NP-MRD: Showing NP-Card for 2-[(2r,5z)-5-[(4e,8e,12e)-4,9,13,17-tetramethyloctadeca-4,8,12,16-tetraen-1-ylidene]oxan-2-yl]prop-2-enoic acid (NP0167487)

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Record Information

Version

2.0

Created at

2022-09-03 03:04:32 UTC

Updated at

2022-09-03 03:04:32 UTC

NP-MRD ID

NP0167487

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(2r,5z)-5-[(4e,8e,12e)-4,9,13,17-tetramethyloctadeca-4,8,12,16-tetraen-1-ylidene]oxan-2-yl]prop-2-enoic acid

Description

Hippospongic acid A, also known as hippospongate a, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 2-[(2r,5z)-5-[(4e,8e,12e)-4,9,13,17-tetramethyloctadeca-4,8,12,16-tetraen-1-ylidene]oxan-2-yl]prop-2-enoic acid was first documented in 2003 (PMID: 12761303). Based on a literature review very few articles have been published on Hippospongic acid A (PMID: 15884945).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032205042D          

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M  END

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M  END


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 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
  9 32  1  0  0  0  0
 32 33  1  0  0  0  0
  6 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0167487

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C1\CC[C@@H](OC1)C(=C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O3/c1-23(2)12-9-15-26(5)17-10-16-24(3)13-7-8-14-25(4)18-11-19-28-20-21-29(33-22-28)27(6)30(31)32/h12-14,17,19,29H,6-11,15-16,18,20-22H2,1-5H3,(H,31,32)/b24-13+,25-14+,26-17+,28-19-/t29-/m1/s1

> <INCHI_KEY>
HJNULIFEXQNJKQ-WJJPFERQSA-N

> <FORMULA>
C30H46O3

> <MOLECULAR_WEIGHT>
454.695

> <EXACT_MASS>
454.344695341

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
56.862767974552845

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2R,5Z)-5-[(4E,8E,12E)-4,9,13,17-tetramethyloctadeca-4,8,12,16-tetraen-1-ylidene]oxan-2-yl]prop-2-enoic acid

> <ALOGPS_LOGP>
7.71

> <JCHEM_LOGP>
8.321759170666668

> <ALOGPS_LOGS>
-5.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.60850156596039

> <JCHEM_PKA_STRONGEST_BASIC>
-4.206812248276401

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
145.04260000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.26e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2R,5Z)-5-[(4E,8E,12E)-4,9,13,17-tetramethyloctadeca-4,8,12,16-tetraen-1-ylidene]oxan-2-yl]prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334  -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      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -14.670  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -16.004  -3.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -17.338  -2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -18.672  -3.080   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -20.005  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -21.339  -3.080   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -20.005  -0.770   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    2    7   33                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   32                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32    9   33                                                       
CONECT   33   32    6                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   66    0
END

View in JSmol

Synonyms

Value	Source
Hippospongate a	Generator

Chemical Formula

C₃₀H₄₆O₃

Average Mass

454.6950 Da

Monoisotopic Mass

454.34470 Da

IUPAC Name

2-[(2R,5Z)-5-[(4E,8E,12E)-4,9,13,17-tetramethyloctadeca-4,8,12,16-tetraen-1-ylidene]oxan-2-yl]prop-2-enoic acid

Traditional Name

2-[(2R,5Z)-5-[(4E,8E,12E)-4,9,13,17-tetramethyloctadeca-4,8,12,16-tetraen-1-ylidene]oxan-2-yl]prop-2-enoic acid

CAS Registry Number

Not Available

SMILES

CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C1\CC[C@@H](OC1)C(=C)C(O)=O

InChI Identifier

InChI=1S/C30H46O3/c1-23(2)12-9-15-26(5)17-10-16-24(3)13-7-8-14-25(4)18-11-19-28-20-21-29(33-22-28)27(6)30(31)32/h12-14,17,19,29H,6-11,15-16,18,20-22H2,1-5H3,(H,31,32)/b24-13+,25-14+,26-17+,28-19-/t29-/m1/s1

