NP-MRD: Showing NP-Card for (+)-(5S)-5-Hydroxylasiodiplodin (NP0078145)

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Record Information

Version

1.0

Created at

2022-04-28 23:16:31 UTC

Updated at

2022-04-28 23:16:32 UTC

NP-MRD ID

NP0078145

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-(5S)-5-Hydroxylasiodiplodin

Description

5R-Htdroxylasiodiplodin 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. (+)-(5S)-5-Hydroxylasiodiplodin is found in Garcinia mangostana, Lasiodiplodia theobromae and Lasiodiplodia theobromae IFO31059. Based on a literature review very few articles have been published on 5R-Htdroxylasiodiplodin.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 46 47  0  0  0  0  0  0  0  0999 V2000
   -4.0131   -2.4868   -1.5343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8116   -1.8396   -1.2758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7281   -0.6672   -0.5237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9439   -0.1725   -0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9773    0.9672    0.7087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1954    1.4401    1.1814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7967    1.6107    0.9674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5827    1.1309    0.4909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5333   -0.0171   -0.2624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3150   -0.6031   -0.8088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4718   -1.1404   -1.9715 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8774   -0.5944   -0.1738 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4271   -1.2511    0.8920 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6990   -2.4622    1.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8207   -1.7278    0.4519 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417   -0.7237   -0.5702 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5227   -1.1365   -1.1309 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4289    0.6589   -0.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7426    1.7064   -0.8656 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8321    2.5666   -0.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3709    2.4124   -0.3842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3781    1.9265    0.8390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6984   -1.8467   -2.1354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8275   -3.4145   -2.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5090   -2.7014   -0.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8666   -0.7147   -0.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5187    1.1224    2.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8408    2.5184    1.5639 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6254   -0.6043    1.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9383   -2.6526    2.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0635   -3.3598    0.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3918   -2.4016    1.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7047   -2.6896   -0.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4938   -1.8723    1.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5703   -0.7124   -1.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6072   -0.7897   -2.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0276    0.6796    1.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5263    0.8921    0.1063 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2335    1.2248   -1.7196 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5594    2.3299   -1.3361 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9942    2.3330    1.0672 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1825    3.6321   -0.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0025    3.4489   -0.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1920    1.8174   -1.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6398    2.8354    1.4195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2552    1.3284    1.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
  9  3  1  0
 22  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
 13 29  1  1
 14 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  6
 17 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
 19 40  1  0
 20 41  1  0
 20 42  1  0
 21 43  1  0
 21 44  1  0
 22 45  1  0
 22 46  1  0
M  END


  Mrv1652304292201162D          

 22 23  0  0  1  0            999 V2000
    6.5347    0.6825    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1583    0.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0024   -0.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2228   -0.9377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5992   -0.3976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8196   -0.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1960   -0.1276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3519    0.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1315    0.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7551    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2874    1.7627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0669    2.0328    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6906    1.4927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2228    2.8429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7283    1.2226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9487    0.9526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7928    0.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4164   -0.3976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0133   -0.1276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8842    2.0328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2605    2.5729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3142    0.9526    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
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  1 13  1  0  0  0  0
 12 14  1  1  0  0  0
  8 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
  7 18  1  0  0  0  0
 17 19  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
  1 22  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0078145

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=CC2=C1C(=O)O[C@@H](C)C[C@H](O)CCCCC2

> <INCHI_IDENTIFIER>
InChI=1S/C17H24O5/c1-11-8-13(18)7-5-3-4-6-12-9-14(19)10-15(21-2)16(12)17(20)22-11/h9-11,13,18-19H,3-8H2,1-2H3/t11-,13+/m0/s1

> <INCHI_KEY>
SMFDUNDNVFMERG-WCQYABFASA-N

> <FORMULA>
C17H24O5

> <MOLECULAR_WEIGHT>
308.374

> <EXACT_MASS>
308.162373873

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
32.81242524581563

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,5R)-5,12-dihydroxy-14-methoxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclododecin-1-one

> <ALOGPS_LOGP>
2.79

> <JCHEM_LOGP>
2.9798491806666663

> <ALOGPS_LOGS>
-3.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.17713351871345

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.64128248852598

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7213218542259465

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
83.48769999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.77e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,5R)-5,12-dihydroxy-14-methoxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-2-benzoxacyclododecin-1-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      12.198   1.274   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.362   0.266   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.071  -1.246   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.616  -1.750   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.452  -0.742   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.997  -1.246   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.833  -0.238   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.124   1.274   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.579   1.778   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      10.743   0.770   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       9.870   3.290   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      11.325   3.794   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.489   2.786   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.616   5.307   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.959   2.282   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.504   1.778   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.213   0.266   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.377  -0.742   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.758  -0.238   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       7.250   3.794   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.086   4.803   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      13.653   1.778   0.000  0.00  0.00           O+0
CONECT    1    2   13   22                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   18                                                  
CONECT    8    7    9   15                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12    1                                                       
CONECT   14   12                                                            
CONECT   15    8   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17    7                                                       
CONECT   19   17                                                            
CONECT   20   15   21                                                       
CONECT   21   20                                                            
CONECT   22    1                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₄O₅

Average Mass

308.3740 Da

Monoisotopic Mass

308.16237 Da

IUPAC Name

(3S,5R)-5,12-dihydroxy-14-methoxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-1H-2-benzoxacyclododecin-1-one

Traditional Name

(3S,5R)-5,12-dihydroxy-14-methoxy-3-methyl-3,4,5,6,7,8,9,10-octahydro-2-benzoxacyclododecin-1-one

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=CC2=C1C(=O)O[C@@H](C)C[C@H](O)CCCCC2

InChI Identifier

InChI=1S/C17H24O5/c1-11-8-13(18)7-5-3-4-6-12-9-14(19)10-15(21-2)16(12)17(20)22-11/h9-11,13,18-19H,3-8H2,1-2H3/t11-,13+/m0/s1

InChI Key

SMFDUNDNVFMERG-WCQYABFASA-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
Garcinia mangostana	LOTUS Database	35616633
Lasiodiplodia theobromae	LOTUS Database	35616633
Lasiodiplodia theobromae IFO31059	Fungi	KNApSAcK

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
Anisole
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Carboxylic acid ester
Lactone
Secondary alcohol
Ether
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	2.79	ALOGPS
logP	2.98	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	8.64	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	83.49 m³·mol⁻¹	ChemAxon
Polarizability	32.81 Å³	ChemAxon
Number of Rings	2	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

8813887

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10638525

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-(5S)-5-Hydroxylasiodiplodin (NP0078145)

MOL for NP0078145 ((+)-(5S)-5-Hydroxylasiodiplodin)

3D MOL for NP0078145 ((+)-(5S)-5-Hydroxylasiodiplodin)

3D SDF for NP0078145 ((+)-(5S)-5-Hydroxylasiodiplodin)

3D-SDF for NP0078145 ((+)-(5S)-5-Hydroxylasiodiplodin)

PDB for NP0078145 ((+)-(5S)-5-Hydroxylasiodiplodin)

3D PDB for NP0078145 ((+)-(5S)-5-Hydroxylasiodiplodin)

SMILES for NP0078145 ((+)-(5S)-5-Hydroxylasiodiplodin)

INCHI for NP0078145 ((+)-(5S)-5-Hydroxylasiodiplodin)

Structure for NP0078145 ((+)-(5S)-5-Hydroxylasiodiplodin)

3D Structure for NP0078145 ((+)-(5S)-5-Hydroxylasiodiplodin)