NP-MRD: Showing NP-Card for {8-formyl-14-hydroxy-2-methoxy-10-methyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradeca-1(9),2,5,7-tetraen-6-yl}methyl acetate (NP0270962)

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Record Information

Version

2.0

Created at

2022-09-08 17:05:15 UTC

Updated at

2022-09-08 17:05:15 UTC

NP-MRD ID

NP0270962

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{8-formyl-14-hydroxy-2-methoxy-10-methyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradeca-1(9),2,5,7-tetraen-6-yl}methyl acetate

Description

{8-Formyl-14-hydroxy-2-methoxy-10-methyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]Tetradeca-1,3(7),5,8-tetraen-6-yl}methyl acetate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. {8-formyl-14-hydroxy-2-methoxy-10-methyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradeca-1(9),2,5,7-tetraen-6-yl}methyl acetate is found in Roldana angulifolia. {8-Formyl-14-hydroxy-2-methoxy-10-methyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]Tetradeca-1,3(7),5,8-tetraen-6-yl}methyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004231520382D          

 25 28  0  0  0  0            999 V2000
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5983   -3.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1503   -4.0006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8953   -4.7852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4474   -5.3983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0884   -4.9567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -1.2680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7  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
  4 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 13 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 17 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  3 25  2  0  0  0  0
 16 25  1  0  0  0  0
M  END


  Mrv1533004231520382D          

 25 28  0  0  0  0            999 V2000
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5983   -3.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1503   -4.0006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8953   -4.7852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4474   -5.3983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0884   -4.9567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -1.2680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7  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
  4 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 13 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 17 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  3 25  2  0  0  0  0
 16 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0270962

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2OC=C(COC(C)=O)C2=C(C=O)C2=C1C(O)C1OC1C2C

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O7/c1-7-11-10(4-19)12-9(5-23-8(2)20)6-24-17(12)16(22-3)13(11)14(21)18-15(7)25-18/h4,6-7,14-15,18,21H,5H2,1-3H3

> <INCHI_KEY>
QSPXRVDTGKRUHN-UHFFFAOYSA-N

> <FORMULA>
C18H18O7

> <MOLECULAR_WEIGHT>
346.335

> <EXACT_MASS>
346.10525292

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
34.54325272062887

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{8-formyl-14-hydroxy-2-methoxy-10-methyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradeca-1(9),2,5,7-tetraen-6-yl}methyl acetate

> <ALOGPS_LOGP>
1.27

> <JCHEM_LOGP>
0.9592882623333336

> <ALOGPS_LOGS>
-3.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.875839296335606

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9997199453774193

> <JCHEM_POLAR_SURFACE_AREA>
98.50000000000001

> <JCHEM_REFRACTIVITY>
86.5959

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.95e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{8-formyl-14-hydroxy-2-methoxy-10-methyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradeca-1(9),2,5,7-tetraen-6-yl}methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.258  -0.533   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.925  -0.533   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      11.592  -3.613   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.925  -6.693   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.258  -6.693   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.591  -7.463   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.459  -4.859   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.983  -6.323   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.014  -7.468   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.538  -8.932   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.568 -10.077   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.032  -9.253   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.554  -3.613   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.459  -2.367   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   25                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7    9                                                       
CONECT    9    8    7   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    4   13                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17   25                                                  
CONECT   17   16   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   17   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24    3   16                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Value	Source
{8-formyl-14-hydroxy-2-methoxy-10-methyl-4,12-dioxatetracyclo[7.5.0.0,.0,]tetradeca-1,3(7),5,8-tetraen-6-yl}methyl acetic acid	Generator
{8-formyl-14-hydroxy-2-methoxy-10-methyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradeca-1,3(7),5,8-tetraen-6-yl}methyl acetic acid	Generator

Chemical Formula

C₁₈H₁₈O₇

Average Mass

346.3350 Da

Monoisotopic Mass

346.10525 Da

IUPAC Name

{8-formyl-14-hydroxy-2-methoxy-10-methyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradeca-1(9),2,5,7-tetraen-6-yl}methyl acetate

Traditional Name

{8-formyl-14-hydroxy-2-methoxy-10-methyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradeca-1(9),2,5,7-tetraen-6-yl}methyl acetate

CAS Registry Number

Not Available

SMILES

COC1=C2OC=C(COC(C)=O)C2=C(C=O)C2=C1C(O)C1OC1C2C

InChI Identifier

InChI=1S/C18H18O7/c1-7-11-10(4-19)12-9(5-23-8(2)20)6-24-17(12)16(22-3)13(11)14(21)18-15(7)25-18/h4,6-7,14-15,18,21H,5H2,1-3H3

InChI Key

QSPXRVDTGKRUHN-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Roldana angulifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Cacalol sesquiterpenoid
Naphthofuran
Tetralin
Benzofuran
Anisole
Alkyl aryl ether
Aryl-aldehyde
Benzenoid
Furan
Heteroaromatic compound
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Organoheterocyclic compound
Dialkyl ether
Oxirane
Ether
Oxacycle
Monocarboxylic acid or derivatives
Alcohol
Aldehyde
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	1.27	ALOGPS
logP	0.96	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	12.88	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	98.5 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	86.6 m³·mol⁻¹	ChemAxon
Polarizability	34.54 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-14-hydroxy-2-methoxy-10-methyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradeca-1(9),2,5,7-tetraen-6-yl}methyl acetate (NP0270962)

MOL for NP0270962 ({8-formyl-14-hydroxy-2-methoxy-10-methyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradeca-1(9),2,5,7-tetraen-6-yl}methyl acetate)

3D MOL for NP0270962 ({8-formyl-14-hydroxy-2-methoxy-10-methyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradeca-1(9),2,5,7-tetraen-6-yl}methyl acetate)

3D SDF for NP0270962 ({8-formyl-14-hydroxy-2-methoxy-10-methyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradeca-1(9),2,5,7-tetraen-6-yl}methyl acetate)

3D-SDF for NP0270962 ({8-formyl-14-hydroxy-2-methoxy-10-methyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradeca-1(9),2,5,7-tetraen-6-yl}methyl acetate)

PDB for NP0270962 ({8-formyl-14-hydroxy-2-methoxy-10-methyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradeca-1(9),2,5,7-tetraen-6-yl}methyl acetate)

3D PDB for NP0270962 ({8-formyl-14-hydroxy-2-methoxy-10-methyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradeca-1(9),2,5,7-tetraen-6-yl}methyl acetate)

SMILES for NP0270962 ({8-formyl-14-hydroxy-2-methoxy-10-methyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradeca-1(9),2,5,7-tetraen-6-yl}methyl acetate)

INCHI for NP0270962 ({8-formyl-14-hydroxy-2-methoxy-10-methyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradeca-1(9),2,5,7-tetraen-6-yl}methyl acetate)

Structure for NP0270962 ({8-formyl-14-hydroxy-2-methoxy-10-methyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradeca-1(9),2,5,7-tetraen-6-yl}methyl acetate)

3D Structure for NP0270962 ({8-formyl-14-hydroxy-2-methoxy-10-methyl-4,12-dioxatetracyclo[7.5.0.0³,⁷.0¹¹,¹³]tetradeca-1(9),2,5,7-tetraen-6-yl}methyl acetate)