NP-MRD: Showing NP-Card for (+)-Micrandilactone B (NP0076865)

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Record Information

Version

2.0

Created at

2022-04-28 22:03:25 UTC

Updated at

2022-04-28 22:03:25 UTC

NP-MRD ID

NP0076865

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Micrandilactone B

Description

Micrandilactone B belongs to the class of organic compounds known as furofurans. These are organic compounds containing a two furan rings fused to each other. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. (+)-Micrandilactone B is found in Kadsura ananosma, Kadsura coccinea, Schisandra chinensis and Schisandra propinqua var.propinqua. (+)-Micrandilactone B was first documented in 2008 (PMID: 18590312). Based on a literature review very few articles have been published on Micrandilactone B (PMID: 31669819).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292200032D          

 37 43  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304292200032D          

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    2.1822   -4.3742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2620   -1.8067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0349   -2.0489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  1  0  0  0
  3  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 17 16  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 21 23  1  0  0  0  0
 16 24  1  1  0  0  0
 15 25  1  6  0  0  0
 12 26  1  6  0  0  0
 11 26  1  6  0  0  0
 10 27  1  1  0  0  0
  6 28  1  6  0  0  0
  2 29  1  0  0  0  0
 29 30  1  0  0  0  0
 31 30  1  6  0  0  0
  1 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
  1 35  1  6  0  0  0
 29 36  1  0  0  0  0
 29 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0076865

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]([C@H](O)[C@H]1OC(=O)C(C)=C1)[C@H]1C[C@@H]2O[C@@]22[C@@H]3CC[C@H]4C(C)(C)O[C@@H]5CC(=O)O[C@]45C[C@@]3(O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C29H40O8/c1-14-10-17(34-24(14)32)23(31)15(2)16-11-21-29(36-21)19-7-6-18-25(3,4)35-20-12-22(30)37-28(18,20)13-27(19,33)9-8-26(16,29)5/h10,15-21,23,31,33H,6-9,11-13H2,1-5H3/t15-,16+,17-,18-,19+,20+,21-,23-,26+,27-,28+,29-/m0/s1

> <INCHI_KEY>
NOPJKUNZSJEAIR-CKJYOAKFSA-N

> <FORMULA>
C29H40O8

> <MOLECULAR_WEIGHT>
516.631

> <EXACT_MASS>
516.272318248

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
55.73142211735956

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,7R,10S,13R,14R,16S,18R,19R)-1-hydroxy-18-[(1S,2S)-1-hydroxy-1-[(2S)-4-methyl-5-oxo-2,5-dihydrofuran-2-yl]propan-2-yl]-9,9,19-trimethyl-4,8,15-trioxahexacyclo[11.8.0.0^{3,7}.0^{3,10}.0^{14,16}.0^{14,19}]henicosan-5-one

> <ALOGPS_LOGP>
3.14

> <JCHEM_LOGP>
2.280313638

> <ALOGPS_LOGS>
-4.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.506732805740882

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.383179950357658

> <JCHEM_PKA_STRONGEST_BASIC>
-3.080833269144285

> <JCHEM_POLAR_SURFACE_AREA>
114.82000000000001

> <JCHEM_REFRACTIVITY>
131.1049

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.91e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3R,7R,10S,13R,14R,16S,18R,19R)-1-hydroxy-18-[(1S,2S)-1-hydroxy-1-[(2S)-4-methyl-5-oxo-2H-furan-2-yl]propan-2-yl]-9,9,19-trimethyl-4,8,15-trioxahexacyclo[11.8.0.0^{3,7}.0^{3,10}.0^{14,16}.0^{14,19}]henicosan-5-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       4.966  -6.910   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.950  -5.370   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.736  -4.422   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.238  -4.781   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.584  -6.175   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.267  -7.556   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.577  -7.786   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.413  -8.837   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.124  -8.738   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.807  -7.357   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.047  -6.076   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.907  -4.868   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.352  -5.402   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.289  -6.941   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.498  -7.896   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.929  -7.327   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.137  -8.281   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -6.075  -9.820   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -7.519 -10.355   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -7.936 -11.837   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -8.474  -9.146   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -7.620  -7.865   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -10.013  -9.208   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -5.151  -5.803   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -3.275  -9.419   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.617  -4.645   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.790  -8.542   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.844  -8.983   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.409  -4.879   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       7.327  -6.115   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.435  -7.370   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.451  -8.910   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.992  -9.401   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.531 -10.871   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       4.073  -8.165   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       6.089  -3.372   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.532  -3.825   0.000  0.00  0.00           C+0
CONECT    1    2    7   31   35                                             
CONECT    2    1    3   29                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8   28                                             
CONECT    7    6    1                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   14   27                                             
CONECT   11   10    5   12   26                                             
CONECT   12   11   13   26                                                  
CONECT   13   12   14                                                       
CONECT   14   13   10   15                                                  
CONECT   15   14   16   25                                                  
CONECT   16   15   17   24                                                  
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21   17                                                       
CONECT   23   21                                                            
CONECT   24   16                                                            
CONECT   25   15                                                            
CONECT   26   12   11                                                       
CONECT   27   10                                                            
CONECT   28    6                                                            
CONECT   29    2   30   36   37                                             
CONECT   30   29   31                                                       
CONECT   31   30    1   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    1                                                       
CONECT   36   29                                                            
CONECT   37   29                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₀O₈

