NP-MRD: Showing NP-Card for pseuboyene A (NP0332946)

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Record Information

Version

2.0

Created at

2024-05-02 08:24:10 UTC

Updated at

2024-11-01 01:37:21 UTC

NP-MRD ID

NP0332946

Natural Product DOI

https://doi.org/10.57994/2228

Secondary Accession Numbers

None

Natural Product Identification

Common Name

pseuboyene A

Description

Pseuboyene A belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review very few articles have been published on pseuboyene A.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01142311012D          

 24 25  0  0  1  0            999 V2000
   -1.8351    0.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0918    0.4731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0301    1.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4101    0.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3332    0.3663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3948    1.1890    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2868    1.6537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1381    1.5469    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6238    2.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3217    0.7426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6525    2.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4775    2.1919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9919    1.5469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8083    0.7426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0650    0.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0650   -0.4404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7795   -0.8529    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7795   -1.6779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4940   -0.4404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2084   -0.8529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9229   -0.4404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4940    0.3846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6329    1.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8355    2.9352    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
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
  8 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  2  0  0  0  0
 15 23  1  0  0  0  0
 11 23  1  0  0  0  0
 12 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0332946

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@H](O)CC12CC(C(=C)CC1)[C@](C)(O2)[C@H](O)CC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C19H30O5/c1-12(2)6-7-16(21)18(4)14-10-19(24-18,9-8-13(14)3)11-15(20)17(22)23-5/h6,14-16,20-21H,3,7-11H2,1-2,4-5H3/t14?,15-,16+,18-,19?/m0/s1

> <INCHI_KEY>
RBEWRVHKVVVJLV-IUKIHODOSA-N

> <FORMULA>
C19H30O5

> <MOLECULAR_WEIGHT>
338.444

> <EXACT_MASS>
338.209324066

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
37.47571404778017

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2S)-2-hydroxy-3-[(7S)-7-[(1R)-1-hydroxy-4-methylpent-3-en-1-yl]-7-methyl-2-methylidene-6-oxabicyclo[3.2.1]octan-5-yl]propanoate

> <JCHEM_LOGP>
1.7994407140000002

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.94100913974999

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.593544879503593

> <JCHEM_PKA_STRONGEST_BASIC>
-3.271179688629544

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
92.28219999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2S)-2-hydroxy-3-[(7S)-7-[(1R)-1-hydroxy-4-methylpent-3-en-1-yl]-7-methyl-2-methylidene-6-oxabicyclo[3.2.1]octan-5-yl]propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 14-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-JAN-23         0                                  
HETATM    1  C   UNK     0      -3.425   0.215   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.038   0.883   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.923   2.419   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.766   0.016   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.622   0.684   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.737   2.219   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.535   3.087   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.125   2.888   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.164   4.092   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.467   1.386   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.085   4.092   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.625   4.092   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.585   2.888   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.242   1.386   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.855   0.718   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.855  -0.822   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.188  -1.592   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.188  -3.132   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.522  -0.822   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.856  -1.592   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.189  -0.822   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.522   0.718   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.048   2.309   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.293   5.479   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                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8   15                                                       
CONECT   11    8   12   23                                                  
CONECT   12   11   13   24                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10   16   23                                             
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19                                                            
CONECT   23   15   11                                                       
CONECT   24   12                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₃₀O₅

Average Mass

338.4440 Da

Monoisotopic Mass

338.20932 Da

IUPAC Name

methyl (2S)-2-hydroxy-3-[(7S)-7-[(1R)-1-hydroxy-4-methylpent-3-en-1-yl]-7-methyl-2-methylidene-6-oxabicyclo[3.2.1]octan-5-yl]propanoate

Traditional Name

methyl (2S)-2-hydroxy-3-[(7S)-7-[(1R)-1-hydroxy-4-methylpent-3-en-1-yl]-7-methyl-2-methylidene-6-oxabicyclo[3.2.1]octan-5-yl]propanoate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@H](O)CC12CC(C(=C)CC1)[C@](C)(O2)[C@H](O)CC=C(C)C

InChI Identifier

InChI=1S/C19H30O5/c1-12(2)6-7-16(21)18(4)14-10-19(24-18,9-8-13(14)3)11-15(20)17(22)23-5/h6,14-16,20-21H,3,7-11H2,1-2,4-5H3/t14?,15-,16+,18-,19?/m0/s1

InChI Key

RBEWRVHKVVVJLV-IUKIHODOSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)	m8545303@163.com	Institute of Oceanology, Chinese Academy of Sciences	Linghong Meng	2024-05-02	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, C2D6OS, experimental)	m8545303@163.com	Institute of Oceanology, Chinese Academy of Sciences	Linghong Meng	2024-05-02	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, C2D6OS, experimental)	m8545303@163.com	Institute of Oceanology, Chinese Academy of Sciences	Linghong Meng	2024-05-02	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, C2D6OS, experimental)	m8545303@163.com	Institute of Oceanology, Chinese Academy of Sciences	Linghong Meng	2024-05-02	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, CDCl3, experimental)	m8545303@163.com	Institute of Oceanology, Chinese Academy of Sciences	Linghong Meng	2024-05-02	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C2D6OS, experimental)	m8545303@163.com	Institute of Oceanology, Chinese Academy of Sciences	Linghong Meng	2024-05-02	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)	m8545303@163.com	Institute of Oceanology, Chinese Academy of Sciences	Linghong Meng	2024-05-02	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)	m8545303@163.com	Institute of Oceanology, Chinese Academy of Sciences	Linghong Meng	2024-05-02	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Pseudallescheria boydii		Not Available

Chemical Taxonomy

Description

This compound 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
Oxepane
Fatty acid ester
Fatty acyl
Methyl ester
Tetrahydrofuran
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
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	1.8	ChemAxon
pKa (Strongest Acidic)	12.59	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	92.28 m³·mol⁻¹	ChemAxon
Polarizability	37.48 Å³	ChemAxon
Number of Rings	2	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

Showing NP-Card for pseuboyene A (NP0332946)

MOL for NP0332946 (pseuboyene A)

3D MOL for NP0332946 (pseuboyene A)

3D SDF for NP0332946 (pseuboyene A)

3D-SDF for NP0332946 (pseuboyene A)

PDB for NP0332946 (pseuboyene A)

3D PDB for NP0332946 (pseuboyene A)

SMILES for NP0332946 (pseuboyene A)

INCHI for NP0332946 (pseuboyene A)

Structure for NP0332946 (pseuboyene A)

3D Structure for NP0332946 (pseuboyene A)