NP-MRD: Showing NP-Card for (1s,3s,3's,4s,4's,6's)-3',4,9-trihydroxy-4'-(methoxycarbonyl)-6'-methyl-5,10-dioxo-3,4-dihydrospiro[naphtho[2,3-c]pyran-1,2'-oxan]-3-ylacetic acid (NP0214502)

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Record Information

Version

2.0

Created at

2022-09-05 13:49:00 UTC

Updated at

2022-09-05 13:49:00 UTC

NP-MRD ID

NP0214502

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3s,3's,4s,4's,6's)-3',4,9-trihydroxy-4'-(methoxycarbonyl)-6'-methyl-5,10-dioxo-3,4-dihydrospiro[naphtho[2,3-c]pyran-1,2'-oxan]-3-ylacetic acid

Description

2-[(1S,3S,3'S,4S,4'S,6'S)-3',4,9-trihydroxy-4'-(methoxycarbonyl)-6'-methyl-5,10-dioxo-3,4,5,10-tetrahydrospiro[naphtho[2,3-c]pyran-1,2'-oxane]-3-yl]acetic acid belongs to the class of organic compounds known as benzoisochromanequinones. These are benzo derivatives of isochromanequinones. Isochromanequinones are structurally characterized by a quinone fused to an isochromane, and forming a naphtho[2,3-c]pyran-6,9-dione skeleton. Based on a literature review very few articles have been published on 2-[(1S,3S,3'S,4S,4'S,6'S)-3',4,9-trihydroxy-4'-(methoxycarbonyl)-6'-methyl-5,10-dioxo-3,4,5,10-tetrahydrospiro[naphtho[2,3-c]pyran-1,2'-oxane]-3-yl]acetic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052215492D          

 33 36  0  0  1  0            999 V2000
    6.9020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1895   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    2.5559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0145    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    2.5559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3645    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8395    1.8414    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  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 10 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
 19 30  1  0  0  0  0
 30 31  2  0  0  0  0
 10 32  1  0  0  0  0
  5 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END

     RDKit          3D

 55 58  0  0  0  0  0  0  0  0999 V2000
   -5.6155   -0.4164    2.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4325   -0.9700    1.8222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4060   -0.1475    1.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5799    1.0820    1.5041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1601   -0.7316    0.7570 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5703   -1.4902   -0.4446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9828   -0.8597   -1.6578 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1941   -1.8411   -2.8192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6387   -0.6260   -1.5768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2524    0.2852   -0.6133 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4160    1.5221   -1.1892 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6618    2.2935   -1.3651 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2821    3.7207   -1.6090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4874    4.3513   -0.5156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7595    4.2374   -0.5036 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0707    5.0755    0.5255 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6846    2.2457   -0.2641 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2695    2.7732    0.9218 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0661    0.8066   -0.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1339   -0.0848   -0.2883 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4916   -1.5173   -0.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5642   -2.3107   -0.3408 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8535   -1.9406    0.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1833   -3.2701    0.3071 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2704   -4.2658    0.1293 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5157   -3.6140    0.6317 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4373   -2.6403    0.8122 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1447   -1.3028    0.6952 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8308   -0.9725    0.3755 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4308    0.4217    0.2307 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3168    1.3074    0.4060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0795    0.2604    0.6402 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6093    1.5213    0.9117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2348   -1.2982    2.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1609    0.2150    1.6543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3971    0.1939    3.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8823   -1.5363    1.5259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6908   -1.4360   -0.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3724   -2.5795   -0.3660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5670    0.0479   -1.9176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2546   -2.0523   -2.9831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6417   -1.5210   -3.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7164   -2.8194   -2.5178 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1748    1.9580   -2.3183 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2421    4.3084   -1.7202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3111    3.8325   -2.5684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3336    4.9538    1.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5968    2.7718   -0.6070 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7359    2.3866    1.7041 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3413   -4.2051   -0.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7053   -4.6728    0.7143 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4520   -2.9175    1.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8907   -0.5230    0.8416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3763    0.0749    1.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2236    1.9162    1.7071 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
 10  9  1  6
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 16  1  0
 14 15  2  0
 12 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 10 32  1  0
 32 33  1  0
 32  5  1  0
 20 10  1  0
 29 23  1  0
 30 19  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  5 37  1  1
  6 38  1  0
  6 39  1  0
  7 40  1  6
  8 41  1  0
  8 42  1  0
  8 43  1  0
 12 44  1  6
 13 45  1  0
 13 46  1  0
 16 47  1  0
 17 48  1  6
 18 49  1  0
 25 50  1  0
 26 51  1  0
 27 52  1  0
 28 53  1  0
 32 54  1  1
 33 55  1  0
M  END


