NP-MRD: Showing NP-Card for methyl (1r,4as,9s,10s,10ar)-10-(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2-oxo-10,10a-dihydro-9h-phenanthrene-1-carboxylate (NP0218544)

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Record Information

Version

2.0

Created at

2022-09-05 19:14:32 UTC

Updated at

2022-09-05 19:14:32 UTC

NP-MRD ID

NP0218544

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,4as,9s,10s,10ar)-10-(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2-oxo-10,10a-dihydro-9h-phenanthrene-1-carboxylate

Description

Leonubiastrin belongs to the class of organic compounds known as 1-hydroxysteroids. These are steroids carrying a hydroxyl group at the 1-position of the steroid backbone. methyl (1r,4as,9s,10s,10ar)-10-(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2-oxo-10,10a-dihydro-9h-phenanthrene-1-carboxylate is found in Chaiturus marrubiastrum. Based on a literature review very few articles have been published on Leonubiastrin.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052221142D          

 30 32  0  0  1  0            999 V2000
   -1.3918   -4.1538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6165   -3.8716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4733   -3.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1053   -2.5288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.7770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4452   -3.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9520   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.4914    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7770   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -3.4914    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1270   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -4.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -4.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -5.6349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.7770    0.0000 C   0  0  1  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
  5  3  1  1  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  2  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 30 25  1  1  0  0  0
 11 30  1  0  0  0  0
  5 30  1  0  0  0  0
M  END


  Mrv1652309052221142D          

 30 32  0  0  1  0            999 V2000
   -1.3918   -4.1538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6165   -3.8716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4733   -3.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1053   -2.5288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.7770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4452   -3.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9520   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.4914    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7770   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -3.4914    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1270   -4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -4.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -4.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -5.6349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.7770    0.0000 C   0  0  1  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
  5  3  1  1  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  2  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 30 25  1  1  0  0  0
 11 30  1  0  0  0  0
  5 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0218544

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@]1(C)[C@@H]2[C@H](OC(C)=O)[C@@H](O)C3=CC(=CC(O)=C3[C@@]2(C)C=CC1=O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C23H28O7/c1-11(2)13-9-14-17(15(25)10-13)22(4)8-7-16(26)23(5,21(28)29-6)20(22)19(18(14)27)30-12(3)24/h7-11,18-20,25,27H,1-6H3/t18-,19+,20+,22+,23-/m0/s1

> <INCHI_KEY>
ROWKODQLOIEBHL-XCWFNORRSA-N

> <FORMULA>
C23H28O7

> <MOLECULAR_WEIGHT>
416.47

> <EXACT_MASS>
416.183503242

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
43.71054563213202

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,4aS,9S,10S,10aR)-10-(acetyloxy)-5,9-dihydroxy-1,4a-dimethyl-2-oxo-7-(propan-2-yl)-1,2,4a,9,10,10a-hexahydrophenanthrene-1-carboxylate

> <JCHEM_LOGP>
3.134998057

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.526302679627488

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.166073482114527

> <JCHEM_PKA_STRONGEST_BASIC>
-3.513814770264557

> <JCHEM_POLAR_SURFACE_AREA>
110.13000000000002

> <JCHEM_REFRACTIVITY>
109.932

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,4aS,9S,10S,10aR)-10-(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2-oxo-10,10a-dihydro-9H-phenanthrene-1-carboxylate

> <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      -2.598  -7.754   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.151  -7.227   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.883  -5.710   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.063  -4.720   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.564  -5.184   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.831  -6.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.206  -3.850   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.746  -3.850   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.564  -2.516   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.104  -2.516   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.874  -3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.644  -2.516   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414  -3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.184  -2.516   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.414  -1.183   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.724  -2.516   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.494  -3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.034  -3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.804  -2.516   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.804  -5.184   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.724  -5.184   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.184  -5.184   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.414  -6.517   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.184  -7.851   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.874  -6.517   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.104  -7.851   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.874  -9.185   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.414  -9.185   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.104 -10.518   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.104  -5.184   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7   30                                             
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   30                                             
CONECT   12   11                                                            
CONECT   13   11   14   22                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   17   22                                                       
CONECT   22   21   13   23                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   25   11    5                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₈O₇

