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Aphidicolin

HCID 457964
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Basic information

CAS
38966-21-1
Standard SMILES
C[C@@]1(CO)[C@H](O)CC[C@@]2(C)[C@H]1CC[C@H]1C[C@@H]3C[C@@]12CC[C@]3(O)CO
InChIKey
NOFOAYPPHIUXJR-APNQCZIXSA-N
Molecular formula
C20H34O4
Average molar mass
338.5 g/mol
Monoisotopic mass
338.24570956

Overview

Aphidicolin is a tetracyclic diterpenoid that has an tetradecahydro-8,11a-methanocyclohepta[a]naphthalene skeleton with two hydroxymethyl substituents at positions 4 and 9, two methyl substituents at positions 4 and 11b and two hydroxy substituents at positions 3 and 9. An antibiotic with antiviral and antimitotical properties. Aphidicolin is a reversible inhibitor of eukaryotic nuclear DNA replication. It has a role as an EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor, an antimicrobial agent, an antineoplastic agent, an antiviral drug, a DNA synthesis inhibitor, an antimitotic, an apoptosis inducer, a fungal metabolite and an Aspergillus metabolite.

Names & identifiers

Preferred name
Aphidicolin
IUPAC
(1S,2S,5R,6R,7R,10S,12R,13R)-6,13-bis(hydroxymethyl)-2,6-dimethyltetracyclo[10.3.1.01,10.02,7]hexadecane-5,13-diol
English name
APHIDICOLIN
Molecular formula
C20H34O4
Molecular weight
338.48

Names & synonyms

aphidicolin38966-21-1(+)-AphidicolinNSC-234714ICI 69653DTXSID5036711(3R,4R,4aR,6aS,8R,9R,11aS,11bS)-4,9-bis(hydroxymethyl)-4,11b-dimethyltetradecahydro-8,11a-methanocyclohepta[a]naphthalene-3,9-diolNSC 234714ICI-69653NSC234714192TJ6PP19CHEBI:2766
Show more names
APC,11a-beta,11b-beta))-APHIDICOLIN USP/EP/BPAphidicolin, Ready Made Solution(+)-APHIDICOLIN, NIGROSPORA ORYZAEAphidicolin, froM Nigrospora oryzae
9,15-Cyclo-C,18-dinor-14,15-secoandrostane-4,17-dimethanol, 3,17-dihydroxy-4-methyl-, (3alpha,4alpha,5alpha,17alpha)-(1S,2S,5R,6R,7R,10S,12R,13R)-6,13-bis(hydroxymethyl)-2,6-dimethyltetracyclo[10.3.1.01,10.02,7]hexadecane-5,13-diolNSC3511408,11A-METHANO-11AH-CYCLOHEPTA(A)NAPHTHALENE-4,9-DIMETHANOL, TETRADECAHYDRO-3,9-DIHYDROXY-4,11B-DIMETHYL-, (3R,4R,4AR,6AS,8R,9R,11AS,11BS)-(1S,2S,5R,6R,7R,10S,12R,13R)-6,13-bis(hydroxymethyl)-2,6-dimethyltetracyclo(10.3.1.01,10.02,7)hexadecane-5,13-diol(3R,4R,4aR,6aS,8R,9R,11aS,11bS)-4,9-bis(hydroxymethyl)-4,11b-dimethyltetradecahydro-8,11a-methanocyclohepta(a)naphthalene-3,9-diolICI69653NSC 351140

Database identifiers

Properties

Computed structural properties

XLogP
2.5
Topological polar surface area
80.9 Ų
Hydrogen bond donors
4
Hydrogen bond acceptors
4
Rotatable bonds
2
Heavy atoms
24
Formal charge
0
Complexity
524

Experimental & physicochemical properties

DrugsPharmaceuticals -> Antibiotics

Physicochemical properties

Melting point
218 · 218-220°C
alpha
27 · D27 +12° (c = 1 in methanol)
Boiling point
394.61 °C · 394.61°C (rough estimate)
Density
1.0057 · 1.0057 (rough estimate)
vapor pressure
0.55 hPa · 0.55 hPa ( 20 °C)
refractive index
1.4434 · 1.4434 (estimate)
Flash point
87 ℃ · 87℃
storage temp.
2 · 2-8°C
solubility
1 mg/mL · ethanol: soluble1mg/mL (stable at least a week at 4°C.)
pka
14.24 · 14.24±0.70(Predicted)
form
White solid
color
colorless
biological source
Nigrospora sphaerica

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Regulatory InformationAphidicoline: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

F
10-21
wgk
3
rtecs
PB9185000
ridadr
NA 1993 / PGIII
hs_code
29419090
Signal word
Warning
Symbol(GHS)
GHS07
safety_code
22-24
Storage Class
10 - Combustible liquids
Hazard statements
H315-H319-H335
Precautionary statements
P271-P280

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 2 items

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.

