NP-MRD: Showing NP-Card for (6s,9s,10s,12r,13s,14s,16r,19s,22s,23s,25r)-16-(acetyloxy)-10,12,14,23-tetrahydroxy-6,10,19-trimethyl-22-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-13-yl 2-hydroxy-2-methylbutanoate (NP0219669)

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Record Information

Version

1.0

Created at

2022-09-05 20:44:31 UTC

Updated at

2022-09-05 20:44:31 UTC

NP-MRD ID

NP0219669

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6s,9s,10s,12r,13s,14s,16r,19s,22s,23s,25r)-16-(acetyloxy)-10,12,14,23-tetrahydroxy-6,10,19-trimethyl-22-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-13-yl 2-hydroxy-2-methylbutanoate

Description

SCHEMBL14052394 belongs to the class of organic compounds known as cerveratrum-type alkaloids. These are steroidal alkaloids containing the cevane (23-methyl-4- azahexacyclo[12.11.0.0^{2,11}.0^{4,9}.0^{15,24}.0^{18,23}]Pentacosane) moiety, which is a six ring system. Cerveratrum alkaloids have 7-9 oxygen atoms and occur as free alkamines or esters of simple aliphatic or aromatic acids. (6s,9s,10s,12r,13s,14s,16r,19s,22s,23s,25r)-16-(acetyloxy)-10,12,14,23-tetrahydroxy-6,10,19-trimethyl-22-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-13-yl 2-hydroxy-2-methylbutanoate is found in Veratrum nigrum. Based on a literature review very few articles have been published on SCHEMBL14052394.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052222442D          

 52 58  0  0  1  0            999 V2000
   -3.6875   -3.2655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8791   -3.1010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6173   -2.3187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1639   -1.7008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8088   -2.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2622   -2.7721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5471   -1.3718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7386   -1.2073    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1181   -1.7643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6947   -1.5581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8710   -0.7114    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5847   -1.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1706   -0.0173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2111    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9737    1.1077    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1403    1.9157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5238    2.4639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2592    2.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6904    3.2719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5661    0.5428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3702    0.7100    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9113    1.3956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7300   -0.0324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1244   -0.6106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3187   -0.3144    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3834   -0.9243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3910   -0.4649    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6337    0.3235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5528   -0.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9125   -0.8345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7354   -0.8942    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0951   -1.6366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9179   -1.6963    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2777   -2.4388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3811   -1.0136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0213   -0.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1985   -0.2115    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8388    0.5310    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7546    1.3517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6324    0.7563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0159    0.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6562    1.3331    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1193    2.0159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8333    1.3928    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4736    2.1352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9367    2.8180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7596    2.7583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5770    3.5604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8346    3.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3194    3.9202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2173    4.3029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6804    4.9856    0.0000 C   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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 25  1  0  0  0  0
 11 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 13 27  1  0  0  0  0
  8 27  1  0  0  0  0
 27 28  1  1  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 31  1  6  0  0  0
 37 38  1  0  0  0  0
 38 39  1  1  0  0  0
 38 40  1  6  0  0  0
 38 41  1  0  0  0  0
 29 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  6  0  0  0
 42 44  1  0  0  0  0
 21 44  1  0  0  0  0
 44 45  1  1  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 46 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 48 51  1  0  0  0  0
 51 52  1  0  0  0  0
M  END


