NP-MRD: Showing NP-Card for 3-[5-(2-{1a,5,6-trimethyl-octahydrocyclopropa[e]naphthalen-5-yl}ethyl)-2-hydroxy-3,6-dihydropyran-2-yl]-4-hydroxybutanoic acid (NP0215688)

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Record Information

Version

2.0

Created at

2022-09-05 15:23:28 UTC

Updated at

2022-09-05 15:23:28 UTC

NP-MRD ID

NP0215688

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[5-(2-{1a,5,6-trimethyl-octahydrocyclopropa[e]naphthalen-5-yl}ethyl)-2-hydroxy-3,6-dihydropyran-2-yl]-4-hydroxybutanoic acid

Description

3-[5-(2-{2,3,5B-trimethyl-decahydrocyclopropa[e]naphthalen-2-yl}ethyl)-2-hydroxy-3,6-dihydro-2H-pyran-2-yl]-4-hydroxybutanoic acid belongs to the class of organic compounds known as heterocyclic fatty acids. These are fatty acids containing a heterocyclic attached to the acyl chain. 3-[5-(2-{1a,5,6-trimethyl-octahydrocyclopropa[e]naphthalen-5-yl}ethyl)-2-hydroxy-3,6-dihydropyran-2-yl]-4-hydroxybutanoic acid is found in Fasciospongia cavernosa. Based on a literature review very few articles have been published on 3-[5-(2-{2,3,5b-trimethyl-decahydrocyclopropa[e]naphthalen-2-yl}ethyl)-2-hydroxy-3,6-dihydro-2H-pyran-2-yl]-4-hydroxybutanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052217232D          

 30 33  0  0  0  0            999 V2000
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0416   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4788   -3.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0915   -3.8065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5287   -4.5061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1414   -5.2346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3169   -5.2634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4884   -6.0703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4481   -5.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0982   -5.0645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9833   -4.2475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5629   -6.3894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1203   -4.5637    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2670   -3.8353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
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  5 12  1  0  0  0  0
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 29 30  1  0  0  0  0
 17 30  1  0  0  0  0
M  END

     RDKit          3D

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    4.2626    0.2092    0.9438 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5547    0.3672    2.3312 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4394    0.8415    0.2389 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4403    2.3541    0.5389 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5169    2.9642   -0.0975 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7400    0.3594    0.8314 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0093   -1.0629    0.7813 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8244   -1.8905    1.7229 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1016    0.9715    0.7658 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4660    0.6934   -0.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8218    2.7776    2.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4227    1.1371    1.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309052217232D          

 30 33  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0215688

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC23CC2(C)CCCC3C1(C)CCC1=CCC(O)(OC1)C(CO)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H40O5/c1-17-6-11-24-16-22(24,2)9-4-5-20(24)23(17,3)10-7-18-8-12-25(29,30-15-18)19(14-26)13-21(27)28/h8,17,19-20,26,29H,4-7,9-16H2,1-3H3,(H,27,28)

> <INCHI_KEY>
RFKUHBLGCIYMDR-UHFFFAOYSA-N

> <FORMULA>
C25H40O5

> <MOLECULAR_WEIGHT>
420.59

> <EXACT_MASS>
420.287574388

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
48.20359928199483

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[5-(2-{5,6,8b-trimethyl-decahydrocyclopropa[e]naphthalen-5-yl}ethyl)-2-hydroxy-3,6-dihydro-2H-pyran-2-yl]-4-hydroxybutanoic acid

> <JCHEM_LOGP>
3.7883638700000004

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.715745807518527

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.291994886169166

> <JCHEM_PKA_STRONGEST_BASIC>
-2.675911000117374

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
116.24939999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-[5-(2-{5,6,8b-trimethyl-octahydrocyclopropa[e]naphthalen-5-yl}ethyl)-2-hydroxy-3,6-dihydropyran-2-yl]-4-hydroxybutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.105   1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.390  -4.440   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.944  -4.440   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.760  -5.746   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.037  -7.105   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.854  -8.411   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.131  -9.771   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.591  -9.825   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.912 -11.331   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.836 -10.402   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.050  -9.454   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.836  -7.929   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.051 -11.927   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.479 -12.504   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.693 -14.029   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -3.692 -11.556   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -0.225  -8.519   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.498  -7.159   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   12                                             
CONECT    6    5    7                                                       
CONECT    7    6    5    8    9                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    5   13                                                  
CONECT   13   12    2   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   30                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22   29                                             
CONECT   21   20                                                            
CONECT   22   20   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   20   30                                                       
CONECT   30   29   17                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
3-[5-(2-{2,3,5b-trimethyl-decahydrocyclopropa[e]naphthalen-2-yl}ethyl)-2-hydroxy-3,6-dihydro-2H-pyran-2-yl]-4-hydroxybutanoate	Generator

