NP-MRD: Showing NP-Card for 5-formyl-13-hydroxy-13-isopropyl-1,9-dimethyl-4-oxatricyclo[10.3.0.0³,⁵]pentadec-8-en-7-yl acetate (NP0191661)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 08:41:48 UTC

Updated at

2022-09-04 08:41:48 UTC

NP-MRD ID

NP0191661

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-formyl-13-hydroxy-13-isopropyl-1,9-dimethyl-4-oxatricyclo[10.3.0.0³,⁵]pentadec-8-en-7-yl acetate

Description

5-Formyl-13-hydroxy-1,9-dimethyl-13-(propan-2-yl)-4-oxatricyclo[10.3.0.0³,⁵]Pentadec-8-en-7-yl acetate belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ). 5-formyl-13-hydroxy-13-isopropyl-1,9-dimethyl-4-oxatricyclo[10.3.0.0³,⁵]pentadec-8-en-7-yl acetate is found in Odontoschisma denudatum. 5-Formyl-13-hydroxy-1,9-dimethyl-13-(propan-2-yl)-4-oxatricyclo[10.3.0.0³,⁵]Pentadec-8-en-7-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241514232D          

 27 29  0  0  0  0            999 V2000
   -0.8611   -1.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6320   -2.0683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2039   -2.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1689   -2.2662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1117   -3.0420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2820   -1.4490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0942   -1.3040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4830   -2.0317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9753   -1.3697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3680   -2.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0956   -1.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8882   -1.5921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6903   -2.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3301   -3.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5429   -4.0127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3393   -4.2279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5511   -5.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3475   -5.2405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9665   -5.6074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9710   -4.6073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1701   -4.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5983   -5.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9411   -3.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1402   -3.4189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9111   -2.6263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4661   -2.6736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6110   -3.4858    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  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
  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
 11 13  1  0  0  0  0
 13 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  2  0  0  0  0
 17 19  1  0  0  0  0
 20 15  1  4  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  4 25  1  0  0  0  0
  8 25  1  0  0  0  0
 13 26  1  0  0  0  0
 26 27  2  0  0  0  0
M  END


  Mrv1533004241514232D          

 27 29  0  0  0  0            999 V2000
   -0.8611   -1.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6320   -2.0683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2039   -2.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1689   -2.2662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1117   -3.0420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2820   -1.4490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0942   -1.3040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4830   -2.0317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9753   -1.3697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3680   -2.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0956   -1.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8882   -1.5921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6903   -2.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3301   -3.1353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5429   -4.0127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3393   -4.2279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5511   -5.0253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3475   -5.2405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9665   -5.6074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9710   -4.6073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1701   -4.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5983   -5.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9411   -3.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1402   -3.4189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9111   -2.6263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4661   -2.6736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6110   -3.4858    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  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
  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
 11 13  1  0  0  0  0
 13 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  2  0  0  0  0
 17 19  1  0  0  0  0
 20 15  1  4  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  4 25  1  0  0  0  0
  8 25  1  0  0  0  0
 13 26  1  0  0  0  0
 26 27  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0191661

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1(O)CCC2(C)CC3OC3(CC(OC(C)=O)C=C(C)CCC12)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H34O5/c1-14(2)22(25)9-8-20(5)12-19-21(13-23,27-19)11-17(26-16(4)24)10-15(3)6-7-18(20)22/h10,13-14,17-19,25H,6-9,11-12H2,1-5H3

> <INCHI_KEY>
GVXDJURQUSZJIH-UHFFFAOYSA-N

> <FORMULA>
C22H34O5

> <MOLECULAR_WEIGHT>
378.509

> <EXACT_MASS>
378.240624195

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
41.5345785749166

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-formyl-13-hydroxy-1,9-dimethyl-13-(propan-2-yl)-4-oxatricyclo[10.3.0.0³,⁵]pentadec-8-en-7-yl acetate

> <ALOGPS_LOGP>
2.83

> <JCHEM_LOGP>
2.8710460783333334

> <ALOGPS_LOGS>
-4.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.08045746078542404

