NP-MRD: Showing NP-Card for (-)-Singapurensine A (NP0066939)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 11:09:31 UTC

Updated at

2022-04-28 11:09:31 UTC

NP-MRD ID

NP0066939

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Singapurensine A

Description

13,15-Dimethyl (1S,2R,6R,14S,15R,16R,18S,20S)-15,20-dihydroxy-17-oxa-3,13-diazaheptacyclo[12.6.2.0¹,¹⁶.0²,⁶.0³,¹⁸.0⁶,¹⁴.0⁷,¹²]Docosa-7,9,11-triene-13,15-dicarboxylate belongs to the class of organic compounds known as aspidofractine alkaloids. These are alkaloids with a structure that is based on the hexacyclic aspidofractine core. These compounds are related to the Aspidosperma group by formation of a C-2 to C-18 bond. (-)-Singapurensine A is found in Kopsia singapurensis. Based on a literature review very few articles have been published on 13,15-dimethyl (1S,2R,6R,14S,15R,16R,18S,20S)-15,20-dihydroxy-17-oxa-3,13-diazaheptacyclo[12.6.2.0¹,¹⁶.0²,⁶.0³,¹⁸.0⁶,¹⁴.0⁷,¹²]Docosa-7,9,11-triene-13,15-dicarboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282213092D          

 32 38  0  0  1  0            999 V2000
    5.4457    0.7361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8887    0.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5076   -0.6915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6833   -0.7273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2403   -0.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6214    0.7003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4265   -0.1859    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3127   -1.2238    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1936   -1.3833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4960   -2.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9824   -2.7966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3119   -2.2729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6143   -3.0405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5013   -1.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5524   -0.8331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3297   -0.6513    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6742    0.0063    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2638    0.7087    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4267    0.6412    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2988   -0.2064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861   -1.0192    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4725   -1.5677    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9842   -2.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1642   -2.1423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3160   -2.9881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8277   -3.6530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7536   -2.3434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8507    0.0348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3548   -0.7132    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9907   -1.4535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9430    1.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6129    0.6713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  7  5  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  6  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
 21 20  1  6  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
  8 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 22 27  1  1  0  0  0
 19 28  1  0  0  0  0
 28 29  1  0  0  0  0
 16 29  1  0  0  0  0
 29 30  1  1  0  0  0
 18 31  1  0  0  0  0
 31 32  1  0  0  0  0
  7 32  1  0  0  0  0
M  END

     RDKit          3D

 58 64  0  0  0  0  0  0  0  0999 V2000
    4.7662    2.3872    0.9420 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8701    1.4867    0.3176 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4726    1.6782    0.3729 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1409    2.7045    1.0186 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6401    0.7622   -0.2592 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1659   -0.3922   -0.9805 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3520   -0.5863   -1.6941 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6065   -1.7981   -2.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6592   -2.7895   -2.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4583   -2.6383   -1.5435 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2451   -1.4309   -0.9222 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1519   -0.8768   -0.0310 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5788   -1.1248    1.3900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6857   -1.5574    2.0523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6801   -1.8475    1.0495 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8516   -0.9969    1.3207 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9142   -1.3420    0.3191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4080   -1.0365   -1.0756 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2924   -2.2085   -1.8386 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0333   -0.4245   -0.9107 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3958   -0.0903   -2.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0112    0.4443   -2.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2285    0.5776   -0.4633 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7718    1.4931   -0.0055 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0107    2.4262   -1.0807 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6379    2.3208    1.1753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7317    3.5722    1.1217 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4042    1.7798    2.4180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2716    2.5760    3.5978 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1374    0.7520    0.0182 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4480    0.3251    1.3025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1679   -1.5026   -0.2403 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2268    1.8891    1.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6048    2.6718    0.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2344    3.2740    1.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0923    0.1867   -1.7625 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5199   -1.9475   -2.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8155   -3.7468   -2.7342 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7277   -3.4130   -1.4789 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3020   -2.0090    1.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1389   -0.3250    1.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0655   -0.8323    2.8035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4793   -2.5530    2.5543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2615   -1.2360    2.3300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0788   -2.4414    0.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8790   -0.8672    0.5278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0960   -0.3041   -1.5552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0934   -2.2659   -2.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3283   -1.0335   -2.8076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0220    0.5954   -2.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7666   -0.1944   -2.4205 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0512    1.5002   -2.3670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9037    2.8356   -0.9223 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1433    3.5773    3.2996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2647    2.7927    4.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4355    2.1529    4.3123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9445    1.4015   -0.3705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1249   -2.3510   -0.9488 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  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  1
 13 14  1  0
 14 15  1  0
 15 32  1  0
 32 20  1  0
 20 21  1  6
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  6
 24 30  1  0
 30 31  1  0
 31 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 24 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 23  5  1  6
 11  6  1  0
 32 12  1  0
 30 20  1  0
 23 12  1  0
 16 15  1  0
 18 20  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  7 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 14 43  1  0
 32 58  1  6
 21 49  1  0
 21 50  1  0
 22 51  1  0
 22 52  1  0
 25 53  1  0
 30 57  1  6
 16 44  1  1
 17 45  1  0
 17 46  1  0
 18 47  1  6
 19 48  1  0
 29 54  1  0
 29 55  1  0
 29 56  1  0
M  END


