NP-MRD: Showing NP-Card for (6beta,7beta,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide (NP0334037)

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Record Information

Version

2.0

Created at

2024-09-09 21:46:33 UTC

Updated at

2024-09-09 21:46:33 UTC

NP-MRD ID

NP0334037

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6beta,7beta,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide

Description

Isolated from sage. (6Beta,7beta,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide is found in herbs and spices.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05252300182D          

 32 36  0  0  1  0            999 V2000
    3.8365    2.8673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9946    2.2805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5159   -0.8413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9518   -0.5165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8381   -0.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0271    1.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0801    0.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2574    1.8703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7357    0.3857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1652    2.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0585   -0.0855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4969    1.1754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6910    0.4510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4011    0.4130    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3375    1.2196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1078   -0.2492    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2848   -0.3063    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6569    0.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0147    1.6907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8544    1.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4055    0.2269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5829    1.3953    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6721    1.1923    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2446    1.6493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3125   -1.1718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0355    2.6535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1718    1.6369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7270    0.3016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1174   -0.3617    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6648   -0.8577    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7519   -0.9361    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4710    0.7074    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  2 10  1  0  0  0  0
  3 11  1  0  0  0  0
  4 21  1  0  0  0  0
  5 21  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7 21  1  0  0  0  0
 22  8  1  0  0  0  0
  9 11  2  0  0  0  0
  9 12  1  0  0  0  0
 23 10  1  6  0  0  0
 14 11  1  0  0  0  0
 23 12  1  0  0  0  0
 12 24  2  0  0  0  0
 14 13  1  0  0  0  0
 13 15  2  0  0  0  0
 16 13  1  0  0  0  0
 14 29  1  1  0  0  0
 14 23  1  0  0  0  0
 15 19  1  0  0  0  0
 22 15  1  6  0  0  0
 16 30  1  6  0  0  0
 16 17  1  0  0  0  0
 16 25  1  1  0  0  0
 17 31  1  6  0  0  0
 17 18  1  0  0  0  0
 17 28  1  0  0  0  0
 18 32  1  0  0  0  0
 18 21  1  0  0  0  0
 22 18  1  0  0  0  0
 23 19  1  0  0  0  0
 19 26  2  0  0  0  0
 22 20  1  0  0  0  0
 20 27  2  0  0  0  0
 20 28  1  0  0  0  0
M  END


  Mrv2104 05252300182D          

 32 36  0  0  1  0            999 V2000
    3.8365    2.8673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9946    2.2805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5159   -0.8413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9518   -0.5165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8381   -0.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0271    1.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0801    0.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2574    1.8703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7357    0.3857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1652    2.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0585   -0.0855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4969    1.1754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6910    0.4510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4011    0.4130    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3375    1.2196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1078   -0.2492    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2848   -0.3063    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6569    0.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0147    1.6907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8544    1.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4055    0.2269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5829    1.3953    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6721    1.1923    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2446    1.6493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3125   -1.1718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0355    2.6535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1718    1.6369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7270    0.3016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1174   -0.3617    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6648   -0.8577    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7519   -0.9361    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4710    0.7074    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  2 10  1  0  0  0  0
  3 11  1  0  0  0  0
  4 21  1  0  0  0  0
  5 21  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7 21  1  0  0  0  0
 22  8  1  0  0  0  0
  9 11  2  0  0  0  0
  9 12  1  0  0  0  0
 23 10  1  6  0  0  0
 14 11  1  0  0  0  0
 23 12  1  0  0  0  0
 12 24  2  0  0  0  0
 14 13  1  0  0  0  0
 13 15  2  0  0  0  0
 16 13  1  0  0  0  0
 14 29  1  1  0  0  0
 14 23  1  0  0  0  0
 15 19  1  0  0  0  0
 22 15  1  6  0  0  0
 16 30  1  6  0  0  0
 16 17  1  0  0  0  0
 16 25  1  1  0  0  0
 17 31  1  6  0  0  0
 17 18  1  0  0  0  0
 17 28  1  0  0  0  0
 18 32  1  0  0  0  0
 18 21  1  0  0  0  0
 22 18  1  0  0  0  0
 23 19  1  0  0  0  0
 19 26  2  0  0  0  0
 22 20  1  0  0  0  0
 20 27  2  0  0  0  0
 20 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334037

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12OC(=O)[C@]3(CCCC(C)(C)C13[H])C1=C([C@@]3([H])C(C)=CC(=O)[C@]3(C(C)C)C1=O)[C@@]2([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C23H28O5/c1-10(2)23-12(24)9-11(3)14(23)13-15(19(23)26)22-8-6-7-21(4,5)18(22)17(16(13)25)28-20(22)27/h9-10,14,16-18,25H,6-8H2,1-5H3/t14-,16-,17-,18?,22-,23+/m1/s1

> <INCHI_KEY>
IEPYKUBVROCHOQ-OQOFFOLUSA-N

> <FORMULA>
C23H28O5

> <MOLECULAR_WEIGHT>
384.472

> <EXACT_MASS>
384.193674002

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
43.02384847193015

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4R,8R,10R,11S)-10-hydroxy-7,13,13-trimethyl-4-(propan-2-yl)-18-oxapentacyclo[9.5.2.0^{1,12}.0^{2,9}.0^{4,8}]octadeca-2(9),6-diene-3,5,17-trione

