NP-MRD: Showing NP-Card for 16alpha-Hydroxydehydrotrametenolic acid (NP0137640)

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Record Information

Version

2.0

Created at

2022-05-31 16:01:33 UTC

Updated at

2022-05-31 16:01:34 UTC

NP-MRD ID

NP0137640

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16alpha-Hydroxydehydrotrametenolic acid

Description

16Alpha-Hydroxydehydrotrametenolic acid belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 16alpha-Hydroxydehydrotrametenolic acid was first documented in 2015 (PMID: 26435185). Based on a literature review a small amount of articles have been published on 16alpha-Hydroxydehydrotrametenolic acid (PMID: 31108794) (PMID: 31090294) (PMID: 27912907).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652305312218012D          

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M  END

     RDKit          3D

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M  END


  Mrv1652305312218012D          

 39 42  0  0  1  0            999 V2000
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    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 12  2  1  1  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  6  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  1  0  0  0
 28 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 23 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 20 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 12 38  1  0  0  0  0
 18 38  1  0  0  0  0
 38 39  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0137640

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@](CCC=C(C)C)(C(O)=O)[C@@]1([H])[C@]([H])(O)C[C@@]2(C)C3=CC[C@@]4([H])C(C)(C)[C@@]([H])(O)CC[C@]4(C)C3=CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O4/c1-18(2)9-8-10-19(26(33)34)25-22(31)17-30(7)21-11-12-23-27(3,4)24(32)14-15-28(23,5)20(21)13-16-29(25,30)6/h9,11,13,19,22-25,31-32H,8,10,12,14-17H2,1-7H3,(H,33,34)/t19-,22-,23+,24+,25+,28-,29-,30+/m1/s1

> <INCHI_KEY>
XSLKAKROJKMHIT-WIUKAADNSA-N

> <FORMULA>
C30H46O4

> <MOLECULAR_WEIGHT>
470.694

> <EXACT_MASS>
470.339609961

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
56.05618778702809

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-[(2S,5S,7R,11R,13R,14R,15R)-5,13-dihydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(17),9-dien-14-yl]-6-methylhept-5-enoic acid

> <JCHEM_LOGP>
4.971711484333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.900497609260086

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.723431771513833

> <JCHEM_PKA_STRONGEST_BASIC>
-0.7785408198271931

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
138.9451

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-[(2S,5S,7R,11R,13R,14R,15R)-5,13-dihydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(17),9-dien-14-yl]-6-methylhept-5-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 31-MAY-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAY-22         0                                  
HETATM    1  H   UNK     0       3.837  -7.079   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.312  -6.868   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.786  -6.657   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.206  -5.231   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.320  -5.020   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.151  -4.015   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.888  -7.500   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       4.417  -8.505   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0       4.215  -4.357   0.000  0.00  0.00           H+0
HETATM   14  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   15  H   UNK     0       5.108  -1.640   0.000  0.00  0.00           H+0
HETATM   16  O   UNK     0       3.851  -2.645   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.159  -1.754   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0      13.330  -3.613   0.000  0.00  0.00           H+0
HETATM   25  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.323  -0.719   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.185  -1.391   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0      15.839  -4.519   0.000  0.00  0.00           H+0
HETATM   30  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9   12                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    2   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    2   13   14   38                                             
CONECT   13   12                                                            
CONECT   14   12   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14   18                                                       
CONECT   18   17   19   20   38                                             
CONECT   19   18                                                            
CONECT   20   18   21   35                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25   33                                             
CONECT   24   23                                                            
CONECT   25   23   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   23   34   35                                             
CONECT   34   33                                                            
CONECT   35   33   20   36                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   12   18   39                                             
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Value	Source
16a-Hydroxydehydrotrametenolate	Generator
16a-Hydroxydehydrotrametenolic acid	Generator
16alpha-Hydroxydehydrotrametenolate	Generator
16Α-hydroxydehydrotrametenolate	Generator
16Α-hydroxydehydrotrametenolic acid	Generator

