NP-MRD: Showing NP-Card for Ulmoidol (NP0086131)

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Record Information

Version

2.0

Created at

2022-04-29 06:29:46 UTC

Updated at

2022-04-29 06:29:46 UTC

NP-MRD ID

NP0086131

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ulmoidol

Description

Ulmoidol belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Ulmoidol is found in Eucommia ulmoides and Ilex asprella. Ulmoidol was first documented in 2012 (PMID: 23183887). Based on a literature review very few articles have been published on ulmoidol (PMID: 34560559).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292208292D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304292208292D          

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    3.8406   -1.1155    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2542   -1.8294    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6656   -1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0792   -1.8281    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  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  6  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  6  0  0  0
 13 16  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 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  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
  6 27  2  0  0  0  0
  5 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
  8 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 18 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 20 36  1  0  0  0  0
 36 37  1  1  0  0  0
 36 38  1  0  0  0  0
 25 38  1  0  0  0  0
 38 39  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0086131

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12O[C@]1([H])[C@]13OC(=O)[C@@]4(CC[C@@H](C)[C@H](C)[C@@]14[H])CC[C@@]3(C)[C@]1(C)CC[C@@]3([H])C(=C)[C@@H](O)[C@H](O)C[C@]3(C)[C@@]21[H]

> <INCHI_IDENTIFIER>
InChI=1S/C29H42O5/c1-14-7-10-28-12-11-27(6)26(5)9-8-17-16(3)19(31)18(30)13-25(17,4)22(26)20-23(33-20)29(27,34-24(28)32)21(28)15(14)2/h14-15,17-23,30-31H,3,7-13H2,1-2,4-6H3/t14-,15+,17+,18-,19-,20+,21-,22-,23+,25+,26-,27+,28+,29-/m1/s1

> <INCHI_KEY>
CGDNMHCUSPXQHB-ASWZSIAWSA-N

> <FORMULA>
C29H42O5

> <MOLECULAR_WEIGHT>
470.65

> <EXACT_MASS>
470.303224452

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
53.453805254911515

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,4S,5R,6S,8R,9R,11R,14R,15S,18S,21R,22S,23R)-8,9-dihydroxy-6,14,15,21,22-pentamethyl-10-methylidene-3,24-dioxaheptacyclo[16.5.2.0^{1,15}.0^{2,4}.0^{5,14}.0^{6,11}.0^{18,23}]pentacosan-25-one

> <ALOGPS_LOGP>
3.71

> <JCHEM_LOGP>
3.937763530999999

> <ALOGPS_LOGS>
-5.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.083144303334613

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.510667631585939

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1820960231969693

> <JCHEM_POLAR_SURFACE_AREA>
79.28999999999999

> <JCHEM_REFRACTIVITY>
126.60669999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.00e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4S,5R,6S,8R,9R,11R,14R,15S,18S,21R,22S,23R)-8,9-dihydroxy-6,14,15,21,22-pentamethyl-10-methylidene-3,24-dioxaheptacyclo[16.5.2.0^{1,15}.0^{2,4}.0^{5,14}.0^{6,11}.0^{18,23}]pentacosan-25-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0      -0.774   2.330   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.715   0.791   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.018  -0.029   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.959  -1.568   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.597  -2.286   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.094  -0.749   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.065   0.350   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.634  -0.710   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.706  -1.466   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0       1.605  -2.716   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0       0.647   0.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.950   0.894   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.537   0.601   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.313   1.932   0.000  0.00  0.00           O+0
HETATM   15  H   UNK     0       3.251  -0.763   0.000  0.00  0.00           H+0
HETATM   16  C   UNK     0       4.077   0.595   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0       4.855   1.924   0.000  0.00  0.00           H+0
HETATM   18  C   UNK     0       4.857  -0.752   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0       5.629  -2.085   0.000  0.00  0.00           H+0
HETATM   20  C   UNK     0       6.397  -0.750   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.625   0.583   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.165   0.585   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.705   0.587   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.473   1.922   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.477  -0.745   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      11.017  -0.743   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -2.558  -0.271   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.285  -3.645   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.880  -3.578   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.529  -2.092   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.375  -3.379   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.089  -2.087   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.254  -3.618   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.861  -3.420   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.401  -3.417   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.169  -2.082   0.000  0.00  0.00           C+0
HETATM   37  H   UNK     0       7.941  -3.415   0.000  0.00  0.00           H+0
HETATM   38  C   UNK     0       8.709  -2.080   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       9.481  -3.413   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9   28                                             
CONECT    6    5    7   27                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13   30                                             
CONECT    9    8    5   10   11                                             
CONECT   10    9                                                            
CONECT   11    9    2   12                                                  
CONECT   12   11                                                            
CONECT   13    8   14   15   16                                             
CONECT   14   13   16                                                       
CONECT   15   13                                                            
CONECT   16   13   14   17   18                                             
CONECT   17   16                                                            
CONECT   18   16   19   20   32                                             
CONECT   19   18                                                            
CONECT   20   18   21   22   36                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   38                                                  
CONECT   26   25                                                            
CONECT   27    6                                                            
CONECT   28    5   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29    8   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   18   33   34                                             
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   20   37   38                                             
CONECT   37   36                                                            
CONECT   38   36   25   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   90    0
END

