NP-MRD: Showing NP-Card for Macrosphelide F (NP0044181)

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Record Information

Version

2.0

Created at

2021-11-12 23:54:44 UTC

Updated at

2021-11-26 17:46:20 UTC

NP-MRD ID

NP0044181

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Macrosphelide F

Description

Macrosphelide F belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. Macrosphelide F is found in Periconia byssoides. Macrosphelide F was first documented in 2001 (Yamada, et al.). Based on a literature review very few articles have been published on Macrosphelide F.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 45  0  0  0  0  0  0  0  0999 V2000
   -3.6102   -1.6158   -0.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5030   -0.6314    0.3835 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1998   -1.3597    0.3526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2507   -2.8103    0.3503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2771   -3.4967    0.9219 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8830   -2.9064    1.5769 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2343   -3.4561    2.6879 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5230   -1.8509    1.0239 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1246   -1.6832   -0.2118 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5078   -2.3450   -0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2387   -0.2534   -0.6561 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4665    0.6892    0.4643 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8419    0.1337    1.5570 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3123    2.0350    0.4138 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2689    2.8220   -0.0454 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4604    3.4058   -1.4010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0869    2.1211    0.0225 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5478    1.9563   -1.2716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0814    2.8924    0.7972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3549    2.6539    0.5547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9071    1.7149   -0.3915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8497    2.1673   -1.1546 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5504    0.4064   -0.5741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5453   -1.0066   -0.0499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3378   -1.9883   -1.0128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6914   -2.4125    0.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7879   -0.2760    1.4004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6408   -1.0305    1.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6716   -1.0374   -0.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0804   -3.3214   -0.1169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3927   -4.5939    0.8779 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6059   -2.2319   -1.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3093   -3.4407   -0.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1184   -2.1401   -1.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9982   -2.0970    0.8393 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1359   -0.1249   -1.3331 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3752   -0.0068   -1.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1797    3.6903    0.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9482    2.7882   -2.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0053    4.4254   -1.4490 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5549    3.4432   -1.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0987    1.1962    0.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0268    2.7263   -1.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7147    3.6078    1.5181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0828    3.2416    1.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23  2  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  1
  3 28  1  0
  3 29  1  0
  4 30  1  0
  5 31  1  0
  9 32  1  6
 10 33  1  0
 10 34  1  0
 10 35  1  0
 11 36  1  0
 11 37  1  0
 15 38  1  1
 16 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  1
 18 43  1  0
 19 44  1  0
 20 45  1  0
M  END


  Mrv1652311132100542D          

 23 23  0  0  1  0            999 V2000
    2.2823    2.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.8054    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7783    1.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5520    1.5649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1868    1.0380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0479    0.2248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6828   -0.3021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2742   -0.0616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1354   -0.8748    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7702   -1.4017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3616   -1.1612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2228   -1.9744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8576   -2.5013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4491   -2.2607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8142   -1.7339    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0405   -2.0202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9531   -0.9206    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7268   -0.6343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3182   -0.3937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4571    0.4195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2308    0.7058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8657    0.1789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3697    1.5191    0.0000 O   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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 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  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  2 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044181

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1C\C=C/C(=O)O[C@H](C)CC(=O)O[C@@H](C)[C@H](O)\C=C/C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C16H22O7/c1-10-5-4-6-14(18)22-11(2)9-16(20)23-12(3)13(17)7-8-15(19)21-10/h4,6-8,10-13,17H,5,9H2,1-3H3/b6-4-,8-7-/t10-,11+,12-,13+/m0/s1

> <INCHI_KEY>
LHDGUPDIEZSEGS-DZQDPMDGSA-N

> <FORMULA>
C16H22O7

> <MOLECULAR_WEIGHT>
326.345

> <EXACT_MASS>
326.136553048

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
32.564882781023975

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R,7Z,10S,13Z,15R,16S)-15-hydroxy-4,10,16-trimethyl-1,5,11-trioxacyclohexadeca-7,13-diene-2,6,12-trione

> <ALOGPS_LOGP>
1.22

> <JCHEM_LOGP>
1.8421726149999993

> <ALOGPS_LOGS>
-2.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.4627180475063

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.74905511208852

> <JCHEM_PKA_STRONGEST_BASIC>
-3.345910658255507

> <JCHEM_POLAR_SURFACE_AREA>
99.13000000000001

> <JCHEM_REFRACTIVITY>
82.02179999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.89e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R,7Z,10S,13Z,15R,16S)-15-hydroxy-4,10,16-trimethyl-1,5,11-trioxacyclohexadeca-7,13-diene-2,6,12-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-21         0                                  
HETATM    1  C   UNK     0       4.260   4.888   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   3.370   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.186   2.387   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.630   2.921   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.815   1.938   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.556   0.420   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.741  -0.564   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       6.112  -0.115   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.853  -1.633   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.038  -2.616   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.408  -2.167   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.149  -3.686   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.334  -4.669   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.705  -4.220   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.520  -3.237   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.076  -3.771   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.779  -1.719   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.223  -1.184   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.594  -0.735   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.853   0.783   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.298   1.318   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.483   0.334   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.557   2.836   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    2                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₂O₇

Average Mass

326.3450 Da

Monoisotopic Mass

326.13655 Da

IUPAC Name

(4R,7Z,10S,13Z,15R,16S)-15-hydroxy-4,10,16-trimethyl-1,5,11-trioxacyclohexadeca-7,13-diene-2,6,12-trione

Traditional Name

(4R,7Z,10S,13Z,15R,16S)-15-hydroxy-4,10,16-trimethyl-1,5,11-trioxacyclohexadeca-7,13-diene-2,6,12-trione

CAS Registry Number

Not Available

SMILES

C[C@H]1C\C=C/C(=O)O[C@H](C)CC(=O)O[C@@H](C)[C@H](O)\C=C/C(=O)O1

InChI Identifier

InChI=1S/C16H22O7/c1-10-5-4-6-14(18)22-11(2)9-16(20)23-12(3)13(17)7-8-15(19)21-10/h4,6-8,10-13,17H,5,9H2,1-3H3/b6-4-,8-7-/t10-,11+,12-,13+/m0/s1

InChI Key

LHDGUPDIEZSEGS-DZQDPMDGSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Periconia byssoides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Tricarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	1.22	ALOGPS
logP	1.84	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	13.75	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	99.13 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	82.02 m³·mol⁻¹	ChemAxon
Polarizability	32.56 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

Not Available

Chemspider ID

78437153

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139585233

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Takeshi Yamada, Masashi Iritani, Mitsunobu Doi, Katsuhiko Minoura, Tadayoshi Itob and Atsushi Numata (2001). Absolute stereostructures of cell-adhesion inhibitors, macrosphelides C, E–G and I, produced by a Periconia species separated from an Aplysia sea hare. Journal of the Chemical Society Perkin Transactions 1, 2001, 1(22):3046-3053. DOI:10.1039/b104337b. Journal of the Chemical Society Perkin Transactions 1.

Showing NP-Card for Macrosphelide F (NP0044181)

MOL for NP0044181 (Macrosphelide F)

3D MOL for NP0044181 (Macrosphelide F)

3D SDF for NP0044181 (Macrosphelide F)

3D-SDF for NP0044181 (Macrosphelide F)

PDB for NP0044181 (Macrosphelide F)

3D PDB for NP0044181 (Macrosphelide F)

SMILES for NP0044181 (Macrosphelide F)

INCHI for NP0044181 (Macrosphelide F)

Structure for NP0044181 (Macrosphelide F)

3D Structure for NP0044181 (Macrosphelide F)