NP-MRD: Showing NP-Card for 6-Tuliposide A (NP0076084)

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Record Information

Version

2.0

Created at

2022-04-28 21:15:38 UTC

Updated at

2022-04-28 21:15:38 UTC

NP-MRD ID

NP0076084

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-Tuliposide A

Description

6-Tuliposide a belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety. Thus, 6-tuliposide a is considered to be an other acyl sugar. 6-Tuliposide A is found in Alstroemeria angustifolia, Alstroemeria aurea, Alstroemeria pelegrina, Alstroemeria pseudospathulata, Alstroemeria revoluta, Spiraea thunbergii, Tulipa gesneriana , Tulipa kaufmanniana and Tulipa turkestanica. 6-Tuliposide A was first documented in 2012 (PMID: 22474185). Based on a literature review a small amount of articles have been published on 6-tuliposide a (PMID: 28029062) (PMID: 27169177) (PMID: 23649245).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 37  0  0  0  0  0  0  0  0999 V2000
    3.1231    1.9576    0.3920 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3306    0.8177   -0.2205 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6935    0.2873   -0.3617 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8508   -1.0579    0.2969 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5741   -0.9646    1.6486 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2029    0.0716   -0.7654 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3948   -1.0331   -1.3602 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8970    0.5009   -0.6744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1607   -0.2892   -1.2359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4960    0.3893   -1.0091 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4681   -0.3910   -1.5555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7358   -0.2129   -1.0981 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.5053   -1.2954   -1.5905 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8856   -0.2370    0.3946 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3361    1.0361    0.7927 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5266   -0.4394    1.0450 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9997   -1.6859    0.8163 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6330    0.6460    0.4602 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2616    1.8776    0.6298 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1427    2.3573    0.5037 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9478    2.5302    0.8053 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4511    0.9825    0.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8673    0.1425   -1.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2238   -1.8350   -0.1489 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9239   -1.3474    0.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2495   -1.8138    2.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.2815   -0.7549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0007   -0.4383   -2.3293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4120    1.3915   -1.5234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2065    0.6937   -1.5649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5584   -2.0277   -0.9276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6121   -0.9809    0.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2060    0.9766    1.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6315   -0.3243    2.1563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3274   -2.1369    0.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6744    0.6901    1.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1265    2.4437   -0.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  2  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 10  1  0
  5 26  1  0
  4 24  1  0
  4 25  1  0
  3 22  1  0
  3 23  1  0
  1 20  1  0
  1 21  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  6
 12 30  1  6
 13 31  1  0
 14 32  1  6
 15 33  1  0
 16 34  1  1
 17 35  1  0
 18 36  1  1
 19 37  1  0
M  END

  Mrv1652304282223152D          

 19 19  0  0  1  0            999 V2000
   -1.4289    1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  4  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  3 17  1  6  0  0  0
  2 18  1  1  0  0  0
  1 19  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0076084

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCCC(=C)C(=O)OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C11H18O8/c1-5(2-3-12)10(16)18-4-6-7(13)8(14)9(15)11(17)19-6/h6-9,11-15,17H,1-4H2/t6-,7-,8+,9-,11-/m1/s1

> <INCHI_KEY>
NABVFHUVYXEKSQ-ZBGLXGBJSA-N

> <FORMULA>
C11H18O8

> <MOLECULAR_WEIGHT>
278.257

> <EXACT_MASS>
278.10016754

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
26.701398685283493

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl 4-hydroxy-2-methylidenebutanoate

> <ALOGPS_LOGP>
-1.54

> <JCHEM_LOGP>
-2.098346929666667

> <ALOGPS_LOGS>
-0.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.691865781728584

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.298274699842022

> <JCHEM_PKA_STRONGEST_BASIC>
-2.4008381427741643

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
60.609399999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl 4-hydroxy-2-methylidenebutanoate

