NP-MRD: Showing NP-Card for [(1r,4ar,5s,6s,8ar)-6-[(2-hydroxy-3-methylbutanoyl)oxy]-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-yl]acetic acid (NP0288333)

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Record Information

Version

1.0

Created at

2022-09-09 17:59:37 UTC

Updated at

2022-09-09 17:59:37 UTC

NP-MRD ID

NP0288333

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1r,4ar,5s,6s,8ar)-6-[(2-hydroxy-3-methylbutanoyl)oxy]-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-yl]acetic acid

Description

Conoideocin A belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. [(1r,4ar,5s,6s,8ar)-6-[(2-hydroxy-3-methylbutanoyl)oxy]-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-yl]acetic acid is found in Conoideocrella tenuis. It was first documented in 2022 (PMID: 36109246). Based on a literature review a significant number of articles have been published on Conoideocin A (PMID: 36087713) (PMID: 36083970) (PMID: 36091400) (PMID: 36088383).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092219592D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309092219592D          

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M  END
> <DATABASE_ID>
NP0288333

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(O)C(=O)O[C@H]1CC[C@]2(C)[C@H](CC(O)=O)C(=C)CC[C@H]2[C@]1(C)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C26H42O5/c1-16(2)9-8-13-26(7)20-11-10-18(5)19(15-22(27)28)25(20,6)14-12-21(26)31-24(30)23(29)17(3)4/h9,17,19-21,23,29H,5,8,10-15H2,1-4,6-7H3,(H,27,28)/t19-,20-,21+,23?,25-,26+/m1/s1

> <INCHI_KEY>
LNOXABRKXZUJQU-YRRRMRBKSA-N

> <FORMULA>
C26H42O5

> <MOLECULAR_WEIGHT>
434.617

> <EXACT_MASS>
434.303224452

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
49.944610898833844

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(1R,4aR,5S,6S,8aR)-6-[(2-hydroxy-3-methylbutanoyl)oxy]-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-decahydronaphthalen-1-yl]acetic acid

> <JCHEM_LOGP>
5.413734264

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.489287339490652

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.551364116228921

> <JCHEM_PKA_STRONGEST_BASIC>
-3.896985719901319

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
122.40419999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,4aR,5S,6S,8aR)-6-[(2-hydroxy-3-methylbutanoyl)oxy]-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-hexahydro-1H-naphthalen-1-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0     -10.669   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.336   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.325   5.800   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.345   5.800   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.872   7.247   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.882   8.427   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.408   9.874   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.418  11.053   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.925  10.141   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.668   0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0     -10.669  -0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   27                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   25                                                  
CONECT    6    5    7    8   14                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    6   15   23                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   14   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24    5   26   27                                             
CONECT   26   25                                                            
CONECT   27   25    2   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₄₂O₅

Average Mass

434.6170 Da

Monoisotopic Mass

434.30322 Da

IUPAC Name

2-[(1R,4aR,5S,6S,8aR)-6-[(2-hydroxy-3-methylbutanoyl)oxy]-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-decahydronaphthalen-1-yl]acetic acid

Traditional Name

[(1R,4aR,5S,6S,8aR)-6-[(2-hydroxy-3-methylbutanoyl)oxy]-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-hexahydro-1H-naphthalen-1-yl]acetic acid

CAS Registry Number

Not Available

SMILES

CC(C)C(O)C(=O)O[C@H]1CC[C@]2(C)[C@H](CC(O)=O)C(=C)CC[C@H]2[C@]1(C)CCC=C(C)C

InChI Identifier

InChI=1S/C26H42O5/c1-16(2)9-8-13-26(7)20-11-10-18(5)19(15-22(27)28)25(20,6)14-12-21(26)31-24(30)23(29)17(3)4/h9,17,19-21,23,29H,5,8,10-15H2,1-4,6-7H3,(H,27,28)/t19-,20-,21+,23?,25-,26+/m1/s1

InChI Key

LNOXABRKXZUJQU-YRRRMRBKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Conoideocrella tenuis	LOTUS Database	35616633

