NP-MRD: Showing NP-Card for 7-O-Acetylhorminone (NP0047013)

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Record Information

Version

2.0

Created at

2022-03-17 20:33:12 UTC

Updated at

2022-03-17 20:33:12 UTC

NP-MRD ID

NP0047013

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-O-Acetylhorminone

Description

7-O-Acetylhorminone belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 7-O-Acetylhorminone is found in Coleus carnosus, Salvia amplexicaulis Lam., Salvia austriaca, Salvia blepharochaena Hedge and Hub. Mor., Salvia blepharochlaena, Salvia bracteata Banks and Sol., Salvia eriophora Boiss and Kotschy, Salvia tomentosa and Salvia verticillata. 7-O-Acetylhorminone is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241212572D          

 27 29  0  0  0  0            999 V2000
   -4.9205   -1.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6350   -1.4732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6350   -2.2982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9205   -2.7107    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2061   -2.2982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2061   -1.4732    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4916   -1.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4916   -2.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7771   -2.2982    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7771   -1.4732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7771    0.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4916   -0.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0627   -1.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0627   -0.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3330   -3.4252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5080   -3.4252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2061   -0.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0627   -2.7107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3482   -1.4732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2061    0.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7771    1.0018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3482    0.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3482    1.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6337   -0.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2698   -3.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6338   -2.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2341   -3.8802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 13  1  0  0  0  0
  7 10  2  0  0  0  0
 12  7  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  2  0  0  0  0
 13 14  1  0  0  0  0
  4 15  1  1  0  0  0
  4 16  1  6  0  0  0
  6 17  1  1  0  0  0
  9 18  1  6  0  0  0
 13 19  2  0  0  0  0
 12 20  2  0  0  0  0
 11 21  1  0  0  0  0
 14 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
M  END


  Mrv0541 02241212572D          

 27 29  0  0  0  0            999 V2000
   -4.9205   -1.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6350   -1.4732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6350   -2.2982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9205   -2.7107    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2061   -2.2982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2061   -1.4732    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4916   -1.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4916   -2.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7771   -2.2982    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7771   -1.4732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7771    0.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4916   -0.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0627   -1.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0627   -0.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3330   -3.4252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5080   -3.4252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2061   -0.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0627   -2.7107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3482   -1.4732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2061    0.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7771    1.0018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3482    0.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3482    1.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6337   -0.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2698   -3.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6338   -2.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2341   -3.8802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 13  1  0  0  0  0
  7 10  2  0  0  0  0
 12  7  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  2  0  0  0  0
 13 14  1  0  0  0  0
  4 15  1  1  0  0  0
  4 16  1  6  0  0  0
  6 17  1  1  0  0  0
  9 18  1  6  0  0  0
 13 19  2  0  0  0  0
 12 20  2  0  0  0  0
 11 21  1  0  0  0  0
 14 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0047013

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=C(O)C(=O)C2=C([C@@H](CC3C(C)(C)CCC[C@]23C)OC(C)=O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O5/c1-11(2)15-18(24)16-13(27-12(3)23)10-14-21(4,5)8-7-9-22(14,6)17(16)20(26)19(15)25/h11,13-14,25H,7-10H2,1-6H3/t13-,14?,22+/m1/s1

> <INCHI_KEY>
XDBVTCDGDQLEKG-QWDRYGJXSA-N

> <FORMULA>
C22H30O5

> <MOLECULAR_WEIGHT>
374.4706

> <EXACT_MASS>
374.20932407

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
41.39385211210723

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4aS,9R)-6-hydroxy-1,1,4a-trimethyl-5,8-dioxo-7-(propan-2-yl)-1,2,3,4,4a,5,8,9,10,10a-decahydrophenanthren-9-yl acetate

> <ALOGPS_LOGP>
3.36

> <JCHEM_LOGP>
3.945984086333334

> <ALOGPS_LOGS>
-4.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.50491453649846

