NP-MRD: Showing NP-Card for (4s,6r,6as,9r,10s,10ar)-6-(acetyloxy)-6a,9,10-trihydroxy-3-(methoxymethyl)-6,9-dimethyl-2-oxo-4h,5h,7h,8h,10h-naphtho[4a,4-b]furan-4-yl acetate (NP0303387)

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Record Information

Version

2.0

Created at

2022-09-10 17:42:01 UTC

Updated at

2022-09-10 17:42:01 UTC

NP-MRD ID

NP0303387

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4s,6r,6as,9r,10s,10ar)-6-(acetyloxy)-6a,9,10-trihydroxy-3-(methoxymethyl)-6,9-dimethyl-2-oxo-4h,5h,7h,8h,10h-naphtho[4a,4-b]furan-4-yl acetate

Description

(4S,6R,6aS,9R,10S,10aR)-4-(acetyloxy)-6a,9,10-trihydroxy-3-(methoxymethyl)-6,9-dimethyl-2-oxo-2H,4H,5H,6H,6aH,7H,8H,9H,10H-naphtho[4a,4-b]furan-6-yl acetate belongs to the class of organic compounds known as cadinanolides. These are sesquiterpene lactones based on 2-dioxonaphtho[4a,4-b]furan. (4s,6r,6as,9r,10s,10ar)-6-(acetyloxy)-6a,9,10-trihydroxy-3-(methoxymethyl)-6,9-dimethyl-2-oxo-4h,5h,7h,8h,10h-naphtho[4a,4-b]furan-4-yl acetate is found in Pseudelephantopus spicatus. Based on a literature review very few articles have been published on (4S,6R,6aS,9R,10S,10aR)-4-(acetyloxy)-6a,9,10-trihydroxy-3-(methoxymethyl)-6,9-dimethyl-2-oxo-2H,4H,5H,6H,6aH,7H,8H,9H,10H-naphtho[4a,4-b]furan-6-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102219422D          

 30 32  0  0  1  0            999 V2000
    0.0022   -3.2237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5600   -2.6159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3126   -1.8288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8704   -1.2210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7066   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0039    0.0068    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7223   -0.3988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4328    0.0204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1511   -0.3852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4249    0.8454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0040    0.8318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7223    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2586    1.8644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1981    1.8745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4876    2.6470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0366    3.2840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3014    2.7825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4328    0.8182    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4407    1.6431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1512    1.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8617    0.8046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8539   -0.0204    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6677    0.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1286   -0.7983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2188   -0.3444    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1276   -1.2510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4250   -0.0068    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0328   -0.5646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6901   -1.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0957   -2.0335    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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  1  0  0  0
 22 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
  5 27  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
  4 29  1  0  0  0  0
 29 30  2  0  0  0  0
M  END

     RDKit          3D

 58 60  0  0  0  0  0  0  0  0999 V2000
    4.0710   -1.7369    2.6142 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9554   -0.9590    2.3460 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9299   -0.6834    0.9606 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7532    0.1327    0.7013 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7488   -0.1097   -0.0589 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3364   -1.2478   -0.9463 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3244   -2.2011   -1.0008 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9996   -2.5537   -2.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0671   -3.5915   -2.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6453   -1.9296   -3.1878 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0111   -1.7781   -0.4632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8424   -0.7188    0.2327 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3245   -0.9934    0.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5856   -0.7578    1.6216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7994   -1.8282    2.4425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5071   -1.8130    3.9101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2611   -2.8785    1.9594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5657    0.6441   -0.2754 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7918    0.6150   -1.6850 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3730    1.7533    0.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1923    2.9046   -0.7541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7792    3.2134   -1.0564 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7302    4.1337   -2.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2524    3.9458    0.0323 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1452    2.0314   -1.2444 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0448    1.4161   -2.4560 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1243    1.0625   -0.1010 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1907    1.7597    1.0562 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4558    1.3549    1.4579 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2012    1.9227    2.3036 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0350   -2.7016    2.0454 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0839   -1.9247    3.7015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9595   -1.1800    2.2814 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0751   -1.5780    0.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8508   -0.0475    0.7986 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1630   -0.8110   -1.9427 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7309   -3.5330   -1.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6705   -3.4708   -3.1065 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5649   -4.5779   -2.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5743   -2.0774   -1.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7693   -2.6420    0.1881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4158   -1.9213   -0.5402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8394   -1.1901    1.0167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8300   -0.1989   -0.5216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4879   -2.1423    4.1389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7022   -0.8054    4.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2203   -2.5074    4.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3089   -0.1637   -1.9436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4326    1.5798    0.3949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9571    2.1128    1.2293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7992    2.6259   -1.6398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6699    3.7753   -0.2845 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3174    4.3046   -2.5792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1291    5.1216   -1.9355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3233    3.7426   -3.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2958    4.6970   -0.2848 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1802    2.4146   -1.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1963    1.9891   -3.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  1
 14 15  1  0
 15 16  1  0
 15 17  2  0
 12 18  1  0
 18 19  1  6
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  1
 22 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  1
 28 29  1  0
 29 30  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 29  4  1  0
 27  5  1  0
 27 18  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  3 35  1  0
  6 36  1  6
 11 40  1  0
 11 41  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
 16 45  1  0
 16 46  1  0
 16 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  0
 21 52  1  0
 23 53  1  0
 23 54  1  0
 23 55  1  0
 24 56  1  0
 25 57  1  1
 26 58  1  0
  9 37  1  0
  9 38  1  0
  9 39  1  0
M  END