Chemical Formula

C₂₅H₄₀O₅

Average Mass

420.5900 Da

Monoisotopic Mass

420.28757 Da

IUPAC Name

3-[5-(2-{5,6,8b-trimethyl-decahydrocyclopropa[e]naphthalen-5-yl}ethyl)-2-hydroxy-3,6-dihydro-2H-pyran-2-yl]-4-hydroxybutanoic acid

Traditional Name

3-[5-(2-{5,6,8b-trimethyl-octahydrocyclopropa[e]naphthalen-5-yl}ethyl)-2-hydroxy-3,6-dihydropyran-2-yl]-4-hydroxybutanoic acid

CAS Registry Number

Not Available

SMILES

CC1CCC23CC2(C)CCCC3C1(C)CCC1=CCC(O)(OC1)C(CO)CC(O)=O

InChI Identifier

InChI=1S/C25H40O5/c1-17-6-11-24-16-22(24,2)9-4-5-20(24)23(17,3)10-7-18-8-12-25(29,30-15-18)19(14-26)13-21(27)28/h8,17,19-20,26,29H,4-7,9-16H2,1-3H3,(H,27,28)

InChI Key

RFKUHBLGCIYMDR-UHFFFAOYSA-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
Fasciospongia cavernosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as heterocyclic fatty acids. These are fatty acids containing a heterocyclic attached to the acyl chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Heterocyclic fatty acids

Alternative Parents

Substituents

Heterocyclic fatty acid
Hydroxy fatty acid
Short-chain hydroxy acid
Pyran
Hemiacetal
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Primary alcohol
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	3.79	ChemAxon
pKa (Strongest Acidic)	4.29	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	116.25 m³·mol⁻¹	ChemAxon
Polarizability	48.2 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	Yes	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

74000332

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-[5-(2-{1a,5,6-trimethyl-octahydrocyclopropa[e]naphthalen-5-yl}ethyl)-2-hydroxy-3,6-dihydropyran-2-yl]-4-hydroxybutanoic acid (NP0215688)

MOL for NP0215688 (3-[5-(2-{1a,5,6-trimethyl-octahydrocyclopropa[e]naphthalen-5-yl}ethyl)-2-hydroxy-3,6-dihydropyran-2-yl]-4-hydroxybutanoic acid)

3D MOL for NP0215688 (3-[5-(2-{1a,5,6-trimethyl-octahydrocyclopropa[e]naphthalen-5-yl}ethyl)-2-hydroxy-3,6-dihydropyran-2-yl]-4-hydroxybutanoic acid)

3D SDF for NP0215688 (3-[5-(2-{1a,5,6-trimethyl-octahydrocyclopropa[e]naphthalen-5-yl}ethyl)-2-hydroxy-3,6-dihydropyran-2-yl]-4-hydroxybutanoic acid)

3D-SDF for NP0215688 (3-[5-(2-{1a,5,6-trimethyl-octahydrocyclopropa[e]naphthalen-5-yl}ethyl)-2-hydroxy-3,6-dihydropyran-2-yl]-4-hydroxybutanoic acid)

PDB for NP0215688 (3-[5-(2-{1a,5,6-trimethyl-octahydrocyclopropa[e]naphthalen-5-yl}ethyl)-2-hydroxy-3,6-dihydropyran-2-yl]-4-hydroxybutanoic acid)

3D PDB for NP0215688 (3-[5-(2-{1a,5,6-trimethyl-octahydrocyclopropa[e]naphthalen-5-yl}ethyl)-2-hydroxy-3,6-dihydropyran-2-yl]-4-hydroxybutanoic acid)

SMILES for NP0215688 (3-[5-(2-{1a,5,6-trimethyl-octahydrocyclopropa[e]naphthalen-5-yl}ethyl)-2-hydroxy-3,6-dihydropyran-2-yl]-4-hydroxybutanoic acid)

INCHI for NP0215688 (3-[5-(2-{1a,5,6-trimethyl-octahydrocyclopropa[e]naphthalen-5-yl}ethyl)-2-hydroxy-3,6-dihydropyran-2-yl]-4-hydroxybutanoic acid)

Structure for NP0215688 (3-[5-(2-{1a,5,6-trimethyl-octahydrocyclopropa[e]naphthalen-5-yl}ethyl)-2-hydroxy-3,6-dihydropyran-2-yl]-4-hydroxybutanoic acid)

3D Structure for NP0215688 (3-[5-(2-{1a,5,6-trimethyl-octahydrocyclopropa[e]naphthalen-5-yl}ethyl)-2-hydroxy-3,6-dihydropyran-2-yl]-4-hydroxybutanoic acid)