InChI Key

HJNULIFEXQNJKQ-WJJPFERQSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Oxane
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	7.71	ALOGPS
logP	8.32	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	4.61	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	145.04 m³·mol⁻¹	ChemAxon
Polarizability	56.86 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	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

8271040

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10095504

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Trost BM, Machacek MR, Tsui HC: Development of aliphatic alcohols as nucleophiles for palladium-catalyzed DYKAT reactions: total synthesis of (+)-hippospongic acid A. J Am Chem Soc. 2005 May 18;127(19):7014-24. doi: 10.1021/ja050340q. [PubMed:15884945 ]
Mizushina Y, Murakami C, Takikawa H, Kasai N, Xu X, Mori K, Oshige M, Yamaguchi T, Saneyoshi M, Shimazaki N, Koiwai O, Yoshida H, Sugawara F, Sakaguchi K: Molecular action mode of Hippospongic acid A, an inhibitor of gastrulation of starfish embryos. J Biochem. 2003 Apr;133(4):541-52. doi: 10.1093/jb/mvg070. [PubMed:12761303 ]
LOTUS database [Link]

Showing NP-Card for 2-[(2r,5z)-5-[(4e,8e,12e)-4,9,13,17-tetramethyloctadeca-4,8,12,16-tetraen-1-ylidene]oxan-2-yl]prop-2-enoic acid (NP0167487)

MOL for NP0167487 (2-[(2r,5z)-5-[(4e,8e,12e)-4,9,13,17-tetramethyloctadeca-4,8,12,16-tetraen-1-ylidene]oxan-2-yl]prop-2-enoic acid)

3D MOL for NP0167487 (2-[(2r,5z)-5-[(4e,8e,12e)-4,9,13,17-tetramethyloctadeca-4,8,12,16-tetraen-1-ylidene]oxan-2-yl]prop-2-enoic acid)

3D SDF for NP0167487 (2-[(2r,5z)-5-[(4e,8e,12e)-4,9,13,17-tetramethyloctadeca-4,8,12,16-tetraen-1-ylidene]oxan-2-yl]prop-2-enoic acid)

3D-SDF for NP0167487 (2-[(2r,5z)-5-[(4e,8e,12e)-4,9,13,17-tetramethyloctadeca-4,8,12,16-tetraen-1-ylidene]oxan-2-yl]prop-2-enoic acid)

PDB for NP0167487 (2-[(2r,5z)-5-[(4e,8e,12e)-4,9,13,17-tetramethyloctadeca-4,8,12,16-tetraen-1-ylidene]oxan-2-yl]prop-2-enoic acid)

3D PDB for NP0167487 (2-[(2r,5z)-5-[(4e,8e,12e)-4,9,13,17-tetramethyloctadeca-4,8,12,16-tetraen-1-ylidene]oxan-2-yl]prop-2-enoic acid)

SMILES for NP0167487 (2-[(2r,5z)-5-[(4e,8e,12e)-4,9,13,17-tetramethyloctadeca-4,8,12,16-tetraen-1-ylidene]oxan-2-yl]prop-2-enoic acid)

INCHI for NP0167487 (2-[(2r,5z)-5-[(4e,8e,12e)-4,9,13,17-tetramethyloctadeca-4,8,12,16-tetraen-1-ylidene]oxan-2-yl]prop-2-enoic acid)

Structure for NP0167487 (2-[(2r,5z)-5-[(4e,8e,12e)-4,9,13,17-tetramethyloctadeca-4,8,12,16-tetraen-1-ylidene]oxan-2-yl]prop-2-enoic acid)

3D Structure for NP0167487 (2-[(2r,5z)-5-[(4e,8e,12e)-4,9,13,17-tetramethyloctadeca-4,8,12,16-tetraen-1-ylidene]oxan-2-yl]prop-2-enoic acid)