NP-MRD: Showing NP-Card for (1r,2s,5s,6r,9s,10s,13s,15r,16s)-6-ethyl-15,16-dihydroxy-5-methyl-17-oxapentacyclo[14.2.1.0¹,¹³.0²,¹⁰.0⁵,⁹]nonadecan-7-one (NP0166201)

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Record Information

Version

2.0

Created at

2022-09-03 01:32:02 UTC

Updated at

2022-09-03 01:32:02 UTC

NP-MRD ID

NP0166201

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,5s,6r,9s,10s,13s,15r,16s)-6-ethyl-15,16-dihydroxy-5-methyl-17-oxapentacyclo[14.2.1.0¹,¹³.0²,¹⁰.0⁵,⁹]nonadecan-7-one

Description

2Alpha,3beta-Dihydroxy-2,19-epoxy-5alpha-pregnane-16-one belongs to the class of organic compounds known as 16-oxosteroids. These are steroid derivatives carrying a C=O group at the 16-position of the steroid skeleton. (1r,2s,5s,6r,9s,10s,13s,15r,16s)-6-ethyl-15,16-dihydroxy-5-methyl-17-oxapentacyclo[14.2.1.0¹,¹³.0²,¹⁰.0⁵,⁹]nonadecan-7-one is found in Melia volkensii and Trichilia claussenii. Based on a literature review very few articles have been published on 2alpha,3beta-Dihydroxy-2,19-epoxy-5alpha-pregnane-16-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309032203322D          

 25 29  0  0  1  0            999 V2000
    6.4008    1.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5871    1.5446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0624    0.9080    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2691    0.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0367   -0.1930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5733   -0.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9367    0.1907    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1208    0.0686    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8135   -0.7017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9953   -0.8288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4734   -0.1781    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6344   -0.4051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0718    0.2391    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7369    0.0758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3441    1.0628    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3986    1.4220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0446    0.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7508    0.6591    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6623    1.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8196    1.7860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6071    0.7142    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9094    1.4818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7253    1.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2390    0.9583    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6198    1.6901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 18 17  1  6  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 18 21  1  0  0  0  0
  8 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
  7 24  1  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  1  0  0  0
M  END


  Mrv1652309032203322D          

 25 29  0  0  1  0            999 V2000
    6.4008    1.4086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5871    1.5446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0624    0.9080    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2691    0.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0367   -0.1930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5733   -0.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9367    0.1907    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1208    0.0686    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8135   -0.7017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9953   -0.8288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4734   -0.1781    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6344   -0.4051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0718    0.2391    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7369    0.0758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3441    1.0628    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3986    1.4220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0446    0.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7508    0.6591    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6623    1.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8196    1.7860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6071    0.7142    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9094    1.4818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7253    1.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2390    0.9583    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6198    1.6901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 11 10  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 18 17  1  6  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 18 21  1  0  0  0  0
  8 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
  7 24  1  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0166201

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H]1C(=O)C[C@H]2[C@@H]3CC[C@H]4C[C@@H](O)[C@]5(O)C[C@]4(CO5)[C@H]3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O4/c1-3-14-17(22)9-16-13-5-4-12-8-18(23)21(24)10-20(12,11-25-21)15(13)6-7-19(14,16)2/h12-16,18,23-24H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,18+,19+,20+,21-/m0/s1

> <INCHI_KEY>
YTQLYPLDMHKTML-JHZVCAIQSA-N

> <FORMULA>
C21H32O4

> <MOLECULAR_WEIGHT>
348.483

> <EXACT_MASS>
348.23005951

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
39.84926732598727

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,5S,6R,9S,10S,13S,15R,16S)-6-ethyl-15,16-dihydroxy-5-methyl-17-oxapentacyclo[14.2.1.0^{1,13}.0^{2,10}.0^{5,9}]nonadecan-7-one

> <ALOGPS_LOGP>
2.09

> <JCHEM_LOGP>
2.630548417

> <ALOGPS_LOGS>
-3.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.076273145715064

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.113266858638164

> <JCHEM_PKA_STRONGEST_BASIC>
-3.565404087477816

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
94.1364

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.56e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,5S,6R,9S,10S,13S,15R,16S)-6-ethyl-15,16-dihydroxy-5-methyl-17-oxapentacyclo[14.2.1.0^{1,13}.0^{2,10}.0^{5,9}]nonadecan-7-one

> <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      11.948   2.629   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.429   2.883   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.450   1.695   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.836   0.204   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      11.269  -0.360   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.537  -0.624   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.348   0.356   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.825   0.128   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.252  -1.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.724  -1.547   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.750  -0.332   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.184  -0.756   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.134   0.446   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.375   0.141   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.642   1.984   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.744   2.654   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.950   1.532   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.268   1.230   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.103   2.901   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.530   3.334   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.867   1.333   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.431   2.766   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.954   2.994   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.913   1.789   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.624   3.155   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   24                                                  
CONECT    8    7    9   21                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17   20                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   11   19   21                                             
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
CONECT   21   18    8   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23    7    3   25                                             
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

View in JSmol

Synonyms

Value	Source
2a,3b-Dihydroxy-2,19-epoxy-5a-pregnane-16-one	Generator
2Α,3β-dihydroxy-2,19-epoxy-5α-pregnane-16-one	Generator

