NP-MRD: Showing NP-Card for (4s,5s,7e,10r,11r)-8-hydroxy-7-methyl-6,9,13-trioxo-4,10-bis(prop-1-en-2-yl)-12-oxabicyclo[9.2.1]tetradeca-1(14),7-dien-5-yl acetate (NP0318917)

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Record Information

Version

2.0

Created at

2022-09-11 19:41:27 UTC

Updated at

2022-09-11 19:41:27 UTC

NP-MRD ID

NP0318917

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4s,5s,7e,10r,11r)-8-hydroxy-7-methyl-6,9,13-trioxo-4,10-bis(prop-1-en-2-yl)-12-oxabicyclo[9.2.1]tetradeca-1(14),7-dien-5-yl acetate

Description

Kollolide C acetate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. (4s,5s,7e,10r,11r)-8-hydroxy-7-methyl-6,9,13-trioxo-4,10-bis(prop-1-en-2-yl)-12-oxabicyclo[9.2.1]tetradeca-1(14),7-dien-5-yl acetate is found in Antillogorgia bipinnata. Based on a literature review very few articles have been published on Kollolide C acetate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309112221412D          

 29 30  0  0  1  0            999 V2000
    4.5113   -0.2528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6877   -0.2045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2341   -0.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3177    0.5329    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5097    0.3664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7267    0.6262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1785    1.2427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7017    1.8806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2566    2.5753    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4584    2.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4101    1.5431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2846    1.0981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8883    3.3819    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4537    4.0832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6291    4.0574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8437    4.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6963    3.5484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7446    4.3720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4794    3.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9330    3.9777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0276    2.6721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7650    3.0421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1941    1.8641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0177    1.8158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9342    1.0811    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6233    0.6274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3607    0.9974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4090    1.8210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0498    0.5438    0.0000 O   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
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
  4 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
M  END


  Mrv1652309112221412D          

 29 30  0  0  1  0            999 V2000
    4.5113   -0.2528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6877   -0.2045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2341   -0.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3177    0.5329    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5097    0.3664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7267    0.6262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1785    1.2427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7017    1.8806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2566    2.5753    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4584    2.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4101    1.5431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2846    1.0981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8883    3.3819    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4537    4.0832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6291    4.0574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8437    4.8102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6963    3.5484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7446    4.3720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4794    3.2886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9330    3.9777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0276    2.6721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7650    3.0421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1941    1.8641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0177    1.8158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9342    1.0811    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6233    0.6274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3607    0.9974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4090    1.8210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0498    0.5438    0.0000 O   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
  4  2  1  6  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
  4 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0318917

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1[C@@H](CCC2=C[C@@H](OC2=O)[C@@H](C(C)=C)C(=O)\C(O)=C(C)/C1=O)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C22H26O7/c1-10(2)15-8-7-14-9-16(29-22(14)27)17(11(3)4)20(26)18(24)12(5)19(25)21(15)28-13(6)23/h9,15-17,21,24H,1,3,7-8H2,2,4-6H3/b18-12+/t15-,16+,17+,21-/m0/s1

> <INCHI_KEY>
KFOAFRGWCVUHFY-XPIXLHGCSA-N

> <FORMULA>
C22H26O7

> <MOLECULAR_WEIGHT>
402.443

> <EXACT_MASS>
402.167853177

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
40.494761891424076

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S,5S,7E,10R,11R)-8-hydroxy-7-methyl-6,9,13-trioxo-4,10-bis(prop-1-en-2-yl)-12-oxabicyclo[9.2.1]tetradeca-1(14),7-dien-5-yl acetate

> <JCHEM_LOGP>
3.3527855333333325

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.45857674539431

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.168863477157397

> <JCHEM_PKA_STRONGEST_BASIC>
-5.467399096313426

> <JCHEM_POLAR_SURFACE_AREA>
106.97000000000003

> <JCHEM_REFRACTIVITY>
106.41839999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4S,5S,7E,10R,11R)-8-hydroxy-7-methyl-6,9,13-trioxo-4,10-bis(prop-1-en-2-yl)-12-oxabicyclo[9.2.1]tetradeca-1(14),7-dien-5-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       8.421  -0.472   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.884  -0.382   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.037  -1.668   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.193   0.995   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.685   0.684   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.223   1.169   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.200   2.320   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.176   3.510   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.346   4.807   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.856   4.418   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.766   2.881   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.531   2.050   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.525   6.313   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.714   7.622   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.174   7.574   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.442   8.979   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.033   6.624   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.123   8.161   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.495   6.139   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.342   7.425   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.518   4.988   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.895   5.679   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.829   3.480   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.366   3.389   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.344   2.018   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.630   1.171   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.007   1.862   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.097   3.399   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      11.293   1.015   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   25                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10    7   12                                                  
CONECT   12   11                                                            
CONECT   13    9   14   17                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   13   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23    4   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   60    0
END

