version

2.0

Created at

2022-09-05 17:36:50 UTC

Updated at

2022-09-05 17:36:51 UTC

NP-MRD ID

NP0217304

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1r,4ar,4br,7s,8ar,10ar)-7-ethenyl-4b-hydroxy-1,4a,7-trimethyl-decahydrophenanthren-1-yl]methyl pentanoate

Description

[(1R,8aalpha,10abeta)-7alpha-Ethenyltetradecahydro-1,4aalpha,7-trimethyl-4balpha-hydroxyphenanthrene]-1alpha-methanol alpha-pentanoate belongs to the class of organic compounds known as hydrophenanthrenes. These are a phenanthrene derivative where at least one ring CC bond is substituted by hydrogenation. Based on a literature review very few articles have been published on [(1R,8aalpha,10abeta)-7alpha-Ethenyltetradecahydro-1,4aalpha,7-trimethyl-4balpha-hydroxyphenanthrene]-1alpha-methanol alpha-pentanoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052219362D          

 28 30  0  0  1  0            999 V2000
   -7.3984   -0.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5859   -1.0618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0556   -0.4298    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.7701   -0.0173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5253   -1.0618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7128   -0.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4307   -0.1433    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9004   -0.7752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9610    0.4887    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6788    1.2640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8663    1.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3360    0.7752    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5236    0.9185    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8057    1.6938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8091    1.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0946    0.9185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3802    1.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3802    2.1560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3343    0.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0488    1.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7633    0.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4777    1.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9933    0.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2754   -0.4887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0879   -0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6182   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3908   -0.7930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7734    0.3455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  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  1  0  0  0
 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 12 26  1  0  0  0  0
  7 26  1  0  0  0  0
 26 27  1  6  0  0  0
  9 28  1  0  0  0  0
  3 28  1  0  0  0  0
M  END


  Mrv1652309052219362D          

 28 30  0  0  1  0            999 V2000
   -7.3984   -0.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5859   -1.0618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0556   -0.4298    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.7701   -0.0173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5253   -1.0618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7128   -0.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4307   -0.1433    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9004   -0.7752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9610    0.4887    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6788    1.2640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8663    1.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3360    0.7752    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5236    0.9185    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8057    1.6938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8091    1.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0946    0.9185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3802    1.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3802    2.1560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3343    0.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0488    1.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7633    0.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4777    1.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9933    0.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2754   -0.4887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0879   -0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6182   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3908   -0.7930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7734    0.3455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  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  1  0  0  0
 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 12 26  1  0  0  0  0
  7 26  1  0  0  0  0
 26 27  1  6  0  0  0
  9 28  1  0  0  0  0
  3 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0217304

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C25H42O3/c1-6-8-10-21(26)28-18-23(4)13-9-14-24(5)20(23)12-11-19-17-22(3,7-2)15-16-25(19,24)27/h7,19-20,27H,2,6,8-18H2,1,3-5H3/t19-,20-,22+,23+,24-,25-/m1/s1

> <INCHI_KEY>
ZYQILNWUKPTLKB-DISYYVGZSA-N

> <FORMULA>
C25H42O3

> <MOLECULAR_WEIGHT>
390.608

> <EXACT_MASS>
390.313395212

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
47.01857683046515

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1R,4aR,4bR,7S,8aR,10aR)-7-ethenyl-4b-hydroxy-1,4a,7-trimethyl-tetradecahydrophenanthren-1-yl]methyl pentanoate

> <JCHEM_LOGP>
5.949752857000001

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
0.26172982645604936

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
113.9738

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,4aR,4bR,7S,8aR,10aR)-7-ethenyl-4b-hydroxy-1,4a,7-trimethyl-decahydrophenanthren-1-yl]methyl pentanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0     -13.810  -1.715   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -12.294  -1.982   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -11.304  -0.802   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -12.637  -0.032   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -10.314  -1.982   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.797  -1.715   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.271  -0.267   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -7.281  -1.447   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -9.260   0.912   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -8.734   2.359   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -7.217   2.627   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.227   1.447   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.711   1.715   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.237   3.162   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.377   2.485   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.043   1.715   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.710   2.485   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.710   4.025   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.624   1.715   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.958   2.485   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.291   1.715   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.625   2.485   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.721   0.535   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.247  -0.912   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.764  -1.180   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.754  -0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -6.330  -1.480   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -10.777   0.645   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   28                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   26                                             
CONECT    8    7                                                            
CONECT    9    7   10   28                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   26                                                  
CONECT   13   12   14   15   23                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   13   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   12    7   27                                             
CONECT   27   26                                                            
CONECT   28    9    3                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Value	Source
[(1R,8Aalpha,10abeta)-7a-ethenyltetradecahydro-1,4aalpha,7-trimethyl-4balpha-hydroxyphenanthrene]-1a-methanol a-pentanoate	Generator
[(1R,8Aalpha,10abeta)-7a-ethenyltetradecahydro-1,4aalpha,7-trimethyl-4balpha-hydroxyphenanthrene]-1a-methanol a-pentanoic acid	Generator
[(1R,8Aalpha,10abeta)-7alpha-ethenyltetradecahydro-1,4aalpha,7-trimethyl-4balpha-hydroxyphenanthrene]-1alpha-methanol alpha-pentanoic acid	Generator
[(1R,8Aalpha,10abeta)-7α-ethenyltetradecahydro-1,4aalpha,7-trimethyl-4balpha-hydroxyphenanthrene]-1α-methanol α-pentanoate	Generator
[(1R,8Aalpha,10abeta)-7α-ethenyltetradecahydro-1,4aalpha,7-trimethyl-4balpha-hydroxyphenanthrene]-1α-methanol α-pentanoic acid	Generator

