NP-MRD: Showing NP-Card for {8-formyl-11,15-dihydroxy-7,7-dimethyl-14-methylidene-2-oxo-3-oxatetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-9-yl}methyl acetate (NP0251845)

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Record Information

Version

1.0

Created at

2022-09-07 15:09:47 UTC

Updated at

2022-09-07 15:09:47 UTC

NP-MRD ID

NP0251845

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{8-formyl-11,15-dihydroxy-7,7-dimethyl-14-methylidene-2-oxo-3-oxatetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-9-yl}methyl acetate

Description

{8-Formyl-11,15-dihydroxy-7,7-dimethyl-14-methylidene-2-oxo-3-oxatetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecan-9-yl}methyl acetate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. {8-formyl-11,15-dihydroxy-7,7-dimethyl-14-methylidene-2-oxo-3-oxatetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-9-yl}methyl acetate is found in Isodon serra. {8-Formyl-11,15-dihydroxy-7,7-dimethyl-14-methylidene-2-oxo-3-oxatetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecan-9-yl}methyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004251514212D          

 29 32  0  0  0  0            999 V2000
    1.8199    2.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4705    2.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6485    2.0173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9430    1.4121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5936    0.6647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0661   -0.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3132   -0.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1184   -0.9782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6765   -0.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4294    0.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4664    1.2406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2475    0.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6242    0.5960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3771    1.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9352    1.9907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7596   -1.4229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9506   -1.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4165   -1.8832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6469   -0.4671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1726    0.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4028    0.5335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1586    1.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0038    1.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5595    1.6408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2474    0.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7854   -0.2403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5987   -0.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1637   -0.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3012   -1.6618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  7 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
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
  6 25  1  0  0  0  0
 19 25  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END


  Mrv1533004251514212D          

 29 32  0  0  0  0            999 V2000
    1.8199    2.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4705    2.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6485    2.0173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9430    1.4121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5936    0.6647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0661   -0.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3132   -0.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1184   -0.9782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6765   -0.3707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4294    0.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4664    1.2406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2475    0.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6242    0.5960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3771    1.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9352    1.9907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7596   -1.4229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9506   -1.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4165   -1.8832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6469   -0.4671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1726    0.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4028    0.5335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1586    1.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0038    1.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5595    1.6408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2474    0.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7854   -0.2403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5987   -0.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1637   -0.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3012   -1.6618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  7 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
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
  6 25  1  0  0  0  0
 19 25  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0251845

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC12C(CCC(C)(C)C1C=O)OC(=O)C13CC(CC(O)C21)C(=C)C3O

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O7/c1-11-13-7-14(25)17-21(8-13,18(11)26)19(27)29-16-5-6-20(3,4)15(9-23)22(16,17)10-28-12(2)24/h9,13-18,25-26H,1,5-8,10H2,2-4H3

> <INCHI_KEY>
SDGHSGBMLDNKAV-UHFFFAOYSA-N

> <FORMULA>
C22H30O7

> <MOLECULAR_WEIGHT>
406.475

> <EXACT_MASS>
406.199153306

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
41.783172368825475

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{8-formyl-11,15-dihydroxy-7,7-dimethyl-14-methylidene-2-oxo-3-oxatetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-9-yl}methyl acetate

> <ALOGPS_LOGP>
0.95

> <JCHEM_LOGP>
0.25901173900000046

> <ALOGPS_LOGS>
-2.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.890589881437766

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.841073513713372

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8601810370707206

> <JCHEM_POLAR_SURFACE_AREA>
110.13000000000002

> <JCHEM_REFRACTIVITY>
101.8352

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.74e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{8-formyl-11,15-dihydroxy-7,7-dimethyl-14-methylidene-2-oxo-3-oxatetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-9-yl}methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       3.397   5.293   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.745   3.898   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.211   3.766   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.627   2.636   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.975   1.241   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.857  -0.022   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.318  -1.491   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.821  -1.826   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.863  -0.692   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.402   0.777   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.471   2.316   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.929   0.976   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.899   1.113   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.437   2.582   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.479   3.716   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       3.285  -2.656   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.774  -2.341   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.778  -3.515   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.208  -0.872   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.322   0.124   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.752   0.996   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.296   2.224   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.874   1.924   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.911   3.063   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.328   0.347   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.466  -0.449   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.984  -0.707   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.306  -1.583   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.562  -3.102   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   13   25                                             
CONECT    7    6    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10    6   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16    7   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   25   28                                             
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23    6   19                                                  
CONECT   26   21   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   19   29                                                  
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
{8-formyl-11,15-dihydroxy-7,7-dimethyl-14-methylidene-2-oxo-3-oxatetracyclo[11.2.1.0,.0,]hexadecan-9-yl}methyl acetic acid	Generator
{8-formyl-11,15-dihydroxy-7,7-dimethyl-14-methylidene-2-oxo-3-oxatetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-9-yl}methyl acetic acid	Generator