  Mrv1652309052215492D          

 33 36  0  0  1  0            999 V2000
    6.9020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1895   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    2.5559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0145    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    4.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    2.5559    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3645    3.2704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8395    1.8414    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  2  0  0  0  0
  5  3  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 10 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
 19 30  1  0  0  0  0
 30 31  2  0  0  0  0
 10 32  1  0  0  0  0
  5 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0214502

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@H]1C[C@H](C)O[C@@]2(O[C@@H](CC(O)=O)[C@@H](O)C3=C2C(=O)C2=C(O)C=CC=C2C3=O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O11/c1-8-6-10(21(30)31-2)20(29)22(32-8)16-15(18(27)12(33-22)7-13(24)25)17(26)9-4-3-5-11(23)14(9)19(16)28/h3-5,8,10,12,18,20,23,27,29H,6-7H2,1-2H3,(H,24,25)/t8-,10-,12-,18+,20-,22-/m0/s1

> <INCHI_KEY>
SEYSFNKYJDJWGS-VYTCDMPXSA-N

> <FORMULA>
C22H22O11

> <MOLECULAR_WEIGHT>
462.407

> <EXACT_MASS>
462.116211528

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
43.61598177138441

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1S,3S,3'S,4S,4'S,6'S)-3',4,9-trihydroxy-4'-(methoxycarbonyl)-6'-methyl-5,10-dioxo-3,4,5,10-tetrahydrospiro[naphtho[2,3-c]pyran-1,2'-oxane]-3-yl]acetic acid

> <JCHEM_LOGP>
0.606236150000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.176261319962972

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4212962445983646

> <JCHEM_PKA_STRONGEST_BASIC>
-3.543938061054802

> <JCHEM_POLAR_SURFACE_AREA>
176.89

> <JCHEM_REFRACTIVITY>
108.00029999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,3'S,4S,4'S,6'S)-3',4,9-trihydroxy-4'-(methoxycarbonyl)-6'-methyl-5,10-dioxo-3,4-dihydrospiro[naphtho[2,3-c]pyran-1,2'-oxane]-3-ylacetic acid

> <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      12.884  -0.564   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      11.344  -0.564   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      10.574   0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      11.344   2.104   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.264  -0.564   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.954  -1.897   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.954   0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.494   3.437   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.724   4.771   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.494   6.105   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.724   7.438   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.184   7.438   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       7.494   8.772   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.184   4.771   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.414   6.105   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.184  -0.564   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.874  -1.897   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.104   4.771   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       8.264   2.104   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       9.034   3.437   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   32                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   20   32                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   12   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   30                                                  
CONECT   20   19   10   21                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   29                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   23   30                                                  
CONECT   30   29   19   31                                                  
CONECT   31   30                                                            
CONECT   32   10    5   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
2-[(1S,3S,3's,4S,4's,6's)-3',4,9-Trihydroxy-4'-(methoxycarbonyl)-6'-methyl-5,10-dioxo-3,4,5,10-tetrahydrospiro[naphtho[2,3-c]pyran-1,2'-oxane]-3-yl]acetate	Generator

Chemical Formula

C₂₂H₂₂O₁₁

Average Mass

462.4070 Da

Monoisotopic Mass

462.11621 Da

IUPAC Name

2-[(1S,3S,3'S,4S,4'S,6'S)-3',4,9-trihydroxy-4'-(methoxycarbonyl)-6'-methyl-5,10-dioxo-3,4,5,10-tetrahydrospiro[naphtho[2,3-c]pyran-1,2'-oxane]-3-yl]acetic acid

Traditional Name

(1S,3S,3'S,4S,4'S,6'S)-3',4,9-trihydroxy-4'-(methoxycarbonyl)-6'-methyl-5,10-dioxo-3,4-dihydrospiro[naphtho[2,3-c]pyran-1,2'-oxane]-3-ylacetic acid

CAS Registry Number

Not Available

SMILES

COC(=O)[C@H]1C[C@H](C)O[C@@]2(O[C@@H](CC(O)=O)[C@@H](O)C3=C2C(=O)C2=C(O)C=CC=C2C3=O)[C@H]1O

InChI Identifier

InChI=1S/C22H22O11/c1-8-6-10(21(30)31-2)20(29)22(32-8)16-15(18(27)12(33-22)7-13(24)25)17(26)9-4-3-5-11(23)14(9)19(16)28/h3-5,8,10,12,18,20,23,27,29H,6-7H2,1-2H3,(H,24,25)/t8-,10-,12-,18+,20-,22-/m0/s1