Average Mass

516.6310 Da

Monoisotopic Mass

516.27232 Da

IUPAC Name

(1S,3R,7R,10S,13R,14R,16S,18R,19R)-1-hydroxy-18-[(1S,2S)-1-hydroxy-1-[(2S)-4-methyl-5-oxo-2,5-dihydrofuran-2-yl]propan-2-yl]-9,9,19-trimethyl-4,8,15-trioxahexacyclo[11.8.0.0^{3,7}.0^{3,10}.0^{14,16}.0^{14,19}]henicosan-5-one

Traditional Name

(1S,3R,7R,10S,13R,14R,16S,18R,19R)-1-hydroxy-18-[(1S,2S)-1-hydroxy-1-[(2S)-4-methyl-5-oxo-2H-furan-2-yl]propan-2-yl]-9,9,19-trimethyl-4,8,15-trioxahexacyclo[11.8.0.0^{3,7}.0^{3,10}.0^{14,16}.0^{14,19}]henicosan-5-one

CAS Registry Number

Not Available

SMILES

C[C@H]([C@H](O)[C@H]1OC(=O)C(C)=C1)[C@H]1C[C@@H]2O[C@@]22[C@@H]3CC[C@H]4C(C)(C)O[C@@H]5CC(=O)O[C@]45C[C@@]3(O)CC[C@]12C

InChI Identifier

InChI=1S/C29H40O8/c1-14-10-17(34-24(14)32)23(31)15(2)16-11-21-29(36-21)19-7-6-18-25(3,4)35-20-12-22(30)37-28(18,20)13-27(19,33)9-8-26(16,29)5/h10,15-21,23,31,33H,6-9,11-13H2,1-5H3/t15-,16+,17-,18-,19+,20+,21-,23-,26+,27-,28+,29-/m0/s1

InChI Key

NOPJKUNZSJEAIR-CKJYOAKFSA-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
Kadsura ananosma	LOTUS Database	35616633
Kadsura coccinea	Plant	KNApSAcK
Schisandra chinensis	LOTUS Database	35616633
Schisandra propinqua var.propinqua	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furofurans. These are organic compounds containing a two furan rings fused to each other. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furofurans

Sub Class

Not Available

Direct Parent

Furofurans

Alternative Parents

Substituents

Furofuran
2-furanone
Dicarboxylic acid or derivatives
Gamma butyrolactone
Oxane
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Tetrahydrofuran
Enoate ester
Lactone
Secondary alcohol
Carboxylic acid ester
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Alcohol
Organooxygen compound
Organic oxygen compound
Carbonyl group
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	3.14	ALOGPS
logP	2.28	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	12.38	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	114.82 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	131.1 m³·mol⁻¹	ChemAxon
Polarizability	55.73 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

C00039766

Chemspider ID

17614264

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16681613

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Cao L, Shehla N, Li B, Jian Y, Peng C, Sheng W, Liu L, Cai X, Man R, Liao DF, Choudhary MI, Rahman AU, Wang W: Schinortriterpenoids from Tujia ethnomedicine Xuetong-The stems of Kadsura heteroclita. Phytochemistry. 2020 Jan;169:112178. doi: 10.1016/j.phytochem.2019.112178. Epub 2019 Oct 24. [PubMed:31669819 ]
Gao XM, Pu JX, Huang SX, Lu Y, Lou LG, Li RT, Xiao WL, Chang Y, Sun HD: Kadcoccilactones A-J, triterpenoids from Kadsura coccinea. J Nat Prod. 2008 Jul;71(7):1182-8. doi: 10.1021/np800078x. Epub 2008 Jul 1. [PubMed:18590312 ]

Showing NP-Card for (+)-Micrandilactone B (NP0076865)

MOL for NP0076865 ((+)-Micrandilactone B)

3D MOL for NP0076865 ((+)-Micrandilactone B)

3D SDF for NP0076865 ((+)-Micrandilactone B)

3D-SDF for NP0076865 ((+)-Micrandilactone B)

PDB for NP0076865 ((+)-Micrandilactone B)

3D PDB for NP0076865 ((+)-Micrandilactone B)

SMILES for NP0076865 ((+)-Micrandilactone B)

INCHI for NP0076865 ((+)-Micrandilactone B)

Structure for NP0076865 ((+)-Micrandilactone B)

3D Structure for NP0076865 ((+)-Micrandilactone B)