  Mrv1652309052222442D          

 52 58  0  0  1  0            999 V2000
   -3.6875   -3.2655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8791   -3.1010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6173   -2.3187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1639   -1.7008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8088   -2.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2622   -2.7721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5471   -1.3718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7386   -1.2073    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1181   -1.7643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6947   -1.5581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8710   -0.7114    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5847   -1.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1706   -0.0173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2111    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9737    1.1077    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1403    1.9157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5238    2.4639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2592    2.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6904    3.2719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5661    0.5428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3702    0.7100    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9113    1.3956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7300   -0.0324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1244   -0.6106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3187   -0.3144    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3834   -0.9243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3910   -0.4649    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6337    0.3235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5528   -0.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9125   -0.8345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7354   -0.8942    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0951   -1.6366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9179   -1.6963    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2777   -2.4388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3811   -1.0136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0213   -0.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1985   -0.2115    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8388    0.5310    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7546    1.3517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6324    0.7563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0159    0.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6562    1.3331    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1193    2.0159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8333    1.3928    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4736    2.1352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9367    2.8180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7596    2.7583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5770    3.5604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8346    3.2007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3194    3.9202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2173    4.3029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6804    4.9856    0.0000 C   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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 25  1  0  0  0  0
 11 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 13 27  1  0  0  0  0
  8 27  1  0  0  0  0
 27 28  1  1  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 31  1  6  0  0  0
 37 38  1  0  0  0  0
 38 39  1  1  0  0  0
 38 40  1  6  0  0  0
 38 41  1  0  0  0  0
 29 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  6  0  0  0
 42 44  1  0  0  0  0
 21 44  1  0  0  0  0
 44 45  1  1  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 46 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 48 51  1  0  0  0  0
 51 52  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0219669

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C(=O)O[C@H]1CC[C@@]2(C)C3C[C@@H](OC(C)=O)C4[C@@]5(O)C(C[C@]24O[C@]13O)C1CN2C[C@@H](C)CC[C@H]2[C@@](C)(O)C1[C@@H](O)[C@@H]5OC(=O)C(C)(O)CC

> <INCHI_IDENTIFIER>
InChI=1S/C39H61NO12/c1-9-20(4)32(43)50-27-13-14-34(6)25-15-24(49-21(5)41)30-37(34,52-39(25,27)48)16-23-22-18-40-17-19(3)11-12-26(40)36(8,46)28(22)29(42)31(38(23,30)47)51-33(44)35(7,45)10-2/h19-20,22-31,42,45-48H,9-18H2,1-8H3/t19-,20?,22?,23?,24+,25?,26-,27-,28?,29+,30?,31-,34-,35?,36+,37+,38-,39-/m0/s1

> <INCHI_KEY>
LJPLLMYELFESAN-FLUUMLQVSA-N

> <FORMULA>
C39H61NO12

> <MOLECULAR_WEIGHT>
735.912

> <EXACT_MASS>
735.419376408

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
113

> <JCHEM_AVERAGE_POLARIZABILITY>
79.84362695720547

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6S,9S,10S,12R,13S,14S,16R,19S,22S,23S,25R)-16-(acetyloxy)-10,12,14,23-tetrahydroxy-6,10,19-trimethyl-22-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0^{2,11}.0^{4,9}.0^{15,25}.0^{18,23}.0^{19,25}]hexacosan-13-yl 2-hydroxy-2-methylbutanoate

> <JCHEM_LOGP>
2.211838308

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.466502652449314

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.87532723259637

> <JCHEM_PKA_STRONGEST_BASIC>
7.971218103335777

> <JCHEM_POLAR_SURFACE_AREA>
192.51999999999998

> <JCHEM_REFRACTIVITY>
184.66870000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(6S,9S,10S,12R,13S,14S,16R,19S,22S,23S,25R)-16-(acetyloxy)-10,12,14,23-tetrahydroxy-6,10,19-trimethyl-22-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0^{2,11}.0^{4,9}.0^{15,25}.0^{18,23}.0^{19,25}]hexacosan-13-yl 2-hydroxy-2-methylbutanoate

