NP-MRD: Showing NP-Card for (1s,8s,9s,16s)-8-(3,4-dihydroxyphenyl)-16-(4-hydroxyphenyl)tetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol (NP0155348)

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Record Information

Version

2.0

Created at

2022-09-02 12:23:34 UTC

Updated at

2022-09-02 12:23:34 UTC

NP-MRD ID

NP0155348

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,8s,9s,16s)-8-(3,4-dihydroxyphenyl)-16-(4-hydroxyphenyl)tetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol

Description

(1S,8S,9S,16S)-8-(3,4-dihydroxyphenyl)-16-(4-hydroxyphenyl)tetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]Hexadeca-2(7),3,5,10(15),11,13-hexaene-4,6,12,14-tetrol belongs to the class of organic compounds known as indanes. Indanes are compounds containing an indane moiety, which consists of a cyclopentane fused to a benzene ring. (1s,8s,9s,16s)-8-(3,4-dihydroxyphenyl)-16-(4-hydroxyphenyl)tetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol is found in Caragana rosea. Based on a literature review very few articles have been published on (1S,8S,9S,16S)-8-(3,4-dihydroxyphenyl)-16-(4-hydroxyphenyl)tetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]Hexadeca-2(7),3,5,10(15),11,13-hexaene-4,6,12,14-tetrol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022214232D          

 35 40  0  0  1  0            999 V2000
    4.7916   -6.4822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6889   -5.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9286   -5.3433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8259   -4.5247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4835   -4.0265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3807   -3.2079    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6581   -2.8098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8788   -3.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7235   -3.8908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2547   -2.5409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4100   -1.7306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7859   -1.1911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1893   -1.4600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8134   -1.9996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2338   -1.3326    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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    5.5395    0.3564    4.5293 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309022214232D          

 35 40  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0155348

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1)[C@@H]1[C@@H]2[C@@H]([C@H](C3=C(O)C=C(O)C=C23)C2=CC=C(O)C(O)=C2)C2=CC(O)=CC(O)=C12

> <INCHI_IDENTIFIER>
InChI=1S/C28H22O7/c29-14-4-1-12(2-5-14)23-25-17(8-15(30)10-21(25)34)28-24(13-3-6-19(32)20(33)7-13)26-18(27(23)28)9-16(31)11-22(26)35/h1-11,23-24,27-35H/t23-,24-,27+,28+/m0/s1

> <INCHI_KEY>
CQANGYATKKFCOC-KBJUPQRZSA-N

> <FORMULA>
C28H22O7

> <MOLECULAR_WEIGHT>
470.477

> <EXACT_MASS>
470.136553048

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
48.75276578526214

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,8S,9S,16S)-8-(3,4-dihydroxyphenyl)-16-(4-hydroxyphenyl)tetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol

> <ALOGPS_LOGP>
3.41

> <JCHEM_LOGP>
5.010589230333333

> <ALOGPS_LOGS>
-4.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.366299479037199

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.91792045250082

> <JCHEM_PKA_STRONGEST_BASIC>
-5.450553458856267

> <JCHEM_POLAR_SURFACE_AREA>
141.61

> <JCHEM_REFRACTIVITY>
129.92289999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.83e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,8S,9S,16S)-8-(3,4-dihydroxyphenyl)-16-(4-hydroxyphenyl)tetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  O   UNK     0       8.944 -12.100   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       8.753 -10.572   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.333  -9.974   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.142  -8.446   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.369  -7.516   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.177  -5.988   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.828  -5.245   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.374  -5.750   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.084  -7.263   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.209  -4.743   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.499  -3.231   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.334  -2.223   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.953  -2.725   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.118  -3.733   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.646  -3.541   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.770  -2.488   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.578  -0.960   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.159  -0.362   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.967   1.166   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.195   2.097   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.003   3.625   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      10.614   1.499   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      11.841   2.429   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.805  -0.029   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.119  -3.231   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.573  -2.725   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      12.863  -1.213   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      13.738  -3.733   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.449  -5.245   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      14.614  -6.252   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      11.994  -5.750   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.829  -4.743   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.301  -4.935   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.788  -8.114   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.980  -9.642   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   34                                                  
CONECT    6    5    7   33                                                  
CONECT    7    6    8   14                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    7   15                                                  
CONECT   15   14   16   33                                                  
CONECT   16   15   17   25                                                  
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   17                                                       
CONECT   25   16   26   32                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   25   33                                                  
CONECT   33   32    6   15                                                  
CONECT   34    5   35                                                       
CONECT   35   34    2                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₂₂O₇