  Mrv1652304282213092D          

 32 38  0  0  1  0            999 V2000
    5.4457    0.7361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8887    0.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5076   -0.6915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6833   -0.7273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2403   -0.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6214    0.7003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4265   -0.1859    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3127   -1.2238    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1936   -1.3833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4960   -2.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9824   -2.7966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3119   -2.2729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6143   -3.0405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5013   -1.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5524   -0.8331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3297   -0.6513    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6742    0.0063    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2638    0.7087    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4267    0.6412    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2988   -0.2064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861   -1.0192    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4725   -1.5677    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9842   -2.2327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1642   -2.1423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3160   -2.9881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8277   -3.6530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7536   -2.3434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8507    0.0348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3548   -0.7132    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9907   -1.4535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9430    1.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6129    0.6713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  7  5  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  6  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
 21 20  1  6  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
  8 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 22 27  1  1  0  0  0
 19 28  1  0  0  0  0
 28 29  1  0  0  0  0
 16 29  1  0  0  0  0
 29 30  1  1  0  0  0
 18 31  1  0  0  0  0
 31 32  1  0  0  0  0
  7 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0066939

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)N1C2=CC=CC=C2[C@]23CCN4[C@H]2[C@]25CC[C@]13[C@@](O)([C@@H]2O[C@H]4C[C@@H]5O)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C23H26N2O7/c1-30-18(27)23(29)17-20-7-8-22(23)21(9-10-24(16(20)21)15(32-17)11-14(20)26)12-5-3-4-6-13(12)25(22)19(28)31-2/h3-6,14-17,26,29H,7-11H2,1-2H3/t14-,15-,16-,17+,20+,21+,22-,23+/m0/s1

> <INCHI_KEY>
SGULZRPTCAQSHB-VTZRMBNPSA-N

> <FORMULA>
C23H26N2O7

> <MOLECULAR_WEIGHT>
442.468

> <EXACT_MASS>
442.174001185

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
44.26279066333377

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
13,15-dimethyl (1S,2R,6R,14S,15R,16R,18S,20S)-15,20-dihydroxy-17-oxa-3,13-diazaheptacyclo[12.6.2.0^{1,16}.0^{2,6}.0^{3,18}.0^{6,14}.0^{7,12}]docosa-7,9,11-triene-13,15-dicarboxylate

> <ALOGPS_LOGP>
-0.01

> <JCHEM_LOGP>
0.57267499

> <ALOGPS_LOGS>
-1.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.445986147200628

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.750320278441611

> <JCHEM_PKA_STRONGEST_BASIC>
6.21470665762042

> <JCHEM_POLAR_SURFACE_AREA>
108.77000000000001

> <JCHEM_REFRACTIVITY>
107.63079999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.96e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13,15-dimethyl (1S,2R,6R,14S,15R,16R,18S,20S)-15,20-dihydroxy-17-oxa-3,13-diazaheptacyclo[12.6.2.0^{1,16}.0^{2,6}.0^{3,18}.0^{6,14}.0^{7,12}]docosa-7,9,11-triene-13,15-dicarboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      10.165   1.374   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.992   0.075   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.281  -1.291   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.742  -1.358   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.915  -0.058   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.627   1.307   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.396  -0.347   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.184  -2.284   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       7.828  -2.582   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       8.393  -4.015   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.434  -5.220   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       9.916  -4.243   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      10.480  -5.676   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.536  -3.287   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.631  -1.555   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.349  -1.216   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.992   0.012   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       4.226   1.323   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       2.663   1.197   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.424  -0.385   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.334  -1.903   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.615  -2.926   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.704  -4.168   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.173  -3.999   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.323  -5.578   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.412  -6.819   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.140  -4.374   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.588   0.065   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.529  -1.331   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       1.849  -2.713   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.494   2.244   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.744   1.253   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   17   32                                             
CONECT    8    7    9   14   22                                             
CONECT    9    8    4   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12                                                            
CONECT   14    8   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21   29                                             
CONECT   17   16    7   18                                                  
CONECT   18   17   19   31                                                  
CONECT   19   18   20   28                                                  
CONECT   20   19   21                                                       
CONECT   21   20   16   22                                                  
CONECT   22   21    8   23   27                                             
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25                                                            
CONECT   27   22                                                            
CONECT   28   19   29                                                       
CONECT   29   28   16   30                                                  
CONECT   30   29                                                            
CONECT   31   18   32                                                       
CONECT   32   31    7                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   76    0
END

