NP-MRD: Showing NP-Card for methyl 2-hydroxy-5,9-dimethyl-20-oxa-3-azaheptacyclo[11.5.2.1³,¹⁰.0¹,⁹.0²,⁶.0¹³,¹⁹.0¹⁶,¹⁹]henicos-16-ene-17-carboxylate (NP0285396)

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Record Information

Version

2.0

Created at

2022-09-09 13:33:21 UTC

Updated at

2022-09-09 13:33:21 UTC

NP-MRD ID

NP0285396

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-hydroxy-5,9-dimethyl-20-oxa-3-azaheptacyclo[11.5.2.1³,¹⁰.0¹,⁹.0²,⁶.0¹³,¹⁹.0¹⁶,¹⁹]henicos-16-ene-17-carboxylate

Description

Methyl 2-hydroxy-5,9-dimethyl-20-oxa-3-azaheptacyclo[11.5.2.1³,¹⁰.0¹,⁹.0²,⁶.0¹³,¹⁹.0¹⁶,¹⁹]Henicos-16-ene-17-carboxylate belongs to the class of organic compounds known as azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom. methyl 2-hydroxy-5,9-dimethyl-20-oxa-3-azaheptacyclo[11.5.2.1³,¹⁰.0¹,⁹.0²,⁶.0¹³,¹⁹.0¹⁶,¹⁹]henicos-16-ene-17-carboxylate is found in Daphniphyllum calycinum. Methyl 2-hydroxy-5,9-dimethyl-20-oxa-3-azaheptacyclo[11.5.2.1³,¹⁰.0¹,⁹.0²,⁶.0¹³,¹⁹.0¹⁶,¹⁹]Henicos-16-ene-17-carboxylate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251508542D          

 28 34  0  0  0  0            999 V2000
    1.6385   -4.0371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5464   -3.2172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2104   -2.7276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9664   -3.0578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1183   -1.9077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4328   -1.4645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5778   -1.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2626   -0.7348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9401   -0.1572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9765    0.6883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6508    1.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5015    1.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3241    0.7057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6377   -0.2697    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5766   -1.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3754   -1.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9807   -2.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2136   -0.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4029    0.0998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8041    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8095    0.4508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9880    0.3747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5126   -0.4601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6805   -1.3315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2124   -0.8101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0873   -1.6255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6436   -0.6261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9035   -0.9463    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  0  0  0  0
  7  8  1  0  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  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 12 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
  5 24  1  0  0  0  0
 23 25  1  0  0  0  0
 14 25  1  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
 23 27  1  0  0  0  0
  6 27  1  0  0  0  0
  9 27  1  0  0  0  0
 27 28  1  0  0  0  0
  9 28  1  0  0  0  0
M  END

     RDKit          3D

 59 65  0  0  0  0  0  0  0  0999 V2000
    3.8278    4.4060    0.5826 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2355    3.1025    0.5121 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3076    2.7778   -0.4570 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9881    3.6622   -1.2888 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7302    1.4291   -0.4866 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0191    0.4639    0.3482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7814   -0.0190    1.5196 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7491   -1.5579    1.4086 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6257   -1.8239    0.3890 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1224   -3.1885    0.3338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1782   -3.4353   -0.3338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0914   -2.2160   -0.4102 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3976   -1.8063    0.9881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0773   -0.4873    1.4319 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1577    0.2083    2.1453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9020    1.0644    1.0957 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7647    2.5111    1.2970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3508    0.4058   -0.0784 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5139    0.6609   -1.4610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8980   -0.5602   -2.1690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7231   -1.1875   -1.4147 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0230   -1.8614   -2.5581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0460   -0.1427   -0.7227 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7050    0.9405   -1.4944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8774    0.3809    0.3192 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4123    1.5781    0.7625 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2247   -0.7031   -0.0678 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1858   -1.4501   -0.9481 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6450    4.3406    1.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1363    4.7246   -0.4158 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0106    5.0624    1.0024 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8492    0.2893    1.4811 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2554    0.3283    2.4160 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7022   -1.9122    0.9767 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5038   -1.9713    2.3837 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8815   -3.8286   -0.2142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1640   -3.6105    1.3803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1685   -4.0486   -1.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7670   -4.1095    0.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0370   -2.6949   -0.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7906   -2.4419    1.7208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4391   -2.1338    1.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6378    0.9375    2.8111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8122   -0.4794    2.6716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9960    0.8181    1.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9342    2.8338    1.9880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7177    3.1004    0.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6723    2.9675    1.8063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8342   -0.6239    0.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2292    1.6072   -1.9203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6162    0.5694   -1.7334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6217   -1.3597   -2.3252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5874   -0.1820   -3.1554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7199   -2.3590   -3.2508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7390   -2.6103   -2.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5268   -1.1076   -3.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2805    0.6028   -2.3535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1314    1.8126   -1.7597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4717    2.3265    0.1569 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  6
 21 23  1  0
 23 24  1  6
 23 27  1  0
 27 28  1  6
 23 25  1  0
 25 26  1  1
 24  5  1  0
 27  6  1  0
 27  9  1  0
  9 28  1  6
 21 12  1  0
 25 14  1  0
 25 18  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  6
 13 41  1  0
 13 42  1  0
 15 43  1  0
 15 44  1  0
 16 45  1  1
 17 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  6
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 22 54  1  0
 22 55  1  0
 22 56  1  0
 24 57  1  0
 24 58  1  0
 26 59  1  0
M  END


