NP-MRD: Showing NP-Card for methyl (7e,9e)-11-[2,4-dihydroxy-4-(2-hydroxyethyl)-6-oxa-3-azabicyclo[3.1.0]hex-2-en-1-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate (NP0309449)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-11 04:03:40 UTC

Updated at

2022-09-11 04:03:41 UTC

NP-MRD ID

NP0309449

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (7e,9e)-11-[2,4-dihydroxy-4-(2-hydroxyethyl)-6-oxa-3-azabicyclo[3.1.0]hex-2-en-1-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate

Description

methyl (7e,9e)-11-[2,4-dihydroxy-4-(2-hydroxyethyl)-6-oxa-3-azabicyclo[3.1.0]hex-2-en-1-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate is found in Neonectria coccinea. Methyl (7E,9E)-11-[2,4-dihydroxy-4-(2-hydroxyethyl)-6-oxa-3-azabicyclo[3.1.0]Hex-2-en-1-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231523212D          

 31 32  0  0  0  0            999 V2000
   -7.3124   -0.8752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9768   -0.1215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1563   -0.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6714   -0.7027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8208    0.7184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3057    1.3859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9701    2.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0003    0.8047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5154    0.1372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8509   -0.6164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6949    0.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2100   -0.4440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5455   -1.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3895   -0.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9046   -1.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0841   -0.9389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5992   -1.6064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9347   -2.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2213   -1.5201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7062   -2.1876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5569   -0.7665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1576   -0.3540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5569    0.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3415    0.3135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0059    1.0671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0560    0.7260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7704    0.3135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4849    0.7260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8264   -0.3540    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3415   -1.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5964   -1.8060    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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  4  0  0  0
  8  5  1  4  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 11  9  1  4  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  2  0  0  0  0
M  END

     RDKit          3D

 60 61  0  0  0  0  0  0  0  0999 V2000
   -9.0180   -0.9498    0.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6681   -0.5474    0.7369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4676   -0.5666    0.4021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1433   -0.5879    0.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2152    0.2394    0.6685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7777    1.0996    1.7213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8304    0.0741    0.3240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7994    0.7622    0.7561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8274    1.8942    1.6916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4654    0.2289    0.3591 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6220    0.8261    0.7261 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9948    0.4044    0.4192 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0004    1.1274    0.8276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6376    2.3990    1.5916 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4074    0.8470    0.6988 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2154    1.7303    1.1990 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9941   -0.3198    0.0699 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2509   -1.1595   -0.7510 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3194   -0.3660   -1.2708 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6387   -1.0835   -1.3986 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6056   -1.9580   -2.4313 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7661   -0.0703   -1.5660 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0958   -0.7898   -1.7240 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3534   -1.5785   -0.6370 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7849   -1.7826   -0.1336 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0666   -1.0509    0.8673 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2788   -1.0329    2.0822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8865   -1.5885   -0.9931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8836   -1.7988   -1.6272 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1048   -1.9448   -1.1290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5088   -2.7807   -2.2424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2252   -2.0232    0.5913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6919   -0.4389    1.2855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4612   -0.5551   -0.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6822    0.1574    1.7443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6419   -1.2014   -0.7130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6398    0.5621    2.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0435    2.1077    1.4685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0143    1.0782    2.5652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6266   -0.7439   -0.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9650    2.5805    1.4371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7463    2.5047    1.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7875    1.6367    2.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3812   -0.6690   -0.2487 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5357    1.7071    1.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1796   -0.5152   -0.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5608    2.9784    1.7553 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0313    2.9516    0.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1720    2.2170    2.5401 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0244    0.3668   -2.0495 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8387   -1.8976   -3.0267 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5311    0.5466   -2.4484 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7971    0.5351   -0.6202 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1659   -1.3077   -2.6829 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9073    0.0107   -1.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2426   -1.0513    0.1875 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3216   -2.6538    0.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4627   -2.3272   -2.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7664   -2.7590   -3.0264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6082   -3.7938   -1.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
 31 30  1  0
 30 28  1  0
 28 29  2  0
 28  3  1  0
  3  2  2  0
  2  1  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 17 15  1  1
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  6
 20 22  1  0
 22 23  1  0
 23 24  1  0
 20 25  1  0
 25 26  1  0
 26 27  2  0
 19 17  1  0
 26 17  1  0
 31 58  1  0
 31 59  1  0
 31 60  1  0
  2 35  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 36  1  0
  6 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  9 41  1  0
  9 42  1  0
  9 43  1  0
 10 44  1  0
 11 45  1  0
 12 46  1  0
 14 47  1  0
 14 48  1  0
 14 49  1  0
 19 50  1  6
 21 51  1  0
 22 52  1  0
 22 53  1  0
 23 54  1  0
 23 55  1  0
 24 56  1  0
 25 57  1  0
M  END


