NP-MRD: Showing NP-Card for (+)-Denudatin B (NP0050450)

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Record Information

Version

2.0

Created at

2022-04-27 21:39:52 UTC

Updated at

2022-04-27 21:39:52 UTC

NP-MRD ID

NP0050450

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Denudatin B

Description

Kadsurenone, also known as denudatin b, belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. (+)-Denudatin B is found in Magnolia biondii, Magnolia denudata , Magnolia soulangeana, Nectandra amazonum, Piper hancei, Piper kadsura and Piper pedicellatum. (+)-Denudatin B was first documented in 2013 (PMID: 23843078). Based on a literature review a small amount of articles have been published on kadsurenone (PMID: 31819371) (PMID: 27452451) (PMID: 30136489) (PMID: 30008927).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304272223392D          

 26 28  0  0  1  0            999 V2000
   -3.1034   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1034   -2.1269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9284   -2.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5549   -1.9309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2223   -2.4158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9284   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3409   -1.4124    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  4  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 11 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 12 21  1  0  0  0  0
  9 21  1  0  0  0  0
 11 22  1  1  0  0  0
 22 23  1  0  0  0  0
 10 24  1  6  0  0  0
  1 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END


  Mrv1652304272223392D          

 26 28  0  0  1  0            999 V2000
   -3.1034   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    0.0165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909   -1.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1034   -2.1269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9284   -2.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5549   -1.9309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2223   -2.4158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9284   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3409   -1.4124    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  4  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 11 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 12 21  1  0  0  0  0
  9 21  1  0  0  0  0
 11 22  1  1  0  0  0
 22 23  1  0  0  0  0
 10 24  1  6  0  0  0
  1 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050450

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1OC)[C@H]1OC2=CC(=O)C(CC=C)=C[C@]2(OC)[C@@H]1C

> <INCHI_IDENTIFIER>
InChI=1S/C21H24O5/c1-6-7-15-12-21(25-5)13(2)20(26-19(21)11-16(15)22)14-8-9-17(23-3)18(10-14)24-4/h6,8-13,20H,1,7H2,2-5H3/t13-,20+,21+/m1/s1

> <INCHI_KEY>
VDYACOATPFOZIO-UBWHGVKJSA-N

> <FORMULA>
C21H24O5

> <MOLECULAR_WEIGHT>
356.418

> <EXACT_MASS>
356.162373873

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
38.56295671180936

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R,3aS)-2-(3,4-dimethoxyphenyl)-3a-methoxy-3-methyl-5-(prop-2-en-1-yl)-2,3,3a,6-tetrahydro-1-benzofuran-6-one

> <ALOGPS_LOGP>
3.54

> <JCHEM_LOGP>
3.235169188666667

> <ALOGPS_LOGS>
-4.65

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.007834189606957

> <JCHEM_POLAR_SURFACE_AREA>
53.99000000000001

> <JCHEM_REFRACTIVITY>
101.20500000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.97e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
kadsurenone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0      -5.793  -1.303   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.023   0.031   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.483   0.031   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.713  -1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.483  -2.637   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.023  -2.637   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -5.793  -3.970   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -7.333  -3.970   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.268  -2.549   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.198   0.237   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.198  -2.843   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.531  -2.073   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.865  -2.843   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.268  -0.057   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.036  -3.604   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.282  -4.510   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.744  -4.013   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -7.333  -1.303   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -8.103  -2.637   0.000  0.00  0.00           C+0
CONECT    1    2    6   25                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    4   10   21                                                  
CONECT   10    9   11   24                                                  
CONECT   11   10   12   17   22                                             
CONECT   12   11   13   21                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16   11                                                       
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   12    9                                                       
CONECT   22   11   23                                                       
CONECT   23   22                                                            
CONECT   24   10                                                            
CONECT   25    1   26                                                       
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
Denudatin b	MeSH
Kadsurenone, (2S-(2alpha,3beta,3abeta))-isomer	MeSH

Chemical Formula

C₂₁H₂₄O₅

Average Mass

356.4180 Da

Monoisotopic Mass

356.16237 Da

IUPAC Name

(2S,3R,3aS)-2-(3,4-dimethoxyphenyl)-3a-methoxy-3-methyl-5-(prop-2-en-1-yl)-2,3,3a,6-tetrahydro-1-benzofuran-6-one