Chemical Formula

C₂₁H₃₂O₄

Average Mass

348.4830 Da

Monoisotopic Mass

348.23006 Da

IUPAC Name

(1R,2S,5S,6R,9S,10S,13S,15R,16S)-6-ethyl-15,16-dihydroxy-5-methyl-17-oxapentacyclo[14.2.1.0^{1,13}.0^{2,10}.0^{5,9}]nonadecan-7-one

Traditional Name

(1R,2S,5S,6R,9S,10S,13S,15R,16S)-6-ethyl-15,16-dihydroxy-5-methyl-17-oxapentacyclo[14.2.1.0^{1,13}.0^{2,10}.0^{5,9}]nonadecan-7-one

CAS Registry Number

Not Available

SMILES

CC[C@H]1C(=O)C[C@H]2[C@@H]3CC[C@H]4C[C@@H](O)[C@]5(O)C[C@]4(CO5)[C@H]3CC[C@]12C

InChI Identifier

InChI=1S/C21H32O4/c1-3-14-17(22)9-16-13-5-4-12-8-18(23)21(24)10-20(12,11-25-21)15(13)6-7-19(14,16)2/h12-16,18,23-24H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,18+,19+,20+,21-/m0/s1

InChI Key

YTQLYPLDMHKTML-JHZVCAIQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Melia volkensii	LOTUS Database	35616633
Trichilia claussenii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 16-oxosteroids. These are steroid derivatives carrying a C=O group at the 16-position of the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Oxosteroids

Direct Parent

16-oxosteroids

Alternative Parents

Substituents

3-hydroxysteroid
2-hydroxysteroid
Hydroxysteroid
16-oxosteroid
3-beta-hydroxysteroid
Oxepane
Cyclic alcohol
Tetrahydrofuran
Hemiacetal
Ketone
Cyclic ketone
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	2.09	ALOGPS
logP	2.63	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	11.11	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	94.14 m³·mol⁻¹	ChemAxon
Polarizability	39.85 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

10267326

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21634667

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,5s,6r,9s,10s,13s,15r,16s)-6-ethyl-15,16-dihydroxy-5-methyl-17-oxapentacyclo[14.2.1.0¹,¹³.0²,¹⁰.0⁵,⁹]nonadecan-7-one (NP0166201)

MOL for NP0166201 ((1r,2s,5s,6r,9s,10s,13s,15r,16s)-6-ethyl-15,16-dihydroxy-5-methyl-17-oxapentacyclo[14.2.1.0¹,¹³.0²,¹⁰.0⁵,⁹]nonadecan-7-one)

3D MOL for NP0166201 ((1r,2s,5s,6r,9s,10s,13s,15r,16s)-6-ethyl-15,16-dihydroxy-5-methyl-17-oxapentacyclo[14.2.1.0¹,¹³.0²,¹⁰.0⁵,⁹]nonadecan-7-one)

3D SDF for NP0166201 ((1r,2s,5s,6r,9s,10s,13s,15r,16s)-6-ethyl-15,16-dihydroxy-5-methyl-17-oxapentacyclo[14.2.1.0¹,¹³.0²,¹⁰.0⁵,⁹]nonadecan-7-one)

3D-SDF for NP0166201 ((1r,2s,5s,6r,9s,10s,13s,15r,16s)-6-ethyl-15,16-dihydroxy-5-methyl-17-oxapentacyclo[14.2.1.0¹,¹³.0²,¹⁰.0⁵,⁹]nonadecan-7-one)

PDB for NP0166201 ((1r,2s,5s,6r,9s,10s,13s,15r,16s)-6-ethyl-15,16-dihydroxy-5-methyl-17-oxapentacyclo[14.2.1.0¹,¹³.0²,¹⁰.0⁵,⁹]nonadecan-7-one)

3D PDB for NP0166201 ((1r,2s,5s,6r,9s,10s,13s,15r,16s)-6-ethyl-15,16-dihydroxy-5-methyl-17-oxapentacyclo[14.2.1.0¹,¹³.0²,¹⁰.0⁵,⁹]nonadecan-7-one)

SMILES for NP0166201 ((1r,2s,5s,6r,9s,10s,13s,15r,16s)-6-ethyl-15,16-dihydroxy-5-methyl-17-oxapentacyclo[14.2.1.0¹,¹³.0²,¹⁰.0⁵,⁹]nonadecan-7-one)

INCHI for NP0166201 ((1r,2s,5s,6r,9s,10s,13s,15r,16s)-6-ethyl-15,16-dihydroxy-5-methyl-17-oxapentacyclo[14.2.1.0¹,¹³.0²,¹⁰.0⁵,⁹]nonadecan-7-one)

Structure for NP0166201 ((1r,2s,5s,6r,9s,10s,13s,15r,16s)-6-ethyl-15,16-dihydroxy-5-methyl-17-oxapentacyclo[14.2.1.0¹,¹³.0²,¹⁰.0⁵,⁹]nonadecan-7-one)

3D Structure for NP0166201 ((1r,2s,5s,6r,9s,10s,13s,15r,16s)-6-ethyl-15,16-dihydroxy-5-methyl-17-oxapentacyclo[14.2.1.0¹,¹³.0²,¹⁰.0⁵,⁹]nonadecan-7-one)