NP-MRD: Showing NP-Card for 22-Hydroxy-3-oxo-12-ursen-30-oic acid (NP0138094)

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Record Information

Version

1.0

Created at

2022-05-31 16:46:28 UTC

Updated at

2022-05-31 16:46:28 UTC

NP-MRD ID

NP0138094

Secondary Accession Numbers

None

Natural Product Identification

Common Name

22-Hydroxy-3-oxo-12-ursen-30-oic acid

Description

22-Hydroxy-3-oxo-12-ursen-30-oic acid belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. It was first documented in 2022 (PMID: 35633614). Based on a literature review a significant number of articles have been published on 22-Hydroxy-3-oxo-12-ursen-30-oic acid (PMID: 35633556) (PMID: 35633535) (PMID: 35633460) (PMID: 35633602) (PMID: 35633552) (PMID: 35633551).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652305312218462D          

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M  END

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M  END


  Mrv1652305312218462D          

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    5.2520   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645   -5.9664    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -5.2520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1895   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -5.2520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6907   -6.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -5.2520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  1  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  6  0  0  0
 10 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  1  0  0  0  0
 20 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 18 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 15 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
  2 39  1  0  0  0  0
 13 39  1  0  0  0  0
 39 40  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0138094

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1(O)C[C@@]([H])(C(O)=O)[C@]([H])(C)[C@@]2([H])C3=CC[C@]4([H])[C@@]5(C)CCC(=O)C(C)(C)C5([H])CC[C@@]4(C)[C@]3(C)CC[C@@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O4/c1-17-18(25(33)34)16-23(32)28(5)14-15-29(6)19(24(17)28)8-9-21-27(4)12-11-22(31)26(2,3)20(27)10-13-30(21,29)7/h8,17-18,20-21,23-24,32H,9-16H2,1-7H3,(H,33,34)/t17-,18+,20?,21+,23?,24-,27-,28-,29+,30+/m0/s1

> <INCHI_KEY>
QGMNTKNSMLYTKS-BAKMLKDBSA-N

> <FORMULA>
C30H46O4

> <MOLECULAR_WEIGHT>
470.694

> <EXACT_MASS>
470.339609961

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
54.68361978688368

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,4aR,6aS,6bR,12aR,12bR,14bS)-4-hydroxy-1,4a,6a,6b,9,9,12a-heptamethyl-10-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylic acid

> <JCHEM_LOGP>
5.658554866333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.691064850460073

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.554365838392054

> <JCHEM_PKA_STRONGEST_BASIC>
-2.946679917326658

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
134.36530000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4aR,6aS,6bR,12aR,12bR,14bS)-4-hydroxy-1,4a,6a,6b,9,9,12a-heptamethyl-10-oxo-1,2,3,4,5,6,7,8,8a,11,12,12b,13,14b-tetradecahydropicene-2-carboxylic 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      -0.976  -9.804   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       0.564  -9.804   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.206 -11.137   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.206  -8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.564  -7.136   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0       1.334  -5.803   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0      -0.206  -5.803   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.746  -5.803   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.564  -4.469   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.104  -7.136   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0       3.644  -7.136   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0       2.874  -5.803   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.874  -8.470   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0       3.644  -9.804   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0       4.414  -8.470   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.184  -7.136   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.724  -7.136   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.494  -8.470   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0       8.264  -9.804   0.000  0.00  0.00           H+0
HETATM   20  C   UNK     0       9.034  -8.470   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.264  -7.136   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.804  -7.136   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.344  -7.136   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.114  -8.470   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      13.654  -8.470   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      11.344  -9.804   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.791 -10.330   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.076 -11.320   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.804  -9.804   0.000  0.00  0.00           C+0
HETATM   30  H   UNK     0      10.574 -11.137   0.000  0.00  0.00           H+0
HETATM   31  C   UNK     0       9.034 -11.137   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.494 -11.137   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.724  -9.804   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.954 -11.137   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.184  -9.804   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.023 -11.335   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.414 -11.137   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.874 -11.137   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.104  -9.804   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       1.334 -11.137   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   39                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7   10                                             
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10   14   15   39                                             
CONECT   14   13                                                            
CONECT   15   13   16   35                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   33                                             
CONECT   19   18                                                            
CONECT   20   18   21   22   29                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26   20   30   31                                             
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   18   34   35                                             
CONECT   34   33                                                            
CONECT   35   33   15   36   37                                             
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38    2   13   40                                             
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   88    0
END

View in JSmol

Synonyms

Value	Source
22-Hydroxy-3-oxo-12-ursen-30-Oate	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

173991-81-6

SMILES

[H]C1(O)C[C@@]([H])(C(O)=O)[C@]([H])(C)[C@@]2([H])C3=CC[C@]4([H])[C@@]5(C)CCC(=O)C(C)(C)C5([H])CC[C@@]4(C)[C@]3(C)CC[C@@]12C

InChI Identifier

InChI=1S/C30H46O4/c1-17-18(25(33)34)16-23(32)28(5)14-15-29(6)19(24(17)28)8-9-21-27(4)12-11-22(31)26(2,3)20(27)10-13-30(21,29)7/h8,17-18,20-21,23-24,32H,9-16H2,1-7H3,(H,33,34)/t17-,18+,20?,21+,23?,24-,27-,28-,29+,30+/m0/s1

InChI Key

QGMNTKNSMLYTKS-BAKMLKDBSA-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
Cyclic alcohol
Cyclic ketone
Secondary alcohol
Ketone
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

