NP-MRD: Showing NP-Card for 4-[6-hydroxy-4-methoxy-1,1-dimethyl-3-(3-methylbut-2-en-1-yl)-2h,2ah,7h,7ah-cyclobuta[a]inden-2-yl]benzene-1,2-diol (NP0256341)

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Record Information

Version

1.0

Created at

2022-09-07 21:08:08 UTC

Updated at

2022-09-07 21:08:08 UTC

NP-MRD ID

NP0256341

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[6-hydroxy-4-methoxy-1,1-dimethyl-3-(3-methylbut-2-en-1-yl)-2h,2ah,7h,7ah-cyclobuta[a]inden-2-yl]benzene-1,2-diol

Description

4-[6-Hydroxy-4-methoxy-1,1-dimethyl-3-(3-methylbut-2-en-1-yl)-1H,2H,2aH,7H,7aH-cyclobuta[a]inden-2-yl]benzene-1,2-diol 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. 4-[6-hydroxy-4-methoxy-1,1-dimethyl-3-(3-methylbut-2-en-1-yl)-2h,2ah,7h,7ah-cyclobuta[a]inden-2-yl]benzene-1,2-diol is found in Artocarpus chama. 4-[6-Hydroxy-4-methoxy-1,1-dimethyl-3-(3-methylbut-2-en-1-yl)-1H,2H,2aH,7H,7aH-cyclobuta[a]inden-2-yl]benzene-1,2-diol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241515552D          

 29 32  0  0  0  0            999 V2000
   -0.2210   -1.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4417   -0.7647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1364   -0.1761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0843    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4938    1.2074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2731    2.0024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2925    1.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9804    1.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6262    0.9433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3375    0.1704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1103   -0.1183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4527   -0.8689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2739   -0.9477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6162   -1.6983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1373   -2.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4797   -3.1207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3161   -2.2913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8372   -2.9631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9738   -1.5407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3990    0.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8601    1.3387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2179    0.5543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5133    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9352   -0.3824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1559   -1.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5778   -1.7660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7985   -2.5609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5973   -2.7672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2204   -3.1495    0.0000 C   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  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
 10 11  1  0  0  0  0
 11 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
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 12 19  1  0  0  0  0
 11 20  1  0  0  0  0
  9 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 10 23  1  0  0  0  0
  7 23  1  0  0  0  0
 23 24  2  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
M  END


  Mrv1533004241515552D          

 29 32  0  0  0  0            999 V2000
   -0.2210   -1.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4417   -0.7647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1364   -0.1761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0843    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4938    1.2074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2731    2.0024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2925    1.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9804    1.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6262    0.9433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3375    0.1704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1103   -0.1183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4527   -0.8689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2739   -0.9477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6162   -1.6983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1373   -2.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4797   -3.1207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3161   -2.2913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8372   -2.9631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9738   -1.5407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3990    0.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8601    1.3387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2179    0.5543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5133    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9352   -0.3824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1559   -1.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5778   -1.7660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7985   -2.5609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5973   -2.7672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2204   -3.1495    0.0000 C   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  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
 10 11  1  0  0  0  0
 11 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
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 12 19  1  0  0  0  0
 11 20  1  0  0  0  0
  9 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 10 23  1  0  0  0  0
  7 23  1  0  0  0  0
 23 24  2  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0256341

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2CC3C(C(C4=CC=C(O)C(O)=C4)C3(C)C)C2=C1CC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C25H30O4/c1-13(2)6-8-15-21(29-5)12-19(27)16-11-17-23(22(15)16)24(25(17,3)4)14-7-9-18(26)20(28)10-14/h6-7,9-10,12,17,23-24,26-28H,8,11H2,1-5H3

> <INCHI_KEY>
GZFNBAIGMIFCNM-UHFFFAOYSA-N

> <FORMULA>
C25H30O4

> <MOLECULAR_WEIGHT>
394.511

> <EXACT_MASS>
394.214409446

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
44.41052365947243

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[6-hydroxy-4-methoxy-1,1-dimethyl-3-(3-methylbut-2-en-1-yl)-1H,2H,2aH,7H,7aH-cyclobuta[a]inden-2-yl]benzene-1,2-diol

> <ALOGPS_LOGP>
4.94

> <JCHEM_LOGP>
5.759332701000001

> <ALOGPS_LOGS>
-5.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.901271300015885

