NP-MRD: Showing NP-Card for Sebiferenic acid (NP0137050)

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Record Information

Version

2.0

Created at

2022-05-30 16:40:12 UTC

Updated at

2022-05-30 16:40:12 UTC

NP-MRD ID

NP0137050

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sebiferenic acid

Description

Sebiferenic acid, also known as sebiferenate, belongs to the class of organic compounds known as scalarane sesterterpenoids. These are sesterterpenoids with a structure based on the scalarane backbone. Scalarane is a tetracyclic compound, which is similar the homoandrostane with five methyl groups at the 4-, 4-, 8-, 17-, 17a-positions. Sebiferenic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Sebiferenic acid has been detected, but not quantified in, fats and oils. Sebiferenic acid is found in Triadica sebifera. This could make sebiferenic acid a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061308412D          

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M  END

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  Mrv0541 05061308412D          

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 19  8  1  0  0  0  0
 20 10  2  0  0  0  0
 21  9  1  0  0  0  0
 22 17  1  0  0  0  0
 23 18  1  0  0  0  0
 25  1  1  0  0  0  0
 25  2  1  0  0  0  0
 25 14  1  0  0  0  0
 25 17  1  0  0  0  0
 26  3  1  0  0  0  0
 26  4  1  0  0  0  0
 26 19  1  0  0  0  0
 26 23  1  0  0  0  0
 27  5  1  0  0  0  0
 27 11  1  0  0  0  0
 27 20  1  0  0  0  0
 27 21  1  0  0  0  0
 28  6  1  0  0  0  0
 28 12  1  0  0  0  0
 28 20  1  0  0  0  0
 28 22  1  0  0  0  0
 29  7  1  0  0  0  0
 29 16  1  0  0  0  0
 29 19  1  0  0  0  0
 29 21  1  0  0  0  0
 30 13  1  0  0  0  0
 30 15  1  0  0  0  0
 30 22  1  0  0  0  0
 30 24  1  0  0  0  0
 31 18  1  0  0  0  0
 32 23  1  0  0  0  0
 33 24  2  0  0  0  0
 34 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137050

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCC2(CC=C3C4(C)CCC5C(C)(C)C(O)C(O)CC5(C)C4CCC3(C)C2C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O4/c1-25(2)14-15-30(24(33)34)13-10-20-27(5)11-8-19-26(3,4)23(32)18(31)16-29(19,7)21(27)9-12-28(20,6)22(30)17-25/h10,18-19,21-23,31-32H,8-9,11-17H2,1-7H3,(H,33,34)

> <INCHI_KEY>
JMJVYEINATYJHM-UHFFFAOYSA-N

> <FORMULA>
C30H48O4

> <MOLECULAR_WEIGHT>
472.6997

> <EXACT_MASS>
472.355260024

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
55.9466123033628

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
10,11-dihydroxy-2,2,6b,9,9,12a,14a-heptamethyl-1,2,3,4,4a,5,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a,14b-icosahydropicene-4a-carboxylic acid

> <ALOGPS_LOGP>
5.88

> <JCHEM_LOGP>
5.519929826333335

> <ALOGPS_LOGS>
-5.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.627313601899676