  Mrv1652309102219422D          

 30 32  0  0  1  0            999 V2000
    0.0022   -3.2237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5600   -2.6159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3126   -1.8288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8704   -1.2210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7066   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0039    0.0068    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7223   -0.3988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4328    0.0204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1511   -0.3852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4249    0.8454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0040    0.8318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7223    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2586    1.8644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1981    1.8745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4876    2.6470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0366    3.2840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3014    2.7825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4328    0.8182    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4407    1.6431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1512    1.2238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8617    0.8046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8539   -0.0204    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6677    0.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1286   -0.7983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2188   -0.3444    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1276   -1.2510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4250   -0.0068    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0328   -0.5646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6901   -1.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0957   -2.0335    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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  1  0  0  0
 22 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
  5 27  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
  4 29  1  0  0  0  0
 29 30  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0303387

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COCC1=C2[C@H](C[C@@](C)(OC(C)=O)[C@@]3(O)CC[C@@](C)(O)[C@H](O)[C@]23OC1=O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O10/c1-10(21)28-13-8-18(4,29-11(2)22)19(26)7-6-17(3,25)16(24)20(19)14(13)12(9-27-5)15(23)30-20/h13,16,24-26H,6-9H2,1-5H3/t13-,16-,17+,18+,19-,20+/m0/s1

> <INCHI_KEY>
UHAQFLNYQMGHEC-HCWJOOGXSA-N

> <FORMULA>
C20H28O10

> <MOLECULAR_WEIGHT>
428.434

> <EXACT_MASS>
428.168247102

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
41.63216545079065

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S,6R,6aS,9R,10S,10aR)-6-(acetyloxy)-6a,9,10-trihydroxy-3-(methoxymethyl)-6,9-dimethyl-2-oxo-2H,4H,5H,6H,6aH,7H,8H,9H,10H-naphtho[4a,4-b]furan-4-yl acetate

> <JCHEM_LOGP>
-1.5595202410000004

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.998762256870439

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.269663485295133

> <JCHEM_PKA_STRONGEST_BASIC>
-3.257827172976418

> <JCHEM_POLAR_SURFACE_AREA>
148.82

> <JCHEM_REFRACTIVITY>
99.17349999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4S,6R,6aS,9R,10S,10aR)-6-(acetyloxy)-6a,9,10-trihydroxy-3-(methoxymethyl)-6,9-dimethyl-2-oxo-4H,5H,7H,8H,10H-naphtho[4a,4-b]furan-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       0.004  -6.017   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.045  -4.883   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.583  -3.414   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.625  -2.279   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.319  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.007   0.013   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.348  -0.745   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.675   0.038   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.015  -0.719   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.660   1.578   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.007   1.553   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.348   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.349   3.480   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.370   3.499   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.910   4.941   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.068   6.130   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.429   5.194   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.675   1.527   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.689   3.067   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.016   2.285   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.342   1.502   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.327  -0.038   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.846   0.215   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.840  -1.490   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.142  -0.643   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.972  -2.335   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.660  -0.013   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.795  -1.054   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.155  -2.455   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.912  -3.796   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   29                                                  
CONECT    5    4    6   27                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    6   12                                                       
CONECT   12   11   13   14   18                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   12   19   20   27                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25    5   18   28                                             
CONECT   28   27   29                                                       
CONECT   29   28    4   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Value	Source
(4S,6R,6AS,9R,10S,10ar)-4-(acetyloxy)-6a,9,10-trihydroxy-3-(methoxymethyl)-6,9-dimethyl-2-oxo-2H,4H,5H,6H,6ah,7H,8H,9H,10H-naphtho[4a,4-b]furan-6-yl acetic acid	Generator

Chemical Formula

C₂₀H₂₈O₁₀

Average Mass

428.4340 Da

Monoisotopic Mass

428.16825 Da

IUPAC Name

(4S,6R,6aS,9R,10S,10aR)-6-(acetyloxy)-6a,9,10-trihydroxy-3-(methoxymethyl)-6,9-dimethyl-2-oxo-2H,4H,5H,6H,6aH,7H,8H,9H,10H-naphtho[4a,4-b]furan-4-yl acetate

Traditional Name

(4S,6R,6aS,9R,10S,10aR)-6-(acetyloxy)-6a,9,10-trihydroxy-3-(methoxymethyl)-6,9-dimethyl-2-oxo-4H,5H,7H,8H,10H-naphtho[4a,4-b]furan-4-yl acetate

