NP-MRD: Showing NP-Card for (3r,3as,7s,7as)-7-hydroxy-3-[(2s,5s)-5-hydroxy-6-methylhept-6-en-2-yl]-7a-methyl-2,3,6,7-tetrahydro-1h-indene-3a,4-dicarbaldehyde (NP0178114)

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Record Information

Version

2.0

Created at

2022-09-03 16:03:11 UTC

Updated at

2022-09-03 16:03:11 UTC

NP-MRD ID

NP0178114

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,3as,7s,7as)-7-hydroxy-3-[(2s,5s)-5-hydroxy-6-methylhept-6-en-2-yl]-7a-methyl-2,3,6,7-tetrahydro-1h-indene-3a,4-dicarbaldehyde

Description

(3R,3aS,7S,7aS)-7-hydroxy-3-[(2S,5S)-5-hydroxy-6-methylhept-6-en-2-yl]-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-indene-3a,4-dicarbaldehyde belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (3r,3as,7s,7as)-7-hydroxy-3-[(2s,5s)-5-hydroxy-6-methylhept-6-en-2-yl]-7a-methyl-2,3,6,7-tetrahydro-1h-indene-3a,4-dicarbaldehyde is found in Dictyota fasciola. Based on a literature review very few articles have been published on (3R,3aS,7S,7aS)-7-hydroxy-3-[(2S,5S)-5-hydroxy-6-methylhept-6-en-2-yl]-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-indene-3a,4-dicarbaldehyde.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309032218032D          

 24 25  0  0  1  0            999 V2000
    4.8525   -0.8511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5670   -1.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5670   -2.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2815   -0.8511    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2815   -0.0261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9960   -1.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7104   -0.8511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4249   -1.2636    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4249   -2.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1394   -0.8511    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.2256   -0.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0326    0.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4451   -0.5736    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.9300    0.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2521   -0.7451    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.8041   -0.1320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5070   -1.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9550   -2.1428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1480   -1.9713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5960   -2.5844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8509   -3.3690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8930   -1.1867    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2800   -1.7387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7950   -2.4062    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
 10  8  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 19 22  1  0  0  0  0
 10 22  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0178114

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O4/c1-13(2)17(23)7-5-14(3)16-9-10-19(4)18(24)8-6-15(11-21)20(16,19)12-22/h6,11-12,14,16-18,23-24H,1,5,7-10H2,2-4H3/t14-,16+,17-,18-,19+,20+/m0/s1

> <INCHI_KEY>
FGQBUPFFWVREBP-KMHDYSICSA-N

> <FORMULA>
C20H30O4

> <MOLECULAR_WEIGHT>
334.456

> <EXACT_MASS>
334.214409446

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
37.053549065539876

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,3aS,7S,7aS)-7-hydroxy-3-[(2S,5S)-5-hydroxy-6-methylhept-6-en-2-yl]-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-indene-3a,4-dicarbaldehyde

> <JCHEM_LOGP>
2.0446121623333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.996206875569733

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.604262972049256

> <JCHEM_PKA_STRONGEST_BASIC>
-1.4881929006316015

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
94.89369999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3R,3aS,7S,7aS)-7-hydroxy-3-[(2S,5S)-5-hydroxy-6-methylhept-6-en-2-yl]-7a-methyl-2,3,6,7-tetrahydro-1H-indene-3a,4-dicarbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       9.058  -1.589   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.392  -2.359   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.392  -3.899   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.725  -1.589   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      11.725  -0.049   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      13.059  -2.359   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.393  -1.589   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.726  -2.359   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.726  -3.899   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.060  -1.589   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.221  -0.057   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.727   0.263   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      19.497  -1.071   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.403   0.175   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.004  -1.391   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      22.034  -0.246   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      21.480  -2.856   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.449  -4.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.943  -3.680   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.912  -4.824   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      18.388  -6.289   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      18.467  -2.215   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      17.323  -3.246   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      16.417  -4.492   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   22                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   22                                             
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   10   13   23                                             
CONECT   23   22   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₀O₄

Average Mass

334.4560 Da

Monoisotopic Mass

334.21441 Da

IUPAC Name

(3R,3aS,7S,7aS)-7-hydroxy-3-[(2S,5S)-5-hydroxy-6-methylhept-6-en-2-yl]-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-indene-3a,4-dicarbaldehyde

