NP-MRD: Showing NP-Card for (2s)-2,9-dihydroxy-3,3-dimethyl-1h,2h,11h-pyrano[3,2-a]carbazole-5-carbaldehyde (NP0306900)

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Record Information

Version

2.0

Created at

2022-09-10 23:40:04 UTC

Updated at

2022-09-10 23:40:04 UTC

NP-MRD ID

NP0306900

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2,9-dihydroxy-3,3-dimethyl-1h,2h,11h-pyrano[3,2-a]carbazole-5-carbaldehyde

Description

2Alpha,9-Dihydroxy-3,3-dimethyl-1,2,3,11-tetrahydropyrano[3,2-a]carbazole-5-carbaldehyde belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring. (2s)-2,9-dihydroxy-3,3-dimethyl-1h,2h,11h-pyrano[3,2-a]carbazole-5-carbaldehyde is found in Clausena excavata. Based on a literature review very few articles have been published on 2alpha,9-Dihydroxy-3,3-dimethyl-1,2,3,11-tetrahydropyrano[3,2-a]carbazole-5-carbaldehyde.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 43  0  0  0  0  0  0  0  0999 V2000
   -3.5205   -0.2898   -1.2356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3015   -0.3368    0.2729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6356   -0.4444    0.9553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5987    0.8373    0.6142 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2153    0.8763    0.4478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5273    2.0805    0.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2925    3.2599    1.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7683    4.3752    1.2456 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8373    2.1208    0.4911 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5486    0.9803    0.1222 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8529   -0.1880   -0.0748 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7569   -1.1485   -0.4242 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9942   -0.6022   -0.4479 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2191   -1.1659   -0.7412 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3542   -0.3715   -0.6913 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5664   -0.9699   -0.9915 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2273    0.9575   -0.3506 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0015    1.5347   -0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8858    0.7283   -0.1092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5304   -0.2601    0.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2258   -1.5785   -0.1512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4827   -1.5498    0.6636 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2459   -2.6886    0.5551 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5129    0.1450   -1.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7663    0.3929   -1.7129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4081   -1.2835   -1.6990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4905   -0.5879    2.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2765    0.4452    0.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1494   -1.3323    0.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3652    3.2002    1.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3958    3.0410    0.6449 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4838   -2.1372   -0.6310 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3100   -2.2192   -1.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1652   -1.4103   -0.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1103    1.5833   -0.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9333    2.5814    0.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5472   -2.3858    0.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4168   -1.6449   -1.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1959   -1.4081    1.7304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1692   -3.1362   -0.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 20 11  1  0
 11 10  2  0
 10  9  1  0
  9  6  2  0
  6  7  1  0
  7  8  2  0
 10 19  1  0
 19 13  2  0
 13 12  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 22  2  1  0
 12 11  1  0
  6  5  1  0
 18 19  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
 21 37  1  0
 21 38  1  0
 22 39  1  1
 23 40  1  0
  9 31  1  0
  7 30  1  0
 12 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
M  END


  Mrv1652309112201402D          

 23 26  0  0  1  0            999 V2000
    1.2520   -3.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8527   -2.6877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1914   -2.1944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3053   -3.3775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1290   -3.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5816   -4.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2106   -4.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6633   -5.4467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4053   -3.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7763   -3.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3236   -2.5463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8397   -1.9027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6113   -2.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3446   -1.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0387   -2.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7719   -1.8844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9995   -3.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2662   -3.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5721   -3.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5000   -2.5934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0473   -1.9037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2237   -1.9509    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7710   -1.2611    0.0000 O   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
  2  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
  7  8  2  0  0  0  0
  6  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  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  2  0  0  0  0
 18 19  1  0  0  0  0
 13 19  2  0  0  0  0
 10 19  1  0  0  0  0
 11 20  1  0  0  0  0
  5 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  2 22  1  0  0  0  0
 22 23  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0306900

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)OC2=C(C[C@@H]1O)C1=C(C=C2C=O)C2=C(N1)C=C(O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C18H17NO4/c1-18(2)15(22)7-13-16-12(5-9(8-20)17(13)23-18)11-4-3-10(21)6-14(11)19-16/h3-6,8,15,19,21-22H,7H2,1-2H3/t15-/m0/s1

> <INCHI_KEY>
WTDDDTFFPLONHZ-HNNXBMFYSA-N

> <FORMULA>
C18H17NO4

> <MOLECULAR_WEIGHT>
311.337

> <EXACT_MASS>
311.115758031

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
33.56865648781308

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2,9-dihydroxy-3,3-dimethyl-1H,2H,3H,11H-pyrano[3,2-a]carbazole-5-carbaldehyde

