NP-MRD: Showing NP-Card for Yunnanxane (NP0074791)

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Record Information

Version

2.0

Created at

2022-04-28 20:07:24 UTC

Updated at

2022-04-28 20:07:24 UTC

NP-MRD ID

NP0074791

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Yunnanxane

Description

Yunnanxane belongs to the class of organic compounds known as taxanes and derivatives. These are diterpenoids with a structure based either on the taxane skeleton, or a derivative thereof. In term of phytochemistry, several derivatives of the taxane skeleton exist: 2(3->20)-Abeotaxane, 3,11-cyclotaxane, 11(15->1),11(10->9)-abeotaxane, 3,8-seco-taxane, and 11(15->1)-abeotaxane, among others. More complex skeletons have been found recently, which include the taxane-derived [3.3.3] Propellane ring system. Yunnanxane is found in Taxus baccata , Taxus chinensis, Taxus cuspidata , Taxus mairei , Taxus wallichiana and Taxus yunnanensis. Yunnanxane was first documented in 2004 (PMID: 14738387). Based on a literature review a small amount of articles have been published on Yunnanxane (PMID: 17144468) (PMID: 25924478) (PMID: 17425097) (PMID: 16268509).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282222072D          

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M  END


  Mrv1652304282222072D          

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   -4.9001    3.9396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7251    3.9380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1362    3.2227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1390    4.6516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6819    1.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7686    0.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1014    0.0897    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3475    0.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6804   -0.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1881   -0.7307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9419   -1.0659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0286   -1.8863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6091   -0.5806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6481    2.1332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9919    0.7024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1670    0.7157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7660    1.4367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7430    0.0080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1021    2.5865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7894    2.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8613    4.6268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 10 14  1  1  0  0  0
  4 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 16 27  1  6  0  0  0
 27 28  2  0  0  0  0
 26 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 17 33  1  6  0  0  0
 15 34  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
  3 38  1  0  0  0  0
  3 39  1  0  0  0  0
  1 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0074791

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](O)[C@@H](C)C(=O)O[C@H]1CC(C)=C2[C@H](C[C@]3(C)CC[C@H](OC(C)=O)C(=C)[C@H]3[C@H](OC(C)=O)[C@H]1C2(C)C)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C31H46O9/c1-15-13-23(40-29(36)16(2)18(4)32)27-28(39-21(7)35)26-17(3)22(37-19(5)33)11-12-31(26,10)14-24(38-20(6)34)25(15)30(27,8)9/h16,18,22-24,26-28,32H,3,11-14H2,1-2,4-10H3/t16-,18+,22+,23+,24+,26+,27+,28+,31+/m1/s1

> <INCHI_KEY>
FMPIEMVVEJGMCY-YYURHUSPSA-N

> <FORMULA>
C31H46O9

> <MOLECULAR_WEIGHT>
562.7

> <EXACT_MASS>
562.314183061

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
60.23241519137832

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,3S,5S,8S,10S,14S)-2,5,10-tris(acetyloxy)-8,12,15,15-tetramethyl-4-methylidenetricyclo[9.3.1.0^{3,8}]pentadec-11-en-14-yl (2R,3S)-3-hydroxy-2-methylbutanoate

> <ALOGPS_LOGP>
3.80

> <JCHEM_LOGP>
2.8813809406666677

> <ALOGPS_LOGS>
-5.23

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.027480528833948

> <JCHEM_PKA_STRONGEST_BASIC>
-2.78678001668803

> <JCHEM_POLAR_SURFACE_AREA>
125.43000000000004

> <JCHEM_REFRACTIVITY>
146.276

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.31e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,3S,5S,8S,10S,14S)-2,5,10-tris(acetyloxy)-8,12,15,15-tetramethyl-4-methylidenetricyclo[9.3.1.0^{3,8}]pentadec-11-en-14-yl (2R,3S)-3-hydroxy-2-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -5.313   7.097   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.762   6.313   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.135   5.058   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.341   3.902   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.953   4.790   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.880   6.387   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.620   4.020   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.286   4.790   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.286   6.330   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.048   4.020   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.381   4.790   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.715   4.020   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.381   6.330   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.048   2.480   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.376   2.632   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -7.954   2.325   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -9.199   3.230   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -9.407   4.791   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -8.374   6.022   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -9.147   7.354   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0     -10.687   7.351   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0     -11.454   6.016   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0     -11.460   8.683   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -10.606   2.605   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -10.768   1.073   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -9.523   0.167   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -8.115   0.793   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -6.870  -0.113   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -9.684  -1.364   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0     -11.092  -1.990   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0     -11.253  -3.521   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0     -12.337  -1.084   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -10.543   3.982   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -5.585   1.311   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -4.045   1.336   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -3.297   2.682   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -3.254   0.015   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -7.657   4.828   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -7.073   3.838   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -5.341   8.637   0.000  0.00  0.00           C+0
CONECT    1    2    6   40                                                  
CONECT    2    1    3   19                                                  
CONECT    3    2    4   38   39                                             
CONECT    4    3    5   15                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10                                                            
CONECT   15    4   16   34                                                  
CONECT   16   15   17   27                                                  
CONECT   17   16   18   24   33                                             
CONECT   18   17   19                                                       
CONECT   19   18    2   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   17   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   16   28                                                  
CONECT   28   27                                                            
CONECT   29   26   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   17                                                            
CONECT   34   15   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38    3                                                            
CONECT   39    3                                                            
CONECT   40    1                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₄₆O₉