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

30647244

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73554051

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Al-Zubaidy NA, Sahib HB: The Antiangiogenic Activity of Flaxseed Oil Alone and Combination with Mefenamic Acid in Vivo and in Vitro Assay. Asian Pac J Cancer Prev. 2022 May 1;23(5):1711-1717. doi: 10.31557/APJCP.2022.23.5.1711. [PubMed:35633556 ]
Qashou E, Al-Hiari Y, Kasabri V, AlBashiti R, AlAlawi S, Telfah A, AlHadid A: Antiproliferative Activities of Lipophililic Fluoroquinolones- Based Scaffold Against a Panel of Solid and Liquid Cancer Cell Lines. Asian Pac J Cancer Prev. 2022 May 1;23(5):1529-1537. doi: 10.31557/APJCP.2022.23.5.1529. [PubMed:35633535 ]
Kang F, Lv QL, Liu J, Meng YS, Wang ZH, Ren XQ, Hu SW: Organic-inorganic calcium lignosulfonate compounds for soil acidity amelioration. Environ Sci Pollut Res Int. 2022 May 28. pii: 10.1007/s11356-022-20461-1. doi: 10.1007/s11356-022-20461-1. [PubMed:35633460 ]
Liu J, Chen J, Xu B, Lin L, Liu S, Ma X, Liu J: 3,4,5-O-tricaffeoylquinic acid with anti-radiation activity suppresses LPS-induced NLRP3 inflammasome activation via autophagy in THP-1 macrophages. Mol Immunol. 2022 May 25;147:187-198. doi: 10.1016/j.molimm.2022.05.011. [PubMed:35633614 ]
Awaad A, Elkady EF, El-Mahdy SM: Time-dependent biodistribution profiles and reaction of polyethylene glycol-coated iron oxide nanoclusters in the spleen after intravenous injection in the mice. Acta Histochem. 2022 May 25;124(5):151907. doi: 10.1016/j.acthis.2022.151907. [PubMed:35633602 ]
Wiriyaukaradecha K, Nimsanor S, Tantirukdham N, Tongsom J, Bunyoo C, Soonklang K, Sritana N, Auewarakul C: Study of CALR, MPL, and c-kit Gene Mutations in Thai Patients with JAK2 V617F Negative Myeloproliferative Neoplasms. Asian Pac J Cancer Prev. 2022 May 1;23(5):1671-1678. doi: 10.31557/APJCP.2022.23.5.1671. [PubMed:35633552 ]
Rahimian L, Kalantari Khandani B, Nemati M, Hoseini-Shahrestanak S, Aminizadeh N, Jafarzadeh A: Reduced Expression of Natural Killer Cell-Related Activating Receptors by Peripheral Blood Mononuclear Cells from Patients with Breast Cancer and Their Improvement by Zoledronic Acid. Asian Pac J Cancer Prev. 2022 May 1;23(5):1661-1669. doi: 10.31557/APJCP.2022.23.5.1661. [PubMed:35633551 ]
Bashari MH, Fadhil M, Aulia Y, Sari AK, Putri T, Qomarilla N, Atmaja H, Sudji IR, Ariyanto EF, Indrati AR, Rohmawaty E: The Ethyl Acetate Fraction of Marine Sponge Stylissa carteri Induces Breast Cancer Cell Death via Upregulation of Mcl-1S: an In vitro Study. Asian Pac J Cancer Prev. 2022 May 1;23(5):1653-1660. doi: 10.31557/APJCP.2022.23.5.1653. [PubMed:35633550 ]
Chtouki M, Bargaz A, Lyamlouli K, Oukarroum A, Zeroual Y: A phospho-compost biological-based approach increases phosphate rock agronomic efficiency in faba bean as compared to chemical and physical treatments. Environ Sci Pollut Res Int. 2022 May 28. pii: 10.1007/s11356-022-21087-z. doi: 10.1007/s11356-022-21087-z. [PubMed:35633456 ]
Oter C: Solid Phase Extraction for the Determination of Methylene Blue Using Lignocellulosic Biosorbent in Aqueous Solutions. Bull Environ Contam Toxicol. 2022 May 28. pii: 10.1007/s00128-022-03543-1. doi: 10.1007/s00128-022-03543-1. [PubMed:35633396 ]

Showing NP-Card for 22-Hydroxy-3-oxo-12-ursen-30-oic acid (NP0138094)

MOL for NP0138094 (22-Hydroxy-3-oxo-12-ursen-30-oic acid)

3D MOL for NP0138094 (22-Hydroxy-3-oxo-12-ursen-30-oic acid)

3D SDF for NP0138094 (22-Hydroxy-3-oxo-12-ursen-30-oic acid)

3D-SDF for NP0138094 (22-Hydroxy-3-oxo-12-ursen-30-oic acid)

PDB for NP0138094 (22-Hydroxy-3-oxo-12-ursen-30-oic acid)

3D PDB for NP0138094 (22-Hydroxy-3-oxo-12-ursen-30-oic acid)

SMILES for NP0138094 (22-Hydroxy-3-oxo-12-ursen-30-oic acid)

INCHI for NP0138094 (22-Hydroxy-3-oxo-12-ursen-30-oic acid)

Structure for NP0138094 (22-Hydroxy-3-oxo-12-ursen-30-oic acid)

3D Structure for NP0138094 (22-Hydroxy-3-oxo-12-ursen-30-oic acid)