NP-MRD: Showing NP-Card for (3'S)-(-)-Hamaudol (NP0072932)

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Record Information

Version

2.0

Created at

2022-04-28 18:12:25 UTC

Updated at

2022-04-28 18:12:26 UTC

NP-MRD ID

NP0072932

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3'S)-(-)-Hamaudol

Description

Hamaudol belongs to the class of organic compounds known as pyranochromenes. These are organic heterocyclic compounds containing a pyran ring fused to a chromene (1-benzopyran) moiety. (3'S)-(-)-Hamaudol is found in Angelica genuflexa, Angelica japonica, Angelica lucida, Ledebouriella seseloides, Peucedanum japonicum, Saposhnikovia divaricata and Saposhnikovia divaricata Schischkin. (3'S)-(-)-Hamaudol was first documented in 2010 (PMID: 21174769). Based on a literature review a small amount of articles have been published on Hamaudol (PMID: 32656897) (PMID: 32351756) (PMID: 31931162) (PMID: 26833192).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
    5.5542   -0.9541    1.3642 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2780   -0.4376    0.8130 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3471    0.5742   -0.1093 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1956    1.0988   -0.6603 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2268    2.0372   -1.5177 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9701    0.5934   -0.2727 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7776    1.0874   -0.7982 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8421    2.1023   -1.7233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4457    0.5854   -0.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4469   -0.4360    0.5217 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7450   -0.9228    1.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9709   -0.4226    0.6578 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1054   -0.8915    1.1568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6811   -0.9385    0.9064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9113   -0.5280    0.3647 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5958    0.4822    1.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7981   -1.7762    0.3100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6894   -0.0611   -1.0342 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8457    0.2742   -1.7064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7107    1.1204   -0.9823 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4120   -1.7230    2.1372 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1288   -0.0968    1.7647 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1745   -1.3999    0.5560 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3033    0.9884   -0.4299 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0833    2.5571   -2.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7338   -1.7187    1.7689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6565    0.5867    0.9282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0504    1.4215    1.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6337    0.0473    2.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5008   -1.6533   -0.5405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2957   -1.9575    1.2739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1240   -2.6463    0.0654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1516   -0.8643   -1.5804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5838    0.4622   -2.6520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1177    1.9620   -0.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6095    1.4475   -2.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 14  1  0
 14 15  1  0
 15 16  1  1
 15 17  1  0
 15 18  1  0
 18 19  1  0
 18 20  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13  2  1  0
 12  6  1  0
 20  9  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  8 25  1  0
 16 27  1  0
 16 28  1  0
 16 29  1  0
 17 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  6
 19 34  1  0
 20 35  1  0
 20 36  1  0
 11 26  1  0
M  END


  Mrv1652304282220122D          

 20 22  0  0  1  0            999 V2000
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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    0.8250    0.0000 C   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
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4372   -0.6996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8245   -0.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    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  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  9 11  1  1  0  0  0
  8 12  1  0  0  0  0
  8 13  1  0  0  0  0
  3 14  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
  1 19  1  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0072932

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(=O)C2=C(O)C3=C(OC(C)(C)[C@@H](O)C3)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O5/c1-7-4-9(16)13-11(19-7)6-10-8(14(13)18)5-12(17)15(2,3)20-10/h4,6,12,17-18H,5H2,1-3H3/t12-/m0/s1

> <INCHI_KEY>
VOTLUFSYIRHICX-LBPRGKRZSA-N

> <FORMULA>
C15H16O5

> <MOLECULAR_WEIGHT>
276.288

> <EXACT_MASS>
276.099773615

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
28.523883441952098

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(7S)-5,7-dihydroxy-2,8,8-trimethyl-4H,6H,7H,8H-pyrano[3,2-g]chromen-4-one

> <ALOGPS_LOGP>
1.87

> <JCHEM_LOGP>
2.1670219393333334

> <ALOGPS_LOGS>
-2.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.849189392669224

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.5496433911016165

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3356231800311953

> <JCHEM_POLAR_SURFACE_AREA>
75.99

> <JCHEM_REFRACTIVITY>
73.88040000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.65e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(7S)-5,7-dihydroxy-2,8,8-trimethyl-6H,7H-pyrano[3,2-g]chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.816  -1.306   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.539  -0.054   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2    6   19                                                  
CONECT    2    1    3   15                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   12   13                                             
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9                                                            
CONECT   12    8                                                            
CONECT   13    8                                                            
CONECT   14    3                                                            
CONECT   15    2   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18    1                                                       
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₆O₅