View in JSmol

Synonyms

Value	Source
13,15-Dimethyl (1S,2R,6R,14S,15R,16R,18S,20S)-15,20-dihydroxy-17-oxa-3,13-diazaheptacyclo[12.6.2.0,.0,.0,.0,.0,]docosa-7,9,11-triene-13,15-dicarboxylic acid	Generator

Chemical Formula

C₂₃H₂₆N₂O₇

Average Mass

442.4680 Da

Monoisotopic Mass

442.17400 Da

IUPAC Name

13,15-dimethyl (1S,2R,6R,14S,15R,16R,18S,20S)-15,20-dihydroxy-17-oxa-3,13-diazaheptacyclo[12.6.2.0^{1,16}.0^{2,6}.0^{3,18}.0^{6,14}.0^{7,12}]docosa-7,9,11-triene-13,15-dicarboxylate

Traditional Name

13,15-dimethyl (1S,2R,6R,14S,15R,16R,18S,20S)-15,20-dihydroxy-17-oxa-3,13-diazaheptacyclo[12.6.2.0^{1,16}.0^{2,6}.0^{3,18}.0^{6,14}.0^{7,12}]docosa-7,9,11-triene-13,15-dicarboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)N1C2=CC=CC=C2[C@]23CCN4[C@H]2[C@]25CC[C@]13[C@@](O)([C@@H]2O[C@H]4C[C@@H]5O)C(=O)OC

InChI Identifier

InChI=1S/C23H26N2O7/c1-30-18(27)23(29)17-20-7-8-22(23)21(9-10-24(16(20)21)15(32-17)11-14(20)26)12-5-3-4-6-13(12)25(22)19(28)31-2/h3-6,14-17,26,29H,7-11H2,1-2H3/t14-,15-,16-,17+,20+,21+,22-,23+/m0/s1

InChI Key

SGULZRPTCAQSHB-VTZRMBNPSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Kopsia singapurensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aspidofractine alkaloids. These are alkaloids with a structure that is based on the hexacyclic aspidofractine core. These compounds are related to the Aspidosperma group by formation of a C-2 to C-18 bond.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aspidofractine alkaloids

Sub Class

Not Available

Direct Parent

Aspidofractine alkaloids

Alternative Parents

Substituents

Aspidofractine skeleton
Aspidosperma alkaloid
Carbazole
Indolecarboxylic acid
Indolecarboxylic acid derivative
Azaspirodecane
Quinolidine
Indole or derivatives
Indolizidine
1,3-oxazinane
Oxane
Oxazinane
Piperidine
N-alkylpyrrolidine
Benzenoid
Pyrrolidine
Methyl ester
Carbamic acid ester
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Carbonic acid derivative
Carboxylic acid ester
Hemiaminal
Organoheterocyclic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Azacycle
Oxacycle
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Carbonyl group
Organooxygen compound
Alcohol
Organic oxygen compound
Organopnictogen compound
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	-0.01	ALOGPS
logP	0.57	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	10.75	ChemAxon
pKa (Strongest Basic)	6.21	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	108.77 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	107.63 m³·mol⁻¹	ChemAxon
Polarizability	44.26 Å³	ChemAxon
Number of Rings	7	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

163038233

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Singapurensine A (NP0066939)

MOL for NP0066939 ((-)-Singapurensine A)

3D MOL for NP0066939 ((-)-Singapurensine A)

3D SDF for NP0066939 ((-)-Singapurensine A)

3D-SDF for NP0066939 ((-)-Singapurensine A)

PDB for NP0066939 ((-)-Singapurensine A)

3D PDB for NP0066939 ((-)-Singapurensine A)

SMILES for NP0066939 ((-)-Singapurensine A)

INCHI for NP0066939 ((-)-Singapurensine A)

Structure for NP0066939 ((-)-Singapurensine A)

3D Structure for NP0066939 ((-)-Singapurensine A)