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.743995837439183

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1598163689737273

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
134.986

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.02e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10,11-dihydroxy-2,2,6b,9,9,12a,14a-heptamethyl-1,3,4,5,7,8,8a,10,11,12,12b,13,14,14b-tetradecahydropicene-4a-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -8.886   3.530   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.171   2.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.074   8.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.789   7.250   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.048   8.057   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.358   4.056   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.262   4.056   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.032   8.057   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.278   4.056   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.588   8.057   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.508   8.057   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.818   4.056   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.128   8.057   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -8.208   5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -7.438   6.724   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.802   4.056   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.898   4.056   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.342   4.056   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.802   6.724   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.818   6.724   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.508   5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.128   5.390   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.112   5.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.668   8.057   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -7.438   4.056   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.342   6.724   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.278   6.724   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.588   5.390   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.032   5.390   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.898   6.724   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.112   2.723   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       5.652   5.390   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -8.208   8.057   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -5.898   9.391   0.000  0.00  0.00           O+0
CONECT    1   25                                                            
CONECT    2   25                                                            
CONECT    3   26                                                            
CONECT    4   26                                                            
CONECT    5   27                                                            
CONECT    6   28                                                            
CONECT    7   29                                                            
CONECT    8   11   19                                                       
CONECT    9   12   21                                                       
CONECT   10   13   20                                                       
CONECT   11    8   27                                                       
CONECT   12    9   28                                                       
CONECT   13   10   30                                                       
CONECT   14   15   25                                                       
CONECT   15   14   30                                                       
CONECT   16   18   29                                                       
CONECT   17   22   25                                                       
CONECT   18   16   23   31                                                  
CONECT   19    8   26   29                                                  
CONECT   20   10   27   28                                                  
CONECT   21    9   27   29                                                  
CONECT   22   17   28   30                                                  
CONECT   23   18   26   32                                                  
CONECT   24   30   33   34                                                  
CONECT   25    1    2   14   17                                             
CONECT   26    3    4   19   23                                             
CONECT   27    5   11   20   21                                             
CONECT   28    6   12   20   22                                             
CONECT   29    7   16   19   21                                             
CONECT   30   13   15   22   24                                             
CONECT   31   18                                                            
CONECT   32   23                                                            
CONECT   33   24                                                            
CONECT   34   24                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Value	Source
Sebiferenate	Generator
2a-Hydroxyaleuritolic acid	HMDB
2a-Hydroxymaprounic acid	HMDB
10,11-Dihydroxy-2,2,6b,9,9,12a,14a-heptamethyl-1,2,3,4,4a,5,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a,14b-icosahydropicene-4a-carboxylate	Generator

Chemical Formula

C₃₀H₄₈O₄

Average Mass

472.6997 Da

Monoisotopic Mass

472.35526 Da

IUPAC Name

10,11-dihydroxy-2,2,6b,9,9,12a,14a-heptamethyl-1,2,3,4,4a,5,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14a,14b-icosahydropicene-4a-carboxylic acid

Traditional Name

10,11-dihydroxy-2,2,6b,9,9,12a,14a-heptamethyl-1,3,4,5,7,8,8a,10,11,12,12b,13,14,14b-tetradecahydropicene-4a-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1(C)CCC2(CC=C3C4(C)CCC5C(C)(C)C(O)C(O)CC5(C)C4CCC3(C)C2C1)C(O)=O

InChI Identifier

InChI=1S/C30H48O4/c1-25(2)14-15-30(24(33)34)13-10-20-27(5)11-8-19-26(3,4)23(32)18(31)16-29(19,7)21(27)9-12-28(20,6)22(30)17-25/h10,18-19,21-23,31-32H,8-9,11-17H2,1-7H3,(H,33,34)

InChI Key

JMJVYEINATYJHM-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
Triadica sebifera	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as scalarane sesterterpenoids. These are sesterterpenoids with a structure based on the scalarane backbone. Scalarane is a tetracyclic compound, which is similar the homoandrostane with five methyl groups at the 4-, 4-, 8-, 17-, 17a-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Scalarane sesterterpenoids

Alternative Parents

Substituents

Scalarane sesterterpenoid
Cyclic alcohol
Secondary alcohol
1,2-diol
Monocarboxylic acid or derivatives
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	5.88	ALOGPS
logP	5.52	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	4.74	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	134.99 m³·mol⁻¹	ChemAxon
Polarizability	55.95 Å³	ChemAxon
Number of Rings	5	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

HMDB0035748

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014478

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

75049017

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Sebiferenic acid (NP0137050)

MOL for NP0137050 (Sebiferenic acid)

3D MOL for NP0137050 (Sebiferenic acid)

3D SDF for NP0137050 (Sebiferenic acid)

3D-SDF for NP0137050 (Sebiferenic acid)

PDB for NP0137050 (Sebiferenic acid)

3D PDB for NP0137050 (Sebiferenic acid)

SMILES for NP0137050 (Sebiferenic acid)

INCHI for NP0137050 (Sebiferenic acid)

Structure for NP0137050 (Sebiferenic acid)

3D Structure for NP0137050 (Sebiferenic acid)