Chemical Formula

C₂₂H₃₀O₇

Average Mass

406.4750 Da

Monoisotopic Mass

406.19915 Da

IUPAC Name

{8-formyl-11,15-dihydroxy-7,7-dimethyl-14-methylidene-2-oxo-3-oxatetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-9-yl}methyl acetate

Traditional Name

{8-formyl-11,15-dihydroxy-7,7-dimethyl-14-methylidene-2-oxo-3-oxatetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-9-yl}methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC12C(CCC(C)(C)C1C=O)OC(=O)C13CC(CC(O)C21)C(=C)C3O

InChI Identifier

InChI=1S/C22H30O7/c1-11-13-7-14(25)17-21(8-13,18(11)26)19(27)29-16-5-6-20(3,4)15(9-23)22(16,17)10-28-12(2)24/h9,13-18,25-26H,1,5-8,10H2,2-4H3

InChI Key

SDGHSGBMLDNKAV-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Isodon serra	LOTUS Database	35616633

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

Diterpene lactone
Diterpenoid
Kaurane diterpenoid
Delta valerolactone
Delta_valerolactone
Dicarboxylic acid or derivatives
Oxane
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Aldehyde
Organooxygen compound
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	0.95	ALOGPS
logP	0.26	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	13.84	ChemAxon
pKa (Strongest Basic)	-2.9	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	4	ChemAxon
Refractivity	101.84 m³·mol⁻¹	ChemAxon
Polarizability	41.78 Å³	ChemAxon
Number of Rings	4	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

LOTUS database [Link]

Showing NP-Card for {8-formyl-11,15-dihydroxy-7,7-dimethyl-14-methylidene-2-oxo-3-oxatetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-9-yl}methyl acetate (NP0251845)

MOL for NP0251845 ({8-formyl-11,15-dihydroxy-7,7-dimethyl-14-methylidene-2-oxo-3-oxatetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-9-yl}methyl acetate)

3D MOL for NP0251845 ({8-formyl-11,15-dihydroxy-7,7-dimethyl-14-methylidene-2-oxo-3-oxatetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-9-yl}methyl acetate)

3D SDF for NP0251845 ({8-formyl-11,15-dihydroxy-7,7-dimethyl-14-methylidene-2-oxo-3-oxatetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-9-yl}methyl acetate)

3D-SDF for NP0251845 ({8-formyl-11,15-dihydroxy-7,7-dimethyl-14-methylidene-2-oxo-3-oxatetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-9-yl}methyl acetate)

PDB for NP0251845 ({8-formyl-11,15-dihydroxy-7,7-dimethyl-14-methylidene-2-oxo-3-oxatetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-9-yl}methyl acetate)

3D PDB for NP0251845 ({8-formyl-11,15-dihydroxy-7,7-dimethyl-14-methylidene-2-oxo-3-oxatetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-9-yl}methyl acetate)

SMILES for NP0251845 ({8-formyl-11,15-dihydroxy-7,7-dimethyl-14-methylidene-2-oxo-3-oxatetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-9-yl}methyl acetate)

INCHI for NP0251845 ({8-formyl-11,15-dihydroxy-7,7-dimethyl-14-methylidene-2-oxo-3-oxatetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-9-yl}methyl acetate)

Structure for NP0251845 ({8-formyl-11,15-dihydroxy-7,7-dimethyl-14-methylidene-2-oxo-3-oxatetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-9-yl}methyl acetate)

3D Structure for NP0251845 ({8-formyl-11,15-dihydroxy-7,7-dimethyl-14-methylidene-2-oxo-3-oxatetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-9-yl}methyl acetate)