NP-MRD: Showing NP-Card for Heraclenin (NP0046569)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-03-17 20:08:02 UTC

Updated at

2022-03-17 20:08:03 UTC

NP-MRD ID

NP0046569

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Heraclenin

Description

Heraclenin is found in Afraegle paniculata, Ammi majus, Angelica genuflexa, Angelica lucida, Angelica ursina, Angelica ursina Maxim, Atalantia ceylanica, Ferula moschata, Ferula sumbul , Glehnia littoralis, Halocnemum strobilaceum, Heracleum pinnatum, Heracleum rapula, Opopanax chironium, Orixa japonica, Phebalium canaliculatum, Phebalium filifolium, Philotheca spicata, Prangos bucharica, Prangos ferulacea, Prangos lipskyi, Prangos lophoptera, Prangos tschimganica, Prangos uloptera, Skimmia laureola, Thamnosma texana and Zeravschania regeliana.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241221202D          

 21 24  0  0  1  0            999 V2000
    0.0000    0.0000    0.0000 O   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
    1.4289    0.0000    0.0000 O   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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   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
    2.1434    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7309    2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559    2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9046    3.5247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3778    2.7051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -0.1576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -1.4924    0.0000 C   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
    2.8579   -1.6500    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
    0.7145   -1.2375    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  5 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
  4 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
  2 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046569

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)O[C@H]1COC1=C2OC=CC2=CC2=C1OC(=O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O5/c1-16(2)11(21-16)8-19-15-13-10(5-6-18-13)7-9-3-4-12(17)20-14(9)15/h3-7,11H,8H2,1-2H3/t11-/m0/s1

> <INCHI_KEY>
CTJZWFCPUDPLME-NSHDSACASA-N

> <FORMULA>
C16H14O5

> <MOLECULAR_WEIGHT>
286.2794

> <EXACT_MASS>
286.084123558

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
29.03452402439358

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-{[(2S)-3,3-dimethyloxiran-2-yl]methoxy}-7H-furo[3,2-g]chromen-7-one

> <ALOGPS_LOGP>
2.78

> <JCHEM_LOGP>
2.323230061666666

> <ALOGPS_LOGS>
-3.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3921706521845603

> <JCHEM_POLAR_SURFACE_AREA>
61.2

> <JCHEM_REFRACTIVITY>
74.65459999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.32e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-{[(2S)-3,3-dimethyloxiran-2-yl]methoxy}furo[3,2-g]chromen-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.231   5.184   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.771   5.184   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.422   6.579   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.305   5.050   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.133  -0.294   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.038  -1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.133  -2.786   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   19                                                  
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8   10                                                       
CONECT   10    9    8   11   12                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    5   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   13   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18    4   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20    2                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₄O₅

Average Mass

286.2794 Da

Monoisotopic Mass

286.08412 Da

IUPAC Name

9-{[(2S)-3,3-dimethyloxiran-2-yl]methoxy}-7H-furo[3,2-g]chromen-7-one

Traditional Name

9-{[(2S)-3,3-dimethyloxiran-2-yl]methoxy}furo[3,2-g]chromen-7-one

CAS Registry Number

Not Available

SMILES

CC1(C)O[C@H]1COC1=C2OC=CC2=CC2=C1OC(=O)C=C2

InChI Identifier

InChI=1S/C16H14O5/c1-16(2)11(21-16)8-19-15-13-10(5-6-18-13)7-9-3-4-12(17)20-14(9)15/h3-7,11H,8H2,1-2H3/t11-/m0/s1

InChI Key

CTJZWFCPUDPLME-NSHDSACASA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Afraegle paniculata	LOTUS Database	35616633
Ammi majus	LOTUS Database	35616633
Angelica genuflexa	LOTUS Database	35616633
Angelica lucida	LOTUS Database	35616633
Angelica ursina	LOTUS Database	35616633
Angelica ursina Maxim	Plant	KNApSAcK
Atalantia ceylanica	Plant	KNApSAcK
Citrus limon	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Daucus carota	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Daucus carota ssp. sativus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ferula moschata	LOTUS Database	35616633
Ferula sumbul	Plant	KNApSAcK
Glehnia littoralis	LOTUS Database	35616633
Halocnemum strobilaceum	LOTUS Database	35616633
Heracleum pinnatum	Plant	KNApSAcK
Heracleum rapula	LOTUS Database	35616633
Opopanax chironium	Plant	KNApSAcK
Orixa japonica	LOTUS Database	35616633
Phebalium canaliculatum	LOTUS Database	35616633
Phebalium filifolium	LOTUS Database	35616633
Philotheca spicata	LOTUS Database	35616633
Prangos bucharica	LOTUS Database	35616633
Prangos ferulacea	LOTUS Database	35616633
Prangos lipskyi	LOTUS Database	35616633
Prangos lophoptera	LOTUS Database	35616633
Prangos tschimganica	LOTUS Database	35616633
Prangos uloptera	LOTUS Database	35616633
Skimmia laureola	LOTUS Database	35616633
Thamnosma texana	LOTUS Database	35616633
Zeravschania regeliana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

Psoralens

Alternative Parents

Substituents

Psoralen
Benzopyran
1-benzopyran
Benzofuran
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Furan
Lactone
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen 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
logP	2.78	ALOGPS
logP	2.32	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.2 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	74.65 m³·mol⁻¹	ChemAxon
Polarizability	29.03 Å³	ChemAxon
Number of Rings	4	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

FDB005034

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

17897

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Heraclenin (NP0046569)

MOL for NP0046569 (Heraclenin)

3D MOL for NP0046569 (Heraclenin)

3D SDF for NP0046569 (Heraclenin)

3D-SDF for NP0046569 (Heraclenin)

PDB for NP0046569 (Heraclenin)

3D PDB for NP0046569 (Heraclenin)

SMILES for NP0046569 (Heraclenin)

INCHI for NP0046569 (Heraclenin)

Structure for NP0046569 (Heraclenin)

3D Structure for NP0046569 (Heraclenin)