  Mrv1533004251508542D          

 28 34  0  0  0  0            999 V2000
    1.6385   -4.0371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5464   -3.2172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2104   -2.7276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9664   -3.0578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1183   -1.9077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4328   -1.4645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5778   -1.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2626   -0.7348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9401   -0.1572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9765    0.6883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6508    1.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5015    1.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3241    0.7057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6377   -0.2697    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5766   -1.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3754   -1.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9807   -2.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2136   -0.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4029    0.0998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8041    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8095    0.4508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9880    0.3747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5126   -0.4601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6805   -1.3315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2124   -0.8101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0873   -1.6255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6436   -0.6261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9035   -0.9463    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  0  0  0  0
  7  8  1  0  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  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 12 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
  5 24  1  0  0  0  0
 23 25  1  0  0  0  0
 14 25  1  0  0  0  0
 18 25  1  0  0  0  0
 25 26  1  0  0  0  0
 23 27  1  0  0  0  0
  6 27  1  0  0  0  0
  9 27  1  0  0  0  0
 27 28  1  0  0  0  0
  9 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0285396

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C2CCC34CCC5CN6CC(C)C7CCC5(C)C(C1)(C23O4)C67O

> <INCHI_IDENTIFIER>
InChI=1S/C23H31NO4/c1-13-11-24-12-14-4-8-20-9-6-17-15(18(25)27-3)10-21(22(17,20)28-20)19(14,2)7-5-16(13)23(21,24)26/h13-14,16,26H,4-12H2,1-3H3

> <INCHI_KEY>
BJFLVMROQKHALJ-UHFFFAOYSA-N

> <FORMULA>
C23H31NO4

> <MOLECULAR_WEIGHT>
385.504

> <EXACT_MASS>
385.225308482

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
42.140300485267424

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-hydroxy-5,9-dimethyl-20-oxa-3-azaheptacyclo[11.5.2.1³,¹⁰.0¹,⁹.0²,⁶.0¹³,¹⁹.0¹⁶,¹⁹]henicos-16-ene-17-carboxylate

> <ALOGPS_LOGP>
2.16

> <JCHEM_LOGP>
2.3460678186145247

> <ALOGPS_LOGS>
-3.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.625883494303395

> <JCHEM_PKA_STRONGEST_BASIC>
10.756273163001522

> <JCHEM_POLAR_SURFACE_AREA>
62.3

> <JCHEM_REFRACTIVITY>
103.26840000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.34e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-hydroxy-5,9-dimethyl-20-oxa-3-azaheptacyclo[11.5.2.1³,¹⁰.0¹,⁹.0²,⁶.0¹³,¹⁹.0¹⁶,¹⁹]henicos-16-ene-17-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       3.059  -7.536   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.887  -6.006   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.126  -5.091   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.537  -5.708   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.954  -3.561   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.675  -2.734   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.079  -2.880   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.490  -1.372   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.755  -0.294   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.823   1.285   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.081   2.251   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.669   1.895   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.205   1.317   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       6.790  -0.503   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       6.676  -2.517   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.167  -2.702   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.297  -3.749   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.865  -1.212   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.219   0.186   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.101   1.156   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.244   0.841   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.711   0.700   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.690  -0.859   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.004  -2.485   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.997  -1.512   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.763  -3.034   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.068  -1.169   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.687  -1.767   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   24                                                  
CONECT    6    5    7   27                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   27   28                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   21                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   25                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   25                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   12   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24   25   27                                             
CONECT   24   23    5                                                       
CONECT   25   23   14   18   26                                             
CONECT   26   25                                                            
CONECT   27   23    6    9   28                                             
CONECT   28   27    9                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   68    0
END

View in JSmol

Synonyms

Value	Source
Methyl 2-hydroxy-5,9-dimethyl-20-oxa-3-azaheptacyclo[11.5.2.1,.0,.0,.0,.0,]henicos-16-ene-17-carboxylic acid	Generator
Methyl 2-hydroxy-5,9-dimethyl-20-oxa-3-azaheptacyclo[11.5.2.1³,¹⁰.0¹,⁹.0²,⁶.0¹³,¹⁹.0¹⁶,¹⁹]henicos-16-ene-17-carboxylic acid	Generator

Chemical Formula

C₂₃H₃₁NO₄

Average Mass

385.5040 Da

Monoisotopic Mass

385.22531 Da

IUPAC Name

methyl 2-hydroxy-5,9-dimethyl-20-oxa-3-azaheptacyclo[11.5.2.1³,¹⁰.0¹,⁹.0²,⁶.0¹³,¹⁹.0¹⁶,¹⁹]henicos-16-ene-17-carboxylate

