(1R,2R,4aS,6aS,6bR,8aR,9R,10R,11R,12aR,12bR,14bS)-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)1,10,11-trihydroxy-1,2,6a,6b,9,12a-hexamethyl-9-(sulfooxymethyl)-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

ID: ALA1078217

PubChem CID: 44254605

Max Phase: Preclinical

Molecular Formula: C36H58O14S

Molecular Weight: 746.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H]1CC[C@]2(C(=O)O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@@H](O)[C@H](O)[C@@](C)(COS(=O)(=O)O)[C@@H]5CC[C@]43C)[C@@H]2[C@]1(C)O

Standard InChI:  InChI=1S/C36H58O14S/c1-18-9-12-36(30(43)50-29-26(41)25(40)24(39)21(16-37)49-29)14-13-33(4)19(27(36)35(18,6)44)7-8-23-31(2)15-20(38)28(42)32(3,17-48-51(45,46)47)22(31)10-11-34(23,33)5/h7,18,20-29,37-42,44H,8-17H2,1-6H3,(H,45,46,47)/t18-,20-,21-,22-,23-,24-,25+,26-,27-,28+,29+,31+,32+,33-,34-,35-,36+/m1/s1

Standard InChI Key:  XBNZAVUJFGQQSI-JVJIQXRHSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA1078217

   [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,2R,4aS,6aR,6aS,6bR,8aR,9R,10R,11R,12aR,14bS)-1,10,11-trihydroxy-1,2,6a,6b,9,12a-hexamethyl-9-(sulfooxymethyl)-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 746.91

Molecular Weight (Monoisotopic): 746.3547

AlogP: 1.23

#Rotatable Bonds: 6

Polar Surface Area: 240.74

Molecular Species: ACID

HBA: 13

HBD: 8

#RO5 Violations: 3

HBA (Lipinski): 14

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: -1.38

CX Basic pKa: ┄

CX LogP: -0.58

CX LogD: -1.60

Aromatic Rings: ┄

Heavy Atoms: 51

QED Weighted: 0.11

Np Likeness Score: 3.03

References

1. Mencherini T, Picerno P, Russo P, Meloni M, Aquino R..  (2009)  Composition of the fresh leaves and stems of Melissa officinalis and evaluation of skin irritation in a reconstituted human epidermis model.,  72  (8): [PMID:19653667] [10.1021/np9003195]

Source

Source(1):

• Scientific Literature