NP-MRD: Showing NP-Card for [16-(acetyloxy)-2,6-dihydroxy-5,9,13-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-5-yl]methyl acetate (NP0260882)

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Record Information

Version

2.0

Created at

2022-09-08 03:09:57 UTC

Updated at

2022-09-08 03:09:58 UTC

NP-MRD ID

NP0260882

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[16-(acetyloxy)-2,6-dihydroxy-5,9,13-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-5-yl]methyl acetate

Description

[16-(Acetyloxy)-2,6-dihydroxy-5,9,13-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadec-14-en-5-yl]methyl acetate belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. [16-(Acetyloxy)-2,6-dihydroxy-5,9,13-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadec-14-en-5-yl]methyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004171504362D          

 30 33  0  0  0  0            999 V2000
    7.0383    3.9389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7337    3.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3459    2.5622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8928    2.9708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5452    2.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8689    1.5668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6578    2.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4084    0.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2401    0.6862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1377    0.1634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3867    0.1087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7879    0.6324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9354   -0.2269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    0.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7751   -0.3706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9423   -0.5650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3427    0.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5387   -0.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9272    0.8213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5276    1.4565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3593    1.1147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7034    1.8951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3651    2.6962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5236    2.0474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0586    1.4117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8851    0.5670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4920    0.0924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5542   -0.8982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1458   -1.6996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4188   -1.3276    0.0000 C   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
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 14 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
  6 25  1  0  0  0  0
 12 25  1  0  0  0  0
 21 26  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
M  END


  Mrv1533004171504362D          

 30 33  0  0  0  0            999 V2000
    7.0383    3.9389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7337    3.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3459    2.5622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8928    2.9708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5452    2.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8689    1.5668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6578    2.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4084    0.9427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2401    0.6862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1377    0.1634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3867    0.1087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7879    0.6324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9354   -0.2269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    0.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7751   -0.3706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9423   -0.5650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3427    0.0619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5387   -0.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9272    0.8213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5276    1.4565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3593    1.1147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7034    1.8951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3651    2.6962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5236    2.0474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0586    1.4117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8851    0.5670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4920    0.0924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5542   -0.8982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1458   -1.6996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4188   -1.3276    0.0000 C   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
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 14 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
  6 25  1  0  0  0  0
 12 25  1  0  0  0  0
 21 26  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0260882

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC1(C)C(O)CCC2(C)C3CCC4(C)C=CC3(C4OC(C)=O)C(O)CC12

> <INCHI_IDENTIFIER>
InChI=1S/C24H36O6/c1-14(25)29-13-23(5)17-12-19(28)24-11-10-21(3,20(24)30-15(2)26)8-6-16(24)22(17,4)9-7-18(23)27/h10-11,16-20,27-28H,6-9,12-13H2,1-5H3

> <INCHI_KEY>
KWCBIWIJIRPENS-UHFFFAOYSA-N

> <FORMULA>
C24H36O6

> <MOLECULAR_WEIGHT>
420.546

> <EXACT_MASS>
420.251188879

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
46.116975084045635

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[16-(acetyloxy)-2,6-dihydroxy-5,9,13-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-5-yl]methyl acetate

> <ALOGPS_LOGP>
2.66

> <JCHEM_LOGP>
1.6798442663333315

> <ALOGPS_LOGS>
-4.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.891841266424432

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.285631557394527

> <JCHEM_PKA_STRONGEST_BASIC>
-2.960549747853136

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
111.38219999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.73e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[16-(acetyloxy)-2,6-dihydroxy-5,9,13-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-5-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      13.138   7.353   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.570   5.880   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      13.712   4.783   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      11.000   5.546   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.351   4.034   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.089   2.925   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.695   4.504   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.096   1.760   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      11.648   1.281   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.590   0.305   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.189   0.203   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.071   1.180   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.346  -0.424   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.541   0.890   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.180  -0.692   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.626  -1.055   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.506   0.116   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.006  -0.550   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.731   1.533   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.851   2.719   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.404   2.081   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.046   3.537   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.415   5.033   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.577   3.822   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.576   2.635   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.519   1.058   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.652   0.172   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.768  -1.677   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       4.005  -3.173   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.382  -2.478   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   25                                             
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   25                                             
CONECT   13   12                                                            
CONECT   14   12   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   26                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   14   22   26                                             
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24    6   12                                                  
CONECT   26   21   17   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
[16-(Acetyloxy)-2,6-dihydroxy-5,9,13-trimethyltetracyclo[11.2.1.0,.0,]hexadec-14-en-5-yl]methyl acetic acid	Generator
[16-(Acetyloxy)-2,6-dihydroxy-5,9,13-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-5-yl]methyl acetic acid	Generator

Chemical Formula

C₂₄H₃₆O₆

Average Mass

420.5460 Da

Monoisotopic Mass

420.25119 Da

IUPAC Name

[16-(acetyloxy)-2,6-dihydroxy-5,9,13-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-5-yl]methyl acetate

Traditional Name

[16-(acetyloxy)-2,6-dihydroxy-5,9,13-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-5-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC1(C)C(O)CCC2(C)C3CCC4(C)C=CC3(C4OC(C)=O)C(O)CC12

InChI Identifier

InChI=1S/C24H36O6/c1-14(25)29-13-23(5)17-12-19(28)24-11-10-21(3,20(24)30-15(2)26)8-6-16(24)22(17,4)9-7-18(23)27/h10-11,16-20,27-28H,6-9,12-13H2,1-5H3

InChI Key

KWCBIWIJIRPENS-UHFFFAOYSA-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 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

Diterpenoid
Beyerane diterpenoid
Steroid
Dicarboxylic acid or derivatives
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	2.66	ALOGPS
logP	1.68	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	14.29	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	111.38 m³·mol⁻¹	ChemAxon
Polarizability	46.12 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 [16-(acetyloxy)-2,6-dihydroxy-5,9,13-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-5-yl]methyl acetate (NP0260882)

MOL for NP0260882 ([16-(acetyloxy)-2,6-dihydroxy-5,9,13-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-5-yl]methyl acetate)

3D MOL for NP0260882 ([16-(acetyloxy)-2,6-dihydroxy-5,9,13-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-5-yl]methyl acetate)

3D SDF for NP0260882 ([16-(acetyloxy)-2,6-dihydroxy-5,9,13-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-5-yl]methyl acetate)

3D-SDF for NP0260882 ([16-(acetyloxy)-2,6-dihydroxy-5,9,13-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-5-yl]methyl acetate)

PDB for NP0260882 ([16-(acetyloxy)-2,6-dihydroxy-5,9,13-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-5-yl]methyl acetate)

3D PDB for NP0260882 ([16-(acetyloxy)-2,6-dihydroxy-5,9,13-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-5-yl]methyl acetate)

SMILES for NP0260882 ([16-(acetyloxy)-2,6-dihydroxy-5,9,13-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-5-yl]methyl acetate)

INCHI for NP0260882 ([16-(acetyloxy)-2,6-dihydroxy-5,9,13-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-5-yl]methyl acetate)

Structure for NP0260882 ([16-(acetyloxy)-2,6-dihydroxy-5,9,13-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-5-yl]methyl acetate)

3D Structure for NP0260882 ([16-(acetyloxy)-2,6-dihydroxy-5,9,13-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadec-14-en-5-yl]methyl acetate)