NP-MRD: Showing NP-Card for (8r,8as,10as)-8,10a-dimethyl-8-[(1e)-4-methylpenta-1,3-dien-1-yl]-6,7,8a,9-tetrahydro-5h-xanthen-2-ol (NP0226294)

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Record Information

Version

2.0

Created at

2022-09-06 05:16:53 UTC

Updated at

2022-09-06 05:16:53 UTC

NP-MRD ID

NP0226294

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(8r,8as,10as)-8,10a-dimethyl-8-[(1e)-4-methylpenta-1,3-dien-1-yl]-6,7,8a,9-tetrahydro-5h-xanthen-2-ol

Description

Riccardiphenol C belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring. (8r,8as,10as)-8,10a-dimethyl-8-[(1e)-4-methylpenta-1,3-dien-1-yl]-6,7,8a,9-tetrahydro-5h-xanthen-2-ol is found in Riccardia crassa. (8r,8as,10as)-8,10a-dimethyl-8-[(1e)-4-methylpenta-1,3-dien-1-yl]-6,7,8a,9-tetrahydro-5h-xanthen-2-ol was first documented in 1995 (PMID: 7561905). Based on a literature review very few articles have been published on riccardiphenol C.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062207162D          

 23 25  0  0  1  0            999 V2000
    1.1168   -6.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6471   -5.7020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4596   -5.8452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3650   -4.9267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8953   -4.2947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6131   -3.5195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6737   -3.5195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    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
    2.1434   -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  2  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
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  6  0  0  0
  7  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  1  1  0  0  0
 12 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
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 22  1  1  0  0  0
 12 23  1  0  0  0  0
  7 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0226294

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=C\C=C\[C@@]1(C)CCC[C@]2(C)OC3=CC=C(O)C=C3C[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O2/c1-15(2)7-5-10-20(3)11-6-12-21(4)19(20)14-16-13-17(22)8-9-18(16)23-21/h5,7-10,13,19,22H,6,11-12,14H2,1-4H3/b10-5+/t19-,20-,21-/m0/s1

> <INCHI_KEY>
YBIYFWSHKKSQQA-NDFCPFBDSA-N

> <FORMULA>
C21H28O2

> <MOLECULAR_WEIGHT>
312.453

> <EXACT_MASS>
312.208930142

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
36.761599605268245

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4aS,9aS)-1,4a-dimethyl-1-[(1E)-4-methylpenta-1,3-dien-1-yl]-2,3,4,4a,9,9a-hexahydro-1H-xanthen-7-ol

> <JCHEM_LOGP>
5.446814911333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.003415001228356

> <JCHEM_PKA_STRONGEST_BASIC>
-4.857075908594566

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
97.20700000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(8R,8aS,10aS)-8,10a-dimethyl-8-[(1E)-4-methylpenta-1,3-dien-1-yl]-6,7,8a,9-tetrahydro-5H-xanthen-2-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       2.085 -11.823   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.075 -10.644   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.591 -10.911   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.548  -9.197   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.538  -8.017   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.011  -6.570   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.991  -6.570   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   23                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   23                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   15   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   12    7                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₈O₂

Average Mass

312.4530 Da

Monoisotopic Mass

312.20893 Da

IUPAC Name

(1R,4aS,9aS)-1,4a-dimethyl-1-[(1E)-4-methylpenta-1,3-dien-1-yl]-2,3,4,4a,9,9a-hexahydro-1H-xanthen-7-ol

Traditional Name

(8R,8aS,10aS)-8,10a-dimethyl-8-[(1E)-4-methylpenta-1,3-dien-1-yl]-6,7,8a,9-tetrahydro-5H-xanthen-2-ol

CAS Registry Number

Not Available

SMILES

CC(C)=C\C=C\[C@@]1(C)CCC[C@]2(C)OC3=CC=C(O)C=C3C[C@@H]12

InChI Identifier

InChI=1S/C21H28O2/c1-15(2)7-5-10-20(3)11-6-12-21(4)19(20)14-16-13-17(22)8-9-18(16)23-21/h5,7-10,13,19,22H,6,11-12,14H2,1-4H3/b10-5+/t19-,20-,21-/m0/s1

InChI Key

YBIYFWSHKKSQQA-NDFCPFBDSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Riccardia crassa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthenes. These are polycyclic aromatic compounds containing a xanthene moiety, which consists of two benzene rings joined to each other by a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthenes

Alternative Parents

Substituents

Xanthene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Oxacycle
Ether
Organic oxygen compound
Hydrocarbon derivative
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	5.45	ChemAxon
pKa (Strongest Acidic)	10	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	97.21 m³·mol⁻¹	ChemAxon
Polarizability	36.76 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

8239668

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10064128

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Perry NB, Foster LM: Sesquiterpene/quinol from a New Zealand liverwort, Riccardia crassa. J Nat Prod. 1995 Jul;58(7):1131-5. doi: 10.1021/np50121a027. [PubMed:7561905 ]
LOTUS database [Link]

Showing NP-Card for (8r,8as,10as)-8,10a-dimethyl-8-[(1e)-4-methylpenta-1,3-dien-1-yl]-6,7,8a,9-tetrahydro-5h-xanthen-2-ol (NP0226294)

MOL for NP0226294 ((8r,8as,10as)-8,10a-dimethyl-8-[(1e)-4-methylpenta-1,3-dien-1-yl]-6,7,8a,9-tetrahydro-5h-xanthen-2-ol)

3D MOL for NP0226294 ((8r,8as,10as)-8,10a-dimethyl-8-[(1e)-4-methylpenta-1,3-dien-1-yl]-6,7,8a,9-tetrahydro-5h-xanthen-2-ol)

3D SDF for NP0226294 ((8r,8as,10as)-8,10a-dimethyl-8-[(1e)-4-methylpenta-1,3-dien-1-yl]-6,7,8a,9-tetrahydro-5h-xanthen-2-ol)

3D-SDF for NP0226294 ((8r,8as,10as)-8,10a-dimethyl-8-[(1e)-4-methylpenta-1,3-dien-1-yl]-6,7,8a,9-tetrahydro-5h-xanthen-2-ol)

PDB for NP0226294 ((8r,8as,10as)-8,10a-dimethyl-8-[(1e)-4-methylpenta-1,3-dien-1-yl]-6,7,8a,9-tetrahydro-5h-xanthen-2-ol)

3D PDB for NP0226294 ((8r,8as,10as)-8,10a-dimethyl-8-[(1e)-4-methylpenta-1,3-dien-1-yl]-6,7,8a,9-tetrahydro-5h-xanthen-2-ol)

SMILES for NP0226294 ((8r,8as,10as)-8,10a-dimethyl-8-[(1e)-4-methylpenta-1,3-dien-1-yl]-6,7,8a,9-tetrahydro-5h-xanthen-2-ol)

INCHI for NP0226294 ((8r,8as,10as)-8,10a-dimethyl-8-[(1e)-4-methylpenta-1,3-dien-1-yl]-6,7,8a,9-tetrahydro-5h-xanthen-2-ol)

Structure for NP0226294 ((8r,8as,10as)-8,10a-dimethyl-8-[(1e)-4-methylpenta-1,3-dien-1-yl]-6,7,8a,9-tetrahydro-5h-xanthen-2-ol)

3D Structure for NP0226294 ((8r,8as,10as)-8,10a-dimethyl-8-[(1e)-4-methylpenta-1,3-dien-1-yl]-6,7,8a,9-tetrahydro-5h-xanthen-2-ol)