> <JCHEM_LOGP>
3.293089614

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.413203469010273

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.483964103939375

> <JCHEM_PKA_STRONGEST_BASIC>
-3.457530718889512

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
103.44039999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4R,8R,10R,11S)-10-hydroxy-4-isopropyl-7,13,13-trimethyl-18-oxapentacyclo[9.5.2.0^{1,12}.0^{2,9}.0^{4,8}]octadeca-2(9),6-diene-3,5,17-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-MAY-23         0                                  
HETATM    1  C   UNK     0       7.161   5.352   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.323   4.257   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.430  -1.570   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.510  -0.964   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.431  -1.243   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.651   2.630   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.749   1.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.214   3.491   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.840   0.720   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.775   3.788   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.576  -0.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.394   2.194   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.023   0.842   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.349   0.771   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.363   2.277   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.935  -0.465   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.398  -0.572   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.093   1.071   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.627   3.156   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.595   2.084   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.490   0.424   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.955   2.605   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.855   2.226   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.790   3.079   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.317  -2.187   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       5.666   4.953   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.321   3.056   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       1.357   0.563   0.000  0.00  0.00           O+0
HETATM   29  H   UNK     0       5.819  -0.675   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.974  -1.601   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.404  -1.747   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       4.613   1.320   0.000  0.00  0.00           H+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4   21                                                            
CONECT    5   21                                                            
CONECT    6    7    8                                                       
CONECT    7    6   21                                                       
CONECT    8    6   22                                                       
CONECT    9   11   12                                                       
CONECT   10    1    2   23                                                  
CONECT   11    3    9   14                                                  
CONECT   12    9   23   24                                                  
CONECT   13   14   15   16                                                  
CONECT   14   11   13   29   23                                             
CONECT   15   13   19   22                                                  
CONECT   16   13   30   17   25                                             
CONECT   17   16   31   18   28                                             
CONECT   18   17   32   21   22                                             
CONECT   19   15   23   26                                                  
CONECT   20   22   27   28                                                  
CONECT   21    4    5    7   18                                             
CONECT   22    8   15   18   20                                             
CONECT   23   10   12   14   19                                             
CONECT   24   12                                                            
CONECT   25   16                                                            
CONECT   26   19                                                            
CONECT   27   20                                                            
CONECT   28   17   20                                                       
CONECT   29   14                                                            
CONECT   30   16                                                            
CONECT   31   17                                                            
CONECT   32   18                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   72    0
END

View in JSmol

Synonyms

Value	Source
(6b,7b,12b,13b)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide	Generator
(6Β,7β,12β,13β)-7-hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide	Generator

Chemical Formula

C₂₃H₂₈O₅

Average Mass

384.4720 Da

Monoisotopic Mass

384.19367 Da

IUPAC Name

(1S,4R,8R,10R,11S)-10-hydroxy-7,13,13-trimethyl-4-(propan-2-yl)-18-oxapentacyclo[9.5.2.0^{1,12}.0^{2,9}.0^{4,8}]octadeca-2(9),6-diene-3,5,17-trione

Traditional Name

(1S,4R,8R,10R,11S)-10-hydroxy-4-isopropyl-7,13,13-trimethyl-18-oxapentacyclo[9.5.2.0^{1,12}.0^{2,9}.0^{4,8}]octadeca-2(9),6-diene-3,5,17-trione

CAS Registry Number

Not Available

SMILES

[H][C@]12OC(=O)[C@]3(CCCC(C)(C)C13[H])C1=C([C@@]3([H])C(C)=CC(=O)[C@]3(C(C)C)C1=O)[C@@]2([H])O

InChI Identifier

InChI=1S/C23H28O5/c1-10(2)23-12(24)9-11(3)14(23)13-15(19(23)26)22-8-6-7-21(4,5)18(22)17(16(13)25)28-20(22)27/h9-10,14,16-18,25H,6-8H2,1-5H3/t14-,16-,17-,18?,22-,23+/m1/s1

InChI Key

IEPYKUBVROCHOQ-OQOFFOLUSA-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 diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpenoid
Diterpene lactone
Fatty alcohol ester
Gamma-keto acid
Fatty acid ester
Fatty acyl
Alpha-branched alpha,beta-unsaturated-ketone
Keto acid
Gamma butyrolactone
Alpha,beta-unsaturated ketone
Tetrahydrofuran
Enone
Cyclic alcohol
Acryloyl-group
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
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	3.29	ChemAxon
pKa (Strongest Acidic)	13.48	ChemAxon
pKa (Strongest Basic)	-3.5	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	1	ChemAxon
Refractivity	103.44 m³·mol⁻¹	ChemAxon
Polarizability	43.02 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

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 (6beta,7beta,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide (NP0334037)

MOL for NP0334037 ((6beta,7beta,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide)

3D MOL for NP0334037 ((6beta,7beta,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide)

3D SDF for NP0334037 ((6beta,7beta,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide)

3D-SDF for NP0334037 ((6beta,7beta,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide)

PDB for NP0334037 ((6beta,7beta,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide)

3D PDB for NP0334037 ((6beta,7beta,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide)

SMILES for NP0334037 ((6beta,7beta,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide)

INCHI for NP0334037 ((6beta,7beta,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide)

Structure for NP0334037 ((6beta,7beta,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide)

3D Structure for NP0334037 ((6beta,7beta,12beta,13beta)-7-Hydroxy-11,16-dioxo-8,14-apianadien-22,6-olide)