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.257031891403399

> <JCHEM_PKA_STRONGEST_BASIC>
-4.8383931152029716

> <JCHEM_POLAR_SURFACE_AREA>
69.92

> <JCHEM_REFRACTIVITY>
116.55019999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.59e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[6-hydroxy-4-methoxy-1,1-dimethyl-3-(3-methylbut-2-en-1-yl)-2H,2aH,7H,7aH-cyclobuta[a]inden-2-yl]benzene-1,2-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -0.412  -2.911   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.824  -1.427   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.255  -0.329   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.157   1.155   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.922   2.254   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.510   3.738   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.413   1.869   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.697   2.719   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.902   1.761   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.363   0.318   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.806  -0.221   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.445  -1.622   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.978  -1.769   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.617  -3.170   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.723  -4.424   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.362  -5.825   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.190  -4.277   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.296  -5.531   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.551  -2.876   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.345   1.222   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.206   2.499   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.873   1.035   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.825   0.385   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.746  -0.714   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.158  -2.198   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.079  -3.296   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.491  -4.780   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.982  -5.165   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.411  -5.879   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   23                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   20                                                  
CONECT   10    9   11   23                                                  
CONECT   11   10   12   20                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   12                                                       
CONECT   20   11    9   21   22                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   10    7   24                                                  
CONECT   24   23    3   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₀O₄

Average Mass

394.5110 Da

Monoisotopic Mass

394.21441 Da

IUPAC Name

4-[6-hydroxy-4-methoxy-1,1-dimethyl-3-(3-methylbut-2-en-1-yl)-1H,2H,2aH,7H,7aH-cyclobuta[a]inden-2-yl]benzene-1,2-diol

Traditional Name

4-[6-hydroxy-4-methoxy-1,1-dimethyl-3-(3-methylbut-2-en-1-yl)-2H,2aH,7H,7aH-cyclobuta[a]inden-2-yl]benzene-1,2-diol

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2CC3C(C(C4=CC=C(O)C(O)=C4)C3(C)C)C2=C1CC=C(C)C

InChI Identifier

InChI=1S/C25H30O4/c1-13(2)6-8-15-21(29-5)12-19(27)16-11-17-23(22(15)16)24(25(17,3)4)14-7-9-18(26)20(28)10-14/h6-7,9-10,12,17,23-24,26-28H,8,11H2,1-5H3

InChI Key

GZFNBAIGMIFCNM-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Artocarpus chama	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
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Monocyclic benzene moiety
Ether
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	4.94	ALOGPS
logP	5.76	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	9.26	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.92 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	116.55 m³·mol⁻¹	ChemAxon
Polarizability	44.41 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-[6-hydroxy-4-methoxy-1,1-dimethyl-3-(3-methylbut-2-en-1-yl)-2h,2ah,7h,7ah-cyclobuta[a]inden-2-yl]benzene-1,2-diol (NP0256341)

MOL for NP0256341 (4-[6-hydroxy-4-methoxy-1,1-dimethyl-3-(3-methylbut-2-en-1-yl)-2h,2ah,7h,7ah-cyclobuta[a]inden-2-yl]benzene-1,2-diol)

3D MOL for NP0256341 (4-[6-hydroxy-4-methoxy-1,1-dimethyl-3-(3-methylbut-2-en-1-yl)-2h,2ah,7h,7ah-cyclobuta[a]inden-2-yl]benzene-1,2-diol)

3D SDF for NP0256341 (4-[6-hydroxy-4-methoxy-1,1-dimethyl-3-(3-methylbut-2-en-1-yl)-2h,2ah,7h,7ah-cyclobuta[a]inden-2-yl]benzene-1,2-diol)

3D-SDF for NP0256341 (4-[6-hydroxy-4-methoxy-1,1-dimethyl-3-(3-methylbut-2-en-1-yl)-2h,2ah,7h,7ah-cyclobuta[a]inden-2-yl]benzene-1,2-diol)

PDB for NP0256341 (4-[6-hydroxy-4-methoxy-1,1-dimethyl-3-(3-methylbut-2-en-1-yl)-2h,2ah,7h,7ah-cyclobuta[a]inden-2-yl]benzene-1,2-diol)

3D PDB for NP0256341 (4-[6-hydroxy-4-methoxy-1,1-dimethyl-3-(3-methylbut-2-en-1-yl)-2h,2ah,7h,7ah-cyclobuta[a]inden-2-yl]benzene-1,2-diol)

SMILES for NP0256341 (4-[6-hydroxy-4-methoxy-1,1-dimethyl-3-(3-methylbut-2-en-1-yl)-2h,2ah,7h,7ah-cyclobuta[a]inden-2-yl]benzene-1,2-diol)

INCHI for NP0256341 (4-[6-hydroxy-4-methoxy-1,1-dimethyl-3-(3-methylbut-2-en-1-yl)-2h,2ah,7h,7ah-cyclobuta[a]inden-2-yl]benzene-1,2-diol)

Structure for NP0256341 (4-[6-hydroxy-4-methoxy-1,1-dimethyl-3-(3-methylbut-2-en-1-yl)-2h,2ah,7h,7ah-cyclobuta[a]inden-2-yl]benzene-1,2-diol)

3D Structure for NP0256341 (4-[6-hydroxy-4-methoxy-1,1-dimethyl-3-(3-methylbut-2-en-1-yl)-2h,2ah,7h,7ah-cyclobuta[a]inden-2-yl]benzene-1,2-diol)