Average Mass

470.4770 Da

Monoisotopic Mass

470.13655 Da

IUPAC Name

(1S,8S,9S,16S)-8-(3,4-dihydroxyphenyl)-16-(4-hydroxyphenyl)tetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol

Traditional Name

(1S,8S,9S,16S)-8-(3,4-dihydroxyphenyl)-16-(4-hydroxyphenyl)tetracyclo[7.7.0.0^{2,7}.0^{10,15}]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)[C@@H]1[C@@H]2[C@@H]([C@H](C3=C(O)C=C(O)C=C23)C2=CC=C(O)C(O)=C2)C2=CC(O)=CC(O)=C12

InChI Identifier

InChI=1S/C28H22O7/c29-14-4-1-12(2-5-14)23-25-17(8-15(30)10-21(25)34)28-24(13-3-6-19(32)20(33)7-13)26-18(27(23)28)9-16(31)11-22(26)35/h1-11,23-24,27-35H/t23-,24-,27+,28+/m0/s1

InChI Key

CQANGYATKKFCOC-KBJUPQRZSA-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
Caragana rosea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indanes. Indanes are compounds containing an indane moiety, which consists of a cyclopentane fused to a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Indanes

Sub Class

Not Available

Direct Parent

Indanes

Alternative Parents

Substituents

Indane
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Polyol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	3.41	ALOGPS
logP	5.01	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	8.92	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	141.61 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	129.92 m³·mol⁻¹	ChemAxon
Polarizability	48.75 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

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

163051280

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,8s,9s,16s)-8-(3,4-dihydroxyphenyl)-16-(4-hydroxyphenyl)tetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol (NP0155348)

MOL for NP0155348 ((1s,8s,9s,16s)-8-(3,4-dihydroxyphenyl)-16-(4-hydroxyphenyl)tetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol)

3D MOL for NP0155348 ((1s,8s,9s,16s)-8-(3,4-dihydroxyphenyl)-16-(4-hydroxyphenyl)tetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol)

3D SDF for NP0155348 ((1s,8s,9s,16s)-8-(3,4-dihydroxyphenyl)-16-(4-hydroxyphenyl)tetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol)

3D-SDF for NP0155348 ((1s,8s,9s,16s)-8-(3,4-dihydroxyphenyl)-16-(4-hydroxyphenyl)tetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol)

PDB for NP0155348 ((1s,8s,9s,16s)-8-(3,4-dihydroxyphenyl)-16-(4-hydroxyphenyl)tetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol)

3D PDB for NP0155348 ((1s,8s,9s,16s)-8-(3,4-dihydroxyphenyl)-16-(4-hydroxyphenyl)tetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol)

SMILES for NP0155348 ((1s,8s,9s,16s)-8-(3,4-dihydroxyphenyl)-16-(4-hydroxyphenyl)tetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol)

INCHI for NP0155348 ((1s,8s,9s,16s)-8-(3,4-dihydroxyphenyl)-16-(4-hydroxyphenyl)tetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol)

Structure for NP0155348 ((1s,8s,9s,16s)-8-(3,4-dihydroxyphenyl)-16-(4-hydroxyphenyl)tetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol)

3D Structure for NP0155348 ((1s,8s,9s,16s)-8-(3,4-dihydroxyphenyl)-16-(4-hydroxyphenyl)tetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-2,4,6,10,12,14-hexaene-4,6,12,14-tetrol)