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
Fatty acid ester
Fatty acyl
Dicarboxylic acid or derivatives
Secondary alcohol
Carboxylic acid ester
Carboxylic acid
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	5.41	ChemAxon
pKa (Strongest Acidic)	4.55	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	122.4 m³·mol⁻¹	ChemAxon
Polarizability	49.94 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

78442416

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139590327

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

O'Byrne LJ, Bodunde EO, Maher GM, Khashan AS, Greene RM, Browne JP, Mccarthy FP: Patient reported outcome measures evaluating postpartum maternal health and wellbeing: a systematic review and evaluation of measurement properties. Am J Obstet Gynecol MFM. 2022 Sep 7:100743. doi: 10.1016/j.ajogmf.2022.100743. [PubMed:36087713 ]
Panchal N, Desai C, Ghosal R: Fecal glucocorticoid metabolite levels in captive Indian leopards (Panthera pardus fusca) housed under three different enrichment regimes. PLoS One. 2022 Sep 9;17(9):e0261796. doi: 10.1371/journal.pone.0261796. eCollection 2022. [PubMed:36083970 ]
Yuksel S, Bonus M, Schwabe T, Pfleger C, Zimmer T, Enke U, Sass I, Gohlke H, Benndorf K, Kusch J: Uncoupling of Voltage- and Ligand-Induced Activation in HCN2 Channels by Glycine Inserts. Front Physiol. 2022 Aug 25;13:895324. doi: 10.3389/fphys.2022.895324. eCollection 2022. [PubMed:36091400 ]
Peter A, Balogh A, Csanadi Z, Danko K, Griger Z: Subclinical systolic and diastolic myocardial dysfunction in polyphasic polymyositis/dermatomyositis: a 2-year longitudinal study. Arthritis Res Ther. 2022 Sep 10;24(1):219. doi: 10.1186/s13075-022-02906-7. [PubMed:36088383 ]
Dagdigian PJ: Theoretical investigation of rotationally inelastic collisions of OH(X(2)Pi) with hydrogen atoms. J Chem Phys. 2022 Sep 14;157(10):104305. doi: 10.1063/5.0110724. [PubMed:36109246 ]
LOTUS database [Link]

Showing NP-Card for [(1r,4ar,5s,6s,8ar)-6-[(2-hydroxy-3-methylbutanoyl)oxy]-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-yl]acetic acid (NP0288333)

MOL for NP0288333 ([(1r,4ar,5s,6s,8ar)-6-[(2-hydroxy-3-methylbutanoyl)oxy]-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-yl]acetic acid)

3D MOL for NP0288333 ([(1r,4ar,5s,6s,8ar)-6-[(2-hydroxy-3-methylbutanoyl)oxy]-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-yl]acetic acid)

3D SDF for NP0288333 ([(1r,4ar,5s,6s,8ar)-6-[(2-hydroxy-3-methylbutanoyl)oxy]-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-yl]acetic acid)

3D-SDF for NP0288333 ([(1r,4ar,5s,6s,8ar)-6-[(2-hydroxy-3-methylbutanoyl)oxy]-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-yl]acetic acid)

PDB for NP0288333 ([(1r,4ar,5s,6s,8ar)-6-[(2-hydroxy-3-methylbutanoyl)oxy]-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-yl]acetic acid)

3D PDB for NP0288333 ([(1r,4ar,5s,6s,8ar)-6-[(2-hydroxy-3-methylbutanoyl)oxy]-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-yl]acetic acid)

SMILES for NP0288333 ([(1r,4ar,5s,6s,8ar)-6-[(2-hydroxy-3-methylbutanoyl)oxy]-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-yl]acetic acid)

INCHI for NP0288333 ([(1r,4ar,5s,6s,8ar)-6-[(2-hydroxy-3-methylbutanoyl)oxy]-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-yl]acetic acid)

Structure for NP0288333 ([(1r,4ar,5s,6s,8ar)-6-[(2-hydroxy-3-methylbutanoyl)oxy]-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-yl]acetic acid)

3D Structure for NP0288333 ([(1r,4ar,5s,6s,8ar)-6-[(2-hydroxy-3-methylbutanoyl)oxy]-5,8a-dimethyl-2-methylidene-5-(4-methylpent-3-en-1-yl)-hexahydro-1h-naphthalen-1-yl]acetic acid)