View in JSmol

Synonyms

Value	Source
Kollolide C acetic acid	Generator

Chemical Formula

C₂₂H₂₆O₇

Average Mass

402.4430 Da

Monoisotopic Mass

402.16785 Da

IUPAC Name

(4S,5S,7E,10R,11R)-8-hydroxy-7-methyl-6,9,13-trioxo-4,10-bis(prop-1-en-2-yl)-12-oxabicyclo[9.2.1]tetradeca-1(14),7-dien-5-yl acetate

Traditional Name

(4S,5S,7E,10R,11R)-8-hydroxy-7-methyl-6,9,13-trioxo-4,10-bis(prop-1-en-2-yl)-12-oxabicyclo[9.2.1]tetradeca-1(14),7-dien-5-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1[C@@H](CCC2=C[C@@H](OC2=O)[C@@H](C(C)=C)C(=O)\C(O)=C(C)/C1=O)C(C)=C

InChI Identifier

InChI=1S/C22H26O7/c1-10(2)15-8-7-14-9-16(29-22(14)27)17(11(3)4)20(26)18(24)12(5)19(25)21(15)28-13(6)23/h9,15-17,21,24H,1,3,7-8H2,2,4-6H3/b18-12+/t15-,16+,17+,21-/m0/s1

InChI Key

KFOAFRGWCVUHFY-XPIXLHGCSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Antillogorgia bipinnata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Pseudopterane diterpenoid
Diterpene lactone
Diterpenoid
Ileabethane, pseudopterane or nor-sandresane diterpenoid
Macrolide
Alpha-acyloxy ketone
2-furanone
Dicarboxylic acid or derivatives
Dihydrofuran
Vinylogous acid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Ketone
Carboxylic acid ester
Cyclic ketone
Organoheterocyclic compound
Enol
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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	3.35	ChemAxon
pKa (Strongest Acidic)	5.17	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	106.97 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	106.42 m³·mol⁻¹	ChemAxon
Polarizability	40.49 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

9878804

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11704081

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4s,5s,7e,10r,11r)-8-hydroxy-7-methyl-6,9,13-trioxo-4,10-bis(prop-1-en-2-yl)-12-oxabicyclo[9.2.1]tetradeca-1(14),7-dien-5-yl acetate (NP0318917)

MOL for NP0318917 ((4s,5s,7e,10r,11r)-8-hydroxy-7-methyl-6,9,13-trioxo-4,10-bis(prop-1-en-2-yl)-12-oxabicyclo[9.2.1]tetradeca-1(14),7-dien-5-yl acetate)

3D MOL for NP0318917 ((4s,5s,7e,10r,11r)-8-hydroxy-7-methyl-6,9,13-trioxo-4,10-bis(prop-1-en-2-yl)-12-oxabicyclo[9.2.1]tetradeca-1(14),7-dien-5-yl acetate)

3D SDF for NP0318917 ((4s,5s,7e,10r,11r)-8-hydroxy-7-methyl-6,9,13-trioxo-4,10-bis(prop-1-en-2-yl)-12-oxabicyclo[9.2.1]tetradeca-1(14),7-dien-5-yl acetate)

3D-SDF for NP0318917 ((4s,5s,7e,10r,11r)-8-hydroxy-7-methyl-6,9,13-trioxo-4,10-bis(prop-1-en-2-yl)-12-oxabicyclo[9.2.1]tetradeca-1(14),7-dien-5-yl acetate)

PDB for NP0318917 ((4s,5s,7e,10r,11r)-8-hydroxy-7-methyl-6,9,13-trioxo-4,10-bis(prop-1-en-2-yl)-12-oxabicyclo[9.2.1]tetradeca-1(14),7-dien-5-yl acetate)

3D PDB for NP0318917 ((4s,5s,7e,10r,11r)-8-hydroxy-7-methyl-6,9,13-trioxo-4,10-bis(prop-1-en-2-yl)-12-oxabicyclo[9.2.1]tetradeca-1(14),7-dien-5-yl acetate)

SMILES for NP0318917 ((4s,5s,7e,10r,11r)-8-hydroxy-7-methyl-6,9,13-trioxo-4,10-bis(prop-1-en-2-yl)-12-oxabicyclo[9.2.1]tetradeca-1(14),7-dien-5-yl acetate)

INCHI for NP0318917 ((4s,5s,7e,10r,11r)-8-hydroxy-7-methyl-6,9,13-trioxo-4,10-bis(prop-1-en-2-yl)-12-oxabicyclo[9.2.1]tetradeca-1(14),7-dien-5-yl acetate)

Structure for NP0318917 ((4s,5s,7e,10r,11r)-8-hydroxy-7-methyl-6,9,13-trioxo-4,10-bis(prop-1-en-2-yl)-12-oxabicyclo[9.2.1]tetradeca-1(14),7-dien-5-yl acetate)

3D Structure for NP0318917 ((4s,5s,7e,10r,11r)-8-hydroxy-7-methyl-6,9,13-trioxo-4,10-bis(prop-1-en-2-yl)-12-oxabicyclo[9.2.1]tetradeca-1(14),7-dien-5-yl acetate)