NP-MRD: Showing NP-Card for (4as,5r,6s)-5-ethenyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-1-one (NP0220428)

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Record Information

Version

2.0

Created at

2022-09-05 21:44:08 UTC

Updated at

2022-09-05 21:44:08 UTC

NP-MRD ID

NP0220428

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4as,5r,6s)-5-ethenyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-1-one

Description

NSC606404 belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. (4as,5r,6s)-5-ethenyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-1-one is found in Amsonia orientalis, Anthocleista grandiflora, Anthocleista nobilis, Anthocleista vogelii, Bhesa paniculata, Calycophyllum spruceanum, Centaurium erythraea, Carapichea ipecacuanha, Chimarrhis turbinata, Chione venosa, Chironia baccifera, Citronella gongonha, Curtia tenuifolia, Desfontainia spinosa, Dipsacus asperoides, Dipsacus laciniatus, Eucnide bartonioides, Fagraea fragrans, Fagraea gracilipes, Gentiana algida, Gentiana lutea, Gentiana macrophylla, Gentiana olivieri, Gentiana punctata, Gentiana scabra, Gentiana septemfida, Gentiana sino-ornata, Gentiana siphonantha, Gentiana thunbergii, Gentiana tibetica, Gentiana verna, Guettarda platypoda, Hydrangea chinensis, Hydrangea macrophylla, Chelonanthus alatus, Lonicera angustifolia, Lonicera caerulea, Lonicera japonica, Lonicera quinquelocularis, Mentzelia decapetala, Nasa ranunculifolia, Nyssa ogeche, Ophiorrhiza japonica, Ophiorrhiza liukiuensis, Potalia amara, Sinoadina racemosa, Strychnos axillaris, Strychnos lucida, Strychnos spinosa, Swertia calycina, Swertia chirayita, Swertia franchetiana, Swertia japonica, Tabernaemontana cymosa, Triplostegia grandiflora, Tripterospermum japonicum and Tripterospermum lanceolatum. Based on a literature review very few articles have been published on NSC606404.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052223442D          

 25 27  0  0  1  0            999 V2000
    2.1434   -2.8875    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  1  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -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  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  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
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 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
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 24  1  1  0  0  0
 19 25  1  0  0  0  0
  3 25  1  0  0  0  0
M  END

     RDKit          3D

 47 49  0  0  0  0  0  0  0  0999 V2000
   -1.5462    1.7432    1.8871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7945    0.6640    1.1786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6886    0.6984   -0.2965 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6608   -0.3229   -0.7298 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6445    0.0480   -0.4246 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3498   -0.8894    0.3188 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3527   -1.5017   -0.3549 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4875   -0.7505   -0.4302 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3087    0.5300   -1.1823 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5461    1.2092   -1.2200 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1461   -0.5306    0.9084 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7075    0.7453    0.8914 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1823   -0.6679    2.0510 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5977    0.1844    3.0692 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7542   -0.4187    1.6574 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5746    0.9783    1.8307 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6986   -0.2974   -2.1724 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9048   -0.6948   -2.7335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0228   -0.3618   -2.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3182   -0.7462   -2.6507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3967   -1.1105   -3.8686 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4396   -0.7061   -1.8083 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3917   -0.0953   -0.5411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9909   -0.2927    0.0586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0312    0.4187   -0.8760 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6088    1.7762    2.9698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2551    2.6785    1.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0688   -0.2510    1.6671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3390    1.7352   -0.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9414   -1.2951   -0.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5625   -1.7191    0.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2231   -1.3584   -1.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9833    0.3598   -2.2164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5817    1.1957   -0.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4474    1.8767   -1.9522 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9799   -1.2505    1.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6302    0.7583    1.2576 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534   -1.7009    2.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8018   -0.2989    3.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0528   -0.8530    2.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7537    1.1502    2.7888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8956   -1.2719   -3.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5123    0.9990   -0.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1464   -0.5046    0.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9657    0.0930    1.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8044   -1.3831    0.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4992    1.4304   -1.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4 17  1  0
 17 18  1  0
 18 19  2  0
 19 25  1  0
 25 24  1  0
 24 23  1  0
 23 22  1  0
 22 20  1  0
 20 21  2  0
 25  3  1  0
  3  2  1  0
  2  1  2  3
  6 15  1  0
 15 16  1  0
 15 13  1  0
 13 14  1  0
 13 11  1  0
 11 12  1  0
 11  8  1  0
  3  4  1  0
 20 19  1  0
 10 35  1  0
  9 33  1  0
  9 34  1  0
  8 32  1  6
  6 31  1  1
  4 30  1  1
 18 42  1  0
 25 47  1  6
 24 45  1  0
 24 46  1  0
 23 43  1  0
 23 44  1  0
  3 29  1  1
  2 28  1  0
  1 26  1  0
  1 27  1  0
 15 40  1  1
 16 41  1  0
 13 38  1  1
 14 39  1  0
 11 36  1  1
 12 37  1  0
M  END