Traditional Name

methyl 2-hydroxy-5,9-dimethyl-20-oxa-3-azaheptacyclo[11.5.2.1³,¹⁰.0¹,⁹.0²,⁶.0¹³,¹⁹.0¹⁶,¹⁹]henicos-16-ene-17-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C2CCC34CCC5CN6CC(C)C7CCC5(C)C(C1)(C23O4)C67O

InChI Identifier

InChI=1S/C23H31NO4/c1-13-11-24-12-14-4-8-20-9-6-17-15(18(25)27-3)10-21(22(17,20)28-20)19(14,2)7-5-16(13)23(21,24)26/h13-14,16,26H,4-12H2,1-3H3

InChI Key

BJFLVMROQKHALJ-UHFFFAOYSA-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
Daphniphyllum calycinum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azaspirodecane derivatives

Sub Class

Not Available

Direct Parent

Azaspirodecane derivatives

Alternative Parents

Substituents

Azaspirodecane
Indole or derivatives
Indolizidine
Oxane
N-alkylpyrrolidine
Piperidine
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Pyrrolidine
Carboxylic acid ester
Hemiaminal
Alkanolamine
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Monocarboxylic acid or derivatives
Azacycle
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic nitrogen 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	2.16	ALOGPS
logP	2.35	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	12.63	ChemAxon
pKa (Strongest Basic)	10.76	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	62.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	103.27 m³·mol⁻¹	ChemAxon
Polarizability	42.14 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

74392112

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 2-hydroxy-5,9-dimethyl-20-oxa-3-azaheptacyclo[11.5.2.1³,¹⁰.0¹,⁹.0²,⁶.0¹³,¹⁹.0¹⁶,¹⁹]henicos-16-ene-17-carboxylate (NP0285396)

MOL for NP0285396 (methyl 2-hydroxy-5,9-dimethyl-20-oxa-3-azaheptacyclo[11.5.2.1³,¹⁰.0¹,⁹.0²,⁶.0¹³,¹⁹.0¹⁶,¹⁹]henicos-16-ene-17-carboxylate)

3D MOL for NP0285396 (methyl 2-hydroxy-5,9-dimethyl-20-oxa-3-azaheptacyclo[11.5.2.1³,¹⁰.0¹,⁹.0²,⁶.0¹³,¹⁹.0¹⁶,¹⁹]henicos-16-ene-17-carboxylate)

3D SDF for NP0285396 (methyl 2-hydroxy-5,9-dimethyl-20-oxa-3-azaheptacyclo[11.5.2.1³,¹⁰.0¹,⁹.0²,⁶.0¹³,¹⁹.0¹⁶,¹⁹]henicos-16-ene-17-carboxylate)

3D-SDF for NP0285396 (methyl 2-hydroxy-5,9-dimethyl-20-oxa-3-azaheptacyclo[11.5.2.1³,¹⁰.0¹,⁹.0²,⁶.0¹³,¹⁹.0¹⁶,¹⁹]henicos-16-ene-17-carboxylate)

PDB for NP0285396 (methyl 2-hydroxy-5,9-dimethyl-20-oxa-3-azaheptacyclo[11.5.2.1³,¹⁰.0¹,⁹.0²,⁶.0¹³,¹⁹.0¹⁶,¹⁹]henicos-16-ene-17-carboxylate)

3D PDB for NP0285396 (methyl 2-hydroxy-5,9-dimethyl-20-oxa-3-azaheptacyclo[11.5.2.1³,¹⁰.0¹,⁹.0²,⁶.0¹³,¹⁹.0¹⁶,¹⁹]henicos-16-ene-17-carboxylate)

SMILES for NP0285396 (methyl 2-hydroxy-5,9-dimethyl-20-oxa-3-azaheptacyclo[11.5.2.1³,¹⁰.0¹,⁹.0²,⁶.0¹³,¹⁹.0¹⁶,¹⁹]henicos-16-ene-17-carboxylate)

INCHI for NP0285396 (methyl 2-hydroxy-5,9-dimethyl-20-oxa-3-azaheptacyclo[11.5.2.1³,¹⁰.0¹,⁹.0²,⁶.0¹³,¹⁹.0¹⁶,¹⁹]henicos-16-ene-17-carboxylate)

Structure for NP0285396 (methyl 2-hydroxy-5,9-dimethyl-20-oxa-3-azaheptacyclo[11.5.2.1³,¹⁰.0¹,⁹.0²,⁶.0¹³,¹⁹.0¹⁶,¹⁹]henicos-16-ene-17-carboxylate)

3D Structure for NP0285396 (methyl 2-hydroxy-5,9-dimethyl-20-oxa-3-azaheptacyclo[11.5.2.1³,¹⁰.0¹,⁹.0²,⁶.0¹³,¹⁹.0¹⁶,¹⁹]henicos-16-ene-17-carboxylate)