Average Mass

276.2880 Da

Monoisotopic Mass

276.09977 Da

IUPAC Name

(7S)-5,7-dihydroxy-2,8,8-trimethyl-4H,6H,7H,8H-pyrano[3,2-g]chromen-4-one

Traditional Name

(7S)-5,7-dihydroxy-2,8,8-trimethyl-6H,7H-pyrano[3,2-g]chromen-4-one

CAS Registry Number

Not Available

SMILES

CC1=CC(=O)C2=C(O)C3=C(OC(C)(C)[C@@H](O)C3)C=C2O1

InChI Identifier

InChI=1S/C15H16O5/c1-7-4-9(16)13-11(19-7)6-10-8(14(13)18)5-12(17)15(2,3)20-10/h4,6,12,17-18H,5H2,1-3H3/t12-/m0/s1

InChI Key

VOTLUFSYIRHICX-LBPRGKRZSA-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
Angelica genuflexa	LOTUS Database	35616633
Angelica japonica	LOTUS Database	35616633
Angelica lucida	LOTUS Database	35616633
Ledebouriella seseloides	Plant	KNApSAcK
Peucedanum japonicum	LOTUS Database	35616633
Saposhnikovia divaricata	LOTUS Database	35616633
Saposhnikovia divaricata Schischkin	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranochromenes. These are organic heterocyclic compounds containing a pyran ring fused to a chromene (1-benzopyran) moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Pyranochromenes

Alternative Parents

Substituents

Pyranochromene
2,2-dimethyl-1-benzopyran
Chromone
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Ether
Oxacycle
Organooxygen compound
Alcohol
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

chromenes (CHEBI:81123 )
chromones (C17483 )

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	1.87	ALOGPS
logP	2.17	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	7.55	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	73.88 m³·mol⁻¹	ChemAxon
Polarizability	28.52 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00033012

Chemspider ID

144403

KEGG Compound ID

C17483

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

164722

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Huang Y, Yu M, Wu T, Hou W, Liu C, Li S: Development of a method to screen and isolate lipoxidase inhibitors from Radix Saposhnikoviae via ultrafiltration liquid chromatography combined with metablism in vitro. Phytochem Anal. 2020 Nov;31(6):937-947. doi: 10.1002/pca.2966. Epub 2020 Jul 12. [PubMed:32656897 ]
Zhang J, Chen L, Qiu J, Zhang Y, Wang L, Jiang L, Jiang Y, Liu B: Simultaneous Determination of Six Chromones in Saposhnikoviae Radix via Quantitative Analysis of Multicomponents by Single Marker. J Anal Methods Chem. 2020 Apr 14;2020:7867046. doi: 10.1155/2020/7867046. eCollection 2020. [PubMed:32351756 ]
Urbagarova BM, Shults EE, Taraskin VV, Radnaeva LD, Petrova TN, Rybalova TV, Frolova TS, Pokrovskii AG, Ganbaatar J: Chromones and coumarins from Saposhnikovia divaricata (Turcz.) Schischk. Growing in Buryatia and Mongolia and their cytotoxicity. J Ethnopharmacol. 2020 Oct 28;261:112517. doi: 10.1016/j.jep.2019.112517. Epub 2020 Jan 10. [PubMed:31931162 ]
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Showing NP-Card for (3'S)-(-)-Hamaudol (NP0072932)

MOL for NP0072932 ((3'S)-(-)-Hamaudol)

3D MOL for NP0072932 ((3'S)-(-)-Hamaudol)

3D SDF for NP0072932 ((3'S)-(-)-Hamaudol)

3D-SDF for NP0072932 ((3'S)-(-)-Hamaudol)

PDB for NP0072932 ((3'S)-(-)-Hamaudol)

3D PDB for NP0072932 ((3'S)-(-)-Hamaudol)

SMILES for NP0072932 ((3'S)-(-)-Hamaudol)

INCHI for NP0072932 ((3'S)-(-)-Hamaudol)

Structure for NP0072932 ((3'S)-(-)-Hamaudol)

3D Structure for NP0072932 ((3'S)-(-)-Hamaudol)