  Mrv1533004231523212D          

 31 32  0  0  0  0            999 V2000
   -7.3124   -0.8752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9768   -0.1215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1563   -0.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6714   -0.7027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8208    0.7184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3057    1.3859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9701    2.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0003    0.8047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5154    0.1372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8509   -0.6164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6949    0.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2100   -0.4440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5455   -1.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3895   -0.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9046   -1.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0841   -0.9389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5992   -1.6064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9347   -2.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2213   -1.5201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7062   -2.1876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5569   -0.7665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1576   -0.3540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5569    0.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3415    0.3135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0059    1.0671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0560    0.7260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7704    0.3135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4849    0.7260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8264   -0.3540    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3415   -1.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5964   -1.8060    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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  4  0  0  0
  8  5  1  4  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 11  9  1  4  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0309449

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(=CC)C=C(C)C=C(C)\C=C\C=C(/C)C(=O)C12OC1C(O)(CCO)NC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H29NO7/c1-6-17(19(27)30-5)13-15(3)12-14(2)8-7-9-16(4)18(26)23-20(31-23)22(29,10-11-25)24-21(23)28/h6-9,12-13,20,25,29H,10-11H2,1-5H3,(H,24,28)/b8-7+,14-12?,15-13?,16-9+,17-6?

> <INCHI_KEY>
FZFYFSUIOSWLHW-QOOVWNLESA-N

> <FORMULA>
C23H29NO7

> <MOLECULAR_WEIGHT>
431.485

> <EXACT_MASS>
431.194402278

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
46.4568624602406

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (7E,9E)-2-ethylidene-11-[4-hydroxy-4-(2-hydroxyethyl)-2-oxo-6-oxa-3-azabicyclo[3.1.0]hexan-1-yl]-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate

> <ALOGPS_LOGP>
2.17

> <JCHEM_LOGP>
2.5345139890000006

> <ALOGPS_LOGS>
-4.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.671840985908355

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.271324736511998

> <JCHEM_PKA_STRONGEST_BASIC>
-2.4354784299534646

> <JCHEM_POLAR_SURFACE_AREA>
125.46000000000001

> <JCHEM_REFRACTIVITY>
118.21069999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.31e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (7E,9E)-2-ethylidene-11-[4-hydroxy-4-(2-hydroxyethyl)-2-oxo-6-oxa-3-azabicyclo[3.1.0]hexan-1-yl]-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0     -13.650  -1.634   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0     -13.023  -0.227   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0     -11.492  -0.066   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0     -10.587  -1.312   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0     -10.865   1.341   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -11.771   2.587   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -11.144   3.994   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -9.334   1.502   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.429   0.256   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -9.055  -1.151   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.897   0.417   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.992  -0.829   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.618  -2.236   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.460  -0.668   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.555  -1.914   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.024  -1.753   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.118  -2.999   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.745  -4.405   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.413  -2.838   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.318  -4.083   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.039  -1.431   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.294  -0.661   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.039   0.109   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.504   0.585   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.878   1.992   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.838   1.355   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.171   0.585   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       6.505   1.355   0.000  0.00  0.00           O+0
HETATM   29  N   UNK     0       3.409  -0.661   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0       2.504  -1.907   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.980  -3.371   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    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23   30                                             
CONECT   22   21   23                                                       
CONECT   23   22   21   24                                                  
CONECT   24   23   25   26   29                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   24   30                                                       
CONECT   30   29   21   31                                                  
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

View in JSmol

Synonyms

Value	Source
Methyl (7E,9E)-11-[2,4-dihydroxy-4-(2-hydroxyethyl)-6-oxa-3-azabicyclo[3.1.0]hex-2-en-1-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoic acid	Generator