View in JSmol

Synonyms

Value	Source
(1S,2S,4S,5R,6S,8R,9R,11R,14R,15S,18S,21R,22S,23R)-8,9-Dihydroxy-6,14,15,21,22-pentamethyl-10-methylidene-3,24-dioxaheptacyclo(16.5.2.01,15.02,4.05,14.06,11.018,23)pentacosan-25-one	MeSH

Chemical Formula

C₂₉H₄₂O₅

Average Mass

470.6500 Da

Monoisotopic Mass

470.30322 Da

IUPAC Name

(1S,2S,4S,5R,6S,8R,9R,11R,14R,15S,18S,21R,22S,23R)-8,9-dihydroxy-6,14,15,21,22-pentamethyl-10-methylidene-3,24-dioxaheptacyclo[16.5.2.0^{1,15}.0^{2,4}.0^{5,14}.0^{6,11}.0^{18,23}]pentacosan-25-one

Traditional Name

(1S,2S,4S,5R,6S,8R,9R,11R,14R,15S,18S,21R,22S,23R)-8,9-dihydroxy-6,14,15,21,22-pentamethyl-10-methylidene-3,24-dioxaheptacyclo[16.5.2.0^{1,15}.0^{2,4}.0^{5,14}.0^{6,11}.0^{18,23}]pentacosan-25-one

CAS Registry Number

Not Available

SMILES

[H][C@@]12O[C@]1([H])[C@]13OC(=O)[C@@]4(CC[C@@H](C)[C@H](C)[C@@]14[H])CC[C@@]3(C)[C@]1(C)CC[C@@]3([H])C(=C)[C@@H](O)[C@H](O)C[C@]3(C)[C@@]21[H]

InChI Identifier

InChI=1S/C29H42O5/c1-14-7-10-28-12-11-27(6)26(5)9-8-17-16(3)19(31)18(30)13-25(17,4)22(26)20-23(33-20)29(27,34-24(28)32)21(28)15(14)2/h14-15,17-23,30-31H,3,7-13H2,1-2,4-6H3/t14-,15+,17+,18-,19-,20+,21-,22-,23+,25+,26-,27+,28+,29-/m1/s1

InChI Key

CGDNMHCUSPXQHB-ASWZSIAWSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Eucommia ulmoides	LOTUS Database	35616633
Ilex asprella	Plant	KNApSAcK

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
Caprolactone
Oxepane
Gamma butyrolactone
Cyclic alcohol
Tetrahydrofuran
1,2-diol
Carboxylic acid ester
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organooxygen compound
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	3.71	ALOGPS
logP	3.94	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	13.51	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.29 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	126.61 m³·mol⁻¹	ChemAxon
Polarizability	53.45 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

C00056270

Chemspider ID

10194525

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15819326

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Han R, Yuan T, Yang Z, Zhang Q, Wang WW, Lin LB, Zhu MQ, Gao JM: Ulmoidol, an unusual nortriterpenoid from Eucommia ulmoides Oliv. Leaves prevents neuroinflammation by targeting the PU.1 transcriptional signaling pathway. Bioorg Chem. 2021 Nov;116:105345. doi: 10.1016/j.bioorg.2021.105345. Epub 2021 Sep 9. [PubMed:34560559 ]
Li C, Li L, Wang C, Yang J, Ye F, Tian J, Si Y, Zhang D: A new ursane-type nor-triterpenoid from the leaves of Eucommia ulmoides Oliv. Molecules. 2012 Nov 26;17(12):13960-8. doi: 10.3390/molecules171213960. [PubMed:23183887 ]

Showing NP-Card for Ulmoidol (NP0086131)

MOL for NP0086131 (Ulmoidol)

3D MOL for NP0086131 (Ulmoidol)

3D SDF for NP0086131 (Ulmoidol)

3D-SDF for NP0086131 (Ulmoidol)

PDB for NP0086131 (Ulmoidol)

3D PDB for NP0086131 (Ulmoidol)

SMILES for NP0086131 (Ulmoidol)

INCHI for NP0086131 (Ulmoidol)

Structure for NP0086131 (Ulmoidol)

3D Structure for NP0086131 (Ulmoidol)