  Mrv1652309052223442D          

 25 27  0  0  1  0            999 V2000
    2.1434   -2.8875    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  1  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -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  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  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
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 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
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 24  1  1  0  0  0
 19 25  1  0  0  0  0
  3 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0220428

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(O[C@@H]2OC=C3[C@@H](CCOC3=O)[C@H]2C=C)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H22O9/c1-2-7-8-3-4-22-14(21)9(8)6-23-15(7)25-16-13(20)12(19)11(18)10(5-17)24-16/h2,6-8,10-13,15-20H,1,3-5H2/t7-,8+,10?,11?,12?,13?,15+,16?/m1/s1

> <INCHI_KEY>
VSJGJMKGNMDJCI-FGNDQDIWSA-N

> <FORMULA>
C16H22O9

> <MOLECULAR_WEIGHT>
358.343

> <EXACT_MASS>
358.126382288

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
34.404326674854

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4aS,5R,6S)-5-ethenyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,3H,4H,4aH,5H,6H-pyrano[3,4-c]pyran-1-one

> <JCHEM_LOGP>
-1.129194730333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.198719032317623

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.20701619363978

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810847615592513

> <JCHEM_POLAR_SURFACE_AREA>
134.91

> <JCHEM_REFRACTIVITY>
81.44799999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4aS,5R,6S)-5-ethenyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3H,4H,4aH,5H,6H-pyrano[3,4-c]pyran-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   25                                                  
CONECT    4    3    5   17                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    6   16                                                  
CONECT   16   15                                                            
CONECT   17    4   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   25                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   19    3                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₂O₉

Average Mass

358.3430 Da

Monoisotopic Mass

358.12638 Da

IUPAC Name

(4aS,5R,6S)-5-ethenyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,3H,4H,4aH,5H,6H-pyrano[3,4-c]pyran-1-one

Traditional Name

(4aS,5R,6S)-5-ethenyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3H,4H,4aH,5H,6H-pyrano[3,4-c]pyran-1-one

CAS Registry Number

Not Available

SMILES

OCC1OC(O[C@@H]2OC=C3[C@@H](CCOC3=O)[C@H]2C=C)C(O)C(O)C1O

InChI Identifier

InChI=1S/C16H22O9/c1-2-7-8-3-4-22-14(21)9(8)6-23-15(7)25-16-13(20)12(19)11(18)10(5-17)24-16/h2,6-8,10-13,15-20H,1,3-5H2/t7-,8+,10?,11?,12?,13?,15+,16?/m1/s1

