NP-MRD: Showing NP-Card for Paraconulone C (NP0332176)

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Record Information

Version

2.0

Created at

2023-11-30 20:03:25 UTC

Updated at

2024-09-03 04:18:15 UTC

NP-MRD ID

NP0332176

Natural Product DOI

https://doi.org/10.57994/1336

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Paraconulone C

Description

Paraconulone C belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. Paraconulone C was first documented in 2023 (PMID: 37159940). Based on a literature review very few articles have been published on Paraconulone C.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 11302320032D          

 22 23  0  0  1  0            999 V2000
   -5.2431    3.9260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9610    3.1507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1485    3.0075    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8663    2.2322    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0539    2.0890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7717    1.3137    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0572    1.7262    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3428    1.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6283    1.7262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0862    1.3137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8006    1.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0862    0.4887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0572    2.5512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2414    0.6817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3360    2.8642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6182    3.6395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4913    2.5188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2091    1.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3966    1.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1145    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3020    0.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0198   -0.0935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  0  0  0  0
  3  4  1  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
  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  2  0  0  0  0
  7 13  1  6  0  0  0
  6 14  1  6  0  0  0
  4 15  1  6  0  0  0
  3 16  1  1  0  0  0
  2 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
  4 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
  6 21  1  0  0  0  0
 21 22  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0332176

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](COC(C)=O)[C@]1(O)C[C@]2(C)[C@H](C)C(=O)C=CC2=CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O5/c1-10(8-22-12(3)18)17(21)9-16(4)11(2)14(19)6-5-13(16)7-15(17)20/h5-7,10-11,21H,8-9H2,1-4H3/t10-,11-,16-,17-/m1/s1

> <INCHI_KEY>
VIJGIIUZBMYZIL-LMCLETFFSA-N

> <FORMULA>
C17H22O5

> <MOLECULAR_WEIGHT>
306.358

> <EXACT_MASS>
306.146723808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
32.32502638327553

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R)-2-[(2R,8S,8aR)-2-hydroxy-8,8a-dimethyl-3,7-dioxo-1,2,3,7,8,8a-hexahydronaphthalen-2-yl]propyl acetate

> <JCHEM_LOGP>
1.5986474196666656

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.7490517152871

> <JCHEM_PKA_STRONGEST_BASIC>
-3.783364779733423

> <JCHEM_POLAR_SURFACE_AREA>
80.67000000000002

> <JCHEM_REFRACTIVITY>
82.53789999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-[(2R,8S,8aR)-2-hydroxy-8,8a-dimethyl-3,7-dioxo-1,8-dihydronaphthalen-2-yl]propyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-NOV-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-NOV-23         0                                  
HETATM    1  O   UNK     0      -9.787   7.329   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -9.260   5.881   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.744   5.614   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.217   4.167   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.701   3.899   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.174   2.452   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.840   3.222   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.506   2.452   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.173   3.222   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.161   2.452   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.495   3.222   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.161   0.912   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -3.840   4.762   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.184   1.273   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -6.227   5.347   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.754   6.794   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -10.250   4.702   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -9.724   3.255   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -8.207   2.987   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -7.680   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.164   1.273   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -5.637  -0.175   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4   16                                                  
CONECT    4    3    5   15   19                                             
CONECT    5    4    6                                                       
CONECT    6    5    7   14   21                                             
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    7                                                            
CONECT   14    6                                                            
CONECT   15    4                                                            
CONECT   16    3                                                            
CONECT   17    2   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    4   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20    6   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₂O₅

Average Mass

306.3580 Da

Monoisotopic Mass

306.14672 Da

IUPAC Name

(2R)-2-[(2R,8S,8aR)-2-hydroxy-8,8a-dimethyl-3,7-dioxo-1,2,3,7,8,8a-hexahydronaphthalen-2-yl]propyl acetate

Traditional Name

(2R)-2-[(2R,8S,8aR)-2-hydroxy-8,8a-dimethyl-3,7-dioxo-1,8-dihydronaphthalen-2-yl]propyl acetate

CAS Registry Number

Not Available

SMILES

C[C@H](COC(C)=O)[C@]1(O)C[C@]2(C)[C@H](C)C(=O)C=CC2=CC1=O

InChI Identifier

InChI=1S/C17H22O5/c1-10(8-22-12(3)18)17(21)9-16(4)11(2)14(19)6-5-13(16)7-15(17)20/h5-7,10-11,21H,8-9H2,1-4H3/t10-,11-,16-,17-/m1/s1

InChI Key

VIJGIIUZBMYZIL-LMCLETFFSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)	dongdong.wang@nih.gov	NCI-Frederick	Dong Wang	2024-05-11	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)	dongdong.wang@nih.gov	NCI-Frederick	Dong Wang	2024-05-11	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, C2D6OS, experimental)	dongdong.wang@nih.gov	NCI-Frederick	Dong Wang	2024-05-11	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)	dongdong.wang@nih.gov	NCI-Frederick	Dong Wang	2024-05-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C2D6OS, experimental)	dongdong.wang@nih.gov	NCI-Frederick	Dong Wang	2024-05-11	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)	dongdong.wang@nih.gov	NCI-Frederick	Dong Wang	2024-05-11	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
Paraconiothyrium sporulosum		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Eremophilane sesquiterpenoid
Fatty alcohol ester
Cyclohexenone
Acyloin
Alpha,beta-unsaturated ketone
Tertiary alcohol
Enone
Alpha-hydroxy ketone
Acryloyl-group
Cyclic ketone
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	1.6	ChemAxon
pKa (Strongest Acidic)	12.75	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	82.54 m³·mol⁻¹	ChemAxon
Polarizability	32.33 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

Sun B, Wang D, Ren J, Wang C, Yan P, Gustafson KR, Jiang W: Paraconulones A-G: Eremophilane Sesquiterpenoids from the Marine-Derived Fungus Paraconiothyrium sporulosum DL-16. J Nat Prod. 2023 May 26;86(5):1360-1369. doi: 10.1021/acs.jnatprod.3c00221. Epub 2023 May 9. [PubMed:37159940 ]
DOI: 10.1021/acs.jnatprod.3c00221

Showing NP-Card for Paraconulone C (NP0332176)

MOL for NP0332176 (Paraconulone C)

3D MOL for NP0332176 (Paraconulone C)

3D SDF for NP0332176 (Paraconulone C)

3D-SDF for NP0332176 (Paraconulone C)

PDB for NP0332176 (Paraconulone C)

3D PDB for NP0332176 (Paraconulone C)

SMILES for NP0332176 (Paraconulone C)

INCHI for NP0332176 (Paraconulone C)

Structure for NP0332176 (Paraconulone C)

3D Structure for NP0332176 (Paraconulone C)