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Home > Encyclopedia > (-)-Deoxypodophyllotoxin

(-)-Deoxypodophyllotoxin

(-)-Deoxypodophyllotoxin structure

(-)-Deoxypodophyllotoxin 

structure
  • CAS No:

    19186-35-7

  • Formula:

    C22H22O7

  • Chemical Name:

    (-)-Deoxypodophyllotoxin

  • Synonyms:

    Furo[3′,4′:6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)-,(5R,5aR,8aR)-;Podophyllotoxin,deoxy-;Furo[3′,4′:6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)-,[5R-(5α,5aβ,8aα)]-;(5R,5aR,8aR)-5,8,8a,9-Tetrahydro-5-(3,4,5-trimethoxyphenyl)furo[3′,4′:6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one;Deoxypodophyllotoxin;Desoxypodophyllotoxin;Anthricin;Silicicolin;4-Deoxypodophyllotoxin;(-)-Deoxypodophyllotoxin;(-)-Anthricin;AS 2-3;(-)-Desoxypodophyllotoxin;518-30-9;1836-86-8;24150-31-0;75805-80-0

  • Categories:

    Natural Products  >  Lignans

Description

ChEBI: A member of the class of furonaphthodioxoles that is (5R,5aR,8aR)-5,8,8a,9-tetrahydro-2H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one substituted a position 5 by a 3,4,5-trimethoxyphenyl group.


Deoxypodophyllotoxin is a member of the class of furonaphthodioxoles that is (5R,5aR,8aR)-5,8,8a,9-tetrahydro-2H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one substituted at position 5 by a 3,4,5-trimethoxyphenyl group. It has a role as a plant metabolite, an antineoplastic agent and an apoptosis inducer. It is a lignan, a furonaphthodioxole, a gamma-lactone and a member of methoxybenzenes.

(-)-Deoxypodophyllotoxin Basic Attributes

398.40588

398.41

45NR8XYU1L

403148

DTXSID30318504

Characteristics

72.4

2.44

1.304±0.06 g/cm3(Predicted)

168 °C

564.5±50.0 °C(Predicted)

247.0±30.2 °C

1.587

Drug Information

Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)|Semisynthetic conjugates of various toxic molecules, including RADIOACTIVE ISOTOPES and bacterial or plant toxins, with specific immune substances such as IMMUNOGLOBULINS; MONOCLONAL ANTIBODIES; and ANTIGENS. The antitumor or antiviral immune substance carries the toxin to the tumor or infected cell where the toxin exerts its poisonous effect. (See all compounds classified as Immunotoxins.)

Deoxypodophyllotoxin has known human metabolites that include 5-(4-Hydroxy-3,5-dimethoxyphenyl)-5a,8,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-6-one, 5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one, and 6,7-Dihydroxy-4-(3,4,5-trimethoxyphenyl)-3a,4,9,9a-tetrahydro-1H-benzo[f][2]benzofuran-3-one.

deoxypicropodophyllin

(-)-Deoxypodophyllotoxin Use and Manufacturing

4-Deoxypodophyllotoxin is a medicinal herb product isolated from Anthriscus sylvestris Hoffm. It is well known for its antitumor, antiviral, and anti-inflammatory activities. 4-Deoxypodophyllotoxin was also shown to inhibit the passive cutaneous anaphylaxis reaction.

Computed Properties

Molecular Weight:398.4
XLogP3:3.1
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:4
Exact Mass:398.13655304
Monoisotopic Mass:398.13655304
Topological Polar Surface Area:72.4
Heavy Atom Count:29
Complexity:598
Defined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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