InChI Key

VSJGJMKGNMDJCI-FGNDQDIWSA-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
Amsonia orientalis	LOTUS Database	35616633
Anthocleista grandiflora	LOTUS Database	35616633
Anthocleista nobilis	LOTUS Database	35616633
Anthocleista vogelii	LOTUS Database	35616633
Bhesa paniculata	LOTUS Database	35616633
Calycophyllum spruceanum	LOTUS Database	35616633
Centaurium erythraea	LOTUS Database	35616633
Cephaelis ipecacuanha	LOTUS Database	35616633
Chimarrhis turbinata	LOTUS Database	35616633
Chione venosa	LOTUS Database	35616633
Chironia baccifera	LOTUS Database	35616633
Citronella gongonha	LOTUS Database	35616633
Curtia tenuifolia	LOTUS Database	35616633
Desfontainia spinosa	LOTUS Database	35616633
Dipsacus asperoides	LOTUS Database	35616633
Dipsacus laciniatus	LOTUS Database	35616633
Eucnide bartonioides	LOTUS Database	35616633
Fagraea fragrans	LOTUS Database	35616633
Fagraea gracilipes	LOTUS Database	35616633
Gentiana algida	LOTUS Database	35616633
Gentiana lutea	LOTUS Database	35616633
Gentiana macrophylla	LOTUS Database	35616633
Gentiana olivieri	LOTUS Database	35616633
Gentiana punctata	LOTUS Database	35616633
Gentiana scabra	LOTUS Database	35616633
Gentiana septemfida	LOTUS Database	35616633
Gentiana sino-ornata	LOTUS Database	35616633
Gentiana siphonantha	LOTUS Database	35616633
Gentiana thunbergii	LOTUS Database	35616633
Gentiana tibetica	LOTUS Database	35616633
Gentiana verna	LOTUS Database	35616633
Guettarda platypoda	LOTUS Database	35616633
Hydrangea chinensis	LOTUS Database	35616633
Hydrangea macrophylla	LOTUS Database	35616633
Irlbachia alata	LOTUS Database	35616633
Lonicera angustifolia	LOTUS Database	35616633
Lonicera caerulea	LOTUS Database	35616633
Lonicera japonica	LOTUS Database	35616633
Lonicera quinquelocularis	LOTUS Database	35616633
Mentzelia decapetala	LOTUS Database	35616633
Nasa ranunculifolia	LOTUS Database	35616633
Nyssa ogeche	LOTUS Database	35616633
Ophiorrhiza japonica	LOTUS Database	35616633
Ophiorrhiza liukiuensis	LOTUS Database	35616633
Potalia amara	LOTUS Database	35616633
Sinoadina racemosa	LOTUS Database	35616633
Strychnos axillaris	LOTUS Database	35616633
Strychnos lucida	LOTUS Database	35616633
Strychnos spinosa	LOTUS Database	35616633
Swertia calycina	LOTUS Database	35616633
Swertia chirata	LOTUS Database	35616633
Swertia franchetiana	LOTUS Database	35616633
Swertia japonica	LOTUS Database	35616633
Tabernaemontana cymosa	LOTUS Database	35616633
Triplostegia grandiflora	LOTUS Database	35616633
Tripterospermum japonicum	LOTUS Database	35616633
Tripterospermum lanceolatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

Hexose monosaccharide
O-glycosyl compound
Delta valerolactone
Delta_valerolactone
Oxane
Monosaccharide
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Carboxylic acid ester
Lactone
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Polyol
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxide
Alcohol
Primary alcohol
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	-1.1	ChemAxon
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	134.91 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	81.45 m³·mol⁻¹	ChemAxon
Polarizability	34.4 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

314630

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

354447

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4as,5r,6s)-5-ethenyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-1-one (NP0220428)

MOL for NP0220428 ((4as,5r,6s)-5-ethenyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-1-one)

3D MOL for NP0220428 ((4as,5r,6s)-5-ethenyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-1-one)

3D SDF for NP0220428 ((4as,5r,6s)-5-ethenyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-1-one)

3D-SDF for NP0220428 ((4as,5r,6s)-5-ethenyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-1-one)

PDB for NP0220428 ((4as,5r,6s)-5-ethenyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-1-one)

3D PDB for NP0220428 ((4as,5r,6s)-5-ethenyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-1-one)

SMILES for NP0220428 ((4as,5r,6s)-5-ethenyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-1-one)

INCHI for NP0220428 ((4as,5r,6s)-5-ethenyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-1-one)

Structure for NP0220428 ((4as,5r,6s)-5-ethenyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-1-one)

3D Structure for NP0220428 ((4as,5r,6s)-5-ethenyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-1-one)