NP-MRD: Showing NP-Card for Sappanol (NP0140302)

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Record Information

Version

2.0

Created at

2022-06-29 21:22:14 UTC

Updated at

2022-06-29 21:22:14 UTC

NP-MRD ID

NP0140302

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sappanol

Description

Sappanol belongs to the class of organic compounds known as homoisoflavans. These are homoisoflavonoids with a structure based on the chromane system. Chromone is a bicyclic compound consisting of a 3,4-dihydro-1-benzopyran. Sappanol is found in Alpinia japonica. Sappanol was first documented in 2013 (PMID: 23154842). Based on a literature review a small amount of articles have been published on sappanol (PMID: 26951869) (PMID: 34607974) (PMID: 32235775) (PMID: 25248564).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
    4.6085    2.0626   -1.9569 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6593    1.2383   -1.3718 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5683    1.1183   -0.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6114    0.2886    0.5442 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7407   -0.4251   -0.2849 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8192   -0.3158   -1.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7878    0.5228   -2.1676 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9481   -1.0297   -2.4922 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3422   -2.1788   -1.9256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3529   -1.6919   -0.6488 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1085   -2.7727   -0.1976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2405   -0.5560   -1.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9664    0.0602    0.0660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2118   -0.3778    0.4585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8969    0.2138    1.5166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3229    1.2749    2.2048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9956    1.8656    3.2537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0808    1.7223    1.8240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5192    2.7898    2.5270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4244    1.1133    0.7676 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7154   -1.3150    0.3302 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3845   -2.4936    0.6954 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3272    3.0251   -2.1255 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2578    1.6839    0.6429 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5489    0.2016    1.6346 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8346    0.5966   -3.2615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4408   -2.5054   -2.6407 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0785   -2.9736   -1.7110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2722   -2.7521    0.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9511   -0.9424   -1.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6374    0.2228   -1.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7108   -1.1964   -0.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8742   -0.1330    1.8215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5692    2.6306    3.7414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6152    3.1526    2.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4542    1.5024    0.5102 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3301   -0.8773    1.2597 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0822   -2.7496    0.0508 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  1  0
 21  5  1  0
  5  6  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  1
 10 12  1  0
 12 13  1  0
 13 20  2  0
 20 18  1  0
 18 19  1  0
 18 16  2  0
 16 17  1  0
 16 15  1  0
 15 14  2  0
  6  7  1  0
  7  2  2  0
  2  1  1  0
  2  3  1  0
  3  4  2  0
 10 21  1  0
 14 13  1  0
  4  5  1  0
 22 38  1  0
 21 37  1  1
  9 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 20 36  1  0
 19 35  1  0
 17 34  1  0
 15 33  1  0
 14 32  1  0
  7 26  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
M  END


  Mrv1652306292223222D          

 22 24  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   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
    0.0000   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5390   -1.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9762   -0.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8006   -0.5954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2378    0.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8505    0.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0260    0.8614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5888    0.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2877    1.5323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0623    0.0754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1517   -1.9371    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  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  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
  4 10  1  0  0  0  0
  8 11  1  0  0  0  0
  3 12  1  6  0  0  0
  2 13  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 17 20  1  0  0  0  0
 16 21  1  0  0  0  0
  2 22  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0140302

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1C2=C(OC[C@]1(O)CC1=CC(O)=C(O)C=C1)C=C(O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O6/c17-10-2-3-11-14(6-10)22-8-16(21,15(11)20)7-9-1-4-12(18)13(19)5-9/h1-6,15,17-21H,7-8H2/t15-,16+/m0/s1

> <INCHI_KEY>
MPGFEHZDABUJFR-JKSUJKDBSA-N

> <FORMULA>
C16H16O6

> <MOLECULAR_WEIGHT>
304.298

> <EXACT_MASS>
304.094688235

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000  -0.000   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.873  -2.364   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.689  -1.058   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.228  -1.111   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.044   0.194   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.321   1.554   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.782   1.608   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.966   0.302   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -6.137   2.860   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -7.583   0.141   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -2.150  -3.616   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   13   22                                             
CONECT    3    2    4   12                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8                                                            
CONECT   12    3                                                            
CONECT   13    2   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20   17                                                            
CONECT   21   16                                                            
CONECT   22    2                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₆O₆