Traditional Name

kadsurenone

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1OC)[C@H]1OC2=CC(=O)C(CC=C)=C[C@]2(OC)[C@@H]1C

InChI Identifier

InChI=1S/C21H24O5/c1-6-7-15-12-21(25-5)13(2)20(26-19(21)11-16(15)22)14-8-9-17(23-3)18(10-14)24-4/h6,8-13,20H,1,7H2,2-5H3/t13-,20+,21+/m1/s1

InChI Key

VDYACOATPFOZIO-UBWHGVKJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Magnolia biondii	LOTUS Database	35616633
Magnolia denudata	Plant	KNApSAcK
Magnolia soulangeana	LOTUS Database	35616633
Nectandra amazonum	LOTUS Database	35616633
Piper hancei	LOTUS Database	35616633
Piper kadsura	LOTUS Database	35616633
Piper pedicellatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
Dimethoxybenzene
O-dimethoxybenzene
Benzofuran
Methoxybenzene
Anisole
Phenoxy compound
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Vinylogous ester
Tetrahydrofuran
Ketone
Cyclic ketone
Oxacycle
Dialkyl ether
Ether
Organoheterocyclic compound
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzofurans (CHEBI:6097 )
Neolignans (C10638 )

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	3.54	ALOGPS
logP	3.24	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	53.99 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	101.2 m³·mol⁻¹	ChemAxon
Polarizability	38.56 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00000719

Chemspider ID

108956

KEGG Compound ID

C10638

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122159

PDB ID

Not Available

ChEBI ID

6097

Good Scents ID

rw1501101

References

General References

He D, Huang JH, Zhang ZY, Du Q, Peng WJ, Yu R, Zhang SF, Zhang SH, Qin YH: A Network Pharmacology-Based Strategy For Predicting Active Ingredients And Potential Targets Of LiuWei DiHuang Pill In Treating Type 2 Diabetes Mellitus. Drug Des Devel Ther. 2019 Nov 28;13:3989-4005. doi: 10.2147/DDDT.S216644. eCollection 2019. [PubMed:31819371 ]
Ding DD, Wang YH, Chen YH, Mei RQ, Yang J, Luo JF, Li Y, Long CL, Kong Y: Amides and neolignans from the aerial parts of Piper bonii. Phytochemistry. 2016 Sep;129:36-44. doi: 10.1016/j.phytochem.2016.07.004. Epub 2016 Jul 21. [PubMed:27452451 ]
Xin H, Peng Z, Jiang D, Fu Q, Jin Y, Liang X: [Separation and purification of compounds from piper kadsura using preparative reversed-phase liquid chromatography and preparative supercritical fluid chromatography]. Se Pu. 2018 May 8;36(5):474-479. doi: 10.3724/SP.J.1123.2017.11054. [PubMed:30136489 ]
Hou T, Lou Y, Li S, Zhao C, Ji Y, Wang D, Tang L, Zhou M, Xu W, Qian M, Wu Z, Zhao J, Wei H, Li Z, Xiao J: Kadsurenone is a useful and promising treatment strategy for breast cancer bone metastases by blocking the PAF/PTAFR signaling pathway. Oncol Lett. 2018 Aug;16(2):2255-2262. doi: 10.3892/ol.2018.8935. Epub 2018 Jun 8. [PubMed:30008927 ]
Zhang N, Li R, Yu H, Shi D, Dong N, Zhang S, Wang H: Development of an LC-MS/MS method for quantification of kadsurenone in rat plasma and its application to a pharmacokinetic study. Biomed Chromatogr. 2013 Dec;27(12):1754-8. doi: 10.1002/bmc.2989. Epub 2013 Jul 11. [PubMed:23843078 ]

Showing NP-Card for (+)-Denudatin B (NP0050450)

MOL for NP0050450 ((+)-Denudatin B)

3D MOL for NP0050450 ((+)-Denudatin B)

3D SDF for NP0050450 ((+)-Denudatin B)

3D-SDF for NP0050450 ((+)-Denudatin B)

PDB for NP0050450 ((+)-Denudatin B)

3D PDB for NP0050450 ((+)-Denudatin B)

SMILES for NP0050450 ((+)-Denudatin B)

INCHI for NP0050450 ((+)-Denudatin B)

Structure for NP0050450 ((+)-Denudatin B)

3D Structure for NP0050450 ((+)-Denudatin B)