NP-MRD: Showing NP-Card for 11-hydroxyvittatine (NP0286627)

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Record Information

Version

2.0

Created at

2022-09-09 15:16:46 UTC

Updated at

2022-09-09 15:16:46 UTC

NP-MRD ID

NP0286627

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11-hydroxyvittatine

Description

11-Hydroxyvittatine belongs to the class of organic compounds known as crinine- and haemanthamine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds with a structure based on the crinine or haemanthamine backbone. Both backbones have a common 5,10b-ethano bridge moiety in their frameworks, which is a very significant taxonomic feature, and the configurations of the 5,10b-ethano bridge are opposite to each other. 11-hydroxyvittatine is found in Leucojum vernum and Pancratium sickenbergeri. Based on a literature review very few articles have been published on 11-Hydroxyvittatine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 42  0  0  0  0  0  0  0  0999 V2000
   -3.0691    2.7291    0.2925 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1620    1.3594    0.5416 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3139    1.0414    1.6902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2268    0.3253    1.6634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7244   -0.2578    0.4223 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7268   -0.0766    0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5456    0.3864    1.1826 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9231    0.5605    0.9736 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3885    0.2363   -0.2807 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5419   -0.2376   -1.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1985   -0.3984   -1.0542 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2888   -0.9047   -2.1337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0908   -0.7507   -1.7917 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5224   -1.9574   -1.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0957   -1.7384    0.3004 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0207   -2.5394    0.6691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3652    0.2856   -0.8379 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7940    0.6225   -0.7123 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7630    0.4850   -0.2573 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0763    1.2092    0.9175 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9671    1.0022    1.7721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6980    3.2401    0.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2409    1.1536    0.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6538    1.4624    2.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6514    0.1286    2.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2243    0.6542    2.1789 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9509   -0.4780   -2.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5362   -2.0014   -2.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5401   -0.4552   -3.1173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6104   -2.1154   -1.2431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0311   -2.8446   -1.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9813   -1.8830    0.9583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3473   -3.4631    0.7141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7813    1.1903   -1.1820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4051   -0.3063   -0.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1112    1.2171   -1.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1985    2.2702    0.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0274    0.8488    1.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  2  0
 10  9  1  0
  9  8  2  0
  8 21  1  0
 21 20  1  0
 20 19  1  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  1  1
  4  3  2  0
  3  2  1  0
  2  1  1  0
  2 18  1  0
 18 17  1  0
  5 15  1  0
 17  5  1  0
 17 13  1  0
  6 11  1  0
 19  9  1  0
 16 33  1  0
 15 32  1  1
 14 30  1  0
 14 31  1  0
 12 28  1  0
 12 29  1  0
 10 27  1  0
 20 37  1  0
 20 38  1  0
  7 26  1  0
  4 25  1  0
  3 24  1  0
  2 23  1  1
  1 22  1  0
 18 35  1  0
 18 36  1  0
 17 34  1  6
M  END


  Mrv1652309092217162D          

 21 25  0  0  1  0            999 V2000
   -0.2368    1.2219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3182    0.6115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0090   -0.1534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4142   -0.8720    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2287   -1.0032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9418   -0.5038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5788   -0.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2651   -0.3559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2118    0.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5277    0.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7858    0.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1089    0.8466    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8737    1.1561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5241    0.6485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4096   -0.1686    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0600   -0.6762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6449   -0.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9945    0.0296    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9783    0.7725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5053    0.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0646   -0.5596    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
 12 11  1  1  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 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  4  1  6  0  0  0
 12 18  1  0  0  0  0
  9 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  8 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0286627

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1CN2CC3=CC4=C(OCO4)C=C3[C@]11C=C[C@@H](O)C[C@H]21

> <INCHI_IDENTIFIER>
InChI=1S/C16H17NO4/c18-10-1-2-16-11-5-13-12(20-8-21-13)3-9(11)6-17(7-15(16)19)14(16)4-10/h1-3,5,10,14-15,18-19H,4,6-8H2/t10-,14+,15?,16+/m1/s1

> <INCHI_KEY>
KWAOMPWGIIXDPH-UJONCCOVSA-N

> <FORMULA>
C16H17NO4

> <MOLECULAR_WEIGHT>
287.315

> <EXACT_MASS>
287.115758031

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
29.698776294899037

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,13S,15S)-5,7-dioxa-12-azapentacyclo[10.5.2.0^{1,13}.0^{2,10}.0^{4,8}]nonadeca-2,4(8),9,16-tetraene-15,18-diol