Average Mass

304.2980 Da

Monoisotopic Mass

304.09469 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

O[C@H]1C2=C(OC[C@]1(O)CC1=CC(O)=C(O)C=C1)C=C(O)C=C2

InChI Identifier

InChI=1S/C16H16O6/c17-10-2-3-11-14(6-10)22-8-16(21,15(11)20)7-9-1-4-12(18)13(19)5-9/h1-6,15,17-21H,7-8H2/t15-,16+/m0/s1

InChI Key

MPGFEHZDABUJFR-JKSUJKDBSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Alpinia japonica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as homoisoflavans. These are homoisoflavonoids with a structure based on the chromane system. Chromone is a bicyclic compound consisting of a 3,4-dihydro-1-benzopyran.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Homoisoflavonoids

Sub Class

Homoisoflavans

Direct Parent

Homoisoflavans

Alternative Parents

Substituents

Homoisoflavan
Chromane
Benzopyran
1-benzopyran
Catechol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Tertiary alcohol
Secondary alcohol
1,2-diol
Polyol
Ether
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Alcohol
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00020149

Chemspider ID

10405207

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sappanol

METLIN ID

Not Available

PubChem Compound

13846649

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mitani K, Takano F, Kawabata T, Allam AE, Ota M, Takahashi T, Yahagi N, Sakurada C, Fushiya S, Ohta T: Suppression of melanin synthesis by the phenolic constituents of sappanwood (Caesalpinia sappan). Planta Med. 2013 Jan;79(1):37-44. doi: 10.1055/s-0032-1327897. Epub 2012 Nov 15. [PubMed:23154842 ]
Mueller M, Weinmann D, Toegel S, Holzer W, Unger FM, Viernstein H: Compounds from Caesalpinia sappan with anti-inflammatory properties in macrophages and chondrocytes. Food Funct. 2016 Mar;7(3):1671-9. doi: 10.1039/c5fo01256b. [PubMed:26951869 ]
Liu N, Wang X, Wu H, Lv X, Xie H, Guo Z, Wang J, Dou G, Zhang C, Sun M: Computational study of effective matrix metalloproteinase 9 (MMP9) targeting natural inhibitors. Aging (Albany NY). 2021 Oct 4;13(19):22867-22882. doi: 10.18632/aging.203581. Epub 2021 Oct 4. [PubMed:34607974 ]
Zhong L, Ravichandran V, Zhang N, Wang H, Bian X, Zhang Y, Li A: Attenuation of Pseudomonas aeruginosa Quorum Sensing by Natural Products: Virtual Screening, Evaluation and Biomolecular Interactions. Int J Mol Sci. 2020 Mar 22;21(6). pii: ijms21062190. doi: 10.3390/ijms21062190. [PubMed:32235775 ]
Uddin GM, Kim CY, Chung D, Kim KA, Jung SH: One-step isolation of sappanol and brazilin from Caesalpinia sappan and their effects on oxidative stress-induced retinal death. BMB Rep. 2015 May;48(5):289-94. doi: 10.5483/bmbrep.2015.48.5.189. [PubMed:25248564 ]

Showing NP-Card for Sappanol (NP0140302)

MOL for NP0140302 (Sappanol)

3D MOL for NP0140302 (Sappanol)

3D SDF for NP0140302 (Sappanol)

3D-SDF for NP0140302 (Sappanol)

PDB for NP0140302 (Sappanol)

3D PDB for NP0140302 (Sappanol)

SMILES for NP0140302 (Sappanol)

INCHI for NP0140302 (Sappanol)

Structure for NP0140302 (Sappanol)

3D Structure for NP0140302 (Sappanol)