Chemical Formula

C₃₀H₄₆O₄

Average Mass

470.6940 Da

Monoisotopic Mass

470.33961 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

176390-66-2

SMILES

[H][C@](CCC=C(C)C)(C(O)=O)[C@@]1([H])[C@]([H])(O)C[C@@]2(C)C3=CC[C@@]4([H])C(C)(C)[C@@]([H])(O)CC[C@]4(C)C3=CC[C@]12C

InChI Identifier

InChI=1S/C30H46O4/c1-18(2)9-8-10-19(26(33)34)25-22(31)17-30(7)21-11-12-23-27(3,4)24(32)14-15-28(23,5)20(21)13-16-29(25,30)6/h9,11,13,19,22-25,31-32H,8,10,12,14-17H2,1-7H3,(H,33,34)/t19-,22-,23+,24+,25+,28-,29-,30+/m1/s1

InChI Key

XSLKAKROJKMHIT-WIUKAADNSA-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
Cholesterol-skeleton
Cholestane-skeleton
Dihydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
Steroid acid
3-hydroxy-delta-7-steroid
3-hydroxysteroid
14-alpha-methylsteroid
Hydroxysteroid
16-alpha-hydroxysteroid
16-hydroxysteroid
3-beta-hydroxysteroid
Steroid
Delta-7-steroid
Medium-chain fatty acid
Hydroxy fatty acid
Fatty acid
Fatty acyl
Unsaturated fatty acid
Cyclic alcohol
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
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

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

8918339

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10743008

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang G, Wang H, Xie W, Wang Q, Wang X, Wang C, Du Y, Huo C, Wang Q: Comparison of triterpene compounds of four botanical parts from Poria cocos (Schw.) wolf using simultaneous qualitative and quantitative method and metabolomics approach. Food Res Int. 2019 Jul;121:666-677. doi: 10.1016/j.foodres.2018.12.036. Epub 2019 Jan 7. [PubMed:31108794 ]
Tian SS, Liu XQ, Feng WH, Zhang QW, Yan LH, Wang ZM, Gao L: [Quality evaluation of Poria based on specific chromatogram and quantitative analysis of multicomponents]. Zhongguo Zhong Yao Za Zhi. 2019 Apr;44(7):1371-1380. doi: 10.19540/j.cnki.cjcmm.20181220.005. [PubMed:31090294 ]
Lee SR, Lee S, Moon E, Park HJ, Park HB, Kim KH: Bioactivity-guided isolation of anti-inflammatory triterpenoids from the sclerotia of Poria cocos using LPS-stimulated Raw264.7 cells. Bioorg Chem. 2017 Feb;70:94-99. doi: 10.1016/j.bioorg.2016.11.012. Epub 2016 Nov 23. [PubMed:27912907 ]
Zeng H, Liu Q, Yu J, Jiang X, Wu Z, Wang M, Chen M, Chen X: One-step separation of nine structural analogues from Poria cocos (Schw.) Wolf. via tandem high-speed counter-current chromatography. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Nov 1;1004:10-6. doi: 10.1016/j.jchromb.2015.09.017. Epub 2015 Sep 26. [PubMed:26435185 ]

Showing NP-Card for 16alpha-Hydroxydehydrotrametenolic acid (NP0137640)

MOL for NP0137640 (16alpha-Hydroxydehydrotrametenolic acid)

3D MOL for NP0137640 (16alpha-Hydroxydehydrotrametenolic acid)

3D SDF for NP0137640 (16alpha-Hydroxydehydrotrametenolic acid)

3D-SDF for NP0137640 (16alpha-Hydroxydehydrotrametenolic acid)

PDB for NP0137640 (16alpha-Hydroxydehydrotrametenolic acid)

3D PDB for NP0137640 (16alpha-Hydroxydehydrotrametenolic acid)

SMILES for NP0137640 (16alpha-Hydroxydehydrotrametenolic acid)

INCHI for NP0137640 (16alpha-Hydroxydehydrotrametenolic acid)

Structure for NP0137640 (16alpha-Hydroxydehydrotrametenolic acid)

3D Structure for NP0137640 (16alpha-Hydroxydehydrotrametenolic acid)