NP-MRD: Showing NP-Card for (6e)-neomanoalide (NP0298158)

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Record Information

Version

2.0

Created at

2022-09-10 09:10:17 UTC

Updated at

2022-09-10 09:10:17 UTC

NP-MRD ID

NP0298158

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6e)-neomanoalide

Description

(6E)-neomanoalide belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (6e)-neomanoalide is found in Hyrtios erectus. (6e)-neomanoalide was first documented in 2011 (PMID: 21548579). Based on a literature review very few articles have been published on (6E)-neomanoalide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102211102D          

 29 30  0  0  1  0            999 V2000
   -8.4669    7.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1814    6.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1814    6.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4669    5.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7525    6.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0380    5.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3235    6.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0380    4.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3235    4.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3235    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0380    3.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0380    2.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3235    1.8777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3235    1.0527    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6561    0.5678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9110   -0.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4261   -0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7360   -0.2169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9910    0.5678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7756    0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9471    1.6297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7525    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4669    3.1152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8959    5.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3656    4.9582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.6104    6.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8959    7.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
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 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
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  2 29  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309102211102D          

 29 30  0  0  1  0            999 V2000
   -8.4669    7.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1814    6.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1814    6.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4669    5.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.9471    1.6297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  2 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0298158

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(CCC1=C(C)CCCC1(C)C)=C/CC\C(CO)=C/C[C@H]1OC(=O)C=C1CO

> <INCHI_IDENTIFIER>
InChI=1S/C25H38O4/c1-18(10-12-22-19(2)8-6-14-25(22,3)4)7-5-9-20(16-26)11-13-23-21(17-27)15-24(28)29-23/h7,11,15,23,26-27H,5-6,8-10,12-14,16-17H2,1-4H3/b18-7+,20-11+/t23-/m1/s1

> <INCHI_KEY>
VOZHIXNCTBMKNV-KXUMGZKHSA-N

> <FORMULA>
C25H38O4

> <MOLECULAR_WEIGHT>
402.575

> <EXACT_MASS>
402.277009704

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
47.3487881985899

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5R)-5-[(2E)-4-hydroxy-3-[(3E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]but-2-en-1-yl]-4-(hydroxymethyl)-2,5-dihydrofuran-2-one

> <JCHEM_LOGP>
4.5033763769999995

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.608207461766444

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.528461371340261

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9452071088562706

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
120.93289999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5R)-5-[(2E)-4-hydroxy-3-[(3E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]but-2-en-1-yl]-4-(hydroxymethyl)-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0     -15.805  13.515   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -17.139  12.745   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -17.139  11.205   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -15.805  10.435   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -14.471  11.205   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -13.138  10.435   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -11.804  11.205   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -13.138   8.895   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -11.804   8.125   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -11.804   6.585   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -13.138   5.815   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -13.138   4.275   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -11.804   3.505   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -11.804   1.965   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0     -10.558   1.060   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0     -11.034  -0.405   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0     -10.129  -1.651   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0     -12.574  -0.405   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -13.050   1.060   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -14.514   1.536   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0     -14.835   3.042   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0     -14.471   6.585   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0     -15.805   5.815   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0     -18.472  10.435   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -17.482   9.255   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -19.462   9.255   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -19.806  11.205   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -19.806  12.745   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -18.472  13.515   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   29                                                  
CONECT    3    2    4   24                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   22                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   14   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   11   23                                                       
CONECT   23   22                                                            
CONECT   24    3   25   26   27                                             
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   24   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    2                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₈O₄

Average Mass

402.5750 Da

Monoisotopic Mass

402.27701 Da

IUPAC Name

(5R)-5-[(2E)-4-hydroxy-3-[(3E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]but-2-en-1-yl]-4-(hydroxymethyl)-2,5-dihydrofuran-2-one

Traditional Name

(5R)-5-[(2E)-4-hydroxy-3-[(3E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]but-2-en-1-yl]-4-(hydroxymethyl)-5H-furan-2-one

CAS Registry Number

Not Available

SMILES

C\C(CCC1=C(C)CCCC1(C)C)=C/CC\C(CO)=C/C[C@H]1OC(=O)C=C1CO

InChI Identifier

InChI=1S/C25H38O4/c1-18(10-12-22-19(2)8-6-14-25(22,3)4)7-5-9-20(16-26)11-13-23-21(17-27)15-24(28)29-23/h7,11,15,23,26-27H,5-6,8-10,12-14,16-17H2,1-4H3/b18-7+,20-11+/t23-/m1/s1

InChI Key

VOZHIXNCTBMKNV-KXUMGZKHSA-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
Hyrtios erectus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Fatty alcohol
2-furanone
Fatty acyl
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Primary alcohol
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

diterpene lactone (CHEBI:67740 )

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	4.5	ChemAxon
pKa (Strongest Acidic)	6.53	ChemAxon
pKa (Strongest Basic)	-1.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	120.93 m³·mol⁻¹	ChemAxon
Polarizability	47.35 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

8494414

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10318950

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Piao SJ, Zhang HJ, Lu HY, Yang F, Jiao WH, Yi YH, Chen WS, Lin HW: Hippolides A-H, acyclic manoalide derivatives from the marine sponge Hippospongia lachne. J Nat Prod. 2011 May 27;74(5):1248-54. doi: 10.1021/np200227s. Epub 2011 May 6. [PubMed:21548579 ]
LOTUS database [Link]

Showing NP-Card for (6e)-neomanoalide (NP0298158)

MOL for NP0298158 ((6e)-neomanoalide)

3D MOL for NP0298158 ((6e)-neomanoalide)

3D SDF for NP0298158 ((6e)-neomanoalide)

3D-SDF for NP0298158 ((6e)-neomanoalide)

PDB for NP0298158 ((6e)-neomanoalide)

3D PDB for NP0298158 ((6e)-neomanoalide)

SMILES for NP0298158 ((6e)-neomanoalide)

INCHI for NP0298158 ((6e)-neomanoalide)

Structure for NP0298158 ((6e)-neomanoalide)

3D Structure for NP0298158 ((6e)-neomanoalide)