> <JCHEM_LOGP>
2.4488567040000007

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.781649604640805

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.588796039255069

> <JCHEM_PKA_STRONGEST_BASIC>
-3.332452063337147

> <JCHEM_POLAR_SURFACE_AREA>
82.55000000000001

> <JCHEM_REFRACTIVITY>
86.82939999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2,9-dihydroxy-3,3-dimethyl-1H,2H,11H-pyrano[3,2-a]carbazole-5-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       2.337  -6.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.458  -5.017   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.224  -4.096   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.303  -6.305   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.841  -6.217   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.686  -7.504   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.993  -8.880   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.838 -10.167   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.223  -7.416   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.916  -6.041   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.071  -4.753   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       9.034  -3.552   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      10.475  -4.097   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.843  -3.391   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.139  -4.223   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      14.508  -3.518   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      13.066  -5.762   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.697  -6.467   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.401  -5.635   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.533  -4.841   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.688  -3.554   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.151  -3.642   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.306  -2.354   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   22                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   20                                                  
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12   20                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   13   10                                                  
CONECT   20   11    5   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21    2   23                                                  
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Value	Source
2a,9-Dihydroxy-3,3-dimethyl-1,2,3,11-tetrahydropyrano[3,2-a]carbazole-5-carbaldehyde	Generator
2Α,9-dihydroxy-3,3-dimethyl-1,2,3,11-tetrahydropyrano[3,2-a]carbazole-5-carbaldehyde	Generator

Chemical Formula

C₁₈H₁₇NO₄

Average Mass

311.3370 Da

Monoisotopic Mass

311.11576 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1(C)OC2=C(C[C@@H]1O)C1=C(C=C2C=O)C2=C(N1)C=C(O)C=C2

InChI Identifier

InChI=1S/C18H17NO4/c1-18(2)15(22)7-13-16-12(5-9(8-20)17(13)23-18)11-4-3-10(21)6-14(11)19-16/h3-6,8,15,19,21-22H,7H2,1-2H3/t15-/m0/s1

InChI Key

WTDDDTFFPLONHZ-HNNXBMFYSA-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
Clausena excavata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

Carbazoles

Alternative Parents

Substituents

Carbazole
2,2-dimethyl-1-benzopyran
Chromane
Benzopyran
Hydroxyindole
1-benzopyran
Indole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aryl-aldehyde
Benzenoid
Heteroaromatic compound
Pyrrole
Secondary alcohol
Azacycle
Oxacycle
Ether
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Aldehyde
Alcohol
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

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

101705068

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2,9-dihydroxy-3,3-dimethyl-1h,2h,11h-pyrano[3,2-a]carbazole-5-carbaldehyde (NP0306900)

MOL for NP0306900 ((2s)-2,9-dihydroxy-3,3-dimethyl-1h,2h,11h-pyrano[3,2-a]carbazole-5-carbaldehyde)

3D MOL for NP0306900 ((2s)-2,9-dihydroxy-3,3-dimethyl-1h,2h,11h-pyrano[3,2-a]carbazole-5-carbaldehyde)

3D SDF for NP0306900 ((2s)-2,9-dihydroxy-3,3-dimethyl-1h,2h,11h-pyrano[3,2-a]carbazole-5-carbaldehyde)

3D-SDF for NP0306900 ((2s)-2,9-dihydroxy-3,3-dimethyl-1h,2h,11h-pyrano[3,2-a]carbazole-5-carbaldehyde)

PDB for NP0306900 ((2s)-2,9-dihydroxy-3,3-dimethyl-1h,2h,11h-pyrano[3,2-a]carbazole-5-carbaldehyde)

3D PDB for NP0306900 ((2s)-2,9-dihydroxy-3,3-dimethyl-1h,2h,11h-pyrano[3,2-a]carbazole-5-carbaldehyde)

SMILES for NP0306900 ((2s)-2,9-dihydroxy-3,3-dimethyl-1h,2h,11h-pyrano[3,2-a]carbazole-5-carbaldehyde)

INCHI for NP0306900 ((2s)-2,9-dihydroxy-3,3-dimethyl-1h,2h,11h-pyrano[3,2-a]carbazole-5-carbaldehyde)

Structure for NP0306900 ((2s)-2,9-dihydroxy-3,3-dimethyl-1h,2h,11h-pyrano[3,2-a]carbazole-5-carbaldehyde)

3D Structure for NP0306900 ((2s)-2,9-dihydroxy-3,3-dimethyl-1h,2h,11h-pyrano[3,2-a]carbazole-5-carbaldehyde)