> <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      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000   3.080   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.334   0.770   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.336   5.390   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -4.001   5.390   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
CONECT    1    2    6   19                                                  
CONECT    2    1    3   18                                                  
CONECT    3    2    4   17                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    4    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17    3                                                            
CONECT   18    2                                                            
CONECT   19    1                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Value	Source
6-(4-Hydroxy-2-methylenebutyryl)-D-glucopyranose	MeSH

Chemical Formula

C₁₁H₁₈O₈

Average Mass

278.2570 Da

Monoisotopic Mass

278.10017 Da

IUPAC Name

[(2R,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl 4-hydroxy-2-methylidenebutanoate

Traditional Name

[(2R,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl 4-hydroxy-2-methylidenebutanoate

CAS Registry Number

Not Available

SMILES

OCCC(=C)C(=O)OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C11H18O8/c1-5(2-3-12)10(16)18-4-6-7(13)8(14)9(15)11(17)19-6/h6-9,11-15,17H,1-4H2/t6-,7-,8+,9-,11-/m1/s1

InChI Key

NABVFHUVYXEKSQ-ZBGLXGBJSA-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
Alstroemeria angustifolia	LOTUS Database	35616633
Alstroemeria aurantiaca	LOTUS Database	35616633
Alstroemeria pelegrina	LOTUS Database	35616633
Alstroemeria pseudospathulata	LOTUS Database	35616633
Alstroemeria revoluta	LOTUS Database	35616633
Spiraea thunbergii	LOTUS Database	35616633
Tulipa gesneriana	Plant	KNApSAcK
Tulipa kaufmanniana	LOTUS Database	35616633
Tulipa turkestanica	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Saccharolipids

Sub Class

Not Available

Direct Parent

Saccharolipids

Alternative Parents

Substituents

Saccharolipid
Fatty acid ester
Monosaccharide
Fatty acyl
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Hemiacetal
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organooxygen compound
Alcohol
Organic oxygen compound
Primary alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	-1.5	ALOGPS
logP	-2.1	ChemAxon
logS	-0.43	ALOGPS
pKa (Strongest Acidic)	11.3	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	60.61 m³·mol⁻¹	ChemAxon
Polarizability	26.7 Å³	ChemAxon
Number of Rings	1	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

C00038311

Chemspider ID

106399

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

119077

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ibrahim MF, Hussain FHS, Zanoni G, Vidari G: The main constituents of Tulipa systola Stapf. roots and flowers; their antioxidant activities. Nat Prod Res. 2017 Sep;31(17):2001-2007. doi: 10.1080/14786419.2016.1272107. Epub 2016 Dec 28. [PubMed:28029062 ]
Amin HI, Ibrahim MF, Hussain FH, Sardar ASh, Vidari G: Phytochemistry and Ethnopharmacology of Some Medicinal Plants Used in the Kurdistan Region of Iraq. Nat Prod Commun. 2016 Mar;11(3):291-6. [PubMed:27169177 ]
Nomura T, Tsuchigami A, Ogita S, Kato Y: Molecular diversity of tuliposide A-converting enzyme in the tulip. Biosci Biotechnol Biochem. 2013;77(5):1042-8. doi: 10.1271/bbb.130021. Epub 2013 May 7. [PubMed:23649245 ]
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Showing NP-Card for 6-Tuliposide A (NP0076084)

MOL for NP0076084 (6-Tuliposide A)

3D MOL for NP0076084 (6-Tuliposide A)

3D SDF for NP0076084 (6-Tuliposide A)

3D-SDF for NP0076084 (6-Tuliposide A)

PDB for NP0076084 (6-Tuliposide A)

3D PDB for NP0076084 (6-Tuliposide A)

SMILES for NP0076084 (6-Tuliposide A)

INCHI for NP0076084 (6-Tuliposide A)

Structure for NP0076084 (6-Tuliposide A)

3D Structure for NP0076084 (6-Tuliposide A)