> <JCHEM_POLAR_SURFACE_AREA>
76.13

> <JCHEM_REFRACTIVITY>
102.95030000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.31e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-formyl-13-hydroxy-13-isopropyl-1,9-dimethyl-4-oxatricyclo[10.3.0.0³,⁵]pentadec-8-en-7-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -1.607  -2.381   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.180  -3.861   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.247  -4.971   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.315  -4.230   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.208  -5.678   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.526  -2.705   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.042  -2.434   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.768  -3.792   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.687  -2.557   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.420  -4.125   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.778  -3.400   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.258  -2.972   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.888  -4.467   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.216  -5.853   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.613  -7.490   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.100  -7.892   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.495  -9.381   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.982  -9.782   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.404 -10.467   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.546  -8.600   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.051  -8.231   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.983  -9.341   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.623  -6.751   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.128  -6.382   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.701  -4.902   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.337  -4.991   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       8.607  -6.507   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6   25                                             
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   25                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11   13                                                       
CONECT   13   12   11   14   26                                             
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   15   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24    4    8                                                  
CONECT   26   13   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Value	Source
5-Formyl-13-hydroxy-1,9-dimethyl-13-(propan-2-yl)-4-oxatricyclo[10.3.0.0,]pentadec-8-en-7-yl acetic acid	Generator
5-Formyl-13-hydroxy-1,9-dimethyl-13-(propan-2-yl)-4-oxatricyclo[10.3.0.0³,⁵]pentadec-8-en-7-yl acetic acid	Generator

Chemical Formula

C₂₂H₃₄O₅

Average Mass

378.5090 Da

Monoisotopic Mass

378.24062 Da

IUPAC Name

5-formyl-13-hydroxy-1,9-dimethyl-13-(propan-2-yl)-4-oxatricyclo[10.3.0.0³,⁵]pentadec-8-en-7-yl acetate

Traditional Name

5-formyl-13-hydroxy-13-isopropyl-1,9-dimethyl-4-oxatricyclo[10.3.0.0³,⁵]pentadec-8-en-7-yl acetate

CAS Registry Number

Not Available

SMILES

CC(C)C1(O)CCC2(C)CC3OC3(CC(OC(C)=O)C=C(C)CCC12)C=O

InChI Identifier

InChI=1S/C22H34O5/c1-14(2)22(25)9-8-20(5)12-19-21(13-23,27-19)11-17(26-16(4)24)10-15(3)6-7-18(20)22/h10,13-14,17-19,25H,6-9,11-12H2,1-5H3

InChI Key

GVXDJURQUSZJIH-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Odontoschisma denudatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Tertiary alcohols

Alternative Parents

Substituents

Tertiary alcohol
Cyclic alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aldehyde
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	2.83	ALOGPS
logP	2.87	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Basic)	-0.08	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	76.13 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	102.95 m³·mol⁻¹	ChemAxon
Polarizability	41.53 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

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 5-formyl-13-hydroxy-13-isopropyl-1,9-dimethyl-4-oxatricyclo[10.3.0.0³,⁵]pentadec-8-en-7-yl acetate (NP0191661)

MOL for NP0191661 (5-formyl-13-hydroxy-13-isopropyl-1,9-dimethyl-4-oxatricyclo[10.3.0.0³,⁵]pentadec-8-en-7-yl acetate)

3D MOL for NP0191661 (5-formyl-13-hydroxy-13-isopropyl-1,9-dimethyl-4-oxatricyclo[10.3.0.0³,⁵]pentadec-8-en-7-yl acetate)

3D SDF for NP0191661 (5-formyl-13-hydroxy-13-isopropyl-1,9-dimethyl-4-oxatricyclo[10.3.0.0³,⁵]pentadec-8-en-7-yl acetate)

3D-SDF for NP0191661 (5-formyl-13-hydroxy-13-isopropyl-1,9-dimethyl-4-oxatricyclo[10.3.0.0³,⁵]pentadec-8-en-7-yl acetate)

PDB for NP0191661 (5-formyl-13-hydroxy-13-isopropyl-1,9-dimethyl-4-oxatricyclo[10.3.0.0³,⁵]pentadec-8-en-7-yl acetate)

3D PDB for NP0191661 (5-formyl-13-hydroxy-13-isopropyl-1,9-dimethyl-4-oxatricyclo[10.3.0.0³,⁵]pentadec-8-en-7-yl acetate)

SMILES for NP0191661 (5-formyl-13-hydroxy-13-isopropyl-1,9-dimethyl-4-oxatricyclo[10.3.0.0³,⁵]pentadec-8-en-7-yl acetate)

INCHI for NP0191661 (5-formyl-13-hydroxy-13-isopropyl-1,9-dimethyl-4-oxatricyclo[10.3.0.0³,⁵]pentadec-8-en-7-yl acetate)

Structure for NP0191661 (5-formyl-13-hydroxy-13-isopropyl-1,9-dimethyl-4-oxatricyclo[10.3.0.0³,⁵]pentadec-8-en-7-yl acetate)

3D Structure for NP0191661 (5-formyl-13-hydroxy-13-isopropyl-1,9-dimethyl-4-oxatricyclo[10.3.0.0³,⁵]pentadec-8-en-7-yl acetate)