Average Mass

562.7000 Da

Monoisotopic Mass

562.31418 Da

IUPAC Name

(1S,2S,3S,5S,8S,10S,14S)-2,5,10-tris(acetyloxy)-8,12,15,15-tetramethyl-4-methylidenetricyclo[9.3.1.0^{3,8}]pentadec-11-en-14-yl (2R,3S)-3-hydroxy-2-methylbutanoate

Traditional Name

(1S,2S,3S,5S,8S,10S,14S)-2,5,10-tris(acetyloxy)-8,12,15,15-tetramethyl-4-methylidenetricyclo[9.3.1.0^{3,8}]pentadec-11-en-14-yl (2R,3S)-3-hydroxy-2-methylbutanoate

CAS Registry Number

Not Available

SMILES

C[C@H](O)[C@@H](C)C(=O)O[C@H]1CC(C)=C2[C@H](C[C@]3(C)CC[C@H](OC(C)=O)C(=C)[C@H]3[C@H](OC(C)=O)[C@H]1C2(C)C)OC(C)=O

InChI Identifier

InChI=1S/C31H46O9/c1-15-13-23(40-29(36)16(2)18(4)32)27-28(39-21(7)35)26-17(3)22(37-19(5)33)11-12-31(26,10)14-24(38-20(6)34)25(15)30(27,8)9/h16,18,22-24,26-28,32H,3,11-14H2,1-2,4-10H3/t16-,18+,22+,23+,24+,26+,27+,28+,31+/m1/s1

InChI Key

FMPIEMVVEJGMCY-YYURHUSPSA-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
Taxus baccata	Plant	KNApSAcK
Taxus chinensis	Plant	KNApSAcK
Taxus cuspidata	Plant	KNApSAcK
Taxus mairei	Plant	KNApSAcK
Taxus wallichiana	LOTUS Database	35616633
Taxus wallichiana var. yunnanensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as taxanes and derivatives. These are diterpenoids with a structure based either on the taxane skeleton, or a derivative thereof. In term of phytochemistry, several derivatives of the taxane skeleton exist: 2(3->20)-Abeotaxane, 3,11-cyclotaxane, 11(15->1),11(10->9)-abeotaxane, 3,8-seco-taxane, and 11(15->1)-abeotaxane, among others. More complex skeletons have been found recently, which include the taxane-derived [3.3.3] Propellane ring system.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Taxanes and derivatives

Alternative Parents

Substituents

Taxane diterpenoid
Tetracarboxylic acid or derivatives
Beta-hydroxy acid
Fatty acid ester
Fatty acyl
Hydroxy acid
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
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	3.8	ALOGPS
logP	2.88	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	15.03	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	125.43 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	146.28 m³·mol⁻¹	ChemAxon
Polarizability	60.23 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00036244

Chemspider ID

59650785

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Yunnanxane

METLIN ID

Not Available

PubChem Compound

102348608

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Cao CM, Huo CH, Zhao YM, Si XT, Li ZP, Shi QW: [Studies on chemical constituents in heartwood of Taxus cuspidata]. Zhongguo Zhong Yao Za Zhi. 2006 Sep;31(18):1510-3. [PubMed:17144468 ]
Bai XY, Lu JM, Zhou YY, Zhu ZR, Jiang RW, Zhang W: [Chemical constituents of Taxus chinensis var. mairei cell cultures]. Yao Xue Xue Bao. 2015 Jan;50(1):70-4. [PubMed:25924478 ]
Bai J, Kitabatake M, Toyoizumi K, Fu L, Zhang S, Dai J, Sakai J, Hirose K, Yamori T, Tomida A, Tsuruo T, Ando M: Production of biologically active taxoids by a callus culture of Taxus cuspidata. J Nat Prod. 2004 Jan;67(1):58-63. doi: 10.1021/np0301083. [PubMed:14738387 ]
Zhao CF, Yu LJ, Li LQ, Xiang F: Simultaneous identification and determination of major taxoids from extracts of Taxus chinensis cell cultures. Z Naturforsch C J Biosci. 2007 Jan-Feb;62(1-2):1-10. doi: 10.1515/znc-2007-1-201. [PubMed:17425097 ]
Zhao CF, Yu LJ: [LC-ESI-MS metabolic profiling analysis of taxanes from the extracts of Taxus chinensis cell cultures]. Yao Xue Xue Bao. 2005 Aug;40(8):734-9. [PubMed:16268509 ]

Showing NP-Card for Yunnanxane (NP0074791)

MOL for NP0074791 (Yunnanxane)

3D MOL for NP0074791 (Yunnanxane)

3D SDF for NP0074791 (Yunnanxane)

3D-SDF for NP0074791 (Yunnanxane)

PDB for NP0074791 (Yunnanxane)

3D PDB for NP0074791 (Yunnanxane)

SMILES for NP0074791 (Yunnanxane)

INCHI for NP0074791 (Yunnanxane)

Structure for NP0074791 (Yunnanxane)

3D Structure for NP0074791 (Yunnanxane)