> <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      -6.883  -6.096   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.374  -5.789   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.886  -4.328   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.906  -3.175   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.376  -4.021   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.356  -5.175   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -2.888  -2.561   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.379  -2.254   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.220  -3.293   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.297  -2.909   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.626  -1.328   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.958  -2.100   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.319  -0.032   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.394   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.818   2.068   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.129   3.576   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.978   4.599   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.484   4.114   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.289   6.108   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.923   1.013   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.424   1.325   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.568   2.605   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.096  -0.060   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.965  -1.140   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.462  -0.587   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.716  -1.725   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.730  -0.868   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.183   0.604   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.632  -0.172   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.303  -1.558   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0       8.839  -1.669   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0       9.511  -3.055   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.047  -3.166   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.718  -4.552   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.911  -1.892   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      11.240  -0.506   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.704  -0.395   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.032   0.991   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       8.875   2.523   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      10.514   1.412   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       7.496   1.103   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       6.825   2.488   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       7.689   3.763   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       5.289   2.600   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       4.617   3.986   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       5.482   5.260   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       7.018   5.149   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0       4.810   6.646   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       3.425   5.975   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       6.196   7.318   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       4.139   8.032   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       5.003   9.307   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   27                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   25                                             
CONECT   12   11                                                            
CONECT   13   11   14   27                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   15   21   25                                                  
CONECT   21   20   22   23   44                                             
CONECT   22   21                                                            
CONECT   23   21   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   20   11   26                                             
CONECT   26   25   27                                                       
CONECT   27   26   13    8   28                                             
CONECT   28   27                                                            
CONECT   29   23   30   41                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   37                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   31   38                                                  
CONECT   38   37   39   40   41                                             
CONECT   39   38                                                            
CONECT   40   38                                                            
CONECT   41   38   29   42                                                  
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   21   45                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   49   50   51                                             
CONECT   49   48                                                            
CONECT   50   48                                                            
CONECT   51   48   52                                                       
CONECT   52   51                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  116    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₉H₆₁NO₁₂

Average Mass

735.9120 Da

Monoisotopic Mass

735.41938 Da

IUPAC Name

(6S,9S,10S,12R,13S,14S,16R,19S,22S,23S,25R)-16-(acetyloxy)-10,12,14,23-tetrahydroxy-6,10,19-trimethyl-22-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0^{2,11}.0^{4,9}.0^{15,25}.0^{18,23}.0^{19,25}]hexacosan-13-yl 2-hydroxy-2-methylbutanoate

Traditional Name

CAS Registry Number

Not Available

SMILES

CCC(C)C(=O)O[C@H]1CC[C@@]2(C)C3C[C@@H](OC(C)=O)C4[C@@]5(O)C(C[C@]24O[C@]13O)C1CN2C[C@@H](C)CC[C@H]2[C@@](C)(O)C1[C@@H](O)[C@@H]5OC(=O)C(C)(O)CC

InChI Identifier

InChI=1S/C39H61NO12/c1-9-20(4)32(43)50-27-13-14-34(6)25-15-24(49-21(5)41)30-37(34,52-39(25,27)48)16-23-22-18-40-17-19(3)11-12-26(40)36(8,46)28(22)29(42)31(38(23,30)47)51-33(44)35(7,45)10-2/h19-20,22-31,42,45-48H,9-18H2,1-8H3/t19-,20?,22?,23?,24+,25?,26-,27-,28?,29+,30?,31-,34-,35?,36+,37+,38-,39-/m0/s1

InChI Key

LJPLLMYELFESAN-FLUUMLQVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Veratrum nigrum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cerveratrum-type alkaloids. These are steroidal alkaloids containing the cevane (23-methyl-4- azahexacyclo[12.11.0.0^{2,11}.0^{4,9}.0^{15,24}.0^{18,23}]Pentacosane) moiety, which is a six ring system. Cerveratrum alkaloids have 7-9 oxygen atoms and occur as free alkamines or esters of simple aliphatic or aromatic acids.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal alkaloids

