NP-MRD: Showing NP-Card for 6-(hydroxymethyl)-1-methylphenanthro[1,2-b]furan-10,11-dione (NP0217855)

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Record Information

Version

2.0

Created at

2022-09-05 18:20:03 UTC

Updated at

2022-09-05 18:20:03 UTC

NP-MRD ID

NP0217855

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-(hydroxymethyl)-1-methylphenanthro[1,2-b]furan-10,11-dione

Description

Tanshinol A belongs to the class of organic compounds known as tanshinones, isotanshinones, and derivatives. These are a group of abietane-type norditerpenoid quinones. 6-(hydroxymethyl)-1-methylphenanthro[1,2-b]furan-10,11-dione is found in Salvia miltiorrhiza. 6-(hydroxymethyl)-1-methylphenanthro[1,2-b]furan-10,11-dione was first documented in 2014 (PMID: 25026357). Based on a literature review a small amount of articles have been published on Tanshinol A (PMID: 33289608) (PMID: 32058595) (PMID: 31678492).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052220202D          

 22 25  0  0  0  0            999 V2000
    5.2939    1.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875    0.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0168    0.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340   -0.2889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629    0.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7114    2.4000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0872    2.1096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705    0.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781   -0.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1539   -1.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6857   -1.7701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  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
  5 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
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 11 22  2  0  0  0  0
 15 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0217855

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=COC2=C1C(=O)C(=O)C1=C3C=CC=C(CO)C3=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C18H12O4/c1-9-8-22-18-13-6-5-11-10(7-19)3-2-4-12(11)15(13)17(21)16(20)14(9)18/h2-6,8,19H,7H2,1H3

> <INCHI_KEY>
RVBZKTGBLGUYDC-UHFFFAOYSA-N

> <FORMULA>
C18H12O4

> <MOLECULAR_WEIGHT>
292.29

> <EXACT_MASS>
292.073558866

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
30.656541024837004

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-(hydroxymethyl)-14-methyl-12-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),2(7),3,5,8,11(15),13-heptaene-16,17-dione

> <JCHEM_LOGP>
2.7145010973333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.126768377515575

> <JCHEM_PKA_STRONGEST_BASIC>
-2.743351511674687

> <JCHEM_POLAR_SURFACE_AREA>
67.51

> <JCHEM_REFRACTIVITY>
81.84920000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
6-(hydroxymethyl)-14-methyl-12-oxatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),2(7),3,5,8,11(15),13-heptaene-16,17-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       9.882   3.020   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.937   1.804   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.365   0.325   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.090  -0.539   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.874   0.406   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.398   1.854   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.405   3.032   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.928   4.480   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.889   2.761   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.896   3.938   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.366   1.312   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.358   0.135   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.835  -1.314   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.319  -1.585   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.326  -0.407   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.810  -0.678   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.287  -2.127   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.280  -3.304   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.182   0.499   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.341   1.947   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.857   2.218   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.850   1.041   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    2    7                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   22                                                  
CONECT   12   11    5   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   11   15                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₂O₄

Average Mass

292.2900 Da

Monoisotopic Mass

292.07356 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1=COC2=C1C(=O)C(=O)C1=C3C=CC=C(CO)C3=CC=C21

InChI Identifier

InChI=1S/C18H12O4/c1-9-8-22-18-13-6-5-11-10(7-19)3-2-4-12(11)15(13)17(21)16(20)14(9)18/h2-6,8,19H,7H2,1H3

InChI Key

RVBZKTGBLGUYDC-UHFFFAOYSA-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
Salvia miltiorrhiza	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tanshinones, isotanshinones, and derivatives. These are a group of abietane-type norditerpenoid quinones.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Tanshinones, isotanshinones, and derivatives

Alternative Parents

Substituents

Tanshinone skeleton
Phenanthrene
Naphthofuran
Naphthalene
O-quinone
Quinone
Aryl ketone
Benzenoid
Heteroaromatic compound
Furan
Ketone
Organoheterocyclic compound
Oxacycle
Aromatic alcohol
Aldehyde
Primary alcohol
Hydrocarbon derivative
Organooxygen compound
Alcohol
Organic oxide
Organic oxygen compound
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

HMDB0258713

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4479302

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5321622

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rafi MO, Al-Khafaji K, Tok TT, Rahman MS: Computer-based identification of potential compounds from Salviae miltiorrhizae against Neirisaral adhesion A regulatory protein. J Biomol Struct Dyn. 2022 Jul;40(10):4301-4313. doi: 10.1080/07391102.2020.1856189. Epub 2020 Dec 8. [PubMed:33289608 ]
Li Y, Chen Y, Huang X, Huang D, Gan H, Yao N, Hu Z, Li R, Zhan X, Xie K, Jiang J, Cai D: Tanshinol A Ameliorates Triton-1339W-Induced Hyperlipidemia and Liver Injury in C57BL/6J Mice by Regulating mRNA Expression of Lipemic-Oxidative Injury Genes. Lipids. 2020 Mar;55(2):127-140. doi: 10.1002/lipd.12217. Epub 2020 Feb 14. [PubMed:32058595 ]
Liu X, Zhang Y, Gao H, Hou Y, Lu JJ, Feng Y, Xu Q, Liu B, Chen X: Induction of an MLKL mediated non-canonical necroptosis through reactive oxygen species by tanshinol A in lung cancer cells. Biochem Pharmacol. 2020 Jan;171:113684. doi: 10.1016/j.bcp.2019.113684. Epub 2019 Nov 1. [PubMed:31678492 ]
Yue S, Hu B, Wang Z, Yue Z, Wang F, Zhao Y, Yang Z, Shen M: Salvia miltiorrhiza compounds protect the liver from acute injury by regulation of p38 and NFkappaB signaling in Kupffer cells. Pharm Biol. 2014 Oct;52(10):1278-85. doi: 10.3109/13880209.2014.889720. Epub 2014 Jul 15. [PubMed:25026357 ]
LOTUS database [Link]

Showing NP-Card for 6-(hydroxymethyl)-1-methylphenanthro[1,2-b]furan-10,11-dione (NP0217855)

MOL for NP0217855 (6-(hydroxymethyl)-1-methylphenanthro[1,2-b]furan-10,11-dione)

3D MOL for NP0217855 (6-(hydroxymethyl)-1-methylphenanthro[1,2-b]furan-10,11-dione)

3D SDF for NP0217855 (6-(hydroxymethyl)-1-methylphenanthro[1,2-b]furan-10,11-dione)

3D-SDF for NP0217855 (6-(hydroxymethyl)-1-methylphenanthro[1,2-b]furan-10,11-dione)

PDB for NP0217855 (6-(hydroxymethyl)-1-methylphenanthro[1,2-b]furan-10,11-dione)

3D PDB for NP0217855 (6-(hydroxymethyl)-1-methylphenanthro[1,2-b]furan-10,11-dione)

SMILES for NP0217855 (6-(hydroxymethyl)-1-methylphenanthro[1,2-b]furan-10,11-dione)

INCHI for NP0217855 (6-(hydroxymethyl)-1-methylphenanthro[1,2-b]furan-10,11-dione)

Structure for NP0217855 (6-(hydroxymethyl)-1-methylphenanthro[1,2-b]furan-10,11-dione)

3D Structure for NP0217855 (6-(hydroxymethyl)-1-methylphenanthro[1,2-b]furan-10,11-dione)