Chemical Formula

C₂₃H₂₉NO₇

Average Mass

431.4850 Da

Monoisotopic Mass

431.19440 Da

IUPAC Name

methyl (7E,9E)-2-ethylidene-11-[4-hydroxy-4-(2-hydroxyethyl)-2-oxo-6-oxa-3-azabicyclo[3.1.0]hexan-1-yl]-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate

Traditional Name

methyl (7E,9E)-2-ethylidene-11-[4-hydroxy-4-(2-hydroxyethyl)-2-oxo-6-oxa-3-azabicyclo[3.1.0]hexan-1-yl]-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate

CAS Registry Number

Not Available

SMILES

COC(=O)C(=CC)C=C(C)C=C(C)\C=C\C=C(/C)C(=O)C12OC1C(O)(CCO)NC2=O

InChI Identifier

InChI=1S/C23H29NO7/c1-6-17(19(27)30-5)13-15(3)12-14(2)8-7-9-16(4)18(26)23-20(31-23)22(29,10-11-25)24-21(23)28/h6-9,12-13,20,25,29H,10-11H2,1-5H3,(H,24,28)/b8-7+,14-12?,15-13?,16-9+,17-6?

InChI Key

FZFYFSUIOSWLHW-QOOVWNLESA-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
Neonectria coccinea	LOTUS Database	35616633

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Farsesane sesquiterpenoid
Sesquiterpenoid
B'-hydroxy-alpha,beta-unsaturated-ketone
Fatty acid ester
Fatty acyl
Alpha-branched alpha,beta-unsaturated-ketone
Para-oxazine
Cyclic carboximidic acid
Alpha,beta-unsaturated ketone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Pyrroline
Enone
Acryloyl-group
Ketone
Carboxylic acid ester
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Alkanolamine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
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	2.17	ALOGPS
logP	2.53	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	10.27	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	125.46 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	118.21 m³·mol⁻¹	ChemAxon
Polarizability	46.46 Å³	ChemAxon
Number of Rings	2	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (7e,9e)-11-[2,4-dihydroxy-4-(2-hydroxyethyl)-6-oxa-3-azabicyclo[3.1.0]hex-2-en-1-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate (NP0309449)

MOL for NP0309449 (methyl (7e,9e)-11-[2,4-dihydroxy-4-(2-hydroxyethyl)-6-oxa-3-azabicyclo[3.1.0]hex-2-en-1-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate)

3D MOL for NP0309449 (methyl (7e,9e)-11-[2,4-dihydroxy-4-(2-hydroxyethyl)-6-oxa-3-azabicyclo[3.1.0]hex-2-en-1-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate)

3D SDF for NP0309449 (methyl (7e,9e)-11-[2,4-dihydroxy-4-(2-hydroxyethyl)-6-oxa-3-azabicyclo[3.1.0]hex-2-en-1-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate)

3D-SDF for NP0309449 (methyl (7e,9e)-11-[2,4-dihydroxy-4-(2-hydroxyethyl)-6-oxa-3-azabicyclo[3.1.0]hex-2-en-1-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate)

PDB for NP0309449 (methyl (7e,9e)-11-[2,4-dihydroxy-4-(2-hydroxyethyl)-6-oxa-3-azabicyclo[3.1.0]hex-2-en-1-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate)

3D PDB for NP0309449 (methyl (7e,9e)-11-[2,4-dihydroxy-4-(2-hydroxyethyl)-6-oxa-3-azabicyclo[3.1.0]hex-2-en-1-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate)

SMILES for NP0309449 (methyl (7e,9e)-11-[2,4-dihydroxy-4-(2-hydroxyethyl)-6-oxa-3-azabicyclo[3.1.0]hex-2-en-1-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate)

INCHI for NP0309449 (methyl (7e,9e)-11-[2,4-dihydroxy-4-(2-hydroxyethyl)-6-oxa-3-azabicyclo[3.1.0]hex-2-en-1-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate)

Structure for NP0309449 (methyl (7e,9e)-11-[2,4-dihydroxy-4-(2-hydroxyethyl)-6-oxa-3-azabicyclo[3.1.0]hex-2-en-1-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate)

3D Structure for NP0309449 (methyl (7e,9e)-11-[2,4-dihydroxy-4-(2-hydroxyethyl)-6-oxa-3-azabicyclo[3.1.0]hex-2-en-1-yl]-2-ethylidene-4,6,10-trimethyl-11-oxoundeca-3,5,7,9-tetraenoate)