Chemical Formula

C₂₅H₄₂O₃

Average Mass

390.6080 Da

Monoisotopic Mass

390.31340 Da

IUPAC Name

[(1R,4aR,4bR,7S,8aR,10aR)-7-ethenyl-4b-hydroxy-1,4a,7-trimethyl-tetradecahydrophenanthren-1-yl]methyl pentanoate

Traditional Name

[(1R,4aR,4bR,7S,8aR,10aR)-7-ethenyl-4b-hydroxy-1,4a,7-trimethyl-decahydrophenanthren-1-yl]methyl pentanoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C25H42O3/c1-6-8-10-21(26)28-18-23(4)13-9-14-24(5)20(23)12-11-19-17-22(3,7-2)15-16-25(19,24)27/h7,19-20,27H,2,6,8-18H2,1,3-5H3/t19-,20-,22+,23+,24-,25-/m1/s1

InChI Key

ZYQILNWUKPTLKB-DISYYVGZSA-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 hydrophenanthrenes. These are a phenanthrene derivative where at least one ring CC bond is substituted by hydrogenation.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Hydrophenanthrenes

Direct Parent

Hydrophenanthrenes

Alternative Parents

Substituents

Hydrophenanthrene
Fatty acid ester
Fatty acyl
Tertiary alcohol
Cyclic alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	5.95	ChemAxon
pKa (Strongest Basic)	0.26	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	113.97 m³·mol⁻¹	ChemAxon
Polarizability	47.02 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	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

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

102061525

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(1r,4ar,4br,7s,8ar,10ar)-7-ethenyl-4b-hydroxy-1,4a,7-trimethyl-decahydrophenanthren-1-yl]methyl pentanoate (NP0217304)

MOL for NP0217304 ([(1r,4ar,4br,7s,8ar,10ar)-7-ethenyl-4b-hydroxy-1,4a,7-trimethyl-decahydrophenanthren-1-yl]methyl pentanoate)

3D MOL for NP0217304 ([(1r,4ar,4br,7s,8ar,10ar)-7-ethenyl-4b-hydroxy-1,4a,7-trimethyl-decahydrophenanthren-1-yl]methyl pentanoate)

3D SDF for NP0217304 ([(1r,4ar,4br,7s,8ar,10ar)-7-ethenyl-4b-hydroxy-1,4a,7-trimethyl-decahydrophenanthren-1-yl]methyl pentanoate)

3D-SDF for NP0217304 ([(1r,4ar,4br,7s,8ar,10ar)-7-ethenyl-4b-hydroxy-1,4a,7-trimethyl-decahydrophenanthren-1-yl]methyl pentanoate)

PDB for NP0217304 ([(1r,4ar,4br,7s,8ar,10ar)-7-ethenyl-4b-hydroxy-1,4a,7-trimethyl-decahydrophenanthren-1-yl]methyl pentanoate)

3D PDB for NP0217304 ([(1r,4ar,4br,7s,8ar,10ar)-7-ethenyl-4b-hydroxy-1,4a,7-trimethyl-decahydrophenanthren-1-yl]methyl pentanoate)

SMILES for NP0217304 ([(1r,4ar,4br,7s,8ar,10ar)-7-ethenyl-4b-hydroxy-1,4a,7-trimethyl-decahydrophenanthren-1-yl]methyl pentanoate)

INCHI for NP0217304 ([(1r,4ar,4br,7s,8ar,10ar)-7-ethenyl-4b-hydroxy-1,4a,7-trimethyl-decahydrophenanthren-1-yl]methyl pentanoate)

Structure for NP0217304 ([(1r,4ar,4br,7s,8ar,10ar)-7-ethenyl-4b-hydroxy-1,4a,7-trimethyl-decahydrophenanthren-1-yl]methyl pentanoate)

3D Structure for NP0217304 ([(1r,4ar,4br,7s,8ar,10ar)-7-ethenyl-4b-hydroxy-1,4a,7-trimethyl-decahydrophenanthren-1-yl]methyl pentanoate)