Traditional Name

(3R,3aS,7S,7aS)-7-hydroxy-3-[(2S,5S)-5-hydroxy-6-methylhept-6-en-2-yl]-7a-methyl-2,3,6,7-tetrahydro-1H-indene-3a,4-dicarbaldehyde

CAS Registry Number

Not Available

SMILES

C[C@@H](CC[C@H](O)C(C)=C)[C@H]1CC[C@]2(C)[C@@H](O)CC=C(C=O)[C@]12C=O

InChI Identifier

InChI=1S/C20H30O4/c1-13(2)17(23)7-5-14(3)16-9-10-19(4)18(24)8-6-15(11-21)20(16,19)12-22/h6,11-12,14,16-18,23-24H,1,5,7-10H2,2-4H3/t14-,16+,17-,18-,19+,20+/m0/s1

InChI Key

FGQBUPFFWVREBP-KMHDYSICSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Dictyota fasciola	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Secondary alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic 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	2.04	ChemAxon
pKa (Strongest Acidic)	14.6	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	94.89 m³·mol⁻¹	ChemAxon
Polarizability	37.05 Å³	ChemAxon
Number of Rings	2	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

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

163014303

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r,3as,7s,7as)-7-hydroxy-3-[(2s,5s)-5-hydroxy-6-methylhept-6-en-2-yl]-7a-methyl-2,3,6,7-tetrahydro-1h-indene-3a,4-dicarbaldehyde (NP0178114)

MOL for NP0178114 ((3r,3as,7s,7as)-7-hydroxy-3-[(2s,5s)-5-hydroxy-6-methylhept-6-en-2-yl]-7a-methyl-2,3,6,7-tetrahydro-1h-indene-3a,4-dicarbaldehyde)

3D MOL for NP0178114 ((3r,3as,7s,7as)-7-hydroxy-3-[(2s,5s)-5-hydroxy-6-methylhept-6-en-2-yl]-7a-methyl-2,3,6,7-tetrahydro-1h-indene-3a,4-dicarbaldehyde)

3D SDF for NP0178114 ((3r,3as,7s,7as)-7-hydroxy-3-[(2s,5s)-5-hydroxy-6-methylhept-6-en-2-yl]-7a-methyl-2,3,6,7-tetrahydro-1h-indene-3a,4-dicarbaldehyde)

3D-SDF for NP0178114 ((3r,3as,7s,7as)-7-hydroxy-3-[(2s,5s)-5-hydroxy-6-methylhept-6-en-2-yl]-7a-methyl-2,3,6,7-tetrahydro-1h-indene-3a,4-dicarbaldehyde)

PDB for NP0178114 ((3r,3as,7s,7as)-7-hydroxy-3-[(2s,5s)-5-hydroxy-6-methylhept-6-en-2-yl]-7a-methyl-2,3,6,7-tetrahydro-1h-indene-3a,4-dicarbaldehyde)

3D PDB for NP0178114 ((3r,3as,7s,7as)-7-hydroxy-3-[(2s,5s)-5-hydroxy-6-methylhept-6-en-2-yl]-7a-methyl-2,3,6,7-tetrahydro-1h-indene-3a,4-dicarbaldehyde)

SMILES for NP0178114 ((3r,3as,7s,7as)-7-hydroxy-3-[(2s,5s)-5-hydroxy-6-methylhept-6-en-2-yl]-7a-methyl-2,3,6,7-tetrahydro-1h-indene-3a,4-dicarbaldehyde)

INCHI for NP0178114 ((3r,3as,7s,7as)-7-hydroxy-3-[(2s,5s)-5-hydroxy-6-methylhept-6-en-2-yl]-7a-methyl-2,3,6,7-tetrahydro-1h-indene-3a,4-dicarbaldehyde)

Structure for NP0178114 ((3r,3as,7s,7as)-7-hydroxy-3-[(2s,5s)-5-hydroxy-6-methylhept-6-en-2-yl]-7a-methyl-2,3,6,7-tetrahydro-1h-indene-3a,4-dicarbaldehyde)

3D Structure for NP0178114 ((3r,3as,7s,7as)-7-hydroxy-3-[(2s,5s)-5-hydroxy-6-methylhept-6-en-2-yl]-7a-methyl-2,3,6,7-tetrahydro-1h-indene-3a,4-dicarbaldehyde)