Direct Parent

Cerveratrum-type alkaloids

Alternative Parents

Substituents

Cerveratrum-type alkaloid
Azasteroid
Quinolizidine
Tricarboxylic acid or derivatives
Alkaloid or derivatives
Oxepane
Fatty acid ester
Piperidine
Fatty acyl
Tertiary alcohol
Tetrahydrofuran
Cyclic alcohol
Amino acid or derivatives
Tertiary amine
1,2-aminoalcohol
Secondary alcohol
Tertiary aliphatic amine
Carboxylic acid ester
Hemiacetal
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Amine
Organonitrogen compound
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	2.21	ChemAxon
pKa (Strongest Acidic)	10.88	ChemAxon
pKa (Strongest Basic)	7.97	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	192.52 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	184.67 m³·mol⁻¹	ChemAxon
Polarizability	79.84 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

10744

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11217

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (6s,9s,10s,12r,13s,14s,16r,19s,22s,23s,25r)-16-(acetyloxy)-10,12,14,23-tetrahydroxy-6,10,19-trimethyl-22-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-13-yl 2-hydroxy-2-methylbutanoate (NP0219669)

MOL for NP0219669 ((6s,9s,10s,12r,13s,14s,16r,19s,22s,23s,25r)-16-(acetyloxy)-10,12,14,23-tetrahydroxy-6,10,19-trimethyl-22-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-13-yl 2-hydroxy-2-methylbutanoate)

3D MOL for NP0219669 ((6s,9s,10s,12r,13s,14s,16r,19s,22s,23s,25r)-16-(acetyloxy)-10,12,14,23-tetrahydroxy-6,10,19-trimethyl-22-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-13-yl 2-hydroxy-2-methylbutanoate)

3D SDF for NP0219669 ((6s,9s,10s,12r,13s,14s,16r,19s,22s,23s,25r)-16-(acetyloxy)-10,12,14,23-tetrahydroxy-6,10,19-trimethyl-22-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-13-yl 2-hydroxy-2-methylbutanoate)

3D-SDF for NP0219669 ((6s,9s,10s,12r,13s,14s,16r,19s,22s,23s,25r)-16-(acetyloxy)-10,12,14,23-tetrahydroxy-6,10,19-trimethyl-22-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-13-yl 2-hydroxy-2-methylbutanoate)

PDB for NP0219669 ((6s,9s,10s,12r,13s,14s,16r,19s,22s,23s,25r)-16-(acetyloxy)-10,12,14,23-tetrahydroxy-6,10,19-trimethyl-22-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-13-yl 2-hydroxy-2-methylbutanoate)

3D PDB for NP0219669 ((6s,9s,10s,12r,13s,14s,16r,19s,22s,23s,25r)-16-(acetyloxy)-10,12,14,23-tetrahydroxy-6,10,19-trimethyl-22-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-13-yl 2-hydroxy-2-methylbutanoate)

SMILES for NP0219669 ((6s,9s,10s,12r,13s,14s,16r,19s,22s,23s,25r)-16-(acetyloxy)-10,12,14,23-tetrahydroxy-6,10,19-trimethyl-22-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-13-yl 2-hydroxy-2-methylbutanoate)

INCHI for NP0219669 ((6s,9s,10s,12r,13s,14s,16r,19s,22s,23s,25r)-16-(acetyloxy)-10,12,14,23-tetrahydroxy-6,10,19-trimethyl-22-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-13-yl 2-hydroxy-2-methylbutanoate)

Structure for NP0219669 ((6s,9s,10s,12r,13s,14s,16r,19s,22s,23s,25r)-16-(acetyloxy)-10,12,14,23-tetrahydroxy-6,10,19-trimethyl-22-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-13-yl 2-hydroxy-2-methylbutanoate)

3D Structure for NP0219669 ((6s,9s,10s,12r,13s,14s,16r,19s,22s,23s,25r)-16-(acetyloxy)-10,12,14,23-tetrahydroxy-6,10,19-trimethyl-22-[(2-methylbutanoyl)oxy]-24-oxa-4-azaheptacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁵.0¹⁸,²³.0¹⁹,²⁵]hexacosan-13-yl 2-hydroxy-2-methylbutanoate)