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.

Applications · 5 items

Description(+)-Aphidicolin is a natural tetracyclic diterpene first isolated from the fungus C. aphidicola and shown to have antiviral activity against herpes simplex. In eukaryotic cells, it is a cell-permeable, reversible inhibitor of DNA replication, specifically blocking the activity of DNA polymerases α, δ, and ε when used at low micromolar levels. Aphidicolin can be used, at 3 μM, to arrest cells in G1/S phase or to increase gene amplification frequency.

UsesA DNA polymerase inhibitor. Blocks the cell cycle at the early S-phase

Uses(+)-Aphidicolin is a naturally occurring tetracyclic diterpene with potential antiviral and antimitotical properties.

UsesAphidicolin is a tetracyclic diterpene antibiotic isolated from fungi, notably Cephalosporium, Nigrospora, Harziella and Phoma. Aphidicolin has antibiotic, antiviral and antimitotic properties, blocking the cell cycle at early S-phase. This property has been used to synchronise cell division and is useful as a tool in cell differentiation research. Aphidicolin is a reversible inhibitor of DNA replication by inhibiting selected DNA polymerases. Aphidicolin induces apoptosis, prolongs the half-life of DNA methyltransferase, is active against Leishmania parasites and acts synergistically with the antitumour agents, vincristine and doxorubicin.

General DescriptionA cell-permeable tetracyclic diterpene antibiotic. Cell synchronization agent. Blocks the cell cycle at the early S-phase. Specific inhibitor of DNA polymerase α and δ in eukaryotic cells and in some viruses of animal origin. Potentiates apoptosis induced by arabinosyl nucleosides in leukemia cell lines. Also induces apoptosis in HeLaS3 cells, but inhibits vincristine-induced apoptosis in the p53-negative human prostate cancer cell line PC-3.

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
CAS
38966-21-1、69926-98-3
PubChem CID
457964
DTXSID
DTXSID5036711
ChEMBL
CHEMBL29711
ChEBI
CHEBI:2766
UNII
192TJ6PP19、6B3F8QW8TU
EC Number
609-602-3
Nikkaji
J19.324K
optical activity
27 · [α]27/D +12°, c = 1 in methanol(lit.)
Water Solubility
-20 ° · Soluble in DMSO or methanol. Insoluble in water. Store solutions at -20°
Merck
13 · 13,734
BRN
4689958 · 4689958
Stability
2 years · Stable for 2 years from date of purchase from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 1 month.
InChI
1S/C20H34O4/c1-17(11-21)15-4-3-13-9-14-10-19(13,7-8-20(14,24)12-22)18(15,2)6-5-16(17)23/h13-16,21-24H,3-12H2,1-2H3/t13-,14+,15-,16+,17-,18-,19-,20-/m0/s1
InChIKey
NOFOAYPPHIUXJR-APNQCZIXSA-N
SMILES
O[C@]1([C@H]2C[C@@]3([C@@]4([C@H]([C@@]([C@@H](CC4)O)(CO)C)CC[C@H]3C2)C)CC1)CO
FDA UNII
192 TJ6PP19 · 192TJ6PP19
UNSPSC Code
51102829 · 51102829
NACRES
85 · NA.85
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H319-H335
Precautionary statements
271 · P271-P280
Safety Statements
22 · 22-24
RIDADR
1993 · NA 1993 / PGIII
WGK Germany
3 · 3
RTECS
9185000 · PB9185000
F
10 · 10-21
HS Code
29419090 · 29419090
Storage Class
10 · 10 - Combustible liquids
Additional notes · 1 item

DefinitionChEBI: A tetracyclic diterpenoid that has an tetradecahydro-8,11a-methanocyclohepta[a]naphthalene skeleton with two hydroxymethyl substituents at positions 4 and 9, two methyl substituents at positions 4 and 11b and two hydroxy substituents at positi ns 3 and 9. An antibiotic with antiviral and antimitotical properties. Aphidicolin is a reversible inhibitor of eukaryotic nuclear DNA replication.