CAS Registry Number

Not Available

SMILES

COCC1=C2[C@H](C[C@@](C)(OC(C)=O)[C@@]3(O)CC[C@@](C)(O)[C@H](O)[C@]23OC1=O)OC(C)=O

InChI Identifier

InChI=1S/C20H28O10/c1-10(21)28-13-8-18(4,29-11(2)22)19(26)7-6-17(3,25)16(24)20(19)14(13)12(9-27-5)15(23)30-20/h13,16,24-26H,6-9H2,1-5H3/t13-,16-,17+,18+,19-,20+/m0/s1

InChI Key

UHAQFLNYQMGHEC-HCWJOOGXSA-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
Pseudelephantopus spicatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cadinanolides. These are sesquiterpene lactones based on 2-dioxonaphtho[4a,4-b]furan.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Cadinanolides

Alternative Parents

Substituents

Cadinanolide skeleton
Sesquiterpenoid
Cadinane sesquiterpenoid
Naphthofuran
Tricarboxylic acid or derivatives
2-furanone
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Carboxylic acid ester
Lactone
Secondary alcohol
Organoheterocyclic compound
Ether
Oxacycle
Dialkyl ether
Carboxylic acid derivative
Polyol
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organooxygen compound
Organic oxygen compound
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	-1.6	ChemAxon
pKa (Strongest Acidic)	12.27	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	148.82 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	99.17 m³·mol⁻¹	ChemAxon
Polarizability	41.63 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	Yes	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

162949336

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4s,6r,6as,9r,10s,10ar)-6-(acetyloxy)-6a,9,10-trihydroxy-3-(methoxymethyl)-6,9-dimethyl-2-oxo-4h,5h,7h,8h,10h-naphtho[4a,4-b]furan-4-yl acetate (NP0303387)

MOL for NP0303387 ((4s,6r,6as,9r,10s,10ar)-6-(acetyloxy)-6a,9,10-trihydroxy-3-(methoxymethyl)-6,9-dimethyl-2-oxo-4h,5h,7h,8h,10h-naphtho[4a,4-b]furan-4-yl acetate)

3D MOL for NP0303387 ((4s,6r,6as,9r,10s,10ar)-6-(acetyloxy)-6a,9,10-trihydroxy-3-(methoxymethyl)-6,9-dimethyl-2-oxo-4h,5h,7h,8h,10h-naphtho[4a,4-b]furan-4-yl acetate)

3D SDF for NP0303387 ((4s,6r,6as,9r,10s,10ar)-6-(acetyloxy)-6a,9,10-trihydroxy-3-(methoxymethyl)-6,9-dimethyl-2-oxo-4h,5h,7h,8h,10h-naphtho[4a,4-b]furan-4-yl acetate)

3D-SDF for NP0303387 ((4s,6r,6as,9r,10s,10ar)-6-(acetyloxy)-6a,9,10-trihydroxy-3-(methoxymethyl)-6,9-dimethyl-2-oxo-4h,5h,7h,8h,10h-naphtho[4a,4-b]furan-4-yl acetate)

PDB for NP0303387 ((4s,6r,6as,9r,10s,10ar)-6-(acetyloxy)-6a,9,10-trihydroxy-3-(methoxymethyl)-6,9-dimethyl-2-oxo-4h,5h,7h,8h,10h-naphtho[4a,4-b]furan-4-yl acetate)

3D PDB for NP0303387 ((4s,6r,6as,9r,10s,10ar)-6-(acetyloxy)-6a,9,10-trihydroxy-3-(methoxymethyl)-6,9-dimethyl-2-oxo-4h,5h,7h,8h,10h-naphtho[4a,4-b]furan-4-yl acetate)

SMILES for NP0303387 ((4s,6r,6as,9r,10s,10ar)-6-(acetyloxy)-6a,9,10-trihydroxy-3-(methoxymethyl)-6,9-dimethyl-2-oxo-4h,5h,7h,8h,10h-naphtho[4a,4-b]furan-4-yl acetate)

INCHI for NP0303387 ((4s,6r,6as,9r,10s,10ar)-6-(acetyloxy)-6a,9,10-trihydroxy-3-(methoxymethyl)-6,9-dimethyl-2-oxo-4h,5h,7h,8h,10h-naphtho[4a,4-b]furan-4-yl acetate)

Structure for NP0303387 ((4s,6r,6as,9r,10s,10ar)-6-(acetyloxy)-6a,9,10-trihydroxy-3-(methoxymethyl)-6,9-dimethyl-2-oxo-4h,5h,7h,8h,10h-naphtho[4a,4-b]furan-4-yl acetate)

3D Structure for NP0303387 ((4s,6r,6as,9r,10s,10ar)-6-(acetyloxy)-6a,9,10-trihydroxy-3-(methoxymethyl)-6,9-dimethyl-2-oxo-4h,5h,7h,8h,10h-naphtho[4a,4-b]furan-4-yl acetate)