> <JCHEM_PKA_STRONGEST_BASIC>
-4.008210381735574

> <JCHEM_POLAR_SURFACE_AREA>
80.67000000000002

> <JCHEM_REFRACTIVITY>
103.27969999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.49e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4aS,9R)-6-hydroxy-7-isopropyl-1,1,4a-trimethyl-5,8-dioxo-2,3,4,9,10,10a-hexahydrophenanthren-9-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -9.185  -1.980   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.519  -2.750   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.519  -4.290   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.185  -5.060   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.851  -4.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.851  -2.750   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.518  -1.980   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.518  -5.060   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.184  -4.290   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.184  -2.750   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.184   0.330   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.518  -0.440   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.850  -1.980   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.850  -0.440   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -9.955  -6.394   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.415  -6.394   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -7.851  -1.210   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -3.850  -5.060   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -2.517  -2.750   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -7.851   0.330   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -5.184   1.870   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.517   0.330   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.517   1.870   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.183  -0.440   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.370  -5.705   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.183  -5.060   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.304  -7.243   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   15   16                                             
CONECT    5    4    6    8                                                  
CONECT    6    1    7    5   17                                             
CONECT    7    6   10   12                                                  
CONECT    8    5    9                                                       
CONECT    9    8   10   18                                                  
CONECT   10    9   13    7                                                  
CONECT   11   12   14   21                                                  
CONECT   12    7   11   20                                                  
CONECT   13   10   14   19                                                  
CONECT   14   11   13   22                                                  
CONECT   15    4                                                            
CONECT   16    4                                                            
CONECT   17    6                                                            
CONECT   18    9   25                                                       
CONECT   19   13                                                            
CONECT   20   12                                                            
CONECT   21   11                                                            
CONECT   22   14   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   18   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₀O₅

Average Mass

374.4706 Da

Monoisotopic Mass

374.20932 Da

IUPAC Name

(4aS,9R)-6-hydroxy-1,1,4a-trimethyl-5,8-dioxo-7-(propan-2-yl)-1,2,3,4,4a,5,8,9,10,10a-decahydrophenanthren-9-yl acetate

Traditional Name

(4aS,9R)-6-hydroxy-7-isopropyl-1,1,4a-trimethyl-5,8-dioxo-2,3,4,9,10,10a-hexahydrophenanthren-9-yl acetate

CAS Registry Number

Not Available

SMILES

CC(C)C1=C(O)C(=O)C2=C([C@@H](CC3C(C)(C)CCC[C@]23C)OC(C)=O)C1=O

InChI Identifier

InChI=1S/C22H30O5/c1-11(2)15-18(24)16-13(27-12(3)23)10-14-21(4,5)8-7-9-22(14,6)17(16)20(26)19(15)25/h11,13-14,25H,7-10H2,1-6H3/t13-,14?,22+/m1/s1

InChI Key

XDBVTCDGDQLEKG-QWDRYGJXSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Coleus carnosus	Plant	KNApSAcK
Salvia amplexicaulis Lam.	Plant	KNApSAcK
Salvia austriaca	Plant	KNApSAcK
Salvia blepharochaena Hedge and Hub. Mor.	Plant	KNApSAcK
Salvia blepharochlaena	Plant	KNApSAcK
Salvia bracteata Banks and Sol.	Plant	KNApSAcK
Salvia eriophora Boiss and Kotschy	Plant	KNApSAcK
Salvia officinalis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Salvia tomentosa	Plant	KNApSAcK
Salvia verticillata	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Abietane diterpenoid
Diterpenoid
Hydrophenanthrene
Phenanthrene
Vinylogous acid
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Enol
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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	3.36	ALOGPS
logP	3.95	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	8.5	ChemAxon
pKa (Strongest Basic)	-4	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	3	ChemAxon
Refractivity	103.28 m³·mol⁻¹	ChemAxon
Polarizability	41.39 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

FDB006981

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 7-O-Acetylhorminone (NP0047013)

MOL for NP0047013 (7-O-Acetylhorminone)

3D MOL for NP0047013 (7-O-Acetylhorminone)

3D SDF for NP0047013 (7-O-Acetylhorminone)

3D-SDF for NP0047013 (7-O-Acetylhorminone)

PDB for NP0047013 (7-O-Acetylhorminone)

3D PDB for NP0047013 (7-O-Acetylhorminone)

SMILES for NP0047013 (7-O-Acetylhorminone)

INCHI for NP0047013 (7-O-Acetylhorminone)

Structure for NP0047013 (7-O-Acetylhorminone)

3D Structure for NP0047013 (7-O-Acetylhorminone)