> <JCHEM_LOGP>
0.1826226556666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.921831969492814

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.049491816751907

> <JCHEM_PKA_STRONGEST_BASIC>
8.128018362533645

> <JCHEM_POLAR_SURFACE_AREA>
62.16000000000001

> <JCHEM_REFRACTIVITY>
76.3529

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,13S,15S)-5,7-dioxa-12-azapentacyclo[10.5.2.0^{1,13}.0^{2,10}.0^{4,8}]nonadeca-2,4(8),9,16-tetraene-15,18-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  O   UNK     0      -0.442   2.281   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.594   1.141   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.017  -0.286   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       0.773  -1.628   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       2.294  -1.873   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.625  -0.940   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.814  -1.519   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.095  -0.664   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.995   0.872   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.718   1.746   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.334   0.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.070   1.580   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.498   2.158   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.712   1.210   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.498  -0.315   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.712  -1.262   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.070  -0.892   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.856   0.055   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.426   1.442   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.410   0.257   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.587  -1.045   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   18                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   21                                                  
CONECT    9    8   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11    2   13   18                                             
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17    4   12                                                  
CONECT   19    9   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    8                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₇NO₄

Average Mass

287.3150 Da

Monoisotopic Mass

287.11576 Da

IUPAC Name

(1S,13S,15S)-5,7-dioxa-12-azapentacyclo[10.5.2.0^{1,13}.0^{2,10}.0^{4,8}]nonadeca-2,4(8),9,16-tetraene-15,18-diol

Traditional Name

(1S,13S,15S)-5,7-dioxa-12-azapentacyclo[10.5.2.0^{1,13}.0^{2,10}.0^{4,8}]nonadeca-2,4(8),9,16-tetraene-15,18-diol

CAS Registry Number

Not Available

SMILES

OC1CN2CC3=CC4=C(OCO4)C=C3[C@]11C=C[C@@H](O)C[C@H]21

InChI Identifier

InChI=1S/C16H17NO4/c18-10-1-2-16-11-5-13-12(20-8-21-13)3-9(11)6-17(7-15(16)19)14(16)4-10/h1-3,5,10,14-15,18-19H,4,6-8H2/t10-,14+,15?,16+/m1/s1

InChI Key

KWAOMPWGIIXDPH-UJONCCOVSA-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
Leucojum vernum	LOTUS Database	35616633
Pancratium sickenbergeri	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as crinine- and haemanthamine-type amaryllidaceae alkaloids. These are amaryllidaceae alkaloids compounds with a structure based on the crinine or haemanthamine backbone. Both backbones have a common 5,10b-ethano bridge moiety in their frameworks, which is a very significant taxonomic feature, and the configurations of the 5,10b-ethano bridge are opposite to each other.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Amaryllidaceae alkaloids

Sub Class

Crinine- and Haemanthamine-type amaryllidaceae alkaloids

Direct Parent

Crinine- and Haemanthamine-type amaryllidaceae alkaloids

Alternative Parents

Substituents

Hemanthamine/crinine alkaloid skeleton
Benzoquinoline
Phenanthridine
Benzazepine
Quinoline
Tetrahydroisoquinoline
Benzodioxole
Indole or derivatives
Azepine
Aralkylamine
N-alkylpyrrolidine
Benzenoid
Pyrrolidine
Tertiary aliphatic amine
1,2-aminoalcohol
Secondary alcohol
Tertiary amine
Oxacycle
Organoheterocyclic compound
Acetal
Azacycle
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

alkaloid (CHEBI:31052 )

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	0.18	ChemAxon
pKa (Strongest Acidic)	14.05	ChemAxon
pKa (Strongest Basic)	8.13	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.16 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	76.35 m³·mol⁻¹	ChemAxon
Polarizability	29.7 Å³	ChemAxon
Number of Rings	5	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

C00027615

Chemspider ID

391811

KEGG Compound ID

C12194

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

443694

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 11-hydroxyvittatine (NP0286627)

MOL for NP0286627 (11-hydroxyvittatine)

3D MOL for NP0286627 (11-hydroxyvittatine)

3D SDF for NP0286627 (11-hydroxyvittatine)

3D-SDF for NP0286627 (11-hydroxyvittatine)

PDB for NP0286627 (11-hydroxyvittatine)

3D PDB for NP0286627 (11-hydroxyvittatine)

SMILES for NP0286627 (11-hydroxyvittatine)

INCHI for NP0286627 (11-hydroxyvittatine)

Structure for NP0286627 (11-hydroxyvittatine)

3D Structure for NP0286627 (11-hydroxyvittatine)