Average Mass

416.4700 Da

Monoisotopic Mass

416.18350 Da

IUPAC Name

methyl (1R,4aS,9S,10S,10aR)-10-(acetyloxy)-5,9-dihydroxy-1,4a-dimethyl-2-oxo-7-(propan-2-yl)-1,2,4a,9,10,10a-hexahydrophenanthrene-1-carboxylate

Traditional Name

methyl (1R,4aS,9S,10S,10aR)-10-(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2-oxo-10,10a-dihydro-9H-phenanthrene-1-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@]1(C)[C@@H]2[C@H](OC(C)=O)[C@@H](O)C3=CC(=CC(O)=C3[C@@]2(C)C=CC1=O)C(C)C

InChI Identifier

InChI=1S/C23H28O7/c1-11(2)13-9-14-17(15(25)10-13)22(4)8-7-16(26)23(5,21(28)29-6)20(22)19(18(14)27)30-12(3)24/h7-11,18-20,25,27H,1-6H3/t18-,19+,20+,22+,23-/m0/s1

InChI Key

ROWKODQLOIEBHL-XCWFNORRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Leonurus marrubiastrum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-hydroxysteroids. These are steroids carrying a hydroxyl group at the 1-position of the steroid backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

1-hydroxysteroids

Alternative Parents

Substituents

Abietane diterpenoid
Diterpenoid
6-hydroxysteroid
1-hydroxysteroid
Hydrophenanthrene
Phenanthrene
Tetralin
Cyclohexenone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Dicarboxylic acid or derivatives
Methyl ester
Carboxylic acid ester
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid derivative
Carbonyl group
Organic oxide
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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	3.13	ChemAxon
pKa (Strongest Acidic)	9.17	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	109.93 m³·mol⁻¹	ChemAxon
Polarizability	43.71 Å³	ChemAxon
Number of Rings	3	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

C00044212

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

15390948

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1r,4as,9s,10s,10ar)-10-(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2-oxo-10,10a-dihydro-9h-phenanthrene-1-carboxylate (NP0218544)

MOL for NP0218544 (methyl (1r,4as,9s,10s,10ar)-10-(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2-oxo-10,10a-dihydro-9h-phenanthrene-1-carboxylate)

3D MOL for NP0218544 (methyl (1r,4as,9s,10s,10ar)-10-(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2-oxo-10,10a-dihydro-9h-phenanthrene-1-carboxylate)

3D SDF for NP0218544 (methyl (1r,4as,9s,10s,10ar)-10-(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2-oxo-10,10a-dihydro-9h-phenanthrene-1-carboxylate)

3D-SDF for NP0218544 (methyl (1r,4as,9s,10s,10ar)-10-(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2-oxo-10,10a-dihydro-9h-phenanthrene-1-carboxylate)

PDB for NP0218544 (methyl (1r,4as,9s,10s,10ar)-10-(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2-oxo-10,10a-dihydro-9h-phenanthrene-1-carboxylate)

3D PDB for NP0218544 (methyl (1r,4as,9s,10s,10ar)-10-(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2-oxo-10,10a-dihydro-9h-phenanthrene-1-carboxylate)

SMILES for NP0218544 (methyl (1r,4as,9s,10s,10ar)-10-(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2-oxo-10,10a-dihydro-9h-phenanthrene-1-carboxylate)

INCHI for NP0218544 (methyl (1r,4as,9s,10s,10ar)-10-(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2-oxo-10,10a-dihydro-9h-phenanthrene-1-carboxylate)

Structure for NP0218544 (methyl (1r,4as,9s,10s,10ar)-10-(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2-oxo-10,10a-dihydro-9h-phenanthrene-1-carboxylate)

3D Structure for NP0218544 (methyl (1r,4as,9s,10s,10ar)-10-(acetyloxy)-5,9-dihydroxy-7-isopropyl-1,4a-dimethyl-2-oxo-10,10a-dihydro-9h-phenanthrene-1-carboxylate)