InChI Key

SEYSFNKYJDJWGS-VYTCDMPXSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoisochromanequinones. These are benzo derivatives of isochromanequinones. Isochromanequinones are structurally characterized by a quinone fused to an isochromane, and forming a naphtho[2,3-c]pyran-6,9-dione skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isochromanequinones

Sub Class

Benzoisochromanequinones

Direct Parent

Benzoisochromanequinones

Alternative Parents

Substituents

Benzoisochromanequinone
Naphthopyranone
Naphthopyran
Naphthoquinone
Naphthalene
Aryl ketone
Quinone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Ketal
Beta-hydroxy acid
Pyranone
Dicarboxylic acid or derivatives
Hydroxy acid
Oxane
Benzenoid
Pyran
Methyl ester
Vinylogous acid
Secondary alcohol
Carboxylic acid ester
Ketone
Polyol
Carboxylic acid derivative
Organoheterocyclic compound
Carboxylic acid
Acetal
Oxacycle
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
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	0.61	ChemAxon
pKa (Strongest Acidic)	3.42	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	176.89 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	108 m³·mol⁻¹	ChemAxon
Polarizability	43.62 Å³	ChemAxon
Number of Rings	4	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

59702143

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162820932

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3s,3's,4s,4's,6's)-3',4,9-trihydroxy-4'-(methoxycarbonyl)-6'-methyl-5,10-dioxo-3,4-dihydrospiro[naphtho[2,3-c]pyran-1,2'-oxan]-3-ylacetic acid (NP0214502)

MOL for NP0214502 ((1s,3s,3's,4s,4's,6's)-3',4,9-trihydroxy-4'-(methoxycarbonyl)-6'-methyl-5,10-dioxo-3,4-dihydrospiro[naphtho[2,3-c]pyran-1,2'-oxan]-3-ylacetic acid)

3D MOL for NP0214502 ((1s,3s,3's,4s,4's,6's)-3',4,9-trihydroxy-4'-(methoxycarbonyl)-6'-methyl-5,10-dioxo-3,4-dihydrospiro[naphtho[2,3-c]pyran-1,2'-oxan]-3-ylacetic acid)

3D SDF for NP0214502 ((1s,3s,3's,4s,4's,6's)-3',4,9-trihydroxy-4'-(methoxycarbonyl)-6'-methyl-5,10-dioxo-3,4-dihydrospiro[naphtho[2,3-c]pyran-1,2'-oxan]-3-ylacetic acid)

3D-SDF for NP0214502 ((1s,3s,3's,4s,4's,6's)-3',4,9-trihydroxy-4'-(methoxycarbonyl)-6'-methyl-5,10-dioxo-3,4-dihydrospiro[naphtho[2,3-c]pyran-1,2'-oxan]-3-ylacetic acid)

PDB for NP0214502 ((1s,3s,3's,4s,4's,6's)-3',4,9-trihydroxy-4'-(methoxycarbonyl)-6'-methyl-5,10-dioxo-3,4-dihydrospiro[naphtho[2,3-c]pyran-1,2'-oxan]-3-ylacetic acid)

3D PDB for NP0214502 ((1s,3s,3's,4s,4's,6's)-3',4,9-trihydroxy-4'-(methoxycarbonyl)-6'-methyl-5,10-dioxo-3,4-dihydrospiro[naphtho[2,3-c]pyran-1,2'-oxan]-3-ylacetic acid)

SMILES for NP0214502 ((1s,3s,3's,4s,4's,6's)-3',4,9-trihydroxy-4'-(methoxycarbonyl)-6'-methyl-5,10-dioxo-3,4-dihydrospiro[naphtho[2,3-c]pyran-1,2'-oxan]-3-ylacetic acid)

INCHI for NP0214502 ((1s,3s,3's,4s,4's,6's)-3',4,9-trihydroxy-4'-(methoxycarbonyl)-6'-methyl-5,10-dioxo-3,4-dihydrospiro[naphtho[2,3-c]pyran-1,2'-oxan]-3-ylacetic acid)

Structure for NP0214502 ((1s,3s,3's,4s,4's,6's)-3',4,9-trihydroxy-4'-(methoxycarbonyl)-6'-methyl-5,10-dioxo-3,4-dihydrospiro[naphtho[2,3-c]pyran-1,2'-oxan]-3-ylacetic acid)

3D Structure for NP0214502 ((1s,3s,3's,4s,4's,6's)-3',4,9-trihydroxy-4'-(methoxycarbonyl)-6'-methyl-5,10-dioxo-3,4-dihydrospiro[naphtho[2,3-c]pyran-1,2'-oxan]-3-ylacetic acid)